$1,950,000 Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail. Step inside to whitewashed oak wood and travertine flooring, setting the tone for a warm and sophisticated ambiance. The open floor plan begins with a private front office, ideal for remote work, and a guest suite with a full bath—perfect for visitors or multi-generational living. The first-floor primary suite serves as a private retreat, featuring direct access to the patio for a peaceful outdoor escape. The spa-like en-suite bathroom boasts dual vanities, a walk-in shower, and a freestanding soaking tub, while the custom-built walk-in closet offers elegant storage solutions. Thoughtful details, like built-in wiring for a wall-mounted TV, enhance both convenience and luxury. At the heart of the home is the gourmet kitchen, designed to impress with a solid walnut breakfast bar, quartzite, Carrara, and travertine countertops, Grohe faucets, and custom pullout/swivel cabinetry. A hidden pantry blends seamlessly into the custom cabinetry, while top-tier Thermador gas appliances, including a 42” refrigerator, make cooking a breeze. Flowing effortlessly into the family room and private courtyard, this space is perfect for entertaining. Upstairs, you'll find stunning Venetian plaster walls and a modern glass stair railing leading to a versatile loft space. Three additional bedrooms are located on this level, each featuring custom-built walk-in closets for optimal organization. One of the upstairs bedrooms includes a private en-suite, while the bonus loft opens to a covered balcony through elegant French doors, providing a tranquil indoor-outdoor retreat. Plush new carpeting in the bedrooms enhances the comfort and style of the upper level. Designed for seamless outdoor living, this home features a custom-built gas fire pit, summer kitchen, and outdoor grill, making it perfect for year-round entertaining. The expansive upstairs balcony offers additional entertainment space, large enough for a ping pong table, outdoor lounge, or media area. A two-car rear side-entry garage, connected to the main house by a charming esplanade walkway, offers both privacy and convenience while enhancing the home’s architectural beauty. The freshly painted exterior adds to the home’s pristine appeal, making it truly move-in ready. Located within one of Winter Park’s most desired school districts, this home is zoned for Audubon K-8 and Winter Park High School. Plus, you’re just minutes from East End Market and Park Avenue, with the area's finest dining, shopping, and cultural attractions. This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today! 5 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code Welcome to 141 Oakwood Way, a one-of-a-kind custom-built estate in the highly desirable south Winter Park/Lake Sue area. This modern Mediterranean-inspired residence seamlessly blends timeless elegance with contemporary luxury, offering an exceptional living experience with high-end finishes, thoughtfully designed spaces, and unmatched attention to detail. Step inside to whitewashed oak wood and travertine flooring, setting the tone for a warm and sophisticated ambiance. The open floor plan begins with a private front office, ideal for remote work, and a guest suite with a full bath—perfect for visitors or multi-generational living. The first-floor primary suite serves as a private retreat, featuring direct access to the patio for a peaceful outdoor escape. The spa-like en-suite bathroom boasts dual vanities, a walk-in shower, and a freestanding soaking tub, while the custom-built walk-in closet offers elegant storage solutions. Thoughtful details, like built-in wiring for a wall-mounted TV, enhance both convenience and luxury. At the heart of the home is the gourmet kitchen, designed to impress with a solid walnut breakfast bar, quartzite, Carrara, and travertine countertops, Grohe faucets, and custom pullout/swivel cabinetry. A hidden pantry blends seamlessly into the custom cabinetry, while top-tier Thermador gas appliances, including a 42” refrigerator, make cooking a breeze. Flowing effortlessly into the family room and private courtyard, this space is perfect for entertaining. Upstairs, you'll find stunning Venetian plaster walls and a modern glass stair railing leading to a versatile loft space. Three additional bedrooms are located on this level, each featuring custom-built walk-in closets for optimal organization. One of the upstairs bedrooms includes a private en-suite, while the bonus loft opens to a covered balcony through elegant French doors, providing a tranquil indoor-outdoor retreat. Plush new carpeting in the bedrooms enhances the comfort and style of the upper level. Designed for seamless outdoor living, this home features a custom-built gas fire pit, summer kitchen, and outdoor grill, making it perfect for year-round entertaining. The expansive upstairs balcony offers additional entertainment space, large enough for a ping pong table, outdoor lounge, or media area. A two-car rear side-entry garage, connected to the main house by a charming esplanade walkway, offers both privacy and convenience while enhancing the home’s architectural beauty. The freshly painted exterior adds to the home’s pristine appeal, making it truly move-in ready. Located within one of Winter Park’s most desired school districts, this home is zoned for Audubon K-8 and Winter Park High School. Plus, you’re just minutes from East End Market and Park Avenue, with the area's finest dining, shopping, and cultural attractions. This is more than a home—it’s an expression of refined living and timeless design. Schedule your private tour today! 141 Oakwood Way, Winter Park
$1,975,000 Elegant French Country Estate in Prestigious Winter ParkNestled in the heart of Winter Park’s picturesque, tree-lined streets near Lake Sue, this exquisite French Country estate blends timeless elegance with modern luxury. Situated on an oversized, gated lot, this stunning home offers privacy, sophistication, and an unparalleled living experience.The expansive primary suite, located on the first floor, is a private retreat with spa-like amenities. The open-concept living and dining areas flow seamlessly into the gourmet kitchen, complete with top-of-the-line gas appliances, custom cabinetry, and a separate catering kitchen—ideal for entertaining. The sun-drenched Florida room, surrounded by floor-to-ceiling windows and French doors, provides breathtaking views of the serene private patio and courtyard.A separate office/den on the first floor offers the perfect work-from-home space, while an elevator leads to the second-floor loft-style living area, two additional bedrooms, and a well-appointed Jack-and-Jill bathroom.The detached three-car garage provides ample storage and the opportunity to add a mother-in-law suite above, making this estate both functional and future-ready. The gated driveway and fully fenced property ensure security and exclusivity, all within one of Winter Park’s most sought-after neighborhoods.This is a rare opportunity to own a luxurious estate in a prestigious Winter Park location, surrounded by the beauty of the Lake Sue neighborhodd and just moments from the best shopping, dining, and cultural experiences the area has to offer. 3 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code Elegant French Country Estate in Prestigious Winter ParkNestled in the heart of Winter Park’s picturesque, tree-lined streets near Lake Sue, this exquisite French Country estate blends timeless elegance with modern luxury. Situated on an oversized, gated lot, this stunning home offers privacy, sophistication, and an unparalleled living experience.The expansive primary suite, located on the first floor, is a private retreat with spa-like amenities. The open-concept living and dining areas flow seamlessly into the gourmet kitchen, complete with top-of-the-line gas appliances, custom cabinetry, and a separate catering kitchen—ideal for entertaining. The sun-drenched Florida room, surrounded by floor-to-ceiling windows and French doors, provides breathtaking views of the serene private patio and courtyard.A separate office/den on the first floor offers the perfect work-from-home space, while an elevator leads to the second-floor loft-style living area, two additional bedrooms, and a well-appointed Jack-and-Jill bathroom.The detached three-car garage provides ample storage and the opportunity to add a mother-in-law suite above, making this estate both functional and future-ready. The gated driveway and fully fenced property ensure security and exclusivity, all within one of Winter Park’s most sought-after neighborhoods.This is a rare opportunity to own a luxurious estate in a prestigious Winter Park location, surrounded by the beauty of the Lake Sue neighborhodd and just moments from the best shopping, dining, and cultural experiences the area has to offer. 140 Dana Way, Winter Park
$1,625,000 Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare find. Step inside to find newly refinished Brazilian Rosewood floors throughout the main living areas. The formal living room features a wood-burning fireplace and two sets of French doors that open to a covered lanai with a remote-controlled motorized screen, perfect for seamless indoor-outdoor living. The formal dining room sets the stage for elegant entertaining, while the spacious open-concept kitchen overlooks the family room. Designed for the culinary enthusiast, the kitchen boasts an Italian porcelain island, a brand-new Kucht Professional 8-burner gas range/oven, double ovens, and a walk-in pantry. The family room offers another wood-burning fireplace and French doors leading to the screened-in saltwater heated pool, refinished just three years ago with new equipment. The first-floor primary suite is a true retreat, featuring serene pool views, a large walk-in closet with California Closet system, and a spacious en-suite bath. Two additional first-floor bedrooms, each with walk-in closets, provide comfort and convenience. Upstairs, a private bedroom, full bath, and large bonus room offer the perfect space for guests or a secondary living area, with easy access to walk-in attic storage. A two-car attached garage includes built-in storage and a private staircase leading to a guest apartment/bedroom suite complete with a wet bar and full bath—ideal for multi-generational living or an au pair. Outdoor living is at its finest with a covered lanai, new tile flooring, and a remote-controlled motorized screen, plus a poolside half bath and outdoor shower. Situated in a Grade A school district and offering easy access to major roadways, this exquisite home blends elegance, comfort, and prime location. Please see attachments for the full list of improvements. 5 Beds ⋅ 6 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code Elegant 5-Bedroom Estate in the Heart of Winter Park. Nestled on a picturesque double lot in the highly sought-after Via’s, this stunning 5-bedroom, 4 full bath, 2 half bath traditional home offers over 4,200 sq. ft. of refined living space. With timeless architectural details, modern upgrades, and an unbeatable location just minutes from Park Avenue’s shops and restaurants, this home is a rare find. Step inside to find newly refinished Brazilian Rosewood floors throughout the main living areas. The formal living room features a wood-burning fireplace and two sets of French doors that open to a covered lanai with a remote-controlled motorized screen, perfect for seamless indoor-outdoor living. The formal dining room sets the stage for elegant entertaining, while the spacious open-concept kitchen overlooks the family room. Designed for the culinary enthusiast, the kitchen boasts an Italian porcelain island, a brand-new Kucht Professional 8-burner gas range/oven, double ovens, and a walk-in pantry. The family room offers another wood-burning fireplace and French doors leading to the screened-in saltwater heated pool, refinished just three years ago with new equipment. The first-floor primary suite is a true retreat, featuring serene pool views, a large walk-in closet with California Closet system, and a spacious en-suite bath. Two additional first-floor bedrooms, each with walk-in closets, provide comfort and convenience. Upstairs, a private bedroom, full bath, and large bonus room offer the perfect space for guests or a secondary living area, with easy access to walk-in attic storage. A two-car attached garage includes built-in storage and a private staircase leading to a guest apartment/bedroom suite complete with a wet bar and full bath—ideal for multi-generational living or an au pair. Outdoor living is at its finest with a covered lanai, new tile flooring, and a remote-controlled motorized screen, plus a poolside half bath and outdoor shower. Situated in a Grade A school district and offering easy access to major roadways, this exquisite home blends elegance, comfort, and prime location. Please see attachments for the full list of improvements. 1470 Place Picardy, Winter Park
$2,599,000 Nestled in the exclusive, sought-after cul-de-sac of Via Tuscany Oaks, this estate offers a rare opportunity to own a premier piece of Winter Park real estate. Situated among only six other distinguished homes and surrounded by a meticulously landscaped central park, this property perfectly blends privacy, elegance, and an unmatched location. The chef’s kitchen is a masterpiece of both design and functionality, featuring custom copper sinks, exquisite marble countertops, and custom cabinetry—an ideal space for both intimate meals and large gatherings. Step outside to find an entertainer’s dream: a custom-built summer kitchen complete with a grill, wet bar, refrigerator, and kegerator. This outdoor space is designed for luxury living, with a pool bath, putting green, and outdoor shower, creating the perfect atmosphere for both relaxation and entertainment. The first-floor Master Suite is a true sanctuary, offering a serene retreat with a spacious spa-like bath that includes a steam shower, vaulted ceilings, and dual walk-in closets—providing both comfort and luxury. Upstairs, four additional bedrooms, two full baths, and a balcony overlooking the central park offer an abundance of space and tranquility, with a perfect balance of privacy and scenic views. Located just steps from the Winter Park Racquet Club and only a short stroll to the renowned Park Avenue, this home places you in the heart of everything Winter Park has to offer—award-winning dining, shopping, and cultural experiences. 5 Beds ⋅ 5 Baths ⋅ Via Tuscany Oaks 47/75 SubDv. ⋅ 32789 Zip Code Nestled in the exclusive, sought-after cul-de-sac of Via Tuscany Oaks, this estate offers a rare opportunity to own a premier piece of Winter Park real estate. Situated among only six other distinguished homes and surrounded by a meticulously landscaped central park, this property perfectly blends privacy, elegance, and an unmatched location. The chef’s kitchen is a masterpiece of both design and functionality, featuring custom copper sinks, exquisite marble countertops, and custom cabinetry—an ideal space for both intimate meals and large gatherings. Step outside to find an entertainer’s dream: a custom-built summer kitchen complete with a grill, wet bar, refrigerator, and kegerator. This outdoor space is designed for luxury living, with a pool bath, putting green, and outdoor shower, creating the perfect atmosphere for both relaxation and entertainment. The first-floor Master Suite is a true sanctuary, offering a serene retreat with a spacious spa-like bath that includes a steam shower, vaulted ceilings, and dual walk-in closets—providing both comfort and luxury. Upstairs, four additional bedrooms, two full baths, and a balcony overlooking the central park offer an abundance of space and tranquility, with a perfect balance of privacy and scenic views. Located just steps from the Winter Park Racquet Club and only a short stroll to the renowned Park Avenue, this home places you in the heart of everything Winter Park has to offer—award-winning dining, shopping, and cultural experiences. 1000 Via Tuscany Oaks Way, Winter Park
$2,325,000 Welcome to this charming one owner home nestled on the shores of Lake Knowles in the heart of Winter Park, located in one of the most sought-after neighborhoods. This home truly has it all and is just steps from Winter Park Racquet Club and minutes to Winter Park’s Interlachen Country Club as well as coveted Park Avenue, that features many restaurants and shops. This 4-bedroom, 3.5 bath pool home has amazing curb appeal with incredible landscaping as well as unique features throughout that will make you never want to leave. From the minute you park, the car to the first step inside, this home will have you wanting to come back for more. As you walk inside, the foyer immediately informs you of the quality of the home. The family room opens into the kitchen and is the perfect place to entertain family or friends. The kitchen has incredible views of Lake Knowles, and kitchen cabinets have been freshly painted. The fireplace in the family room is surrounded by built-in cabinets which provide ample storage. The French doors that lead out to the pool area provide a tremendous amount of natural light. The downstairs is finished off by an office, an additional sitting room, a dining room and a half bath. Located upstairs, 2 bedrooms share a bathroom and have doors that lead out to the covered patio. The owner’s retreat features a fireplace, crown molding, a large walk-in closet and a large master bathroom. Now that we saved one of the best parts for last let’s make our way outside! The back porch overlooks the serene pool and the screen enclosure is perfect for keeping those pesky bugs away. The rear hedge provides wonderful privacy from rear neighbors. Don’t miss the opportunity to have incredible sunsets from your very own private balcony - call today to set up your private showing. 4 Beds ⋅ 4 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code Welcome to this charming one owner home nestled on the shores of Lake Knowles in the heart of Winter Park, located in one of the most sought-after neighborhoods. This home truly has it all and is just steps from Winter Park Racquet Club and minutes to Winter Park’s Interlachen Country Club as well as coveted Park Avenue, that features many restaurants and shops. This 4-bedroom, 3.5 bath pool home has amazing curb appeal with incredible landscaping as well as unique features throughout that will make you never want to leave. From the minute you park, the car to the first step inside, this home will have you wanting to come back for more. As you walk inside, the foyer immediately informs you of the quality of the home. The family room opens into the kitchen and is the perfect place to entertain family or friends. The kitchen has incredible views of Lake Knowles, and kitchen cabinets have been freshly painted. The fireplace in the family room is surrounded by built-in cabinets which provide ample storage. The French doors that lead out to the pool area provide a tremendous amount of natural light. The downstairs is finished off by an office, an additional sitting room, a dining room and a half bath. Located upstairs, 2 bedrooms share a bathroom and have doors that lead out to the covered patio. The owner’s retreat features a fireplace, crown molding, a large walk-in closet and a large master bathroom. Now that we saved one of the best parts for last let’s make our way outside! The back porch overlooks the serene pool and the screen enclosure is perfect for keeping those pesky bugs away. The rear hedge provides wonderful privacy from rear neighbors. Don’t miss the opportunity to have incredible sunsets from your very own private balcony - call today to set up your private showing. 1522 Lake Knowles Circle, Winter Park
$1,400,000 Tuscan-inspired Mediterranean gem in the Via’s of olde Winter Park. Step into the charm of an Italian villa with this elegant residence located on a quiet tree-lined street off Via Tuscany and near the Winter Park Racquet Club. Featuring hardwood floors throughout, this residence combines timeless elegance with modern functionality. The open-concept kitchen boasts a central island, casual dining and overlooks the spacious gathering room. A wall of French doors floods in natural light and opens onto a tranquil outdoor retreat — a gorgeous pool surrounded by a brick-paver deck, evoking the serenity of a quaint European escape. The home offers a formal dining room or works well for a private den/office by adding French doors. The first-floor primary suite is a true sanctuary, with more French doors offering picturesque backyard views. The luxurious primary bath is designed for relaxation, featuring a large soaking tub, dual sinks, a walk-in closet, and a private water closet. The second level of the home hosts two spacious bedrooms, ideal for family or guests. The mudroom/laundry area provides access to a half bath en route to a 2-car attached garage — complete with a cabinet system — adds convenience to everyday living. The meticulously maintained landscaping enhances the home’s curb appeal, while its location in a grade-A school district offers access to quality education. The immediate Via’s neighborhood includes Chain of Lakes access through a park-like setting with boat ramp leading to Lake Maitland only footsteps away at the intersection of Venetian Way & Poinciana Lane (1 block to the S of this property). Also, easy access to major roadways for stress-free commutes and just minutes from the vibrant shopping and dining of downtown Winter Park, this home is a unique jewel box. 3 Beds ⋅ 3 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code Tuscan-inspired Mediterranean gem in the Via’s of olde Winter Park. Step into the charm of an Italian villa with this elegant residence located on a quiet tree-lined street off Via Tuscany and near the Winter Park Racquet Club. Featuring hardwood floors throughout, this residence combines timeless elegance with modern functionality. The open-concept kitchen boasts a central island, casual dining and overlooks the spacious gathering room. A wall of French doors floods in natural light and opens onto a tranquil outdoor retreat — a gorgeous pool surrounded by a brick-paver deck, evoking the serenity of a quaint European escape. The home offers a formal dining room or works well for a private den/office by adding French doors. The first-floor primary suite is a true sanctuary, with more French doors offering picturesque backyard views. The luxurious primary bath is designed for relaxation, featuring a large soaking tub, dual sinks, a walk-in closet, and a private water closet. The second level of the home hosts two spacious bedrooms, ideal for family or guests. The mudroom/laundry area provides access to a half bath en route to a 2-car attached garage — complete with a cabinet system — adds convenience to everyday living. The meticulously maintained landscaping enhances the home’s curb appeal, while its location in a grade-A school district offers access to quality education. The immediate Via’s neighborhood includes Chain of Lakes access through a park-like setting with boat ramp leading to Lake Maitland only footsteps away at the intersection of Venetian Way & Poinciana Lane (1 block to the S of this property). Also, easy access to major roadways for stress-free commutes and just minutes from the vibrant shopping and dining of downtown Winter Park, this home is a unique jewel box. 907 Moss Lane, Winter Park
$5,400,000 *Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home. Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a gas fireplace invites you to unwind and enjoy Florida's beautiful weather. Relax in the hot tub or take a dip in the pool equipped with an Ultraviolet System which ensures the healthiest pool water possible, complete with an outdoor shower. The outdoor home lighting creates an enchanting ambiance, while the boat dock with a covered electronic boat lift offers easy access to water adventures. Experience breathtaking sunrises and sunsets over Rollins and Knowles Chapel from your own piece of paradise. The first floor of this home is designed for both comfort and style. Anderson doors and windows fill the space with natural light, highlighting the wood floors and architectural details like coffered ceilings with wood beams in the open family room. The master suite serves as a private retreat, featuring a spa bathroom, custom closets, and ample storage. Two additional bedrooms, a bathroom, and a half bath provide versatility and convenience. The kitchen is a chef's delight, boasting Caesarstone concrete countertops, a copper hood range, top-of-the-line Subzero and Viking appliances, walk-in pantry. A walk-in bar and wine room enhance the home's functionality, while a Pelican whole house water filtration system and a Kangen Leveluk water purifier ensure the highest quality water. The second floor is perfect for entertaining, offering a spacious area with a bonus room, bar, kitchenette, and an additional bedroom with an en-suite bath. This versatile space is ideal for hosting guests or creating a personal retreat. The city of Winter Park has approved plans to add an enclosed 385 square feet to the second floor, providing potential for additional space. Don't miss the opportunity to own this extraordinary lakefront home in one of Winter Park's most sought-after neighborhoods. Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer. 4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code *Price Improvement* The sellers received an unexpected opportunity and are relocating out of state, so the house is priced to sell quickly. Walk in with instant equity in this once in a lifetime lake home. Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a gas fireplace invites you to unwind and enjoy Florida's beautiful weather. Relax in the hot tub or take a dip in the pool equipped with an Ultraviolet System which ensures the healthiest pool water possible, complete with an outdoor shower. The outdoor home lighting creates an enchanting ambiance, while the boat dock with a covered electronic boat lift offers easy access to water adventures. Experience breathtaking sunrises and sunsets over Rollins and Knowles Chapel from your own piece of paradise. The first floor of this home is designed for both comfort and style. Anderson doors and windows fill the space with natural light, highlighting the wood floors and architectural details like coffered ceilings with wood beams in the open family room. The master suite serves as a private retreat, featuring a spa bathroom, custom closets, and ample storage. Two additional bedrooms, a bathroom, and a half bath provide versatility and convenience. The kitchen is a chef's delight, boasting Caesarstone concrete countertops, a copper hood range, top-of-the-line Subzero and Viking appliances, walk-in pantry. A walk-in bar and wine room enhance the home's functionality, while a Pelican whole house water filtration system and a Kangen Leveluk water purifier ensure the highest quality water. The second floor is perfect for entertaining, offering a spacious area with a bonus room, bar, kitchenette, and an additional bedroom with an en-suite bath. This versatile space is ideal for hosting guests or creating a personal retreat. The city of Winter Park has approved plans to add an enclosed 385 square feet to the second floor, providing potential for additional space. Don't miss the opportunity to own this extraordinary lakefront home in one of Winter Park's most sought-after neighborhoods. Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer. 541 Virginia Drive, Winter Park
$2,530,000 This stunning one-story home, situated on a nearly half acre lot in the heart of the Vias in Winter Park, offers a rare combination of luxury, comfort, and modern amenities. Boasting soaring ceilings between 12' and 17' and an expansive private pool area, this home is designed for both entertaining and everyday living. The home features solid maple cabinetry, maple hardwood floors, and custom built-ins throughout. Pella thermal pane windows provide excellent energy efficiency and natural light. Two remote-controlled gas fireplaces add warmth and elegance to the living/dining rooms and primary bedroom. Multi-slide glass pocket doors create a seamless flow between the interior and outdoor spaces, perfect for enjoying the resort-style pool area. A true culinary haven, the kitchen includes granite countertops, a 30” double Thermador convection oven, a 48” built-in Sub-Zero refrigerator, Bosch dishwasher, Viking wine refrigerator, and Dacor 6-burner gas cooktop—ideal for both intimate meals and large gatherings. The luxurious primary suite is a true retreat, with its own fireplace, his and her custom-designed walk-in closets, and an updated spa-like bathroom. The home offers an idyllic backyard with lush landscaping and a completely private pool and spa area. Retractable screens on the patio allow you to enjoy the outdoors in comfort, even on cooler days or without the presence of insects. Recent updates include a new tile roof in (2023), a renovated guest half bath (2023), and a renovated primary bath and closet (2024). The home has also been freshly painted inside (2022) and out (2024). A circular drive and 3-car garage provide ample parking and convenience, while the porte-cochère adds a touch of elegance to the entrance. The well-appointed laundry room includes a Leibherr 36” refrigerator, washer and dryer, sink, and pantry for extra storage. Set on a double lot (120 X 165), this home offers expansive outdoor space, providing privacy and room for relaxation or recreation. Nestled on a charming “Olde” Winter Park brick street, this home enjoys both tranquility and proximity to the best that Winter Park has to offer. This home is truly a rare find—combining luxury, comfort, and practicality in one exceptional package. It’s perfect for those who appreciate the single-story style, ample space, and the ability to entertain year-round! 4 Beds ⋅ 5 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code This stunning one-story home, situated on a nearly half acre lot in the heart of the Vias in Winter Park, offers a rare combination of luxury, comfort, and modern amenities. Boasting soaring ceilings between 12' and 17' and an expansive private pool area, this home is designed for both entertaining and everyday living. The home features solid maple cabinetry, maple hardwood floors, and custom built-ins throughout. Pella thermal pane windows provide excellent energy efficiency and natural light. Two remote-controlled gas fireplaces add warmth and elegance to the living/dining rooms and primary bedroom. Multi-slide glass pocket doors create a seamless flow between the interior and outdoor spaces, perfect for enjoying the resort-style pool area. A true culinary haven, the kitchen includes granite countertops, a 30” double Thermador convection oven, a 48” built-in Sub-Zero refrigerator, Bosch dishwasher, Viking wine refrigerator, and Dacor 6-burner gas cooktop—ideal for both intimate meals and large gatherings. The luxurious primary suite is a true retreat, with its own fireplace, his and her custom-designed walk-in closets, and an updated spa-like bathroom. The home offers an idyllic backyard with lush landscaping and a completely private pool and spa area. Retractable screens on the patio allow you to enjoy the outdoors in comfort, even on cooler days or without the presence of insects. Recent updates include a new tile roof in (2023), a renovated guest half bath (2023), and a renovated primary bath and closet (2024). The home has also been freshly painted inside (2022) and out (2024). A circular drive and 3-car garage provide ample parking and convenience, while the porte-cochère adds a touch of elegance to the entrance. The well-appointed laundry room includes a Leibherr 36” refrigerator, washer and dryer, sink, and pantry for extra storage. Set on a double lot (120 X 165), this home offers expansive outdoor space, providing privacy and room for relaxation or recreation. Nestled on a charming “Olde” Winter Park brick street, this home enjoys both tranquility and proximity to the best that Winter Park has to offer. This home is truly a rare find—combining luxury, comfort, and practicality in one exceptional package. It’s perfect for those who appreciate the single-story style, ample space, and the ability to entertain year-round! 1215 Via Salerno, Winter Park
$615,000 Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets, stainless steel appliances, a pantry, and a cozy eat-in nook. A convenient half bath completes the main floor. The second floor opens with a wonderful family room featuring a fireplace and French doors that lead to a picturesque balcony overlooking the street. Two generously sized bedrooms, one with custom built-ins, share a spacious bathroom, and there’s also an indoor laundry closet for added convenience. The third-floor primary retreat is a sanctuary, with a large bathroom boasting travertine details, a jetted tub, a separate shower, dual sinks, and a large walk-in closet. The oversized bedroom is bright and airy, with French doors that open to a private balcony. A dedicated office with built-in furniture completes the third floor. This home is as functional as it is beautiful, featuring a metal lifetime roof - installed 12 years ago, whole-house replumbing in 2022, and premium new carpeting with the thickest padding installed throughout the home in 2022. Additional updates include a new water heater and irrigation system added in 2023. A two-car carport and an unbeatable location short distance to Rollins College and the iconic dining and shopping of Park Avenue complete the package. Experience the best of Winter Park living! Motivated Seller all reasonable offers will be considered. 3 Beds ⋅ 3 Baths ⋅ Trotter Rep SubDv. ⋅ 32789 Zip Code Welcome to this elegant three-story townhouse in the heart of Winter Park! Step through French doors into a welcoming foyer leading to a bright and open living room, seamlessly connected to the dining area. Adorned with crown molding and charming Spanish tile, this space is bathed in natural light from sliding glass doors that open to a private outdoor patio. The kitchen features white cabinets, stainless steel appliances, a pantry, and a cozy eat-in nook. A convenient half bath completes the main floor. The second floor opens with a wonderful family room featuring a fireplace and French doors that lead to a picturesque balcony overlooking the street. Two generously sized bedrooms, one with custom built-ins, share a spacious bathroom, and there’s also an indoor laundry closet for added convenience. The third-floor primary retreat is a sanctuary, with a large bathroom boasting travertine details, a jetted tub, a separate shower, dual sinks, and a large walk-in closet. The oversized bedroom is bright and airy, with French doors that open to a private balcony. A dedicated office with built-in furniture completes the third floor. This home is as functional as it is beautiful, featuring a metal lifetime roof - installed 12 years ago, whole-house replumbing in 2022, and premium new carpeting with the thickest padding installed throughout the home in 2022. Additional updates include a new water heater and irrigation system added in 2023. A two-car carport and an unbeatable location short distance to Rollins College and the iconic dining and shopping of Park Avenue complete the package. Experience the best of Winter Park living! Motivated Seller all reasonable offers will be considered. 735 Maryland Avenue, Winter Park
$580,000 Nestled in the heart of Winter Park, this stunning two-story townhome seamlessly blends modern comfort with urban convenience. Offering approximately 1,936 square feet of thoughtfully designed living space, this three bedroom, two and one-half bath home is ideal for those seeking a cultured, low-maintenance lifestyle in one of Central Florida’s most desirable neighborhoods. Head inside to discover elegant finishes, high ceilings, and an open-concept floor plan filled with natural light. Hardwood floors run throughout the main living areas, creating a warm and inviting atmosphere. The spacious kitchen features ample cabinetry, granite countertops, and a layout that’s perfect for both everyday living and entertaining. The serene primary suite offers a spacious retreat, complete with hardwood flooring, a ceiling fan, and a spa-like en-suite bathroom with a stylish vanity and abundant natural light. Two additional bedrooms and a well-placed half bath provide flexible space for guests, a home office, or additional living needs. French doors in the dining room open to a private, cozy patio shaded by mature trees—perfect for morning coffee or evening relaxation. A brand-new roof, installed in March 2024, adds long-term value and peace of mind. Located just minutes from the Park Avenue District, Rollins College, and Winter Park’s acclaimed shops, restaurants, and cultural attractions, this townhome offers the perfect balance of charm and convenience. With easy access to parks, top-rated schools, and major roadways, this move-in-ready gem truly checks all the boxes. Schedule your private showing today and experience the best of Winter Park living! REDUCED FOR QUICK SALE! MOVE-IN READY! 3 Beds ⋅ 3 Baths ⋅ Indiana Place Twnhms Tr A SubDv. ⋅ 32789 Zip Code Nestled in the heart of Winter Park, this stunning two-story townhome seamlessly blends modern comfort with urban convenience. Offering approximately 1,936 square feet of thoughtfully designed living space, this three bedroom, two and one-half bath home is ideal for those seeking a cultured, low-maintenance lifestyle in one of Central Florida’s most desirable neighborhoods. Head inside to discover elegant finishes, high ceilings, and an open-concept floor plan filled with natural light. Hardwood floors run throughout the main living areas, creating a warm and inviting atmosphere. The spacious kitchen features ample cabinetry, granite countertops, and a layout that’s perfect for both everyday living and entertaining. The serene primary suite offers a spacious retreat, complete with hardwood flooring, a ceiling fan, and a spa-like en-suite bathroom with a stylish vanity and abundant natural light. Two additional bedrooms and a well-placed half bath provide flexible space for guests, a home office, or additional living needs. French doors in the dining room open to a private, cozy patio shaded by mature trees—perfect for morning coffee or evening relaxation. A brand-new roof, installed in March 2024, adds long-term value and peace of mind. Located just minutes from the Park Avenue District, Rollins College, and Winter Park’s acclaimed shops, restaurants, and cultural attractions, this townhome offers the perfect balance of charm and convenience. With easy access to parks, top-rated schools, and major roadways, this move-in-ready gem truly checks all the boxes. Schedule your private showing today and experience the best of Winter Park living! REDUCED FOR QUICK SALE! MOVE-IN READY! 1392 Indiana Avenue, Winter Park
$449,000 Welcome to your fully renovated pool home in the heart of Winter Park, FL! As you enter, you will be greeted by a stunning shiplap statement wall in the open concept living space, perfect for entertaining friends and family. The spacious kitchen features marble counters, ample cabinets, and opens up to the dining room, which is centered beside the living area. The gorgeous waterproof, luxury laminated floors throughout this home create a seamless design. Imagine spending time in the kitchen while being surrounded by natural light pouring in from the wall-to-wall windows with plantation shutters, offering a view of the living room and the back of the house with 2 double French doors. It's a serene and inviting space that brings the outdoors in. A bonus room provides extra space and leads to the huge backyard complete with a sparkling pool and banana trees. This home truly is move-in ready, with updated touches throughout, including a Bluetooth speaker in the bathroom for your shower karaoke sessions. The primary bedroom even has direct access to the pool, creating a relaxing retreat right in your own backyard. The roof was added in 2023, and electrical and plumbing were updated as well. The one car garage and laundry room combo can be entered from the dining room for ease with chores. Do you have a boat or a camper? The vinyl fence has a double gate and plenty of space on the side of the home for private parking. Every inch of this home has been curated with lots of love and an exquisite eye for style. Located in a highly desirable area, this home is just a stone's throw from Lake Killarney and a short drive to I-4. It is a dream to have such quick access to all that Winter Park has to give. Winter Park Village, Trader Joe's, and a variety of shopping and dining options are all within minutes from your doorstep. Don't miss out on the opportunity to own this gem of a home in Winter Park! 3 Beds ⋅ 1 Baths ⋅ Orange Terrace SubDv. ⋅ 32789 Zip Code Welcome to your fully renovated pool home in the heart of Winter Park, FL! As you enter, you will be greeted by a stunning shiplap statement wall in the open concept living space, perfect for entertaining friends and family. The spacious kitchen features marble counters, ample cabinets, and opens up to the dining room, which is centered beside the living area. The gorgeous waterproof, luxury laminated floors throughout this home create a seamless design. Imagine spending time in the kitchen while being surrounded by natural light pouring in from the wall-to-wall windows with plantation shutters, offering a view of the living room and the back of the house with 2 double French doors. It's a serene and inviting space that brings the outdoors in. A bonus room provides extra space and leads to the huge backyard complete with a sparkling pool and banana trees. This home truly is move-in ready, with updated touches throughout, including a Bluetooth speaker in the bathroom for your shower karaoke sessions. The primary bedroom even has direct access to the pool, creating a relaxing retreat right in your own backyard. The roof was added in 2023, and electrical and plumbing were updated as well. The one car garage and laundry room combo can be entered from the dining room for ease with chores. Do you have a boat or a camper? The vinyl fence has a double gate and plenty of space on the side of the home for private parking. Every inch of this home has been curated with lots of love and an exquisite eye for style. Located in a highly desirable area, this home is just a stone's throw from Lake Killarney and a short drive to I-4. It is a dream to have such quick access to all that Winter Park has to give. Winter Park Village, Trader Joe's, and a variety of shopping and dining options are all within minutes from your doorstep. Don't miss out on the opportunity to own this gem of a home in Winter Park! 2112 Staunton Avenue, Winter Park
$1,650,000 Rare opportunity to own this exclusive 2 bedrooms / 2 bathrooms condominium within the highly sought after Villa Siena. Nestled in the heart of quaint downtown Winter Park, Fl this meticulously maintained, 2nd floor, condo has been elegantly updated. Interior features include a split plan floorplan, travertine flooring, bright kitchen with quartz countertops, Sub-Zero refrigerator and Wolf gas stove, breakfast bar, dining area with custom built-in bar and wine refrigerator, crown molding within the living room, primary suite and guest bedroom offer tray ceilings, recessed lighting, walk-in closets, and french doors that lead out onto private balconies overlooking the tree lined brick street and award winning Alfond Inn and Spa, new primary bathroom with dual sinks, separate tub and shower and Toto toilet, spacious utility room with cabinetry and wash sink. Villa Siena offers secured underground parking, Club room with bar and outdoor sitting area great for entertaining guests, fitness center, roof top terrace, conference room, guest parking, and an onsite property manager to assist with Resident needs. Steps to the charming Park Avenue shopping District known for it’s celebrated restaurants, boutique stores, Central Park, 9 hole golf course, museums, train station, and Rollins College. Welcome Home! Video Tour: https://youtu.be/AMDbRupc4GM 2 Beds ⋅ 2 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code Rare opportunity to own this exclusive 2 bedrooms / 2 bathrooms condominium within the highly sought after Villa Siena. Nestled in the heart of quaint downtown Winter Park, Fl this meticulously maintained, 2nd floor, condo has been elegantly updated. Interior features include a split plan floorplan, travertine flooring, bright kitchen with quartz countertops, Sub-Zero refrigerator and Wolf gas stove, breakfast bar, dining area with custom built-in bar and wine refrigerator, crown molding within the living room, primary suite and guest bedroom offer tray ceilings, recessed lighting, walk-in closets, and french doors that lead out onto private balconies overlooking the tree lined brick street and award winning Alfond Inn and Spa, new primary bathroom with dual sinks, separate tub and shower and Toto toilet, spacious utility room with cabinetry and wash sink. Villa Siena offers secured underground parking, Club room with bar and outdoor sitting area great for entertaining guests, fitness center, roof top terrace, conference room, guest parking, and an onsite property manager to assist with Resident needs. Steps to the charming Park Avenue shopping District known for it’s celebrated restaurants, boutique stores, Central Park, 9 hole golf course, museums, train station, and Rollins College. Welcome Home! Video Tour: https://youtu.be/AMDbRupc4GM 315 E New England Avenue Unit 9, Winter Park
$1,895,000 Welcome to an extraordinary custom-built pool home that beautifully harmonizes contemporary elegance with traditional charm. This stunning residence is a true masterpiece, showcasing top-tier details and finishes that elevate it to a league of its own. Upon entering, you are greeted by exquisite new white oak wood flooring that flows gracefully throughout the home. The grand foyer opens into a living room, highlighting a breathtaking two-story ceiling that reaches 20 feet. The dining area is equally impressive, featuring elegant built-ins and under-counter wine and beverage refrigerators, perfect for hosting dinner parties and celebrations. At the heart of this home lies a stunning new chef-inspired kitchen designed for culinary enthusiasts and family gatherings alike. Equipped with a state-of-the-art Monogram appliance package, this kitchen boasts a commercial-grade gas range with six burners and dual dishwashers for optimal efficiency. A built-in microwave conveniently situated in the island, along with custom cabinetry and luxurious thick porcelain countertops, elevates the space further. The expansive center island invites creativity and connection, making it the ideal backdrop for memorable meals. Adjacent to the kitchen, the open family room features a cozy corner gas fireplace and three sets of French doors that seamlessly connect the indoor space to the covered and screened lanai, where you can unwind and enjoy serene views of the sparkling saltwater pool. Step outside to discover your private oasis, perfect for entertaining. The outdoor living area includes a fully equipped summer kitchen featuring a Wolf grill, concrete counters, a sink, and an under-counter fridge. A charming outdoor pool bath with a shower adds convenience. Back inside, connecting the kitchen to the spacious two-car garage with 14-foot ceilings, you'll find a well-appointed mudroom complete with laundry facilities, newly added storage cabinetry, a walk-in pantry, and a double wash basin, ensuring both functionality and organization. Ascend the wide, oversized staircase to the second level, where you'll discover two generously sized secondary bedrooms complemented by a newly updated hall bath. The sprawling primary suite is a true retreat, featuring two large walk-in closets and a luxurious spa bath equipped with a cast iron clawfoot tub, a bidet, and a seamless glass shower. This suite also includes a serene and secluded nook, perfect for creating a peaceful office space or nursery. The suite also boasts easy access to a screened balcony. Additionally, the home features a private first-floor guest suite with an ensuite bath, perfect for hosting friends or family. Every inch of this residence reflects exceptional craftsmanship, from the tasteful custom cabinetry to the elegant wood trim. The atmosphere exudes grandeur and comfort, enhanced by 11-foot ceilings and oversized baseboards. Nestled in a tranquil corner of the backyard, the air-conditioned shed serves as the perfect sanctuary for a gym or yoga studio, offering a peaceful bonus space that everyone will adore. The backyard showcases low-maintenance turf along with energy-efficient, drought-tolerant landscaping that beautifully enhances the home's overall appeal. Enjoy a stunning outdoor space that requires minimal upkeep while remaining environmentally friendly! Conveniently located just minutes away from the vibrant shops and restaurants and within the highly sought-after Winter Park school district. 4 Beds ⋅ 5 Baths ⋅ Parklando #3 SubDv. ⋅ 32789 Zip Code Welcome to an extraordinary custom-built pool home that beautifully harmonizes contemporary elegance with traditional charm. This stunning residence is a true masterpiece, showcasing top-tier details and finishes that elevate it to a league of its own. Upon entering, you are greeted by exquisite new white oak wood flooring that flows gracefully throughout the home. The grand foyer opens into a living room, highlighting a breathtaking two-story ceiling that reaches 20 feet. The dining area is equally impressive, featuring elegant built-ins and under-counter wine and beverage refrigerators, perfect for hosting dinner parties and celebrations. At the heart of this home lies a stunning new chef-inspired kitchen designed for culinary enthusiasts and family gatherings alike. Equipped with a state-of-the-art Monogram appliance package, this kitchen boasts a commercial-grade gas range with six burners and dual dishwashers for optimal efficiency. A built-in microwave conveniently situated in the island, along with custom cabinetry and luxurious thick porcelain countertops, elevates the space further. The expansive center island invites creativity and connection, making it the ideal backdrop for memorable meals. Adjacent to the kitchen, the open family room features a cozy corner gas fireplace and three sets of French doors that seamlessly connect the indoor space to the covered and screened lanai, where you can unwind and enjoy serene views of the sparkling saltwater pool. Step outside to discover your private oasis, perfect for entertaining. The outdoor living area includes a fully equipped summer kitchen featuring a Wolf grill, concrete counters, a sink, and an under-counter fridge. A charming outdoor pool bath with a shower adds convenience. Back inside, connecting the kitchen to the spacious two-car garage with 14-foot ceilings, you'll find a well-appointed mudroom complete with laundry facilities, newly added storage cabinetry, a walk-in pantry, and a double wash basin, ensuring both functionality and organization. Ascend the wide, oversized staircase to the second level, where you'll discover two generously sized secondary bedrooms complemented by a newly updated hall bath. The sprawling primary suite is a true retreat, featuring two large walk-in closets and a luxurious spa bath equipped with a cast iron clawfoot tub, a bidet, and a seamless glass shower. This suite also includes a serene and secluded nook, perfect for creating a peaceful office space or nursery. The suite also boasts easy access to a screened balcony. Additionally, the home features a private first-floor guest suite with an ensuite bath, perfect for hosting friends or family. Every inch of this residence reflects exceptional craftsmanship, from the tasteful custom cabinetry to the elegant wood trim. The atmosphere exudes grandeur and comfort, enhanced by 11-foot ceilings and oversized baseboards. Nestled in a tranquil corner of the backyard, the air-conditioned shed serves as the perfect sanctuary for a gym or yoga studio, offering a peaceful bonus space that everyone will adore. The backyard showcases low-maintenance turf along with energy-efficient, drought-tolerant landscaping that beautifully enhances the home's overall appeal. Enjoy a stunning outdoor space that requires minimal upkeep while remaining environmentally friendly! Conveniently located just minutes away from the vibrant shops and restaurants and within the highly sought-after Winter Park school district. 2612 Parkland Drive, Winter Park
$2,750,000 425 Alberta Drive is a Gamble Rogers-designed lakefront home with a boathouse built in 1938 that has not been registered historical and is being sold as is. Bring your builder to build your future home. The home itself has lots of character if you want to take on a project but the value is in the lot. Spectacular views, location is wonderful with brick street, mature landscaping and the backyard faces west for great sunsets. Take your boat through the chain of lakes and enjoy the boating lifestyle. Close to downtown Park Avenue with all the shops and dining. 3 Beds ⋅ 2 Baths ⋅ Osceola Summit SubDv. ⋅ 32789 Zip Code 425 Alberta Drive is a Gamble Rogers-designed lakefront home with a boathouse built in 1938 that has not been registered historical and is being sold as is. Bring your builder to build your future home. The home itself has lots of character if you want to take on a project but the value is in the lot. Spectacular views, location is wonderful with brick street, mature landscaping and the backyard faces west for great sunsets. Take your boat through the chain of lakes and enjoy the boating lifestyle. Close to downtown Park Avenue with all the shops and dining. 425 Alberta Drive, Winter Park
$662,500 Explore this unique and profitable opportunity to invest in this charming duplex in historic Winter Park! Nestled among luxury and lakefront homes in the much sought after "College Quarter." This duplex features 2 units, each with a 2-bedroom, 1-bathroom units both with a light and airy sunroom, functional laundry room, courtyard area, and 2 parking spots (4 total). Unit 600 is approximately 1193 square feet and features a beautiful sunroom, courtyard, kitchen and UPDATED bathroom. Rental income for 600 is presently $1900/month which expires 7/31/25. Unit 602 is approximately 1303 square feet and features an UPDATED bathroom, lawn space and nicely appointed kitchen. Rental income for 602 is presently $1800/month which expires 5/31/25. Both units in this duplex include the washer and dryer. This duplex is a 5 to 10 minute stroll to Lake Virginia, Rollins College, Dinky Dock and the Winter Park Tennis Center. Also within walking and bicycling distance are the Park Ave shops and restaurants and the Winter Park Farmer's Market. I-4 is 10 minutes away and the Orlando International Airport is 30 minutes away. Duplexes such as this are a rare find in this area and don't come on the market often. Take advantage of this opportunity to invest and prosper in the Winter Park community TODAY! Roof 2007, Plumbing 2018. Unit 600- HVAC 2018, Water Heater 2012. Unit 602- HVAC 2017, Water Heater 2004. 4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code Explore this unique and profitable opportunity to invest in this charming duplex in historic Winter Park! Nestled among luxury and lakefront homes in the much sought after "College Quarter." This duplex features 2 units, each with a 2-bedroom, 1-bathroom units both with a light and airy sunroom, functional laundry room, courtyard area, and 2 parking spots (4 total). Unit 600 is approximately 1193 square feet and features a beautiful sunroom, courtyard, kitchen and UPDATED bathroom. Rental income for 600 is presently $1900/month which expires 7/31/25. Unit 602 is approximately 1303 square feet and features an UPDATED bathroom, lawn space and nicely appointed kitchen. Rental income for 602 is presently $1800/month which expires 5/31/25. Both units in this duplex include the washer and dryer. This duplex is a 5 to 10 minute stroll to Lake Virginia, Rollins College, Dinky Dock and the Winter Park Tennis Center. Also within walking and bicycling distance are the Park Ave shops and restaurants and the Winter Park Farmer's Market. I-4 is 10 minutes away and the Orlando International Airport is 30 minutes away. Duplexes such as this are a rare find in this area and don't come on the market often. Take advantage of this opportunity to invest and prosper in the Winter Park community TODAY! Roof 2007, Plumbing 2018. Unit 600- HVAC 2018, Water Heater 2012. Unit 602- HVAC 2017, Water Heater 2004. 600 Huntington Avenue, Winter Park
$1,100,000 One or more photo(s) has been virtually staged. Welcome to 708 Balmoral Road, located in the desirable heart of Winter Park. This charming single-story home boasts 4 bedrooms, 3 baths, and a generous 2786 sq. ft. of living space on a sprawling, elevated 15,161 sq. ft. corner lot. The spacious and open floor plan features soaring beams in many rooms, adding to the home's character and warmth. The living and dining area is bright and welcoming with hardwood floors and three sets of windows, flowing seamlessly into the family room. The updated kitchen includes newer (2020) stainless steel appliances, granite countertops, and a cozy breakfast nook with a picturesque view of the pool and backyard. The family room, with its hardwood floors, floor-to-ceiling windows, soaring beams, and charming brick wood-burning fireplace, offers a perfect spot to relax and entertain. On the left side of the home, you'll find two spacious bedrooms and two full bathrooms, including the primary suite. The right side houses two additional bedrooms, one bathroom, a laundry area, and a stairwell leading to the oversized garage. The backyard is an entertainer's dream with a covered patio featuring a vaulted wood ceiling and Chicago brick flooring. The pool is a highlight during the summer months, offering a refreshing retreat. Additional updates include a new HVAC system (2024), New Roof (2025), updated plumbing, Updated electrical panels, newer windows in most of the house and vinyl fencing, . This fantastic location provides easy access to shopping, dining, and the popular Park Avenue with its boutique shopping and great restaurants. 4 Beds ⋅ 3 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code One or more photo(s) has been virtually staged. Welcome to 708 Balmoral Road, located in the desirable heart of Winter Park. This charming single-story home boasts 4 bedrooms, 3 baths, and a generous 2786 sq. ft. of living space on a sprawling, elevated 15,161 sq. ft. corner lot. The spacious and open floor plan features soaring beams in many rooms, adding to the home's character and warmth. The living and dining area is bright and welcoming with hardwood floors and three sets of windows, flowing seamlessly into the family room. The updated kitchen includes newer (2020) stainless steel appliances, granite countertops, and a cozy breakfast nook with a picturesque view of the pool and backyard. The family room, with its hardwood floors, floor-to-ceiling windows, soaring beams, and charming brick wood-burning fireplace, offers a perfect spot to relax and entertain. On the left side of the home, you'll find two spacious bedrooms and two full bathrooms, including the primary suite. The right side houses two additional bedrooms, one bathroom, a laundry area, and a stairwell leading to the oversized garage. The backyard is an entertainer's dream with a covered patio featuring a vaulted wood ceiling and Chicago brick flooring. The pool is a highlight during the summer months, offering a refreshing retreat. Additional updates include a new HVAC system (2024), New Roof (2025), updated plumbing, Updated electrical panels, newer windows in most of the house and vinyl fencing, . This fantastic location provides easy access to shopping, dining, and the popular Park Avenue with its boutique shopping and great restaurants. 708 Balmoral Road, Winter Park
$1,850,000 This beautifully designed David Weekley home is perfectly situated on nearly a quarter-acre lot along a picturesque tree-lined street in the heart of Winter Park. The exterior features immaculate landscaping and striking wood accents, creating exceptional curb appeal. Inside, warm wood floors lead to a thoughtfully designed first floor that includes a guest bedroom with an adjacent full bath, a dedicated office with glass French doors, and a spacious primary suite. The primary suite boasts tray ceilings large windows, and a spa-like bathroom with dual vanities, a soaking tub, a walk-in shower, and a custom-built walk-in closet. The open-concept living area features a stunning kitchen with stone countertops, stainless steel appliances, a convection cooktop with hood, a dedicated beverage refrigerator, and a large island with seating. Everything flows seamlessly into a formal dining room with wainscoting and the living room with soaring ceilings, custom light fixtures, and French doors opening to a covered patio. Upstairs, two additional bedrooms with walk-in closets share a Jack-and-Jill bath with private vanities, while a versatile bonus room offers additional family space. Outside, the patio overlooks a heated saltwater pool and spa, surrounded by low-maintenance artificial turf and a fully fenced yard with a buried propane tank to service the pool and a hookup line for a gas-fired grill. Additional highlights include crown molding and plantation shutters throughout, an indoor laundry room with built-in storage, and recently replaced roof and AC system in 2022. Located just minutes from iconic Park Avenue's shopping and dining district, this home offers a prime location in Winter Park’s highly desirable "Tree Streets” neighborhood near top-rated schools. 4 Beds ⋅ 4 Baths ⋅ Winter Park Heights SubDv. ⋅ 32789 Zip Code This beautifully designed David Weekley home is perfectly situated on nearly a quarter-acre lot along a picturesque tree-lined street in the heart of Winter Park. The exterior features immaculate landscaping and striking wood accents, creating exceptional curb appeal. Inside, warm wood floors lead to a thoughtfully designed first floor that includes a guest bedroom with an adjacent full bath, a dedicated office with glass French doors, and a spacious primary suite. The primary suite boasts tray ceilings large windows, and a spa-like bathroom with dual vanities, a soaking tub, a walk-in shower, and a custom-built walk-in closet. The open-concept living area features a stunning kitchen with stone countertops, stainless steel appliances, a convection cooktop with hood, a dedicated beverage refrigerator, and a large island with seating. Everything flows seamlessly into a formal dining room with wainscoting and the living room with soaring ceilings, custom light fixtures, and French doors opening to a covered patio. Upstairs, two additional bedrooms with walk-in closets share a Jack-and-Jill bath with private vanities, while a versatile bonus room offers additional family space. Outside, the patio overlooks a heated saltwater pool and spa, surrounded by low-maintenance artificial turf and a fully fenced yard with a buried propane tank to service the pool and a hookup line for a gas-fired grill. Additional highlights include crown molding and plantation shutters throughout, an indoor laundry room with built-in storage, and recently replaced roof and AC system in 2022. Located just minutes from iconic Park Avenue's shopping and dining district, this home offers a prime location in Winter Park’s highly desirable "Tree Streets” neighborhood near top-rated schools. 1660 Oneco Avenue, Winter Park
$950,000 **Stunning Winter Park Home Near Rollins College, Park Ave & Lake Virginia** Located in historic Winter Park, this exceptional 3-bedroom, 2.5-bathroom home offers the perfect blend of modern luxury and classic charm. Just minutes from Rollins College, the upscale dining and shopping of Park Avenue, and the serene beauty of Lake Virginia, this home is ideally situated in a vibrant yet peaceful neighborhood. **Private Backyard Oasis** Step outside to your own private retreat. The fully fenced-in yard features a free-form pool, a large deck, and a pergola, offering a perfect space for outdoor relaxation and entertaining. Whether you’re enjoying a quiet afternoon by the pool or hosting guests, this backyard provides an ideal setting for any occasion. **Interior Features for Comfortable Living** Inside, the home boasts a spacious and functional layout. The chef’s kitchen is equipped with high-end appliances, custom cabinetry, and ample counter space, perfect for preparing meals and entertaining. The open-concept living and dining areas create a seamless flow throughout the home. The oversized primary bedroom is a serene escape, featuring a luxurious en-suite bathroom with a soaking tub, separate walk-in shower, and elegant finishes. The massive walk-in closet offers plenty of storage space for all your needs. **Modern Updates for Peace of Mind** This home is move-in ready, with a brand-new A/C system, new A/C ducts, and a newer roof, ensuring long-term comfort and reliability. **Ample Parking & Storage** With a 2-car garage and multiple driveways accommodating up to 12 cars, parking is never a concern. Additionally, a side gate allows access to a secured side yard that can store up to 2 more cars, adding extra convenience and protection. **Top-Rated Schools & Prime Location** Located in a highly-rated school district, this home offers access to excellent educational opportunities. It’s also ideally positioned for easy access to major highways, making downtown Orlando and surrounding areas easily reachable while maintaining the tranquility of Winter Park. **Development Potential** Sitting on a large 12,000-square-foot lot, this property presents a prime opportunity for future development. Whether you’re looking to build your dream home or invest in a high-demand Winter Park location, this lot offers significant potential. --- With its prime location, stylish updates, and ample outdoor space, this home is a rare find. Don’t miss your chance to own a piece of Winter Park—schedule a private tour today! 3 Beds ⋅ 3 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code **Stunning Winter Park Home Near Rollins College, Park Ave & Lake Virginia** Located in historic Winter Park, this exceptional 3-bedroom, 2.5-bathroom home offers the perfect blend of modern luxury and classic charm. Just minutes from Rollins College, the upscale dining and shopping of Park Avenue, and the serene beauty of Lake Virginia, this home is ideally situated in a vibrant yet peaceful neighborhood. **Private Backyard Oasis** Step outside to your own private retreat. The fully fenced-in yard features a free-form pool, a large deck, and a pergola, offering a perfect space for outdoor relaxation and entertaining. Whether you’re enjoying a quiet afternoon by the pool or hosting guests, this backyard provides an ideal setting for any occasion. **Interior Features for Comfortable Living** Inside, the home boasts a spacious and functional layout. The chef’s kitchen is equipped with high-end appliances, custom cabinetry, and ample counter space, perfect for preparing meals and entertaining. The open-concept living and dining areas create a seamless flow throughout the home. The oversized primary bedroom is a serene escape, featuring a luxurious en-suite bathroom with a soaking tub, separate walk-in shower, and elegant finishes. The massive walk-in closet offers plenty of storage space for all your needs. **Modern Updates for Peace of Mind** This home is move-in ready, with a brand-new A/C system, new A/C ducts, and a newer roof, ensuring long-term comfort and reliability. **Ample Parking & Storage** With a 2-car garage and multiple driveways accommodating up to 12 cars, parking is never a concern. Additionally, a side gate allows access to a secured side yard that can store up to 2 more cars, adding extra convenience and protection. **Top-Rated Schools & Prime Location** Located in a highly-rated school district, this home offers access to excellent educational opportunities. It’s also ideally positioned for easy access to major highways, making downtown Orlando and surrounding areas easily reachable while maintaining the tranquility of Winter Park. **Development Potential** Sitting on a large 12,000-square-foot lot, this property presents a prime opportunity for future development. Whether you’re looking to build your dream home or invest in a high-demand Winter Park location, this lot offers significant potential. --- With its prime location, stylish updates, and ample outdoor space, this home is a rare find. Don’t miss your chance to own a piece of Winter Park—schedule a private tour today! 241 W Lake Sue Avenue, Winter Park
$435,000 Discover the charm of this beautifully updated 4-bedroom, 3-bathroom home in Winter Park! As you step inside, you’re welcomed by an open-concept living space featuring a cozy wood-burning fireplace, real wood floors, and a stylish kitchen complete with granite countertops, stainless steel appliances, and a spacious dining area. French doors lead to an inviting 11x10 Florida room that overlooks a large screened patio and a fully fenced backyard, perfect for entertaining or relaxing on peaceful Florida evenings. The split floor plan highlights a luxurious master suite with exposed beams, dual closets, a dedicated shoe closet, and a spa-inspired bathroom with dual sinks, a granite vanity, and a rain shower. French doors open from the master to the patio, creating a tranquil retreat. Three additional generously sized bedrooms are located on the opposite side of the home, including one with its own en-suite bathroom, while a third full bathroom is conveniently situated in the hallway. This home also features a versatile bonus room, currently used as an office, and a laundry room. Renovated in 2015, updates include a new roof COMING January 2025, NEW HVAC 2024, windows, plumbing, and electrical work, ensuring peace of mind. With just under 2,000 square feet of space, this home is an entertainer's dream. Conveniently located minutes from I-4, Home Depot, Whole Foods, and Winter Park Village’s array of restaurants and shops, this home has it all. Call today to schedule your private tour! 4 Beds ⋅ 3 Baths ⋅ Lake Bell Terrace SubDv. ⋅ 32789 Zip Code Discover the charm of this beautifully updated 4-bedroom, 3-bathroom home in Winter Park! As you step inside, you’re welcomed by an open-concept living space featuring a cozy wood-burning fireplace, real wood floors, and a stylish kitchen complete with granite countertops, stainless steel appliances, and a spacious dining area. French doors lead to an inviting 11x10 Florida room that overlooks a large screened patio and a fully fenced backyard, perfect for entertaining or relaxing on peaceful Florida evenings. The split floor plan highlights a luxurious master suite with exposed beams, dual closets, a dedicated shoe closet, and a spa-inspired bathroom with dual sinks, a granite vanity, and a rain shower. French doors open from the master to the patio, creating a tranquil retreat. Three additional generously sized bedrooms are located on the opposite side of the home, including one with its own en-suite bathroom, while a third full bathroom is conveniently situated in the hallway. This home also features a versatile bonus room, currently used as an office, and a laundry room. Renovated in 2015, updates include a new roof COMING January 2025, NEW HVAC 2024, windows, plumbing, and electrical work, ensuring peace of mind. With just under 2,000 square feet of space, this home is an entertainer's dream. Conveniently located minutes from I-4, Home Depot, Whole Foods, and Winter Park Village’s array of restaurants and shops, this home has it all. Call today to schedule your private tour! 1944 Bering Avenue, Winter Park
$1,500,000 On one of Winter Park's most desirable streets, this charming two-story, four-bedroom, 3.5-bath home offers over 4,200 square feet of a bright-open floor plan with high ceilings, and lots of glass walls of windows and doors. Featuring wood and tile floors in the main living areas, this home has been well maintained by owners! Roof replaced 2019, Pella windows replaced 2019 and pool redone 2020. The main level includes all living areas such as kitchen, family room, living room, dining room, half bath and laundry, plus two secondary bedrooms that share a bath. The open kitchen with a cozy breakfast area opens to French doors that lead to a private paver patio and a sparkling pool with spa, ideal for outdoor entertaining. The expansive primary suite includes room for a sitting area and a generous walk-in closet. Across from Lake Virginia lakefront homes on the Winter Park Chain of Lakes, enjoy leisurely days on the pool deck or visit nearby Park Avenue’s vibrant shopping and dining scene. Note: Tremendous value in the land alone at this price as well, with lots of redevelopment in and around this neighborhood. This property is not subject to the historical district and under standard City of Winter Park building codes, to be verified with the city building department again by buyer/builder during any inspection period. Just a short distance from Rollins College and downtown Winter Park. Additionally, well located only 10-15 minutes to downtown Orlando, hospitals and major roadways, this home offers luxury and convenience in one of Winter Park’s most sought-after neighborhoods. 4 Beds ⋅ 4 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code On one of Winter Park's most desirable streets, this charming two-story, four-bedroom, 3.5-bath home offers over 4,200 square feet of a bright-open floor plan with high ceilings, and lots of glass walls of windows and doors. Featuring wood and tile floors in the main living areas, this home has been well maintained by owners! Roof replaced 2019, Pella windows replaced 2019 and pool redone 2020. The main level includes all living areas such as kitchen, family room, living room, dining room, half bath and laundry, plus two secondary bedrooms that share a bath. The open kitchen with a cozy breakfast area opens to French doors that lead to a private paver patio and a sparkling pool with spa, ideal for outdoor entertaining. The expansive primary suite includes room for a sitting area and a generous walk-in closet. Across from Lake Virginia lakefront homes on the Winter Park Chain of Lakes, enjoy leisurely days on the pool deck or visit nearby Park Avenue’s vibrant shopping and dining scene. Note: Tremendous value in the land alone at this price as well, with lots of redevelopment in and around this neighborhood. This property is not subject to the historical district and under standard City of Winter Park building codes, to be verified with the city building department again by buyer/builder during any inspection period. Just a short distance from Rollins College and downtown Winter Park. Additionally, well located only 10-15 minutes to downtown Orlando, hospitals and major roadways, this home offers luxury and convenience in one of Winter Park’s most sought-after neighborhoods. 1321 Lakeview Drive, Winter Park
$3,900,000 This custom lakefront home on Winter Park's Chain of Lakes offers stunning views of Lake Virginia and is in the historic Virginia Heights neighborhood, just a short walk from Rollins College and downtown Park Avenue. Facing north, it provides picturesque sunrise views over the lake, highlighting Rollins College and its chapel. Lovingly maintained and improved over time, the 4279 square feet does not include an additional 310 square foot finished bonus room with separate HVAC, perfect for game room or office. Upon entering, you are greeted by lake views and a foyer that leads to separate formal living and dining spaces, featuring wood floors, crown molding, plantation shutters, and 10’ ceilings throughout the first floor. The main living space showcases an open-concept kitchen and family room, and flows to the outdoor patio. The spacious kitchen has a gas cooktop, a built-in desk, island seating, an eat-in breakfast space, a walk-in pantry, and a built-in bar with beverage refrigerator. The family room has custom built-ins and a gas fireplace, and overlooks the manicured backyard, pool, and lake. The large downstairs owners’ retreat with picture windows overlooks the lake and a private screened porch with unobstructed views, and the updated bathroom has double vanities and sinks, glass shower, spa tub, and custom walk-in closet. Upstairs there are three bedrooms with attached bathrooms, two bonus spaces, and a media room, offering abundant flex space and storage. Comfort, luxury, and tranquility abound in the backyard with a pool surrounded by paver patio, grassy yard, and boathouse with a lift. The property also includes an oversized two-car garage. Improvements include new roof/2023, whole-house generator/2021, boathouse deck replaced with Trex decking and new roof/2021. 4 Beds ⋅ 4 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code This custom lakefront home on Winter Park's Chain of Lakes offers stunning views of Lake Virginia and is in the historic Virginia Heights neighborhood, just a short walk from Rollins College and downtown Park Avenue. Facing north, it provides picturesque sunrise views over the lake, highlighting Rollins College and its chapel. Lovingly maintained and improved over time, the 4279 square feet does not include an additional 310 square foot finished bonus room with separate HVAC, perfect for game room or office. Upon entering, you are greeted by lake views and a foyer that leads to separate formal living and dining spaces, featuring wood floors, crown molding, plantation shutters, and 10’ ceilings throughout the first floor. The main living space showcases an open-concept kitchen and family room, and flows to the outdoor patio. The spacious kitchen has a gas cooktop, a built-in desk, island seating, an eat-in breakfast space, a walk-in pantry, and a built-in bar with beverage refrigerator. The family room has custom built-ins and a gas fireplace, and overlooks the manicured backyard, pool, and lake. The large downstairs owners’ retreat with picture windows overlooks the lake and a private screened porch with unobstructed views, and the updated bathroom has double vanities and sinks, glass shower, spa tub, and custom walk-in closet. Upstairs there are three bedrooms with attached bathrooms, two bonus spaces, and a media room, offering abundant flex space and storage. Comfort, luxury, and tranquility abound in the backyard with a pool surrounded by paver patio, grassy yard, and boathouse with a lift. The property also includes an oversized two-car garage. Improvements include new roof/2023, whole-house generator/2021, boathouse deck replaced with Trex decking and new roof/2021. 1341 College Point, Winter Park
$1,630,000 One or more photo(s) has been virtually staged. This one-of-a-kind duplex in the heart of Winter Park stands out as the best value in town. Discover an unparalleled living experience in over 3,100 square feet of sophisticated space. Every detail- from the exquisite wood craftmanship which exudes classic Americana to the meticulously finished gourmet kitchen, this home truly speaks of timeless elegance. The stunning condo features three spacious ensuite bedrooms, including a primary suite with a charming fireplace and generous setback terrace. A private elevator ensures seamless access, while a lovely atrium, perfect for morning coffee or an evening glass of wine, enhances the serene ambiance. Pella windows and beautiful wood plantation shutters provide both tranquility and refined style. Step outside, and you’re immersed in the heart of Winter Park, surrounded by charming boutiques, renowned restaurants, lush parks, and vibrant entertainment. Prefer a lighter aesthetic? A paint quote and virtual renderings with lighter wood tones are available upon request. 3 Beds ⋅ 4 Baths ⋅ Winter Park Residential Condominium 9541/3489 Unit SubDv. ⋅ 32789 Zip Code One or more photo(s) has been virtually staged. This one-of-a-kind duplex in the heart of Winter Park stands out as the best value in town. Discover an unparalleled living experience in over 3,100 square feet of sophisticated space. Every detail- from the exquisite wood craftmanship which exudes classic Americana to the meticulously finished gourmet kitchen, this home truly speaks of timeless elegance. The stunning condo features three spacious ensuite bedrooms, including a primary suite with a charming fireplace and generous setback terrace. A private elevator ensures seamless access, while a lovely atrium, perfect for morning coffee or an evening glass of wine, enhances the serene ambiance. Pella windows and beautiful wood plantation shutters provide both tranquility and refined style. Step outside, and you’re immersed in the heart of Winter Park, surrounded by charming boutiques, renowned restaurants, lush parks, and vibrant entertainment. Prefer a lighter aesthetic? A paint quote and virtual renderings with lighter wood tones are available upon request. 101 S New York Ave Unit 302, Winter Park
$2,400,000 New price is $150K below a November 2024 appraisal! Home has been pre-inspected; seller is willing to share the 4PT Report as well as the appraisal. Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market. This stunning home, set on a prime lot adjacent to the Winter Park Golf Course, provides the perfect balance of privacy and convenience. Upon entering through custom double front doors, you’re greeted by an impressive foyer with soaring ceilings and a striking wall-mounted water fountain. The luxurious primary suite is privately situated on one side of the home and features an elegant bath, dual sinks, exquisite shower, and customized his-and-her walk-in closets. A second bedroom or office/study (with a private ensuite bath and walk-in closet) is also on the first floor across from the primary bedroom. This flexible space includes a custom walnut Murphy bed, allowing for dual use as a guest room or office.Continue into the open-concept home as it seamlessly flows from the living room to the dining room. A massive double-sided gas fireplace serves as a centerpiece between the dining room and family room areas. The gourmet kitchen is a chef's dream, outfitted with Sub-Zero Wolf appliances, a reverse osmosis water system, and a large island with bar-top seating that joins the family room. Oversized windows allow natural light to flood these spaces. Sliding doors open to an expansive 35-foot covered lanai, ideal for entertaining or al fresco dining. The lanai features a summer kitchen (with Egg grill) and retractable screens, leading out to a private saltwater pool and spa, which can be heated quickly through a mobile app. A fenced yard includes a small, turfed area, perfect for pets or play. A gate leads right out to the adjacent golf course. Upstairs, you’ll find a private third bedroom with an ensuite bath, along with a versatile multi-use space that can be used as a gym, theater room, or additional living area. For added privacy, a separate fourth bedroom suite is located at the rear of the home. This "apartment-like" suite includes a bedroom, private bath, living area with small refrigerator and sink along with a large second-story private terrace with sweeping views of the golf course. This living area features its own outside entry and security system, offering complete independence from the rest of the home and a door within that can be locked to separate, if desired. Additional features include a whole-home Briggs & Stratton generator, water softener system, tankless water heaters, two newer Trane 16 seer HVAC systems, a security system with multiple cameras, and exterior painting with a lifetime transferable warranty. With its unparalleled location and exceptional design, 1010 N Pennsylvania Ave is a rare opportunity to own a home that combines luxury living with modern convenience. Don’t miss your chance to make this exceptional property your next home! Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home! 4 Beds ⋅ 5 Baths ⋅ Tantums Additions To Winter Park SubDv. ⋅ 32789 Zip Code New price is $150K below a November 2024 appraisal! Home has been pre-inspected; seller is willing to share the 4PT Report as well as the appraisal. Located in the heart of Winter Park's downtown corridor, 1010 N Pennsylvania Ave offers a luxurious Mediterranean-inspired design with so many modern upgrades, all just steps from Park Avenue’s shops, Winter Park Village, and Whole Foods Market. This stunning home, set on a prime lot adjacent to the Winter Park Golf Course, provides the perfect balance of privacy and convenience. Upon entering through custom double front doors, you’re greeted by an impressive foyer with soaring ceilings and a striking wall-mounted water fountain. The luxurious primary suite is privately situated on one side of the home and features an elegant bath, dual sinks, exquisite shower, and customized his-and-her walk-in closets. A second bedroom or office/study (with a private ensuite bath and walk-in closet) is also on the first floor across from the primary bedroom. This flexible space includes a custom walnut Murphy bed, allowing for dual use as a guest room or office.Continue into the open-concept home as it seamlessly flows from the living room to the dining room. A massive double-sided gas fireplace serves as a centerpiece between the dining room and family room areas. The gourmet kitchen is a chef's dream, outfitted with Sub-Zero Wolf appliances, a reverse osmosis water system, and a large island with bar-top seating that joins the family room. Oversized windows allow natural light to flood these spaces. Sliding doors open to an expansive 35-foot covered lanai, ideal for entertaining or al fresco dining. The lanai features a summer kitchen (with Egg grill) and retractable screens, leading out to a private saltwater pool and spa, which can be heated quickly through a mobile app. A fenced yard includes a small, turfed area, perfect for pets or play. A gate leads right out to the adjacent golf course. Upstairs, you’ll find a private third bedroom with an ensuite bath, along with a versatile multi-use space that can be used as a gym, theater room, or additional living area. For added privacy, a separate fourth bedroom suite is located at the rear of the home. This "apartment-like" suite includes a bedroom, private bath, living area with small refrigerator and sink along with a large second-story private terrace with sweeping views of the golf course. This living area features its own outside entry and security system, offering complete independence from the rest of the home and a door within that can be locked to separate, if desired. Additional features include a whole-home Briggs & Stratton generator, water softener system, tankless water heaters, two newer Trane 16 seer HVAC systems, a security system with multiple cameras, and exterior painting with a lifetime transferable warranty. With its unparalleled location and exceptional design, 1010 N Pennsylvania Ave is a rare opportunity to own a home that combines luxury living with modern convenience. Don’t miss your chance to make this exceptional property your next home! Feel free to request an upgrades and features sheet outlining all the wonderful aspects of this home! 1010 N Pennsylvania Avenue, Winter Park
$405,000 **FULLY RENOVATED WINTER PARK GEM in the HIGHLY DESIRABLE 32789 ZIP CODE!** This meticulously renovated home offers a blend of stylish upgrades and classic charm, with an expansive screened-in porch and private backyard perfect for enjoying Florida’s outdoor lifestyle. This home has been thoughtfully designed and professionally renovated by McCree Construction. (NEW ROOF 2021, NEW AC & Ductwork 2024, NEW Plumbing 2024, Updated Electrical 2024, NEW Blown In Insulation, NEW Luxury Vinyl Plank flooring, NEW Kitchen and baths and fixtures, NEW Light fixtures, NEW Hardware, NEW Blinds, NEW doors, trim and door jambs, NEW Paint inside and out, NEW Fence, NEW Landscaping). Step inside to discover a bright, open-concept layout. The inviting living room is bathed in natural light from a large picture window and refinished original hardwood floors are located throughout the living room and two guest rooms. The brand NEW kitchen features stainless steel appliances, mission style wood cabinetry, Quartz countertops, and a warm gray subway tile backsplash. Just off the kitchen the dining room overlooks the backyard and french doors lead to the expansive screened-in porch. This is the perfect outdoor space for hosting guests or relaxing outdoors free of Florida bugs! The HUGE private backyard is fully fenced and plenty of room for furry family members, an urban garden, or space to play. The split floor plan offers a private main suite with an attached bathroom FULLY Renovated with a walk-shower with frameless glass door. The two guest rooms share the FULLY renovated hall bathroom with marble tile. Located just minutes from top-rated schools (Dommerich Elementary, Maitland Middle and Winter Park High). Minutes to Park Ave shopping and dining, various parks and major roads. Don’t miss your chance to own this exceptional property in a prime location. The current owners have thought of everything to make this a comfortable beautiful space for the next owners! 3 Beds ⋅ 2 Baths ⋅ Temple Terrace SubDv. ⋅ 32789 Zip Code **FULLY RENOVATED WINTER PARK GEM in the HIGHLY DESIRABLE 32789 ZIP CODE!** This meticulously renovated home offers a blend of stylish upgrades and classic charm, with an expansive screened-in porch and private backyard perfect for enjoying Florida’s outdoor lifestyle. This home has been thoughtfully designed and professionally renovated by McCree Construction. (NEW ROOF 2021, NEW AC & Ductwork 2024, NEW Plumbing 2024, Updated Electrical 2024, NEW Blown In Insulation, NEW Luxury Vinyl Plank flooring, NEW Kitchen and baths and fixtures, NEW Light fixtures, NEW Hardware, NEW Blinds, NEW doors, trim and door jambs, NEW Paint inside and out, NEW Fence, NEW Landscaping). Step inside to discover a bright, open-concept layout. The inviting living room is bathed in natural light from a large picture window and refinished original hardwood floors are located throughout the living room and two guest rooms. The brand NEW kitchen features stainless steel appliances, mission style wood cabinetry, Quartz countertops, and a warm gray subway tile backsplash. Just off the kitchen the dining room overlooks the backyard and french doors lead to the expansive screened-in porch. This is the perfect outdoor space for hosting guests or relaxing outdoors free of Florida bugs! The HUGE private backyard is fully fenced and plenty of room for furry family members, an urban garden, or space to play. The split floor plan offers a private main suite with an attached bathroom FULLY Renovated with a walk-shower with frameless glass door. The two guest rooms share the FULLY renovated hall bathroom with marble tile. Located just minutes from top-rated schools (Dommerich Elementary, Maitland Middle and Winter Park High). Minutes to Park Ave shopping and dining, various parks and major roads. Don’t miss your chance to own this exceptional property in a prime location. The current owners have thought of everything to make this a comfortable beautiful space for the next owners! 2609 Madeline Avenue, Winter Park
$2,859,000 Welcome to your mid-century modern dream home! This stunning five-bedroom, five-and-a-half-bathroom residence spans almost 5,000 square feet across three levels, meticulously restored to highlight its architectural beauty. Nestled on nearly an acre of lush corner land in the sought-after Via’s, this property invites you to explore its open floor plan, featuring striking brick accents, original Terrazzo flooring, and vaulted tongue and groove ceilings throughout. Step into the inviting living room With a grand double sided fireplace shared with the beautiful dining room, which flows seamlessly into a gorgeous screened-in porch overlooking a sparkling 9-foot deep pool and expansive backyard. The completely renovated kitchen boasts French doors that open to a charming deck, perfect for enjoying the serene side yard with a natural gas fire pit and 20-foot tall bamboo, providing privacy and a lush backdrop.The lower level offers a spacious flex room that leads directly to the pool, along with a full bedroom and bath, plus an indoor storage area equipped with an extra refrigerator and wine fridge. On the upper level, you’ll find three generously sized bedrooms, each with its own walk-in closet and full bath. The main floor’s fully renovated primary suite is a true sanctuary, featuring stunning views and a luxurious shower illuminated by two skylights. Step outside to discover a backyard that opens to a walking path leading directly to the Winter Park Racquet Club, offering easy access to tennis, events, and lakeside dining. The expansive property provides ample space for a pool house, boat garage, or simply to relish the lush surroundings. With a brand-new roof, doors, windows, 4 a/c units and fresh interior and exterior paint completed in 2022, this extraordinary gem is ready for you to call it home. Don’t miss the opportunity to make it yours! 5 Beds ⋅ 6 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code Welcome to your mid-century modern dream home! This stunning five-bedroom, five-and-a-half-bathroom residence spans almost 5,000 square feet across three levels, meticulously restored to highlight its architectural beauty. Nestled on nearly an acre of lush corner land in the sought-after Via’s, this property invites you to explore its open floor plan, featuring striking brick accents, original Terrazzo flooring, and vaulted tongue and groove ceilings throughout. Step into the inviting living room With a grand double sided fireplace shared with the beautiful dining room, which flows seamlessly into a gorgeous screened-in porch overlooking a sparkling 9-foot deep pool and expansive backyard. The completely renovated kitchen boasts French doors that open to a charming deck, perfect for enjoying the serene side yard with a natural gas fire pit and 20-foot tall bamboo, providing privacy and a lush backdrop.The lower level offers a spacious flex room that leads directly to the pool, along with a full bedroom and bath, plus an indoor storage area equipped with an extra refrigerator and wine fridge. On the upper level, you’ll find three generously sized bedrooms, each with its own walk-in closet and full bath. The main floor’s fully renovated primary suite is a true sanctuary, featuring stunning views and a luxurious shower illuminated by two skylights. Step outside to discover a backyard that opens to a walking path leading directly to the Winter Park Racquet Club, offering easy access to tennis, events, and lakeside dining. The expansive property provides ample space for a pool house, boat garage, or simply to relish the lush surroundings. With a brand-new roof, doors, windows, 4 a/c units and fresh interior and exterior paint completed in 2022, this extraordinary gem is ready for you to call it home. Don’t miss the opportunity to make it yours! 845 Via Lombardy, Winter Park
$1,050,000 Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando. 3 Beds ⋅ 2 Baths ⋅ Lords Sub SubDv. ⋅ 32789 Zip Code Experience lakeside living in Winter Park, FL with this custom LAKEFRONT PROPERTY on the shores of Lake Killarney, a 234 acre PRIVATE LAKE. There are a limited number of lakefront properties within the City, especially on skiable lakes, so this home presents a unique opportunity. Boasting an EXPANSIVE DOCK, one that’s grander than current building standards allow (but is grandfathered in), this backyard provides an ideal place to launch your water adventures, soak up scenic sunsets, and travel by lake to Hillstone for a meal. The CUSTOM POOL is waiting to be enjoyed! It features a custom waterfall, grotto, built-in seating/table and adjacent koi pond, all with a lake view. Recent updates to the home include: shingled roof (2018), DOUBLE PANE WINDOWS (2015), and HVAC (2016). Travertine and tile floors cover the entire home, there is no carpet. The back family room has multiple French doors and offers an expansive view of the lake. Fireplaces are featured in both the office and living room. The convenience of 632 Country Club is unmatched. It is approximately .6 miles from grocery shopping like Whole Foods and Publix or the Winter Park Village - a vast outdoor mall featuring a 20-screen Regal Cinema, Ruth's Chris Steakhouse and Bar Italia, to name a few. For everyday errands like HomeGoods, or workouts at LA Fitness, there is an even closer shopping plaza. An Interstate 4 (I-4) onramp is approximately 2 miles away. Winter Park is bursting with Old Florida charm and was named #38 historic world destinations in 2008 by National Geographic Magazine. At its heart is Park Avenue, famed for its cobblestoned and tree-lined streets with over 140 boutiques, museums, a train station, and world-class dining. 632 Country Club is approximately 1.5 miles from luxurious Park Avenue and 5 miles from downtown Orlando. 632 Country Club Drive, Winter Park
$3,125,000 Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As you step through the front door, you’re greeted by captivating lake views that flow from front to back. The spacious foyer leads to a charming living room, complete with a brick wood-burning fireplace. This area seamlessly transitions into the Florida room, an entertainer’s paradise featuring a wet bar, seating area and pool table, with easy access to a full bathroom that is equipped with a steamer shower. Open the French doors to reveal a tranquil outdoor oasis, where mature landscaping ensures privacy for the heated spa, creating a resort-like atmosphere in your own backyard. The heart of the home is a state-of-the-art chef's kitchen, boasting a large island, oversized GE refrigerator, Thermador dual ovens, elegant custom cabinetry, granite countertops, and a cozy breakfast nook. The spacious formal dining and living rooms offer beautiful lake views and lead out to a tranquil front terrace. For those who work from home, a private office on the main floor with a lake view provides an ideal and serene workspace. The large family room is perfect for everyday gatherings and is conveniently located next to a half bath. Upstairs, the primary suite overlooks the lake and features a walk-in closet and ensuite bathroom with a standalone Jacuzzi tub and separate shower. Two additional bedrooms share a full bath, while a generous fourth bedroom serves as a secondary primary suite with its own ensuite and walk-in closet. The property includes a paver circular driveway leading to a side-entry two-car garage. Cross the brick paved road to a sprawling lakefront lawn, leading to a private boat dock with a lift, perfect for enjoying all the water activities. Located on Lake Sue, a private ski lake, this home is just minutes from Park Avenue's shopping and dining, Downtown Orlando, Baldwin Park, playgrounds, parks and excellent public schools. Don’t miss the opportunity to make this stunning lakefront home your own! 4 Beds ⋅ 5 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code Discover this exquisite lakefront property located in the heart of Winter Park! Nestled on over an acre with more than 125 feet of water frontage, this home offers breathtaking views and absolutely stunning sunsets. As you step through the front door, you’re greeted by captivating lake views that flow from front to back. The spacious foyer leads to a charming living room, complete with a brick wood-burning fireplace. This area seamlessly transitions into the Florida room, an entertainer’s paradise featuring a wet bar, seating area and pool table, with easy access to a full bathroom that is equipped with a steamer shower. Open the French doors to reveal a tranquil outdoor oasis, where mature landscaping ensures privacy for the heated spa, creating a resort-like atmosphere in your own backyard. The heart of the home is a state-of-the-art chef's kitchen, boasting a large island, oversized GE refrigerator, Thermador dual ovens, elegant custom cabinetry, granite countertops, and a cozy breakfast nook. The spacious formal dining and living rooms offer beautiful lake views and lead out to a tranquil front terrace. For those who work from home, a private office on the main floor with a lake view provides an ideal and serene workspace. The large family room is perfect for everyday gatherings and is conveniently located next to a half bath. Upstairs, the primary suite overlooks the lake and features a walk-in closet and ensuite bathroom with a standalone Jacuzzi tub and separate shower. Two additional bedrooms share a full bath, while a generous fourth bedroom serves as a secondary primary suite with its own ensuite and walk-in closet. The property includes a paver circular driveway leading to a side-entry two-car garage. Cross the brick paved road to a sprawling lakefront lawn, leading to a private boat dock with a lift, perfect for enjoying all the water activities. Located on Lake Sue, a private ski lake, this home is just minutes from Park Avenue's shopping and dining, Downtown Orlando, Baldwin Park, playgrounds, parks and excellent public schools. Don’t miss the opportunity to make this stunning lakefront home your own! 1900 W Fawsett Road, Winter Park
$537,000 One or more photo(s) has been virtually staged. What!!! Under $540,000 in 32789??!! Yup!! Welcome to this charming ranch-style home located in Winter Park and best of all, NO HOA! Nestled on a spacious corner lot, this property offers a CIRCULAR DRIVEWAY for easy access and ample parking. Inside, you’ll find an updated kitchen with beautiful GRANITE countertops, perfect for hosting or enjoying family meals. Both bathrooms have been tastefully renovated for modern comfort. Cozy up by the WOOD BURNING FIREPLACE or enjoy the Florida lifestyle on the SCREENED-IN PORCH overlooking the FENCED-IN backyard great for pets, and/or outdoor entertaining. There’s also a hot tub with a brand-new motor for the ultimate relaxation. Major updates like a RE-ROOF(2016) and septic drain field (2016) add value and peace of mind. This home is ready to provide a blend of comfort, convenience, and modern updates, all with the freedom of no HOA restrictions. Plus, it includes a 2 car OVERSIZED GRAGE for extra storage or workshop space. Don't miss the chance to make this Winter Park gem your own! 4 Beds ⋅ 2 Baths ⋅ Fairbanks Shores 5th Add SubDv. ⋅ 32789 Zip Code One or more photo(s) has been virtually staged. What!!! Under $540,000 in 32789??!! Yup!! Welcome to this charming ranch-style home located in Winter Park and best of all, NO HOA! Nestled on a spacious corner lot, this property offers a CIRCULAR DRIVEWAY for easy access and ample parking. Inside, you’ll find an updated kitchen with beautiful GRANITE countertops, perfect for hosting or enjoying family meals. Both bathrooms have been tastefully renovated for modern comfort. Cozy up by the WOOD BURNING FIREPLACE or enjoy the Florida lifestyle on the SCREENED-IN PORCH overlooking the FENCED-IN backyard great for pets, and/or outdoor entertaining. There’s also a hot tub with a brand-new motor for the ultimate relaxation. Major updates like a RE-ROOF(2016) and septic drain field (2016) add value and peace of mind. This home is ready to provide a blend of comfort, convenience, and modern updates, all with the freedom of no HOA restrictions. Plus, it includes a 2 car OVERSIZED GRAGE for extra storage or workshop space. Don't miss the chance to make this Winter Park gem your own! 2891 Naples Drive, Winter Park
$658,125 Discover the ease of turnkey living in this beautifully renovated 3-bedroom condo, located off Minnesota Ave., between Pennsylvania and Orange Ave. Just steps from the Winter Park Tennis Center and minutes from Park Avenue, the condo offers a prime location with easy access to dining, shopping, and entertainment. Thoughtfully designed by Wolfe-Rizor Interiors, this home showcases gorgeous “rustic” style engineered wood floors, a modern kitchen with a breezy coastal feel, and stylish bathrooms. Elegant blackout drapes and stunning chandeliers throughout the home add an extra layer of sophistication. The sunny living area is delightful yet cozy, with a wood-burning fireplace and (3) sets of French doors opening to (2) balconies, perfect for outdoor dining and relaxing. The spacious primary suite has a walk-in closet and pocket doors opening to a stylish bathroom with dual sinks and a glass shower. 2 additional bedrooms share a 2nd full bathroom, and a laundry closet located in the hallway offers a stackable washer and dryer, plus great storage space. On the ground level, a detached 2-car garage (with new motors) can be utilized for private parking or storage, while a driveway and street parking provide ample space for your guests. Zoned for Audubon K-8 and close to top schools, this condo is directly across the street from the tennis courts and the Azalea Lane park/playground, and minutes from Baldwin Park, the Corrine Drive corridor, and downtown Winter Park. Enjoy a low-maintenance lifestyle in a prime location! 3 Beds ⋅ 2 Baths ⋅ Azalea Lane SubDv. ⋅ 32789 Zip Code Discover the ease of turnkey living in this beautifully renovated 3-bedroom condo, located off Minnesota Ave., between Pennsylvania and Orange Ave. Just steps from the Winter Park Tennis Center and minutes from Park Avenue, the condo offers a prime location with easy access to dining, shopping, and entertainment. Thoughtfully designed by Wolfe-Rizor Interiors, this home showcases gorgeous “rustic” style engineered wood floors, a modern kitchen with a breezy coastal feel, and stylish bathrooms. Elegant blackout drapes and stunning chandeliers throughout the home add an extra layer of sophistication. The sunny living area is delightful yet cozy, with a wood-burning fireplace and (3) sets of French doors opening to (2) balconies, perfect for outdoor dining and relaxing. The spacious primary suite has a walk-in closet and pocket doors opening to a stylish bathroom with dual sinks and a glass shower. 2 additional bedrooms share a 2nd full bathroom, and a laundry closet located in the hallway offers a stackable washer and dryer, plus great storage space. On the ground level, a detached 2-car garage (with new motors) can be utilized for private parking or storage, while a driveway and street parking provide ample space for your guests. Zoned for Audubon K-8 and close to top schools, this condo is directly across the street from the tennis courts and the Azalea Lane park/playground, and minutes from Baldwin Park, the Corrine Drive corridor, and downtown Winter Park. Enjoy a low-maintenance lifestyle in a prime location! 1086 Azalea Lane, Winter Park
$1,129,000 Stunning, custom-built home in the Winter Park Tree Streets. This beautifully designed, Mediterranean-style home features 4 bedrooms, 3 full-baths, and an open layout complimented by engineered wood and travertine flooring, high ceilings, crown molding, and bright natural light. First floor layout includes a spacious living/dining room and open concept kitchen/family room. The kitchen offers stainless steel appliances, a built-it oven and microwave, gas range, granite counters, bar top seating, and a walk-in pantry. Off the family room are French doors that open to a screened patio which overlooks the perfectly manicured backyard. The first floor primary bedroom is very comfortably sized and has a private en suite with double vanities, a walk-in shower, and jetted tub. There’s an additional guest room with full bath on the first floor as well, ideal for visiting guests. Upstairs are two generously sized bedrooms, each with ample closet space, and a shared hall bath. Additional highlights include natural gas, a Rinnai tankless hot water heater system, paver walkways, a detached Tuff Shed, tile roof, and more. Located in Winter Park’s desirable “tree streets” neighborhood this home is zoned for the A-rated Winter Park School District and is close proximity to the Winter Park Raquet Club, Interlachen Golf & Country Club, Rollins College, Park Avenue, and all of the fantastic shops and dining the area has to offer. This charming home won't last so schedule your showing today. 4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code Stunning, custom-built home in the Winter Park Tree Streets. This beautifully designed, Mediterranean-style home features 4 bedrooms, 3 full-baths, and an open layout complimented by engineered wood and travertine flooring, high ceilings, crown molding, and bright natural light. First floor layout includes a spacious living/dining room and open concept kitchen/family room. The kitchen offers stainless steel appliances, a built-it oven and microwave, gas range, granite counters, bar top seating, and a walk-in pantry. Off the family room are French doors that open to a screened patio which overlooks the perfectly manicured backyard. The first floor primary bedroom is very comfortably sized and has a private en suite with double vanities, a walk-in shower, and jetted tub. There’s an additional guest room with full bath on the first floor as well, ideal for visiting guests. Upstairs are two generously sized bedrooms, each with ample closet space, and a shared hall bath. Additional highlights include natural gas, a Rinnai tankless hot water heater system, paver walkways, a detached Tuff Shed, tile roof, and more. Located in Winter Park’s desirable “tree streets” neighborhood this home is zoned for the A-rated Winter Park School District and is close proximity to the Winter Park Raquet Club, Interlachen Golf & Country Club, Rollins College, Park Avenue, and all of the fantastic shops and dining the area has to offer. This charming home won't last so schedule your showing today. 1571 Oneco Avenue, Winter Park