Homesinorlando.forsale Search Results

$3,600,000

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

4 Beds ⋅ 4 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Nestled on a sprawling 0.89-acre estate, this luxurious home offers the perfect balance of privacy and convenience, just moments from the vibrant downtown Winter Park. A rare gem, this 1935 James Gamble Rogers masterpiece blends Old World charm with European influences, creating an inviting, character-rich ambiance. The main home features 3 bedrooms, 2 1/2 bathrooms, and 3,908 square feet of elegant living space, complemented by a 1-bedroom, 1-bathroom guest cottage, adding 406 square feet, for a total of 4,314 square feet. Accessed via a long, secluded driveway, this estate seamlessly blends indoor and outdoor living with lush gardens, expansive courtyards, and tranquil patios. Inside, arched doorways, reclaimed doors, and rounded stucco walls evoke a Santa Barbara Mediterranean feel. The kitchen is outfitted with stainless steel appliances, granite countertops, and a butler’s pantry—ideal for entertaining. The formal dining room opens to a living room with a curved barrel ceiling, a fireplace, and French doors leading to a garden patio. A sunlit sunroom offers panoramic garden and pool views, perfect for relaxation. The expansive downstairs owner's suite features vaulted ceilings, French doors to the patio, a cozy fireplace, and a lavish marble bath with a Jacuzzi tub, double sinks, and a dressing area with custom cabinetry and two large walk-in closets. Upstairs, two bedrooms share a beautifully renovated marble bath. The detached 2-car garage is adjacent to the laundry room, while the guest house offers a studio layout with terra-cotta floors, a kitchenette, a full bath, and French doors overlooking the pool. The backyard is an oasis of tranquility with a stunning resort-style pool, an expansive patio, and lush landscaping, providing ultimate privacy. This home offers the best of both worlds: a rare opportunity to own a piece of Winter Park history, yet lovingly maintained with modern updates and conveniences throughout.

851 Georgia Avenue, Winter Park

$2,594,550

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today!

3 Beds ⋅ 3 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code

Experience modern elegance in this stunning Lake Sylvan estate with breathtaking lake views and seamless indoor-outdoor living. The open-concept design features a gourmet kitchen (renovated 2023) with quartzite countertops, a wet bar, and luxe appliances. French doors, a custom gas fireplace, and designer lighting add refined charm to the living room. Step outside to nearly 1500 sqft of additional living space on the lake featuring a heated pool, spa, covered patio with gas fireplace, summer kitchen and lakeside firepit. With three bedrooms and a versatile office (easily a fourth), this home adapts to your needs. The first-floor primary suite opens to the pool, while an upstairs primary suite has dual custom closets, a spa-like bath, and a private flex space. Upgrades include a new roof with gutters and gutter guards (2022), new water heaters (2023), interior paint (2021) exterior paint (2023), water filtration, system, dual propane tanks, security system, plantation shutters, and three AC units. The above garage attic is accessible by staircase and can easily be enclosed to make a 5th bedroom, game room or flex space. This lakefront sanctuary offers privacy, sophistication, and modern convenience plus is located just minutes from Park Avenue's charming shops and restaurants. Don’t miss the opportunity to make this lake front home yours. Schedule your private showing today!

254 Sylvan Boulevard, Winter Park

$2,910,000

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

4 Beds ⋅ 6 Baths ⋅ Stonehurst Estates SubDv. ⋅ 32789 Zip Code

Set on a sprawling half-acre, surrounded by meticulously manicured landscaping, this custom-built traditional estate exemplifies refined luxury, modern convenience, and an unparalleled lifestyle. The red brick façade, covered porches with glass doors, and gated side porte-cochere set a timeless tone, while two-story fluted columns add stately elegance. Inside, classic architectural details merge with modern design, highlighted by two-story coffered ceilings, intricate millwork, and expansive windows and French doors that flood the home with natural light. Thoughtfully designed for both entertaining and everyday living, the gourmet kitchen includes a 6-burner Viking gas cooktop, double dishwashers and sinks, a paneled refrigerator and separate full-sized freezer, a walk-in pantry, and an oversized island with breakfast bar seating. The first floor features a private primary retreat, two powder rooms, a workstation/mudroom accessible off the porte-cochere, and one of two laundry rooms. Upstairs offers three spacious bedroom suites with walk-in closets, a versatile bonus room, and a second laundry room. Embrace the Florida lifestyle from a two-story covered brick patio with a built-in gas grill, overlooking the private, fenced-in backyard oasis and breathtaking saltwater pool and heated spa, all elevated by a three-tier fountain and fire pit area, and wrapped in lush landscaping; this outdoor space is truly magical and not easily replicated in Winter Park! A circular driveway provides ample parking, while a gated side drive leads to an oversized, detached three-car garage with a bonus room above—ideal for a gym or studio. This particularly grand, wide street in the City of Winter Park is something truly special. Ideally located near Baldwin Park, Corrine Drive, and Park Avenue, and zoned for highly regarded Audubon K-8, this estate is more than a home—it’s a statement in timeless elegance. *Ask for a list of improvements, the floorplan and click on the virtual tour!

1911 Stonehurst Road, Winter Park

$3,200,000

Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code

Located in the heart of Winter Park this exquisite modern residence built by Vimaro Homes features almost 5,000 square feet of luxury living space. As you step through the glass front doors, you’re immediately greeted by the grandeur of the marble entry floors and custom archways, setting the tone for the exceptional finishes throughout this stunning home. From the gorgeous wood floors laid in a herring bone pattern, to the designer light fixtures, arched doorways, and beautiful mill work, no expense was spared in the construction of this remarkable residence. The chef’s kitchen features exquisite custom cabinetry, marble countertops, a massive butler’s pantry, top of the line appliances including a ILVE Nostalgie range, and a wine cellar. The great room features a wall of glass that opens to the spacious covered lanai blending the indoor and outdoor spaces. The primary bedroom suite overlooks the private back yard and features a spa bath that would rival even the most prominent spas. Last but not least there is a massive walk in closet with separate his and hers sections, and a washer and dryer. Additional features include a first-floor game room, home office, formal dining room, a second floor loft area, 4 additional bedrooms, and second floor laundry room. Situated on a spacious lot, this property features a circular driveway, and a large, fenced yard with mature landscaping, perfect for outdoor activities and entertaining. The highlight of this home is the inviting pool, providing a refreshing oasis for those hot summer days. Jump on your golf cart and within minutes you’re transported to Park Ave, with its amazing shops, fine dining, and everything else that Winter Park has to offer. Don’t miss your opportunity to own this stunning Winter Park home crafted by renowned builder Vimaro Homes.

1833 Loch Berry Road, Winter Park

$1,305,000

Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

4 Beds ⋅ 4 Baths ⋅ Sevilla SubDv. ⋅ 32789 Zip Code

Back on the market at no fault of the seller. Step into the charm of old Florida with this stunning historic home in the heart of Winter Park's exclusive Sevilla neighborhood. Built in 1973 by Charles Clayton, this beautifully preserved residence seamlessly blends timeless elegance with modern comforts. Featuring original hardwood floors, intricate crown molding, and a cozy wood-burning fireplace, every detail reflects meticulous craftsmanship and a timeless aesthetic. The updated gourmet kitchen boasts high-end appliances while maintaining its classic appeal. Nestled on a tree-lined brick street, the home sits on a lushly landscaped lot with a spacious backyard, including a 64,000 gallon custom pool, perfect for enjoying Florida's warm evenings. Just minutes from Park Avenue's boutiques, restaurants, and within walking distance of A-rated schools, this rare gem offers the perfect blend of history, luxury, and location. Don't miss your chance to own a piece of Winter Park's rich heritage!

1600 Barcelona Way, Winter Park

$1,850,000

This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

5 Beds ⋅ 5 Baths ⋅ Windsong Elizabeths Walk 43/81 SubDv. ⋅ 32789 Zip Code

This Mediterranean-style, Windsong pool home is sure to check every box, with a 3-car garage, screened rear patio, heated spa and pool, and an ideal, 3-way split-bedroom floorplan on the 1st floor. The large kitchen sits at the heart of the home with a dinette showcasing pool views, an island with a gas cooktop, and a breakfast bar overlooking the sunny family room. Separate living and dining rooms off the foyer offer flexibility and additional space to entertain with ease. To the left of the foyer, enjoy a large, private office with a storage closet. Just past the office, the Primary Suite is situated on one end of the home for optimal privacy and features his and hers walk-in closets, a renovated bathroom, and access to the screened rear patio. At the other end of the home, a secondary bedroom with a full en-suite bathroom makes a great guest or in-law suite, while 2 additional bedrooms, a full hall bath, storage closet, and spacious laundry room complete the 1st floor. Upstairs, the private bonus room, complete with a walk-in closet and full en-suite bathroom, makes a perfect 5th bedroom. French doors from the family room, living room, and Primary bedroom all lead to a screened rear patio that overlooks a fully-fenced backyard where lush landscaping wraps around the resort-style heated pool and spa with water features. In addition to the massive driveway and expanded parking pad, the oversized 3-car garage provides extra parking and storage space. As one of the most coveted neighborhoods in Winter Park, Windsong offers countless amenities, including private lake access for residents. This premium location is just steps from Baldwin Park, East End Market, the Corrine Drive corridor, and minutes from downtown Park Avenue.

1627 Elizabeths Walk, Winter Park

$602,500

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

3 Beds ⋅ 3 Baths ⋅ Arbors/Aragon SubDv. ⋅ 32789 Zip Code

This beautifully updated 3 bedroom, 3 bath home offers a perfect blend of rustic charm and modern convenience in a highly desirable location. The open floor plan is warm and inviting, with stylish finishes and thoughtful updates that make it truly move-in ready. Each bedroom features its own ensuite bath and a spacious walk-in closet, with both upstairs suites offering the flexibility to serve as a primary retreat. Recent improvements include a brand new hot water heater, new refrigerator, an added mini-split in the garage for enhanced comfort, a water softener system, and a recently replaced A/C. The fenced backyard has been upgraded to turf for easy maintenance, complemented by a private deck—perfect for relaxing or entertaining. Two balconies, including one with a view of the Rollins College baseball field, provide additional peaceful retreats. The attached two-car garage offers both convenience and extra security. Located within walking distance of Park Avenue, Rollins College, and Hannibal Square, this home provides easy access to shopping, dining, and entertainment while maintaining a quiet and private feel. A rare opportunity in an unbeatable location—don’t miss it!

777 S Denning Drive Unit B, Winter Park

$1,500,000

Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of elegance and convenience. Just minutes from shopping, fantastic dining, popular Phelps Park, the YMCA, the renowned Interlachen Country Club, and the lively Park Avenue, this location has it all. As you approach, a charming front porch shaded by majestic oak trees welcomes you home. Step inside to discover a beautifully designed main floor, featuring a formal dining room, a versatile office space, and a kitchen that effortlessly flows into the family room. The kitchen is every chef’s dream, with gorgeous granite countertops, premium stainless steel appliances, a large breakfast bar, and a cozy breakfast nook. From here, enjoy stunning views of the lagoon-style pool, making meal prep a breeze. The family room, complete with custom built-in shelving and French doors, opens up to a screened-in lanai, offering the perfect space for relaxation or entertaining. The spacious primary suite on the main floor is a true sanctuary, featuring a walk-in closet, a luxurious soaking tub, dual sinks, and a spacious shower. Large windows provide beautiful views of the pool and tranquil backyard. A generously sized laundry room, a full bathroom, and a flexible room complete the main floor. The flexible room, conveniently located just off the kitchen, could serve as a guest room or playroom. Upstairs, you'll find three spacious bedrooms and a Jack and Jill bathroom with a soaking tub, separate shower, and dual sinks. The third bedroom can easily function as a bonus room, depending on your needs. Entertain in style in the private, peaceful backyard, where the lagoon-style pool and spa with a rock feature and waterfall from the spa create a serene ambiance. The screened-in lanai is the perfect spot to sip your morning coffee or unwind with a glass of wine while enjoying nature’s beauty. Plus, with top-rated Winter Park Schools, this home offers everything you need!

4 Beds ⋅ 3 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Nestled in the heart of Winter Park, this stunning 4-bedroom, 3-bathroom pool home offers the perfect balance of elegance and convenience. Just minutes from shopping, fantastic dining, popular Phelps Park, the YMCA, the renowned Interlachen Country Club, and the lively Park Avenue, this location has it all. As you approach, a charming front porch shaded by majestic oak trees welcomes you home. Step inside to discover a beautifully designed main floor, featuring a formal dining room, a versatile office space, and a kitchen that effortlessly flows into the family room. The kitchen is every chef’s dream, with gorgeous granite countertops, premium stainless steel appliances, a large breakfast bar, and a cozy breakfast nook. From here, enjoy stunning views of the lagoon-style pool, making meal prep a breeze. The family room, complete with custom built-in shelving and French doors, opens up to a screened-in lanai, offering the perfect space for relaxation or entertaining. The spacious primary suite on the main floor is a true sanctuary, featuring a walk-in closet, a luxurious soaking tub, dual sinks, and a spacious shower. Large windows provide beautiful views of the pool and tranquil backyard. A generously sized laundry room, a full bathroom, and a flexible room complete the main floor. The flexible room, conveniently located just off the kitchen, could serve as a guest room or playroom. Upstairs, you'll find three spacious bedrooms and a Jack and Jill bathroom with a soaking tub, separate shower, and dual sinks. The third bedroom can easily function as a bonus room, depending on your needs. Entertain in style in the private, peaceful backyard, where the lagoon-style pool and spa with a rock feature and waterfall from the spa create a serene ambiance. The screened-in lanai is the perfect spot to sip your morning coffee or unwind with a glass of wine while enjoying nature’s beauty. Plus, with top-rated Winter Park Schools, this home offers everything you need!

1741 Pine Avenue, Winter Park

$1,800,000

Under Construction. Modern elegance and timeless sophistication define 1682 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can be used as a fifth bedroom, offering flexible living space to accommodate a variety of needs. The gourmet kitchen is a standout feature, boasting Thermador appliances, custom cabinetry, and an expansive island, making it ideal for both daily use and entertaining. Included appliances are a 36” gas range, microwave drawer, 36” refrigerator, and dishwasher. Flowing effortlessly into the living and dining areas, the home is bathed in natural light, enhancing its modern yet warm aesthetic. The primary suite, located on the second floor, offers a spa-like retreat with dual vanities, a soaking tub, and a walk-in shower. Also on the second floor are bedrooms three, four, and a conditioned attic space, which serves as an optional fifth bedroom. The first floor includes bedroom two and a dedicated office, offering privacy and convenience. The outdoor living spaces have been thoughtfully curated to provide the ultimate in relaxation and entertainment, featuring a private pool surrounded by lush, manicured landscaping. A separate, elegantly appointed pool cabana further enhances the home’s allure, creating an idyllic space for leisure or hosting guests in style. Located just moments from Park Avenue, this home offers unrivaled access to Winter Park’s finest boutique shopping, gourmet dining, and the vibrant lifestyle for which the area is known. Utilities include electricity, water, sewer, and gas connection. 1682 Arbor Park Dr is a rare opportunity to experience the pinnacle of luxury living, where modern sophistication and timeless charm come together to create an exceptional residence. Please note: Images shown are renderings and are for illustrative purposes only. Final construction details, finishes, and features may vary.

4 Beds ⋅ 4 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code

Under Construction. Modern elegance and timeless sophistication define 1682 Arbor Park Dr, a meticulously crafted new construction home in the heart of Winter Park, FL. Spanning 2,950 square feet, this 4-bedroom, 3.5-bathroom residence also features a dedicated office and a conditioned attic that can be used as a fifth bedroom, offering flexible living space to accommodate a variety of needs. The gourmet kitchen is a standout feature, boasting Thermador appliances, custom cabinetry, and an expansive island, making it ideal for both daily use and entertaining. Included appliances are a 36” gas range, microwave drawer, 36” refrigerator, and dishwasher. Flowing effortlessly into the living and dining areas, the home is bathed in natural light, enhancing its modern yet warm aesthetic. The primary suite, located on the second floor, offers a spa-like retreat with dual vanities, a soaking tub, and a walk-in shower. Also on the second floor are bedrooms three, four, and a conditioned attic space, which serves as an optional fifth bedroom. The first floor includes bedroom two and a dedicated office, offering privacy and convenience. The outdoor living spaces have been thoughtfully curated to provide the ultimate in relaxation and entertainment, featuring a private pool surrounded by lush, manicured landscaping. A separate, elegantly appointed pool cabana further enhances the home’s allure, creating an idyllic space for leisure or hosting guests in style. Located just moments from Park Avenue, this home offers unrivaled access to Winter Park’s finest boutique shopping, gourmet dining, and the vibrant lifestyle for which the area is known. Utilities include electricity, water, sewer, and gas connection. 1682 Arbor Park Dr is a rare opportunity to experience the pinnacle of luxury living, where modern sophistication and timeless charm come together to create an exceptional residence. Please note: Images shown are renderings and are for illustrative purposes only. Final construction details, finishes, and features may vary.

1682 Arbor Park Drive, Winter Park

$939,000

Top floor direct lakefront view of this Renovated condominium. Professional pictures coming.

2 Beds ⋅ 2 Baths ⋅ Cloisters The SubDv. ⋅ 32789 Zip Code

Top floor direct lakefront view of this Renovated condominium. Professional pictures coming.

100 S Interlachen Avenue Unit 502D, Winter Park

$205,000

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

3 Beds ⋅ 2 Baths ⋅ Waterfall Cove At Winter Park SubDv. ⋅ 32789 Zip Code

This property located in a peaceful community IN WINTER PARK. and easy access to FL I-4 , short drive distance to Rollins College, UCF, Valencia college, Hospitals, shopping center, restaurants and Orlando Theme Park. This unit located on the second floor, it has 3 bedrooms 2, bathrooms, open floor plan. The community amenities include a large pool with lounge chairs, playground and gazebo. This property can be leased. You must see for any possibilities come and check for yourself. Registered owner is brother of the realtor. SELLER MIGHT HOLD FIRST MORTGAGE WITH A GOOD DOWN PAYMENT.

1695 Lee Road Unit C202, Winter Park

$4,100,000

Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park. Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft. masterpiece, including white oak floors, beams, and wood details in most rooms, 5 BRs, and 4.5 BAs. The first floor features a primary suite and guest suite as well as an office, great room, dedicated bar, dining area, and exquisite kitchen with a secret pass-through door to the scullery. The second level boasts three generously sized bedrooms and two baths. Cable wire railing, stone, wood inlay details, custom front door, oversized lanai with summer kitchen, outdoor fireplace, huge pool with firepit and separate firepit conversation area, the list goes on and on... This unique lot is a rare find in Winter Park - oversized in both width and depth with dimensions of 155’ deep and 143’ wide. The interior features over 6600 square feet under roof and a 4-car garage with a work-bench area included. The outdoor area features a 34-foot patio with a built-in gas grill, gas fireplace, and large-format porcelain pavers. The remote screen provides you with ease of access to your custom-designed pool with pebbletec, an outdoor shower, and a firepit nestled amongst the landscaping. The rear yard is completely irrigated and includes a well for irrigation to keep water expenses down significantly. The custom-designed pool is large for Winter Park, featuring a lounging shelf as well as a 10’ fire feature and swim-out. The massive deck is adorned with wood-like porcelain pavers with a porcelain coping. Smart home features in this home include wireless controls for audio, a/c, garage doors, pool equipment, lighting, and exterior cameras. Additionally there is upgraded spray foam insulation, gas appliances (water heaters, fireplaces, washer, range), and an elevation featuring Cultured stone, Hardi Siding, and a Jeldwyn 10’ front entry door. Herringbone pavers lead you from the cobblestone street to the magnificent front entry. Buyers will enjoy the extensive landscaping and privacy hedges. The landscaping is mature for a brand-new home! Privacy abounds everywhere in this home. Custom landscape lighting adds to the estate feel of this home. The gourmet kitchen features all Wolf and Sub-zero appliances, which include a Wolf range, Wolf 2cd oven, steam oven, Sharp microwave, Cove dishwasher with custom wood panel, a Sub-zero Refrigerator with custom panel, and a Sub-zero Freezer also with a custom panel. Disguised between the refrigerator and freezer is a secret hidden door to the scullery. Exotic countertops abound throughout the house. Quartzite like you have never seen before is evident in the kitchen and bar. Antolini Italian marble that was specially treated with “Zerocare Plus” can be found on the kitchen counters and kitchen backsplash. Custom cabinetry throughout the house, featuring white oak. Additional appliances include 3 beverage refrigerators, 1 wine refrigerator, ice maker, and a secondary 36” refrigerator. Every detail has been thought-out and implemented for you in this breathtaking home! Do not wait - the work has been done for you with NO waiting time for new construction. This elegant home will not last!

5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Welcome home to this one-of-a-kind custom-designed and built home by Ferrarini Custom Homes, Inc. in February 2024. This singular mid-century modern home is like no other in Winter Park. Boasting an ideal location just steps from Phelps Park as well as only 1.5 miles from Park Avenue makes it the ideal home for the most discerning buyer. Custom features abound in this stunning 4582 sq. ft. masterpiece, including white oak floors, beams, and wood details in most rooms, 5 BRs, and 4.5 BAs. The first floor features a primary suite and guest suite as well as an office, great room, dedicated bar, dining area, and exquisite kitchen with a secret pass-through door to the scullery. The second level boasts three generously sized bedrooms and two baths. Cable wire railing, stone, wood inlay details, custom front door, oversized lanai with summer kitchen, outdoor fireplace, huge pool with firepit and separate firepit conversation area, the list goes on and on... This unique lot is a rare find in Winter Park - oversized in both width and depth with dimensions of 155’ deep and 143’ wide. The interior features over 6600 square feet under roof and a 4-car garage with a work-bench area included. The outdoor area features a 34-foot patio with a built-in gas grill, gas fireplace, and large-format porcelain pavers. The remote screen provides you with ease of access to your custom-designed pool with pebbletec, an outdoor shower, and a firepit nestled amongst the landscaping. The rear yard is completely irrigated and includes a well for irrigation to keep water expenses down significantly. The custom-designed pool is large for Winter Park, featuring a lounging shelf as well as a 10’ fire feature and swim-out. The massive deck is adorned with wood-like porcelain pavers with a porcelain coping. Smart home features in this home include wireless controls for audio, a/c, garage doors, pool equipment, lighting, and exterior cameras. Additionally there is upgraded spray foam insulation, gas appliances (water heaters, fireplaces, washer, range), and an elevation featuring Cultured stone, Hardi Siding, and a Jeldwyn 10’ front entry door. Herringbone pavers lead you from the cobblestone street to the magnificent front entry. Buyers will enjoy the extensive landscaping and privacy hedges. The landscaping is mature for a brand-new home! Privacy abounds everywhere in this home. Custom landscape lighting adds to the estate feel of this home. The gourmet kitchen features all Wolf and Sub-zero appliances, which include a Wolf range, Wolf 2cd oven, steam oven, Sharp microwave, Cove dishwasher with custom wood panel, a Sub-zero Refrigerator with custom panel, and a Sub-zero Freezer also with a custom panel. Disguised between the refrigerator and freezer is a secret hidden door to the scullery. Exotic countertops abound throughout the house. Quartzite like you have never seen before is evident in the kitchen and bar. Antolini Italian marble that was specially treated with “Zerocare Plus” can be found on the kitchen counters and kitchen backsplash. Custom cabinetry throughout the house, featuring white oak. Additional appliances include 3 beverage refrigerators, 1 wine refrigerator, ice maker, and a secondary 36” refrigerator. Every detail has been thought-out and implemented for you in this breathtaking home! Do not wait - the work has been done for you with NO waiting time for new construction. This elegant home will not last!

1691 Chestnut Avenue, Winter Park

$640,000

Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances. $64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on sliding doors, a storage shed, privacy fencing, upgraded switches and dimmers, and custom cabinetry. The laundry room includes a butcher block folding table for added convenience. With a 2023 roof, HVAC, electrical, and plumbing systems, this home is ready for immediate occupancy. Located just minutes from Park Avenue, offering a variety of shopping, dining, and entertainment options in Winter Park. Contact us today to schedule a showing!

4 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully designed home in Winter Park! This residence features an open floor plan, modern finishes, and a spacious two-car garage. The home includes tile flooring throughout the living areas, quartz countertops, upgraded light fixtures, and premium appliances. $64,900 in recent upgrades add tremendous value, including a $30,000 lanai, plantation shutters, custom blinds on sliding doors, a storage shed, privacy fencing, upgraded switches and dimmers, and custom cabinetry. The laundry room includes a butcher block folding table for added convenience. With a 2023 roof, HVAC, electrical, and plumbing systems, this home is ready for immediate occupancy. Located just minutes from Park Avenue, offering a variety of shopping, dining, and entertainment options in Winter Park. Contact us today to schedule a showing!

2739 Riddle Drive, Winter Park

$2,800,000

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

3 Beds ⋅ 4 Baths ⋅ Trovillion Condo SubDv. ⋅ 32789 Zip Code

Discover the pinnacle of luxury and privacy in this stunning Villa Siena penthouse residence, perfectly positioned in the charming brick-lined streets of Winter Park. While nestled in the heart of the city's vibrant dining, shopping, and cultural scene, this exclusive retreat offers unparalleled tranquility and seclusion. Designed for those who appreciate sophistication, this secured building boasts lavish amenities that extend your living space beyond the walls of your penthouse. Host guests in the elegant resident lounge, complete with a bar for entertaining, marvel at rocket launches from the spectacular rooftop terrace, or take advantage of the private conference room, ideal for high-level meetings or remote work. Stay active in the state-of-the-art exercise room, offering convenience and wellness steps from your front door. With private, secured covered parking and concierge-level service, every detail has been designed to elevate your lifestyle. Inside, refined elegance meets cutting-edge technology—custom millwork, exquisite tile work, and smart-home automation blend seamlessly with high-end video conferencing capabilities. Expansive living spaces, soaring ceilings, and generous room sizes create an inviting atmosphere, while every bedroom features a spa-like ensuite and a private balcony to take in the beauty of Winter Park. Enjoy world-class restaurants, boutique shopping, and lively events at the park, all just steps from your front door. With the nearby train station providing effortless access to Orlando and even Miami, your next adventure is always within reach. This penthouse is a rare opportunity—luxury, location, and lifestyle converge in perfect harmony. Schedule your private tour today!

315 E New England Avenue Unit 30, Winter Park

$5,400,000

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

5 Beds ⋅ 9 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code

Extraordinary Waterfront Neoclassical Italian Estate situated on a prime .72-acre corner lot in one of Winter Park's most sought-after locations. This 7,916 SF property includes a main residence of over 7,100 SF, a detached guest house, and a poolside catering suite. The private covered boat dock is located just steps away, across the street, in the historic Kraft Azalea Garden, providing direct lake access with boat and personal watercraft storage on Lake Maitland, without the upkeep of a waterfront backyard. Inside, fresh neutral interiors and beautiful landscaping frame elegant arrival and living spaces. The thoughtful layout offers 5 bedrooms and 5 full plus 4 half baths, including a 550 SF guest house. Expansive entertaining areas flow seamlessly into a private courtyard with a heated pool and spa, covered dining, an outdoor grill, a wood-burning fireplace, and multiple terraces. Highlights include a grand primary suite with dual bathrooms and closets, a two-story wardrobe with an office in one of the primary closets, an impressive entertainment room, and a gourmet kitchen outfitted with Viking appliances, a newly replaced double oven, and a trash compactor. For large-scale entertaining, the detached pool house doubles as a catering suite with prep sink, refrigerator, and wall-to-wall storage. Built by renowned builder Charles Clayton and designed by Marc-Michaels, the home is a masterpiece of solid block construction and timeless detail featuring imported Parisian fireplaces, solid marble columns, both marble and travertine floors, and Venetian plaster walls. A new barrel tile roof (2023) adds lasting value and peace of mind. Ideally located across from Kraft Azalea Garden and near Rollins College, the estate offers a rare combination of waterfront tranquility and walkable access to Park Avenue’s world-class dining, boutiques, and museums. The Winter Park Racquet Club is also just a short golf cart ride away. A rare opportunity to acquire a legacy property with major aesthetic updates already completed and future equity positioned for growth.

1400 Alabama Drive, Winter Park

$1,400,000

Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timberlane Shores. The heart of this home is a chef's dream kitchen, featuring a professional WOLF range, custom two-tone cabinetry in rich wood and sophisticated navy blue, and premium stone countertops that extend to a generous entertainment island. Gleaming terrazzo floors flow seamlessly through the open-concept living spaces, where abundant windows frame views of the lush gardens and flood the home with natural light. The thoughtfully designed floor plan incorporates two distinct living areas - one integrated with the kitchen for casual gatherings, and a separate space with soaring vaulted ceilings and custom built-ins perfect for formal entertaining or quiet evenings. The primary retreat offers a private sanctuary with vaulted ceilings, spa-like ensuite bath, and walk-in closet, while three additional bedroom suites provide comfortable accommodations for family or guests. Step outside to discover multiple outdoor living spaces, including a patio ideal for al fresco dining and a spacious backyard with mature landscaping and room for a future pool. Located in one of Orlando's most sought after neighborhoods, this turnkey home offers access to top-rated schools including Audubon K-8 and Winter Park High School. This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of.

4 Beds ⋅ 4 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code

Welcome to this masterfully renovated Winter Park residence, where modern luxury meets timeless comfort in coveted Timberlane Shores. The heart of this home is a chef's dream kitchen, featuring a professional WOLF range, custom two-tone cabinetry in rich wood and sophisticated navy blue, and premium stone countertops that extend to a generous entertainment island. Gleaming terrazzo floors flow seamlessly through the open-concept living spaces, where abundant windows frame views of the lush gardens and flood the home with natural light. The thoughtfully designed floor plan incorporates two distinct living areas - one integrated with the kitchen for casual gatherings, and a separate space with soaring vaulted ceilings and custom built-ins perfect for formal entertaining or quiet evenings. The primary retreat offers a private sanctuary with vaulted ceilings, spa-like ensuite bath, and walk-in closet, while three additional bedroom suites provide comfortable accommodations for family or guests. Step outside to discover multiple outdoor living spaces, including a patio ideal for al fresco dining and a spacious backyard with mature landscaping and room for a future pool. Located in one of Orlando's most sought after neighborhoods, this turnkey home offers access to top-rated schools including Audubon K-8 and Winter Park High School. This is more than a house - it's an invitation to experience the refined Winter Park lifestyle you've been dreaming of.

1750 Winchester Drive, Winter Park

$649,000

Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida room brings in natural light and opens to the screened-in patio and pool—ready for relaxing weekends. The primary suite offers sliding glass doors to the patio, a walk-in closet, and an en-suite bathroom. Two additional bedrooms share a hall bath with an updated vanity and a shower/tub combo. Outside, the screened patio and pool create a private oasis, with a low-maintenance yard offering potential for customization. Additional features include a two-car garage, plantation shutters throughout, 2021 roof, 2018 AC, and whole-house re-plumbed in 2004. Conveniently located minutes from Park Avenue, Baldwin Park, and Winter Park's dining and shopping scene. Call today to schedule your private showing!

3 Beds ⋅ 2 Baths ⋅ Lake Virginia Shores SubDv. ⋅ 32789 Zip Code

Charming pool home zoned for Audubon K-8 and Winter Park High, tucked behind a private courtyard with artificial turf that feels like your own little secret garden. Vaulted ceilings with tongue-and-groove details add warmth and character to the living and dining areas. The eat-in kitchen features a large passthrough window overlooking the great room, perfect for entertaining. The bright Florida room brings in natural light and opens to the screened-in patio and pool—ready for relaxing weekends. The primary suite offers sliding glass doors to the patio, a walk-in closet, and an en-suite bathroom. Two additional bedrooms share a hall bath with an updated vanity and a shower/tub combo. Outside, the screened patio and pool create a private oasis, with a low-maintenance yard offering potential for customization. Additional features include a two-car garage, plantation shutters throughout, 2021 roof, 2018 AC, and whole-house re-plumbed in 2004. Conveniently located minutes from Park Avenue, Baldwin Park, and Winter Park's dining and shopping scene. Call today to schedule your private showing!

721 Glenridge Way, Winter Park

$1,265,000

Data entry only.

3 Beds ⋅ 4 Baths ⋅ Sylvan Park SubDv. ⋅ 32789 Zip Code

Data entry only.

420 Sylvan Drive, Winter Park

$4,273,211

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

4 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code

Steeped in history and masterfully reimagined, this 1926 Winter Park estate blends architectural provenance with modern refinement. Thoughtfully restored by E2 Homes, the residence honors its past while offering contemporary sophistication. Unlike many historic properties, it is free from preservation restrictions, allowing for seamless enhancements. On the shores of Lake Virginia along the desirable Winter Park Chain of Lakes, this 3,181-square-foot estate features four bedrooms, three full baths and two half baths, with three bedrooms in main house plus detached one-bedroom guest cottage. The second-floor primary suite is a private retreat with a Juliet balcony, dual closets and an elegantly appointed bath with an expansive dual-sink vanity, a separate water closet, and a washroom with a shower-tub combination. A Jack and Jill bath, adorned with Maharam wallpaper, serves the additional upstairs bedrooms. The Poliform TWELVE kitchen showcases European craftsmanship with Gaggenau and Sub-Zero appliances, sleek Italian cabinetry, and natural basalt countertops. The formal dining room, framed by arched windows and French doors, opens to a vine-covered courtyard, while the sunroom offers uninterrupted lake views. A fireplace in the living room, flanked by custom built-ins, adds warmth to the home’s contemporary aesthetic. Beyond its striking interiors, the estate is an architectural rarity, featuring original woodwork by Gene Leedy, a key figure in the Sarasota School of Architecture. The home is crowned with sought-after Ludowici-Celadon Imperial roof tiles. Poliform built-ins extend throughout, including a dedicated upstairs office/library. An integration of art and architecture, the property features site-specific installations by acclaimed artist Matt Olson. His No Separation project finds a compelling continuation here, with a sculptural installation of galvanized steel surrounding a crepe myrtle, accompanied by a matching bike rack. The entryway, designed by Olson’s firm OOIEE and inspired by Sol LeWitt, makes a striking first impression. Designed for seamless indoor-outdoor living, the estate’s exterior spaces are as refined as its interiors. A covered deck overlooks a heated saltwater pool and spa, while a custom cedar hot tub blends into the landscape. A wood-clad pergola shelters the outdoor kitchen, featuring a Röshults system with a professional-grade grill, sink and storage. The boathouse includes a partial bath, creating a waterfront sanctuary. A Sonos-integrated sound system extends from the main house to the patio, guesthouse and boathouse, ensuring a seamless sensory experience. The detached guesthouse is a private retreat with a full bedroom, bath, kitchenette and Poliform built-ins. Floor-to-ceiling windows frame manicured grounds and lake views, while a private covered porch provides a tranquil space for relaxation. Every detail has been meticulously curated, from designer lighting to motorized roller shades and a wood-burning fireplace anchoring the living room. A private wine library enhances the home’s sophisticated appeal. Meticulously maintained by E2 Concierge services, the residence undergoes routine wellness checks and meticulous upkeep. A distinctive home of this caliber is rarely available, a residence where history, architecture and art converge in harmony. This is a once-in-a-lifetime opportunity to own one of Winter Park’s architecturally and artistically significant properties.

1336 College Point, Winter Park

$1,835,000

A timeless masterpiece, this 1935 English Cottage, designed by the renowned Gamble Rogers, stands as a testament to classic elegance and enduring craftsmanship. Nestled on nearly half an acre in one of Winter Park’s most coveted neighborhoods, this home has been thoughtfully updated with modern luxuries while preserving its original charm. Inside, warm Heart of Pine floors, beadboard vaulted ceilings, restored period hardware, and custom built-ins create an inviting ambiance. Spacious formal and casual living areas include a dining room, separate living and family rooms, an office, and a versatile flex space. The expanded and renovated kitchen is a chef’s dream, now featuring marble countertops, custom white cabinetry, a Wolf gas range, stainless steel appliances, a built-in Miele espresso machine, and a farmhouse sink. The thoughtful redesign includes a custom range hood, a new ventilation system, and an integrated refrigerator/freezer drawer in the island. The first-floor primary suite is a private retreat with serene backyard views, two walk-in closets, and a bathroom with dual vanities, a clawfoot tub, and a separate shower. Upstairs, two bedrooms share a charming bathroom. Outside, a lushly landscaped backyard offers an idyllic escape with a newly installed pool heater (2023), a restored koi pond, and extensive hardscape additions. A covered porch and a newly added summer kitchen with plumbing make this home an entertainer’s paradise. The fully fenced property is surrounded by mature landscaping, refreshed with new perennials and heirloom camellias. Additional recent upgrades include a new roof (2021), restored siding, new gutters with leaf guards, and a new irrigation system. A detached guest house with a sitting area and loft provides the perfect private space for visitors. Located just minutes from Park Avenue, downtown Orlando, and zoned for the sought-after Audubon Park K-8 and Winter Park High School, this home embodies the perfect blend of historic elegance and modern convenience.

4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code

A timeless masterpiece, this 1935 English Cottage, designed by the renowned Gamble Rogers, stands as a testament to classic elegance and enduring craftsmanship. Nestled on nearly half an acre in one of Winter Park’s most coveted neighborhoods, this home has been thoughtfully updated with modern luxuries while preserving its original charm. Inside, warm Heart of Pine floors, beadboard vaulted ceilings, restored period hardware, and custom built-ins create an inviting ambiance. Spacious formal and casual living areas include a dining room, separate living and family rooms, an office, and a versatile flex space. The expanded and renovated kitchen is a chef’s dream, now featuring marble countertops, custom white cabinetry, a Wolf gas range, stainless steel appliances, a built-in Miele espresso machine, and a farmhouse sink. The thoughtful redesign includes a custom range hood, a new ventilation system, and an integrated refrigerator/freezer drawer in the island. The first-floor primary suite is a private retreat with serene backyard views, two walk-in closets, and a bathroom with dual vanities, a clawfoot tub, and a separate shower. Upstairs, two bedrooms share a charming bathroom. Outside, a lushly landscaped backyard offers an idyllic escape with a newly installed pool heater (2023), a restored koi pond, and extensive hardscape additions. A covered porch and a newly added summer kitchen with plumbing make this home an entertainer’s paradise. The fully fenced property is surrounded by mature landscaping, refreshed with new perennials and heirloom camellias. Additional recent upgrades include a new roof (2021), restored siding, new gutters with leaf guards, and a new irrigation system. A detached guest house with a sitting area and loft provides the perfect private space for visitors. Located just minutes from Park Avenue, downtown Orlando, and zoned for the sought-after Audubon Park K-8 and Winter Park High School, this home embodies the perfect blend of historic elegance and modern convenience.

160 Glenridge Way, Winter Park

$2,250,000

Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access. Featuring a private boat lift, dock, and spacious outdoor entertaining areas, this property is perfect for boating enthusiasts and nature lovers alike, including boat, canoe, kayak, ski, fish, windsurf or jet ski on this pristine lake. Come early for your appointment and drive the entire quaint neighborhood and see why this neighborhood for lakefront living is so sought after. Where else can you boat and dock at Trader Joe's, Hillstone's Restaurant, some of Winter Park's most desirable shopping and restaurant establishments? The home is located just minutes from Park Ave., I-4, Rollins College, Winter Park Village, Winter Park's Ravaudage and ALL OF Winter Park's restaurants and shopping!! Inside, you’ll find an open-concept layout with high ceilings, large windows, and modern finishes. The gourmet kitchen boasts stainless steel appliances, quartz countertops, and an extra-large island, ideal for entertaining. The home boasts 4 bedrooms, 4 full baths, 2 half baths, 3694 square feet of living space, with 2 primary suites including a spa-like bathroom and a private deck overlooking the lake view; A 3-car garage with a gym area and sauna, an outdoor kitchen and a boat dock with an electric boatlift. Don’t miss this rare opportunity to own a slice of paradise on Lake Killarney! Contact us today to schedule a private tour.

4 Beds ⋅ 6 Baths ⋅ Shores Lake Killarney Sec 02 SubDv. ⋅ 32789 Zip Code

Nestled along the serene shores of Lake Killarney, one of Winter Park's best-kept secrets Lake Killarney is one of Winter Park's largest freshwater spring-fed lakes (240 acres) this stunning lakefront home offers breathtaking views and direct water access. Featuring a private boat lift, dock, and spacious outdoor entertaining areas, this property is perfect for boating enthusiasts and nature lovers alike, including boat, canoe, kayak, ski, fish, windsurf or jet ski on this pristine lake. Come early for your appointment and drive the entire quaint neighborhood and see why this neighborhood for lakefront living is so sought after. Where else can you boat and dock at Trader Joe's, Hillstone's Restaurant, some of Winter Park's most desirable shopping and restaurant establishments? The home is located just minutes from Park Ave., I-4, Rollins College, Winter Park Village, Winter Park's Ravaudage and ALL OF Winter Park's restaurants and shopping!! Inside, you’ll find an open-concept layout with high ceilings, large windows, and modern finishes. The gourmet kitchen boasts stainless steel appliances, quartz countertops, and an extra-large island, ideal for entertaining. The home boasts 4 bedrooms, 4 full baths, 2 half baths, 3694 square feet of living space, with 2 primary suites including a spa-like bathroom and a private deck overlooking the lake view; A 3-car garage with a gym area and sauna, an outdoor kitchen and a boat dock with an electric boatlift. Don’t miss this rare opportunity to own a slice of paradise on Lake Killarney! Contact us today to schedule a private tour.

301 Rippling Lane, Winter Park

$835,000

Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High School. This home is a true gem, meticulously and completely remodeled for a coastal feel that blends modern elegance with comfort. Featuring 4 spacious bedrooms + office, the residence is designed to impress. The entry showcases a custom, German-made solid front door that opens into a bright, airy living space with engineered wood floors throughout. The raised ceilings enhance the sense of openness, complemented by beautiful wood beams that add character to the home. A shiplap-clad eat-in area creates a charming focal point, while the kitchen is equipped with premium Badger Woodworks self-closing cabinetry, gorgeous granite countertops, and new appliances including espresso bar and wine fridge. No detail has been overlooked in this home, with recent upgrades including a new HVAC system and ductwork in 2024, as well as completely updated plumbing, windows, and light fixtures. Replumbed with Pex piping in 2015. The walls have been professionally retextured, and the home also offers the convenience of an interior laundry room and brand new barn door. Outside, the covered porch provides the perfect space for entertaining, with the hot tub conveys for relaxation. The outdoor bar showcases a custom millwork bar with a grill, kegerator, and fountain, ideal for hosting gatherings. A shed on a concrete slab and a workshop area in the garage offer ample storage and workspace. The property is fully fenced, ensuring privacy and security. 625 Worthington home is located in the heart of Winter Park, home to Rollins College, one of America's top-ranked liberal arts colleges. With its prime location, luxury finishes, and family-friendly neighborhood, this home offers an exceptional living experience in one of Central Florida’s most desirable areas. With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million.

4 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code

Completely remodeled, coastal-inspired home is located in the highly sought-after Winter Park neighborhood of Kenilworth Shores in Winter Park 32789. Minutes from the world-renowned Park Avenue and upscale shopping, dining, parks, community events, Sunrail and more lifestyle. The home is zoned for some of Winter Park's most desirable schools, including Brookshire Elementary, Glenridge Middle, and Winter Park High School. This home is a true gem, meticulously and completely remodeled for a coastal feel that blends modern elegance with comfort. Featuring 4 spacious bedrooms + office, the residence is designed to impress. The entry showcases a custom, German-made solid front door that opens into a bright, airy living space with engineered wood floors throughout. The raised ceilings enhance the sense of openness, complemented by beautiful wood beams that add character to the home. A shiplap-clad eat-in area creates a charming focal point, while the kitchen is equipped with premium Badger Woodworks self-closing cabinetry, gorgeous granite countertops, and new appliances including espresso bar and wine fridge. No detail has been overlooked in this home, with recent upgrades including a new HVAC system and ductwork in 2024, as well as completely updated plumbing, windows, and light fixtures. Replumbed with Pex piping in 2015. The walls have been professionally retextured, and the home also offers the convenience of an interior laundry room and brand new barn door. Outside, the covered porch provides the perfect space for entertaining, with the hot tub conveys for relaxation. The outdoor bar showcases a custom millwork bar with a grill, kegerator, and fountain, ideal for hosting gatherings. A shed on a concrete slab and a workshop area in the garage offer ample storage and workspace. The property is fully fenced, ensuring privacy and security. 625 Worthington home is located in the heart of Winter Park, home to Rollins College, one of America's top-ranked liberal arts colleges. With its prime location, luxury finishes, and family-friendly neighborhood, this home offers an exceptional living experience in one of Central Florida’s most desirable areas. With the neighborhood rapidly evolving, many homes around this property are being torn down to make way for new, custom-built estates, including expansive 4,000 square foot homes valued at over $3 million.

625 Worthington Drive, Winter Park

$2,495,000

Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom, cozy living room with a fireplace, and a large welcoming family room. The gourmet kitchen features custom wood cabinets, quartzite counters, a convenient office nook and an adjoining breakfast room, while the formal dining room boasts elegant moldings and built-in corner cabinets. A secret basement presents options for additional storage or a wine cellar. The second floor features a generously- sized master suite, two additional bedrooms, two updated baths, and a versatile nursery or bonus room, perfect for a study or home office. The property includes a detached two-car garage and a charming guest house with a bedroom, bath, and loft area. Newly renovated resort back yard includes heated salt water pool and spa, multiple seating areas, complete with gas hookups for fire pit and outdoor kitchen and a maintenance-free travertine and turf pool scape. You’ll love the inviting ambiance of both this home and its vibrant Winter Park location.

5 Beds ⋅ 4 Baths ⋅ Cortland Park SubDv. ⋅ 32789 Zip Code

Welcome to this beautifully renovated century home on one of the most picturesque brick streets in Olde Winter Park. Take a leisurely stroll down to Lake Mizell or enjoy the views from its large front patio. This classic pool home is filled with charm, natural light and is designed for easy entertaining. The spacious layout offers multiple rooms for every occasion, including a bright sunroom, cozy living room with a fireplace, and a large welcoming family room. The gourmet kitchen features custom wood cabinets, quartzite counters, a convenient office nook and an adjoining breakfast room, while the formal dining room boasts elegant moldings and built-in corner cabinets. A secret basement presents options for additional storage or a wine cellar. The second floor features a generously- sized master suite, two additional bedrooms, two updated baths, and a versatile nursery or bonus room, perfect for a study or home office. The property includes a detached two-car garage and a charming guest house with a bedroom, bath, and loft area. Newly renovated resort back yard includes heated salt water pool and spa, multiple seating areas, complete with gas hookups for fire pit and outdoor kitchen and a maintenance-free travertine and turf pool scape. You’ll love the inviting ambiance of both this home and its vibrant Winter Park location.

140 Cortland Avenue, Winter Park

$4,950,000

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

5 Beds ⋅ 7 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code

New Hamptons-style residence offering a seamless blend of elegance and modern sophistication. A gated entrance opening to a circular driveway and motor court, set the stage for enjoying this exceptional estate. As you enter home, an impressive 2-story foyer with a glass-paneled staircase wraps around a temperature-controlled wine room and a transparent glass elevator, effortlessly connecting all levels including an expansive third-floor multi-purpose space. Designed for contemporary living, the thoughtfully curated floor plan features a spacious open concept kitchen/gathering room along with the dining area enjoy a wall of glass doors and picture window overlooking an expansive lanai, and serene backyard with a sparkling pool and spa. The main residence offers 4 bedrooms, private home office, and multiple flex spaces, complemented by a detached pool cabana that serves as a 5th guest retreat or versatile use building. The gourmet kitchen is an entertainer’s dream, featuring dual 10-foot stone islands, a 60-inch Wolf range, dual 36-inch Sub-Zero refrigerator and freezer columns, a warming drawer, beverage center and a 146-bottle Sub-Zero dual-zone wine cooler. A separate pantry kitchen is equipped with a Dacor induction cooktop, convection oven, additional refrigerator, microwave, dishwasher and ample cabinetry, ideal for catering and meal preparation. The 1st-level primary suite is a tranquil retreat, offering a sitting area, an all-marble bath with a glass-enclosed shower, multiple body sprays, a soaking tub, and French doors leading to a secluded Zen garden with an outdoor shower and fountain. There is also a hidden private home office near the front of home. The second level hosts 3 additional en-suite bedrooms, a generous lounge area, bar, and a well-appointed laundry room with extra storage cabinetry. As noted previously, there is also a unique 3rd level accessible by a staircase or elevator. The outdoor living is elevated with a spacious lanai featuring motorized screens, a gas fireplace, dining space, and a summer kitchen with a 54-inch Coyote wood and gas grill, plus a separate burner beneath a remote-controlled louvered roof. There is also a detached cabana perfectly suited for a guest suite, fitness studio, additional office or game room, complete with a full bath, mini kitchen, and washer/dryer. Crafted with meticulous attention to detail, this home showcases Anderson windows, 10-foot solid doors, high-end lighting, plumbing and electrical fixtures, custom cabinetry built-ins, as well as Trane HVAC systems, ensuring quality and comfort... Lush landscaping, including magnolia trees, bamboo and cypress, surrounds the property, creating a private sanctuary. An attached side-entry garage features a powered car lift providing space for up to three vehicles. Ideally near Interlachen Country Club, Winter Park Racquet Club, Phelps Park/YMCA, and renowned Park Avenue. Note: Partial staging by RH and the furniture package can be purchased separately...

1660 Palmer Avenue, Winter Park

$480,000

NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter Park Welcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations. Prime Location: 5 minutes to Whole Foods and Trader Joe’s 8 minutes to Downtown Orlando via I-4 (Exits 87 & 88) Surrounded by Winter Park’s historic charm Private library with an excellent book collection Weekly Farmers’ Market just minutes away Extensively Renovated in 2019: New Roof, New Windows, New A/C New Electrical Wiring & Plumbing New Driveway & Fully Fenced Yard with Entry Gate New Porch & Open-Concept Kitchen Versatile Living Space: This single-family home offers flexible living arrangements and can also function as a duplex: Downstairs: 1 bed, 1 bath, spacious living room with modern kitchen combo Upstairs: 2 beds, 2 baths, large family room, and a covered porch with scenic views Outdoor space on the porch for entertaining All permits are available on the Orange County Property Permit website for complete peace of mind. Don't miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location! Contact us today for a private showing.

3 Beds ⋅ 3 Baths ⋅ Killarney Circle SubDv. ⋅ 32789 Zip Code

NO HOA! Beautifully Remodeled Home with Expansive Garden in Winter Park Welcome to this charming and fully remodeled two-story, 3-bedroom, 3-bathroom home nestled in the heart of Winter Park. Offering a blend of modern upgrades and historic charm, this property is surrounded by a vibrant community with easy access to top destinations. Prime Location: 5 minutes to Whole Foods and Trader Joe’s 8 minutes to Downtown Orlando via I-4 (Exits 87 & 88) Surrounded by Winter Park’s historic charm Private library with an excellent book collection Weekly Farmers’ Market just minutes away Extensively Renovated in 2019: New Roof, New Windows, New A/C New Electrical Wiring & Plumbing New Driveway & Fully Fenced Yard with Entry Gate New Porch & Open-Concept Kitchen Versatile Living Space: This single-family home offers flexible living arrangements and can also function as a duplex: Downstairs: 1 bed, 1 bath, spacious living room with modern kitchen combo Upstairs: 2 beds, 2 baths, large family room, and a covered porch with scenic views Outdoor space on the porch for entertaining All permits are available on the Orange County Property Permit website for complete peace of mind. Don't miss this rare opportunity to own a beautifully updated home with endless potential in a highly desirable location! Contact us today for a private showing.

423 Ololu Drive, Winter Park

$1,516,500

A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course. Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space. High ceilings, elegant crown molding, and a seamless mix of tile and gleaming hardwood floors in every bedroom create a sense of lightness and luxury. The expansive family room extends off the back of the home, opening effortlessly to a screened-in patio, perfect for enjoying the Florida lifestyle year-round. With an ideal blend of charm, location, and livability, this home is a true treasure in the heart of Winter Park. Enter through the foyer and prepare for seamless indoor/outdoor entertaining, with an inviting living room and dining room, elegantly separated by a gorgeous double-sided gas fireplace, and lined with sliding glass doors that lead to the open, paver patio. The kitchen is complete with stainless steel appliances, a natural-gas cooktop, timeless cabinetry that offers an abundance of storage, and a built-in breakfast bar. You’ll love the ideal split-bedroom floor plan, featuring an oversized primary suite that overlooks the expansive side patio accessible through sliding glass doors. Off the front living room hallway are 2 secondary bedrooms with walk-in closets, and a full bathroom. Wrapped in low-maintenance landscaping with elegant uplighting, all surrounded by concrete privacy walls with gates, this turnkey home is perfect for an active lifestyle. A private alley drive for Beloit homeowners leads to a spacious 2-car garage with built-in cabinets and attic storage. Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park!!

3 Beds ⋅ 2 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code

A special opportunity awaits on one of Winter Park’s most sought-after streets, BELOIT AVENUE! This charming 3-bedroom, 2-bathroom home is perfectly positioned just two blocks from the vibrant energy of Park Avenue and steps from the lush greens of the Winter Park 9 Golf Course. Brimming with character and warmth, this jewel box offers over 2,400 square feet of beautifully designed living space. High ceilings, elegant crown molding, and a seamless mix of tile and gleaming hardwood floors in every bedroom create a sense of lightness and luxury. The expansive family room extends off the back of the home, opening effortlessly to a screened-in patio, perfect for enjoying the Florida lifestyle year-round. With an ideal blend of charm, location, and livability, this home is a true treasure in the heart of Winter Park. Enter through the foyer and prepare for seamless indoor/outdoor entertaining, with an inviting living room and dining room, elegantly separated by a gorgeous double-sided gas fireplace, and lined with sliding glass doors that lead to the open, paver patio. The kitchen is complete with stainless steel appliances, a natural-gas cooktop, timeless cabinetry that offers an abundance of storage, and a built-in breakfast bar. You’ll love the ideal split-bedroom floor plan, featuring an oversized primary suite that overlooks the expansive side patio accessible through sliding glass doors. Off the front living room hallway are 2 secondary bedrooms with walk-in closets, and a full bathroom. Wrapped in low-maintenance landscaping with elegant uplighting, all surrounded by concrete privacy walls with gates, this turnkey home is perfect for an active lifestyle. A private alley drive for Beloit homeowners leads to a spacious 2-car garage with built-in cabinets and attic storage. Enjoy a NEW A/C unit (2024), new washer/dryer (2024), and one of the best locations in the City of Winter Park!!

335 Beloit Avenue, Winter Park

$430,000

Discover a true slice of paradise just minutes from downtown Orlando, nestled along the serene shores of Lake Fair. This meticulously maintained 3-bedroom, 2-bathroom home, built in 1958, reflects an era when craftsmanship and attention to detail were paramount. The moment you step through the front door, you’ll be captivated by the original pine floors, gleaming with character and charm. Straight ahead, a massive living room invites you to unwind, complete with a Yamaha surround sound system—perfect for movie nights or entertaining. To your left, the spacious dining room and kitchen boast a 9-foot solid surface island with a farmhouse sink, 42" quiet-close cabinets, and a real tile backsplash (no peel-and-stick here!). The bathrooms have been beautifully renovated, offering a touch of modern luxury while maintaining the home's timeless appeal. The primary suite is a true retreat, featuring plantation shutters that add elegance and privacy. Step outside to a lush, tropical oasis where palms and landscaping create an ultra-private setting—ideal for cozy evenings around a firepit or swaying in a hammock with a gentle lake breeze. A 20x10 screened porch overlooks the lake, providing a perfect spot for morning coffee or unwinding at sunset. Adjacent to the kitchen, the laundry room is conveniently located just outside the side door. The enormous 2-car carport offers ample coverage for your vehicles, keeping them protected from the elements after a trip to the store. And for fishing enthusiasts? The seller has reeled in 5 lb. bass right from the backyard! Beyond this stunning home, the location is unbeatable. You're just minutes from the vibrant dining and shopping scene of Winter Park, home to award-winning restaurants, charming boutiques, and cultural hotspots like the Winter Park Farmers’ Market and Park Avenue. Downtown Orlando is a short drive away, offering easy access to the city's best entertainment, including Lake Eola Park, where you can enjoy fireworks, swan boat rides, concerts, and year-round festivals like the Orlando Film Festival and the Spring Fiesta in the Park. For nature lovers, this home is just minutes from Leu Gardens, a breathtaking 50-acre botanical garden featuring stunning tropical plants, butterfly gardens, and scenic walking trails. It also hosts outdoor movie nights, educational workshops, and seasonal events like the Dazzling Nights light festival. Also nearby is Mead Botanical Garden, a 47-acre nature preserve in Winter Park, offering hiking trails, butterfly gardens, a boardwalk, and even a community garden. It’s the perfect place for birdwatching, photography, or a peaceful escape into nature. Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today!

3 Beds ⋅ 2 Baths ⋅ Fairbanks Shores Sixth Add SubDv. ⋅ 32789 Zip Code

Discover a true slice of paradise just minutes from downtown Orlando, nestled along the serene shores of Lake Fair. This meticulously maintained 3-bedroom, 2-bathroom home, built in 1958, reflects an era when craftsmanship and attention to detail were paramount. The moment you step through the front door, you’ll be captivated by the original pine floors, gleaming with character and charm. Straight ahead, a massive living room invites you to unwind, complete with a Yamaha surround sound system—perfect for movie nights or entertaining. To your left, the spacious dining room and kitchen boast a 9-foot solid surface island with a farmhouse sink, 42" quiet-close cabinets, and a real tile backsplash (no peel-and-stick here!). The bathrooms have been beautifully renovated, offering a touch of modern luxury while maintaining the home's timeless appeal. The primary suite is a true retreat, featuring plantation shutters that add elegance and privacy. Step outside to a lush, tropical oasis where palms and landscaping create an ultra-private setting—ideal for cozy evenings around a firepit or swaying in a hammock with a gentle lake breeze. A 20x10 screened porch overlooks the lake, providing a perfect spot for morning coffee or unwinding at sunset. Adjacent to the kitchen, the laundry room is conveniently located just outside the side door. The enormous 2-car carport offers ample coverage for your vehicles, keeping them protected from the elements after a trip to the store. And for fishing enthusiasts? The seller has reeled in 5 lb. bass right from the backyard! Beyond this stunning home, the location is unbeatable. You're just minutes from the vibrant dining and shopping scene of Winter Park, home to award-winning restaurants, charming boutiques, and cultural hotspots like the Winter Park Farmers’ Market and Park Avenue. Downtown Orlando is a short drive away, offering easy access to the city's best entertainment, including Lake Eola Park, where you can enjoy fireworks, swan boat rides, concerts, and year-round festivals like the Orlando Film Festival and the Spring Fiesta in the Park. For nature lovers, this home is just minutes from Leu Gardens, a breathtaking 50-acre botanical garden featuring stunning tropical plants, butterfly gardens, and scenic walking trails. It also hosts outdoor movie nights, educational workshops, and seasonal events like the Dazzling Nights light festival. Also nearby is Mead Botanical Garden, a 47-acre nature preserve in Winter Park, offering hiking trails, butterfly gardens, a boardwalk, and even a community garden. It’s the perfect place for birdwatching, photography, or a peaceful escape into nature. Don’t miss the chance to own this lakefront gem—a perfect blend of historic charm, modern upgrades, and an unbeatable location. Schedule your private tour today!

328 Lake Fair Lane, Winter Park

$380,000

Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning Fire place, Bar sink, Ceiling Fans, Both bedrooms have large walk-in closets and the primary has a walk out balcony patio. The Primary bath offers double shower heads & double vanity. Outside Storage closet & Enclosed screen patio. The pool is set with majestic sunset views of the lake where you can fish off the dock or kayak the lake. HOA updates include repaved asphalt parking & exterior paint, dock repainted & pool sealant in 2020. Fees include exterior maintenance, pool, dock & trash.

2 Beds ⋅ 3 Baths ⋅ Killarney Bay Condo SubDv. ⋅ 32789 Zip Code

Winter Park location with access to Lake Killarney & walking distance to Trader Joes & Winter Park Village. Renovated 2 bedroom 2.5 bath 2 story condo with Pool & lake view amenities. Gorgeous wood floors throughout, Granite counters, Stainless Steele appliances , Soft close cabinets & glass tile backsplash. Inside Laundry room with Washer/Dryer included. Under stair storage. Wood burning Fire place, Bar sink, Ceiling Fans, Both bedrooms have large walk-in closets and the primary has a walk out balcony patio. The Primary bath offers double shower heads & double vanity. Outside Storage closet & Enclosed screen patio. The pool is set with majestic sunset views of the lake where you can fish off the dock or kayak the lake. HOA updates include repaved asphalt parking & exterior paint, dock repainted & pool sealant in 2020. Fees include exterior maintenance, pool, dock & trash.

350 Killarney Bay Court Unit 5, Winter Park

$987,500

Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, you’ll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta-styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chef’s dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open-concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort-style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree-lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, you’re less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world-class dining and shopping. Top-rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character-filled home offers a perfect blend of privacy, luxury, and location. Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood!

4 Beds ⋅ 3 Baths ⋅ Lake Knowles Terrace SubDv. ⋅ 32789 Zip Code

Charming Spanish-Style Bungalow with Private Oasis in the Heart of Winter Park. Step into the elegance of Old Florida with this exquisite Spanish-style bungalow, nestled in Winter Park. Offering the perfect blend of historic charm and modern luxury, this 4-bedroom, 2.5-bath retreat is a hidden gem surrounded by lush, mature landscaping, creating a private sanctuary just minutes from the best Winter Park has to offer. From the moment you arrive, you’ll be captivated by the stunning curb appeal, featured on the front cover of Home & Garden magazine. The beautifully maintained exterior, with its 2023 terracotta-styled flat roof sets the stage for what lies within. Inside, timeless character meets contemporary upgrades. French terracotta flooring, antique hardware, and neutral warm tones create an inviting atmosphere, while thoughtful renovations ensure every modern convenience is at your fingertips. The kitchen is a chef’s dream, boasting vanilla quartz countertops with gold flecks, beautifully complementing the bronze accents and upgraded appliances. The open-concept design seamlessly connects the kitchen, dining, and living area ideal for entertaining. For more intimate gatherings, unwind in the spacious family room or soak in the natural light from the attached sunroom, which overlooks the lush backyard retreat. Step outside to a tranquil space perfect for morning coffee or evening cocktails, all while enjoying the peaceful sounds of nature. The pool and jacuzzi (new heater installed in 2021) add a touch of resort-style living, surrounded by meticulously curated landscaping with extensive landscape lighting (2022) that enhances the homes enchanting ambiance. Situated in a vibrant, walkable neighborhood known for its tree-lined streets and friendly atmosphere, this home is just a short stroll to Lake Knowles, the YMCA, and Phelps Park. Bring your golf cart and enjoy easy access to Interlachen Golf & Country Club or the Winter Park Racquet Club. Plus, you’re less than a mile from the newly renovated Winter Park Hospital and just minutes from Park Ave world-class dining and shopping. Top-rated schools: Zoned for Lakemont Elementary, Maitland Middle, and Winter Park High School. This rare, character-filled home offers a perfect blend of privacy, luxury, and location. Don’t miss your chance to own a piece of Winter Parks most desirable neighborhood!

1585 Chestnut Avenue, Winter Park

$1,877,500

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

5 Beds ⋅ 6 Baths ⋅ Orwin Manor Westminster Sec SubDv. ⋅ 32789 Zip Code

Nestled in the highly sought-after Orwin Manor neighborhood of Winter Park, this stunning Spanish Revival home at 1446 Berkshire Ave, offers a luxurious lifestyle with unparalleled proximity to Winter Park’s finest amenities including Historic Park Avenue and Rollins College. Located on a tree-lined street, this residence exudes timeless elegance, complemented by a circular driveway that leads you to its impressive facade. The home has been thoughtfully updated with fresh interior and exterior paint, along with the addition of three new HVAC systems, ensuring modern comfort throughout. Boasting over 4,000 square feet of living space, the home features five generously sized bedrooms, including a second-floor Primary Suite that offers both luxury and privacy. The suite is complete with a private sitting area, a terrace overlooking the lushly landscaped grounds, and a spa-like bath with dual sinks, jetted tub, and a walk-in shower. A spacious walk-in closet provides ample storage space and custom built-ins. In addition to the three bedrooms, the second-floor features a spearate bonus room that is perfect for a private office, or could be converted to an in-law/guest suite, adding versatile living space to the property. The chef’s kitchen is a culinary dream, featuring solid wood 42” cabinetry, elegant granite countertops and a new subway tile backsplash. Adding to the Kitchen's functionality and sophistication are Copper prep and main sinks, Wolf Natural Gas Range, dual dishwashers, under counter ice maker and a walk-in pantry, A separate casual dining space and an island/breakfast bar seamlessly open into the family room, creating an ideal setting for everyday living and entertaining. Off the Kitchen and family room is a full guest bathroom with built in desk area and a multifunctional game room that could convert to a 6th bedroom. Outside, the private oasis is designed for both relaxation and entertainment. A resort-style pool with tranquil fountains serves as the centerpiece, while a beautifully crafted Spanish styled privacy wall, accented with lighting and peaceful bamboo, offers a serene atmosphere. Enjoy the cooler evening relaxing around the piped natural gas fire pit. Enjoy the expansive Cabana area includes a summer kitchen, as well as dedicated seating and dining areas, all overlooking the pool and lush landscaping. With its prime Winter Park location, exceptional privacy, and resort-style amenities, this remarkable home offers the perfect blend of style, comfort, and convenience in one of Winter Park’s most desirable neighborhoods.

1446 Berkshire Avenue, Winter Park