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$5,999,000
6 Beds ⋅ 8 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code
Welcome to the epitome of refined luxury. Nestled in the heart of "The Vias" in Winter Park, this exceptional estate is the ultimate blend of timeless sophistication with contemporary comfort. Boasting 7,535 square feet of living space on a sprawling half-acre lot, this residence was built with impeccable craftsmanship and an array of upscale amenities, including a charming guest house and a distinctive natural slate roof complemented by timeless copper gutters. Designed with meticulous attention to detail, this distinguished home boasts 6 bedrooms and 8 bathrooms. The main level hosts an inviting primary suite with dual oversized walk-in closets, along with a chef's kitchen meticulously appointed to accommodate a dinner party of any size. Featuring dual Wolf ovens, dual Miele dishwashers, a Sub-Zero refrigerator and wine fridge, custom Busby cabinets, and rare Italian Calacatta Gold marble countertops, this kitchen is a culinary haven. Adjacent, the living room showcases exquisite Pecky Cypress beams and one of three wood-burning fireplaces placed throughout the residence. Floor-to-ceiling accordion glass doors in the great room seamlessly blend indoor and outdoor spaces, leading to the picturesque Hampton's style pool and a fully equipped summer kitchen, ideal for both entertaining and enjoying the meticulously landscaped grounds. The spacious second floor reveals four generously proportioned bedrooms and three bathrooms, each complete with spacious custom walk-in closets. Additionally, the upper level features a convenient second laundry room, private home gym, and a sizable flex space adaptable to various lifestyle needs. Above one of the two-car garages, a detached mother-in-law suite awaits, comprising a full bedroom, a bathroom, and a separate living room, offering unparalleled comfort and privacy. Come experience the laid-back elegance and vibrant energy 1460 Via Tuscany has to offer.

1460 Via Tuscany, Winter Park
$445,000
2 Beds ⋅ 1 Baths ⋅ Carver Town SubDv. ⋅ 32789 Zip Code
Discover the charm of easy downtown living in this thoughtfully remodeled two-bedroom home located in the vibrant heart of Winter Park. This delightful residence features an expansive study, which can easily be transformed into a third bedroom, offering flexibility to suit your needs. In 2019, this home underwent a comprehensive renovation, which included updates to the flooring, fresh paint throughout, and the installation of modern, energy-efficient windows. The HVAC system and insulation were completely replaced, ensuring comfort year-round. The heart of the home, the kitchen, was fully remodeled with contemporary fixtures and fittings, alongside a redesigned bath and a convenient interior washer/dryer setup. Step outside into the fenced backyard, where fresh landscaping creates a serene environment perfect for relaxation or hosting gatherings under the Florida sun. The property's prime location places you just a short stroll from the boutique shops of Park Avenue, the cultural charm of Hannibal Square, the trendy spots in Winter Park Village, and the esteemed Rollins College. Ideal for those who value the blend of modern updates and prime location, this home offers an excellent opportunity to enjoy the best of downtown Winter Park living without the luxury price tag.

678 W Webster Avenue, Winter Park
$290,000
2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code
Step into comfort and convenience with this delightful upstairs residence in the highly sought-after Village Condominiums. Positioned perfectly in a neighborly setting, this gem is only a short, pleasant walk from Park Avenue and the lively Winter Park Village, ensuring you're never far from boutique shopping, dining, and entertainment. Unit G offers a tranquil, inviting atmosphere with its exclusive upper-level location and limited sharing of space, promoting a private and serene living environment. You'll appreciate the ease of access to major routes such as I-4 and 17/92, which make commuting straightforward and stress-free. Inside, each room is bathed in natural light through charming plantation shutters. Warm laminate flooring and elegant crown molding enhance the welcoming ambiance. Everyday conveniences are covered with an in-unit washer and dryer and a kitchen equipped with stainless steel appliances, granite countertops, and a practical breakfast bar. A closet pantry keeps essentials organized and within easy reach. The two bedrooms are crafted with individual character, the main bedroom features a spacious walk-in closet, while the second bedroom offers direct access to the communal patios—a collection of cozy spots perfect for socializing, enjoying the outdoors, or unwinding in the quaint courtyard seating areas. Living in Village Condominiums means embracing an effortless lifestyle where everything you need is just a stroll away. Whether it's exploring Hannibal Square, picking up groceries at Whole Foods, playing a round at Winter Park Golf Course, or enjoying a leisurely day of shopping and dining, this location truly has it all. Discover your urban sanctuary at Village Condominiums, where comfort meets convenience in a friendly community setting. Welcome to your new home, where every day feels like a walk in the park.

500 N Pennsylvania Avenue Unit G, Winter Park
$1,200,000
4 Beds ⋅ 3 Baths ⋅ Temple Estates SubDv. ⋅ 32789 Zip Code
Welcome to this rare, single-story residence nestled in the heart of Winter Park! This remarkable 4-bedroom, 3-bathroom home sits on a spacious CORNER lot, boasting a highly sought-after 3-car garage. Upon entry through the foyer, you'll be delighted by the timeless layout, featuring elegant formal living and dining areas. Sunlight pours through the expansive bay windows, casting a warm and welcoming glow throughout. The kitchen is appointed with wood cabinets, a convenient pantry, and counter-height bar seating. Adjacent to the kitchen, a delightful dinette area overlooks the expansive living room, adorned with custom built-ins. Accessible through sliding doors, a fully covered rear porch offers an ideal spot for gatherings and everyday relaxation. The primary suite features vaulted ceilings and an ensuite bathroom, complete with a luxurious soaking tub, dual sinks, a large walk-in shower, and a generously sized cedar-planked walk-in closet. The intelligently designed split floor plan situates two additional guest rooms with ample closet space, sharing a well-appointed full bathroom. Meanwhile, a fourth guest room boasts an ensuite bathroom and direct access to the rear porch. Enjoy the convenience of a BRAND NEW ROOF (2024) ensuring peace of mind and protection for years to come. The home's exterior has also received a complete repaint (2024), with the addition of new exterior lighting. Conveniently located just minutes away from Winter Park's upscale retail and dining options, don’t miss your opportunity to make this home yours today!

1503 Palmer Avenue, Winter Park
$4,100,000
5 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code
Amazing opportunity to own a lakefront home on Lake Virginia footsteps from Rollins College, nestled in walking distance to downtown Park Avenue shops and restaurants, and located on the coveted Chain-of-Lakes! A magnificent five-bedroom, four-and-a-half-bath home offers breathtaking lake views, capturing the essence of Florida living at its finest. This sprawling 5,600-plus square foot residence sits on an expansive .84-acre lot with a huge backyard, gracing a charming brick street, and includes an additional parcel across the street, featuring a covered boat dock/lift, ensuring endless days of waterfront lifestyle enjoyment. Step inside to discover an impressive layout designed for both grand entertaining and comfortable living. Generously sized rooms include formal living and dining areas, a cozy den/library, and a sprawling 18-by-27-foot family room seamlessly connected to the centrally located kitchen. Enjoy the sun-filled 40-by-16-foot Florida room, featuring two sets of sliding glass doors that open to the pool and lush backyard. The second floor features the primary suite with beautiful lake views, a spacious ensuite bath and two large walk-in closets. Three additional bedrooms grace this level, one with a private bath and two sharing a Jack and Jill bath, providing ample space for family and guests. A convenient fifth-bedroom suite on the first floor offers versatility, ideal for guests, a nanny, or an in-law retreat. Step outside to your private paradise, complete with a putting green, gazebo, expansive lawn, and a tropical pool perfect for refreshing dips on warm summer days. With a spacious driveway and a three-car attached garage, there's plenty of room for parking and storage. Location is key, and this home delivers. Again, enjoy the convenience of being steps away from Rollins College and within walking distance to the charming boutiques and eateries of Park Avenue. Don't miss your chance to own this exceptional lakefront estate property, where every day feels like a vacation. Schedule your private tour today!

1135 Lakeview Drive, Winter Park
$2,150,000
4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Welcome to 1651 Oakhurst Avenue, a stunningly renovated Key West style home on a charming bricked street. This meticulously maintained property offers a spacious and open floor plan, perfect for modern living. With 4 bedrooms and 3.5 bathrooms, this home provides ample space for comfortable family living. The downstairs primary bedroom offers convenience and privacy. The updated baths add a touch of luxury to this already impressive home. Situated on an oversized lot measuring 100 x 157, this property boasts a huge pool, ideal for outdoor entertaining and relaxation. The expansive backyard provides plenty of space for outdoor activities and gatherings. The new kitchen is a chef's dream, featuring top-of-the-line appliances and stylish finishes. The open layout seamlessly connects the kitchen to the living and dining areas, creating a perfect space for entertaining guests. Spanning approximately 3,059 square feet, this home offers generous living spaces and abundant natural light throughout. The tasteful renovations and meticulous attention to detail make this property truly stand out. Located in Winter Park, this home is surrounded by a vibrant community and offers easy access to a variety of amenities, including shopping, dining, and entertainment options. The area is known for its excellent schools and proximity to beautiful parks and lakes. Don't miss the opportunity to own this exceptional property. Contact us today to schedule a private viewing and make this your dream home.

1651 Oakhurst Avenue, Winter Park
$1,325,000
4 Beds ⋅ 3 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Luxurious custom pool home in highly desired Winter Park on a beautiful brick street with mature trees! From the moment you walk into the grand entry, you will see that every detail was impeccably thought through from the custom carpentry, including extensive crown molding, to the 10’ ceilings to the ¼” hardwood oak flooring to the built-in living room and office bookshelves and cabinets to the spacious kitchen to multiple storage closets to the electronic lift for storing items in the attic in the garage. This four-bedroom, three-bathroom home has it all. The kitchen is equipped with stainless steel appliances, soft close Busby cabinets, gas cook top, double convection ovens, warming drawer, a custom-built Busby pantry, and a large island for food preparation and/or entertaining. Whether it is casual dining in the breakfast nook with pool views through the bay windows surrounded by beautiful wainscoting and bench seating with storage or entertaining in your formal dining room with an elegant tray ceiling, you, your family, and guests will feel at home. The Butler’s Pantry, located between the kitchen and formal dining room, is equipped with a wine fridge and is the perfect place to stage food when entertaining or for use as a bar or coffee station. The first-floor bedroom can be used as a bedroom, library or office. It is equipped with a walk-in closet and has an ensuite bathroom with a curbless walk-in shower. A beautiful hardwood staircase leads you to the second floor where you will find the remaining bedrooms and laundry room, which includes a laundry tub, built-in storage, built-in ironing board and attic storage with plywood decking. The front of the home has a beautiful porch with ceiling fans for relaxing and waving to the neighbors, while the back porch, also with ceiling fans, offers privacy and a summer kitchen with a beverage cooler and a DCS multipurpose grill that includes rotisserie and smoker options. The pool will invite you in on hot summer days and the hot tub will take all your worries away. The Plantation Shutters throughout the home let the natural light in or provide privacy. The grill, stove and fireplace are fueled by propane. The fireplace can be wood burning as well. There is a vinyl gate that can be closed across the driveway for additional privacy. The detached garage is oversized and will store two cars. There is lots of attic storage with plywood decking and is accessed by wood stairs and the electronic lift for ease of putting items in the attic! Pool/spa heater (2024). Water Heater (2020). Roof (2020). Two HVACs (2016 and 2019). Your stunning new Winter Park home is conveniently located between Park Avenue and Baldwin Park offering a wide array of restaurants and shopping options. This home is covered by a 2-10 Home Buyers Warranty during the listing period only. Buyer has opportunity to continue coverage at closing. Please ask your real estate agent for more details. See links for WALKTHROUGH VIDEO and MATTERPORT TOUR.

1741 Laurel Road, Winter Park
$1,099,000
3 Beds ⋅ 2 Baths ⋅ Timberlane Shores SubDv. ⋅ 32789 Zip Code
Don't miss this charming and updated home, situated on an expansive 12,000-square-foot corner lot, in the highly sought-after Timberlane Shores neighborhood! Boasting an inviting open floor plan and starting with the living space offering stunning engineered wood floors, crown molding and a big window bay, that invites natural light to illuminate the space. The refreshed kitchen complete with a built-in breakfast nook, an abundance of white cabinetry with granite counters and stainless appliances, seamlessly flows into the family room, featuring an electric fireplace and cozy window seating with wonderful views of the spacious lanai entertainment space and the screened-in saltwater pool. The owner's retreat is a haven of tranquility with a lovely renewed en-suite bath and direct access to the pool, while the generously sized secondary bedrooms boast walk-in closets. A perfect laundry room offers plenty of additional storage & built in ironing center. Complementing the rest of the features of this special home is the convenience of the oversized two-car garage with workshop/hobby area. The curb appeal and exterior are enviable displaying a lush landscape with enchanting flowering gardens, recently re-sodded backyard & charming playhouse. Recent improvements include a new 2023 roof, new HVAC 2022, along with replaced windows, interior doors, and baseboards. The added bonus is the superior Winter Park Schools! With all these fabulous highlights combined, this home promises an exceptional living experience!

1880 Shiloh Lane, Winter Park
$1,629,000
5 Beds ⋅ 5 Baths ⋅ Green Oaks Rep 02 SubDv. ⋅ 32789 Zip Code
Welcome to 1801 Legion Drive, a stunning Southern traditional with a huge front porch and white picket fence in one of the best neighborhoods in Winter Park. The main house has 4 bedrooms and 3.5 baths and a separate office. There is an additional bedroom and full bath in the detached guest quarters. A large gourmet kitchen with white cabinetry, a stainless steel Thermador gas range and GE Monogram built-in refrigerator and microwave. The adjacent family room that opens to the kitchen has custom-built in shelving surrounding the brick fireplace and is the perfect place for family night movies. French doors lead to the large covered porch with another brick fireplace and an open patio for dining al fresco and also leads to the detached guest quarters which makes a perfect place for a home gym. Take a cool dip in the saltwater pool that was installed in 2018 or after a long day jump in the hot tub! The living room is located off the porch as well with French doors and features a wet bar and yet another brick fireplace (3). The master bedroom has French doors and two custom built-shelved closets, one is a large walk-in. A central laundry room is conveniently located between the split bedroom plan. There is a secondary master with en-suite and two more bedrooms and a shared bath. Roof 2019. Conveniently located between Maitland and Winter Park, enjoy easy access to top-rated schools, upscale shopping, dining destinations, and recreational amenities. Embrace the quintessential Florida lifestyle in this prestigious community. Don't miss your opportunity to own this exceptional residence in Winter Park. Schedule your private tour today and discover the luxury and sophistication of 1801 Legion Dr.

1801 Legion Drive, Winter Park
$1,700,000
5 Beds ⋅ 4 Baths ⋅ Temple Heights SubDv. ⋅ 32789 Zip Code
Nestled on one of Winter Park's coveted and charming brick streets, this meticulously crafted 5-bedroom residence embodies traditional elegance with modern amenities, offering a NEWER ROOF (2022) and other recent updates for a fresh feel. Its exterior, a testament to Florida living, boasts a sprawling saltwater pool with a sun shelf, surrounded by 900 SF of Chicago brick, and complemented by lush landscaping and enchanting lighting for evenings of magic, while custom-irrigated garden boxes for cultivating fresh herbs and vegetables await those with green thumbs. Inside, natural hardwood floors grace the entire home, accented by updated fixtures. The family room and living areas include built-ins, one gas fireplace, and 4 glass doors that lead to the backyard. An open kitchen awaits, complete with a breakfast bar, walk-in pantry, and bright, sunlit dinette framed by plantation shutters. The front room off the foyer makes a great office or dining room, with access to the kitchen. The large DOWNSTAIRS Main suite treats residents to a renovated, spa-like bathroom, adorned with a large zero-entry shower and separate soaking tub. A massive walk-in closet (Closets by Design), equipped with a dedicated washer & dryer, provides organization and convenience. You will sleep sound with the electronic blackout shades behind the plantation shutters. Upstairs features 4 additional bedrooms with hardwood floors, along with 2 full baths and a second laundry room, affirming practicality and comfort for every member of the household. This is an enchanting traditional home has so much to offer on this brick street. This ideal location is just a few blocks from the WP YMCA, grocery stores, restaurants and shopping off Aloma, and a mile or so from Park Ave!

1333 Mayfield Avenue, Winter Park
$1,800,000
4 Beds ⋅ 4 Baths ⋅ Osceola Shores Sec 01 SubDv. ⋅ 32789 Zip Code
Welcome to 160 Trismen Terrace. This brilliant home has much to offer. Spotlighting an inviting formal living room, formal dining room with built in cabinetry and side board, a luminous family room with french doors to the pool deck, expansive kitchen with stainless steel appliances, prep sink, numerous cabinets, and vaulted ceilings complete with breakfast area. The generous primary en-suite bedroom features his and hers custom closets, newly remodeled primary contemporary bath with a stand alone tub, walk-in shower, dual vanities and water closet. Guest en-suite bedroom with new modern updated bath, 3rd bedroom can be used for the perfect office featuring views of the pool, and 4th bedroom with new Jack and Jill bathroom. This vibrant home also features a circular drive way with a considerable two car garage, crown moldings, recessed lighting through the entire home, built in bookshelves in the main hall, pristine polished terrazzo and high gloss snowwhite floors, ample inside laundry room with storage, dual HVAC systems with added air purification system, ADT security system, heated immense pool with travertine pool decking, and an abundant half acre lot with vinyl fencing for privacy. Termite bond conveys with the property. Roof replaced in 2019, Pex plumbing 2023, HVAC 2019, Pool 2018, Pella sliding and french doors 2024. This alluring Winter Park home is conveniently located just minutes from all the shops and restaurants of Historic Park Avenue, Trismen Park and so much more. 160 Trismen Terrace is truly a home for those who appreciate entertaining.

160 Trismen Terrace, Winter Park
$1,050,000
3 Beds ⋅ 2 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Welcome to your dream home in the coveted Waterbridge neighborhood! This stunning one-story pool home boasts everything you've been searching for and more, including a three-car garage. Situated on a spacious corner lot, this residence offers both elegance and comfort. Step inside to discover a welcoming ambiance, highlighted by a gathering living room featuring a double-sided gas fireplace, perfect for cozy evenings or entertaining guests. The dining room is conveniently located off the kitchen, complete with double built-in ovens and overlooking the inviting family room. A sunny Florida room extends off the family room, offering picturesque views of the lush backyard oasis and sparkling pool—a true haven for relaxation and enjoyment. Retreat to the primary suite, featuring a spacious walk-in closet for all your wardrobe needs. Two additional bedrooms, each boasting generous walk-in closets, ensure ample space for family or guests. Plantation shutters throughout add a touch of sophistication, while the large laundry room with cabinetry provides convenience and storage. Step outside to your own private paradise, where a gorgeous pool awaits, complete with a heated spa, sun shelf, and seating bench—all within the confines of a large privacy fenced backyard. Waterbridge residents enjoy access to community amenities including a park and tennis courts, fostering a sense of community and recreation. Conveniently located near shopping, restaurants, and minutes from Park Avenue, this home offers easy access to all the best Winter Park has to offer. Plus, with sought-after Winter Park schools just a stone's throw away, you'll enjoy peace of mind knowing your family is in a top-notch educational environment.

1203 Germaine Drive, Winter Park
$4,923,750
5 Beds ⋅ 6 Baths ⋅ Sicilian Shores SubDv. ⋅ 32789 Zip Code
Luxurious lakefront living with unparalleled view of Lake Maitland, part of the famed Winter Park chain of lakes with 180 feet of water frontage. Enjoy tranquil views from the lake from almost every room. This custom home is located in the Via's of Winter Park and is close distance to downtown Park Ave and the Winter Park Racquet Club. This home was built by Gallimore and features five bedroom, five & one half bath. As you enter the foyer, you are immediately greeted by high ceilings, open floor plan and panoramic views of the lake. The family room is a fantastic place for entertaining, featuring a gas fireplace, wet bar with refrigerator and opens to the screened pool and gorgeous lakefront. The gourmet kitchen is a chef’s dream featuring a large center island, custom cabinetry, quartz surfaces, top of the line Thermador appliances, and walk-in pantry. The spacious master bedroom is a retreat of its own with amazing views of the lake and a sitting area. The master bathroom has custom cabinets with dual sinks, makeup vanity, modern stand alone tub, walk-in shower and a large walk around closet. There is a guest suite on the first floor with en suite bathroom and walk in closet. Two additional bedrooms upstairs with en suite bathrooms and a huge bonus room or fifth bedroom. This home also features a 3 car garage, a home office, laundry room and walk-in storage room with a large wine refrigerator. Step outside to the backyard paradise, where the pool, heated spa and sun shelf beckons you to relax and unwind. The large covered boat dock is a perfect place to watch the colorful sunset at night and has a separate enclosed storage room. Bring your boat and all your toys and enjoy lakefront living at its best! Roof and boathouse roof updated 2022.

1761 Pinetree Road, Winter Park
$350,000
3 Beds ⋅ 2 Baths ⋅ Park Green SubDv. ⋅ 32789 Zip Code
Welcome to your future home at 1244 Park Green Place, nestled in the vibrant heart of Winter Park, FL. This move-in-ready townhouse offers a seamless blend of comfort and convenience, making it the perfect setting for both new beginnings and cherished memories. Step inside this inviting residence and be greeted by an expansive living space, bathed in natural light, thanks to the high, vaulted ceilings that create an airy and open feel. The hard flooring throughout the home is not only elegant but also promises easy maintenance and durability. This townhouse features three cozy bedrooms and two well-appointed bathrooms, providing ample space for family, guests, or a home office. A/C was recently replaced and roof was replaced within the last 8 years. At the heart of this home is a modern kitchen, boasting luscious granite countertops that offer both beauty and practicality. Whether you're a seasoned chef or a culinary novice, this kitchen is designed to inspire delightful dining experiences. Entertaining is a breeze with the enclosed back porch, providing a perfect backdrop for gatherings or a peaceful retreat after a long day. The fenced-in yard adds an extra layer of privacy and security, making it a safe haven for both relaxation and play. Located conveniently close to shopping centers, appetizing restaurants, world-famous theme parks, and major roads, 1244 Park Green Place ensures that you're never far from where you need to be. Embrace the opportunity to live in a home that combines practicality with endless possibilities for leisure and enjoyment. This townhouse is not just a dwelling; it's a foundation for a life filled with ease, accessibility, and joy. Don't miss the chance to make 1244 Park Green Place your own — a place where every day feels like a breath of fresh air. Welcome home.

1244 Park Green Place, Winter Park
$1,800,000
4 Beds ⋅ 4 Baths ⋅ Woodmere Terrace Rep SubDv. ⋅ 32789 Zip Code
Located within the heart of the Vias, this premier property boasts an expansive, almost half-acre lot spanning 19,800 square feet, with dimensions of 120 by 165 feet, all set along a picturesque brick street. Representing a rare find in an "A location" lot, its over 100-foot width opens up a realm of design possibilities, making it an ideal canvas for your dream home. At the heart of this property stands a spacious four-bedroom home, offering over 4,700 square feet of living space. This dwelling is currently vacant and impeccably maintained, presenting a "move-in condition" option for those seeking immediate occupancy or rental income while planning their custom residence. Alternatively, delve into the meticulously crafted proposed remodel plans, designed by Ashley Martin Home and brought to life by M Lahr Homes. These plans, with an investment of approximately $50,000 by the seller, outline a renovation encompassing around 5,400 square feet, promising a blend of modern luxury and timeless charm. While the value lies predominantly in the land and its generous proportions, the existing home exudes a blend of elegance and functionality. Primarily one-level living, it features an owner's suite along with two additional spacious bedrooms, each with en suite facilities, offering the utmost comfort and privacy. A private office, discreetly positioned behind the garage with a separate entrance, adds versatility to the space, catering to various needs from work to creative pursuits. The interior unfolds with an array of captivating features, including soaring ceilings, plantation shutters, crown molding, and solid oak floors throughout. The primary retreat boasts a luxurious en suite and a large walk-in closet, ensuring indulgent relaxation. A gourmet kitchen, adorned with expansive cabinetry and stainless steel appliances, adjoins a charming eat-in area, offering the perfect setting for culinary endeavors. Entertainment options abound with a formal dining room, a living room adorned with a wood-burning fireplace, and a den complete with a wet bar, ideal for hosting guests or unwinding in style. The enclosed Florida room adds a touch of serenity, overlooking the lush backyard oasis. Upstairs, a second potential owner's suite awaits, boasting its own entrance, vaulted ceilings, and a spacious closet. French doors lead to a private covered balcony, offering scenic views of the meticulously landscaped grounds below. Outside, the allure continues with a park-like setting, characterized by mature landscaping, majestic trees, and an expansive brick patio, covered porch, and pergola. This outdoor haven provides the perfect backdrop for al fresco dining, relaxation, and gatherings with loved ones. Situated in the highly sought-after Vias neighborhood of Old Winter Park, this property offers unparalleled convenience and ambiance, with proximity to WPRC, ICC, and downtown Park Avenue. Embrace the opportunity to create your own haven of luxury and sophistication in this coveted locale. Experience the essence of timeless elegance and modern comfort at this remarkable address.

1251 Woodmere Drive, Winter Park
$330,000
2 Beds ⋅ 1 Baths ⋅ Virginia Heights Condo SubDv. ⋅ 32789 Zip Code
PRIME LOCATION for walking to all WINTER PARK offers! Charming first floor 2/1 renovated condo with custom wood-work, hard pine wood floors, and an abundance of natural light throughout is ready for its new owner to enjoy immediately! The covered wrap-around front porch welcomes friends and family to enjoy time together! Glass French doors open into the spacious family room with floor to ceiling windows and views to the side garden. The renovated eat-in kitchen is a delight with Calacatta marble countertops and a bar for sitting while watching or assisting the chef plus a picturesque breakfast nook surrounded by windows. Nearby is a door with a built-in doggy door opening to the fenced courtyard with brick flooring and twinkle lights! A special spot for morning coffee, grilling or having a container garden! The home's hallway leads to the primary bedroom offering privacy, a ceiling fan, French doors and an abundance of windows. The main bath has dual glass bowl vanities with the shower/ tub combo separate and secluded. The other bedroom would also make a wonderful home office, guest or exercise room. Barn style storage and parking is in the space closest to your door!! This unit also has lake access at Virginia Heights Community Dock on College Point to enjoy Lake Virginia and the WP Chain! Walk to Park Avenue, WP9 Hole, Rollins, Winter Park Tennis Center, and the new WP outdoor area almost completed. HOA is self managed with only 6 friendly owners who love the property and are responsive. Indoor laundry with washer/dryer, roof is 2019 and HVAC, 2017.

1302 S Pennsylvania Avenue Unit 4, Winter Park
$1,102,000
4 Beds ⋅ 4 Baths ⋅ Conwill Estates SubDv. ⋅ 32789 Zip Code
TAKE IN ALL THE CHARM, TRADITION and ELEDANCE THIS WINTER PARK HOME HAS TO OFFER. Situated on a quiet, tree-lined street this 3,100 square feet home boasts 4 bedrooms, 3.5 bathrooms (half bath in located in the laundry room area), double primary suites plus an office. The main first floor living area features recently refurbished original hardwood floors, and a wood-burning fireplace surrounded by built-in shelving in the family room, updated lighting and recently updated kitchen cabinets. Enjoy holiday meals or intimate dinner parties in the lovely dining room, accented with a tongue and groove wood ceiling. Upstairs is bright and airy with natural light flooding in from skylights. Both second floor primary suites feature dedicated bathrooms and multiple closets. Off the second suite upstairs youll find a private balcony overlooking the lush back yard. The other suite upstairs includes another wood burning fireplace. The first floor has two bedrooms plus a bathroom including the office. The exterior of this charming home was recently lime washer and the horseshoe driveway complete with pavers was recently expanded. The exterior view of the home on this tree-lined road is only something you would find in a storybook. To complete the exterior, you will find an extended driveway leading to the 2-car garage and mature landscaping. The private backyard, complete with a new brick patio area, is the perfect place unwind or entertain, with ample space to add a pool. Enhancements include a new roof (2021), AC (2019) and new hot water heater (2023). Located in the sought-after Winter Park school district, this outstanding location is just a short walk from Phelps Park, the YMCA and Lakemont Elementary School. All this could be yours so schedule your private showing today!

1725 Pine Avenue, Winter Park
$215,000
2 Beds ⋅ 2 Baths ⋅ Lakeside Manor Apts Condo SubDv. ⋅ 32789 Zip Code
Nice 2-bedroom 2 bath 1st floor condo on Lake Killarney in quiet development. Close to Hwy 4 and downtown Winter Park, stores, Winter Park Library, parks. Condo has been renovated. New ceramic floors, paint, bathrooms, new kitchen sink, faucet and disposal. A/C 2021, , newer plumbing in complex. Boat dock slips $30 a month when available. Boat ramp available for daily use, only for condo owners, Kayak, canoe storage by lake. Enclosed bicycle storage unit available for $15 year if available. Pool and community room. Water included in HOA fee. 1 reserved parking spot but a second is available for $35 extra monthly fee if available. Sorry no pets, motorcycles, RV or work trucks. No rentals first 2 years.

2500 Lee Road Unit 107, Winter Park
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Unlock the potential of building your dream home with this rare opportunity on an oversized corner lot. The home and property are being sold in as-is condition with all value being placed in the land. An A-plus location and a wonderful setting to embark on the journey of creating a custom masterpiece from the ground up. Situated on almost half an acre along one of Winter Park's most enchanting streets, this property is a canvas awaiting your vision. Enjoy the prime location, offering a swift drive to Winter Park's vibrant Park Avenue. Surrounded by multi-million dollar homes, this property embodies exclusivity and prestige, inviting you to become part of this distinguished neighborhood.

810 Bonita Drive, Winter Park
$2,120,000
4 Beds ⋅ 5 Baths ⋅ Flora Park First Add SubDv. ⋅ 32789 Zip Code
Stunning transitional modern home located in the heart of Winter Park. This immaculate residence features a bright open floor plan and boasts a chef's kitchen with a large center island and a prep sink, custom cabinetry, quartz counter tops, top of the line Wolf and Sub-Zero appliances, a walk-in pantry. The kitchen has an abundance of natural light that creates an inviting atmosphere for culinary creativity and entertaining, it opens to a spacious great room with a fireplace and a wall of glass that pockets into the wall combining the indoor and outdoor living spaces. The primary bedroom suite features a separate sitting area overlooking the backyard and a spa bath with a walk-in shower and large tub for soaking away the stresses of the day. The walk-in closet even has washer and dryer hookups for the ultimate convenience. Additional features include a home office, 2nd floor loft area, 3 additional bedrooms, and a 2nd floor laundry. Step outside to discover a private backyard oasis, complete with a covered lanai with retractable screens, a summer kitchen, and a sparkling pool surrounded by travertine pavers. The pergola adds a touch of elegance to this outdoor retreat, perfect for relaxing or hosting gatherings with friends and family. For those with multiple vehicles, the property features an extra-long driveway and an oversized 2-car garage with electric vehicle charger. This home truly embodies modern luxury and indoor-outdoor living, offering a perfect blend of comfort, style, and functionality. Located a short golf cart ride from Park Ave’s incredible restaurants and shopping, and walking distance to Phelps Park and the YMCA, the location is impossible to beat.

1616 Hibiscus Avenue, Winter Park
$2,320,000
4 Beds ⋅ 4 Baths ⋅ Osceola Shores SubDv. ⋅ 32789 Zip Code
Exquisite total remodel in downtown Winter Park. Walk to Park Avenue, restaurants, shops and parks. No detail was overlooked! From the flooring to the appliances, light fixtures, and magnificent primary closet! You will feel like you are in Palm Beach inside and out, especially outside on the oversized lot, at the pool, on the porch, or in the summer kitchen. You will feel like you are at a five-star resort! This is a gem!

440 Lakewood Drive, Winter Park
$550,000
3 Beds ⋅ 3 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
***SELLER IS OFFERING $10,000 IN CONCESSIONS TOWARDS CLOSING COSTS***This exquisite residence offers sophistication and comfort without HOA constraints. Its fresh stucco facade and welcoming patio lead to a beautifully landscaped oasis. Inside, recessed lighting illuminates a captivating accent wall and a step-down entertainment area, perfect for relaxation or gatherings. The kitchen features luxurious shaker-style cabinetry, calacatta waterfall countertops, and high-end stainless steel appliances. The primary bedroom is a tranquil retreat with natural light, while the en-suite bathroom boasts a glass shower and freestanding soaking tub. Outside, a newly paved patio and lush landscaping extend the home’s luxury. Discover refined elegance at 2612 Lafayette Avenue in Winter Park

2612 Lafayette Avenue, Winter Park
$1,725,000
4 Beds ⋅ 4 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
Welcome to this ideal corner of Winter Park, part of the highly desirable Via's, and this stylishly renovated home. This four-bedroom, four-bath home spans over 3,400 square feet and ideally combines modern updates and timeless charm. The open floorplan seamlessly integrates the living, dining and kitchen areas, creating an ideal space for entertaining and everyday living. Natural light fills the interior, accentuating the sleek finishes and designer touches. Designer lighting, custom hood and gas stovetop make the kitchen an ideal place for preparing and hosting meals. The main level also features the primary bedroom, offering a tranquil retreat complete with a spacious en-suite bath with dual shower heads, a rain shower and a soaking tub. The expansive closet space in the primary bedroom is envious. Step outside into your private paradise, where a saltwater pool with sun shelf awaits. The covered patio with multiple fans ensures you can enjoy the outdoors comfortably, whether lounging poolside or dining alfresco. There is also a summer kitchen with additional refrigeration, ideal for entertaining. For those who love to stay active, there is an additional climate-controlled space with endless possibilities, whether a home gym, yoga studio, art space or office. Location is key, and this home is ideally in a highly desirable neighborhood, zoned for top-rated schools, including the No. 1 elementary school in Orange County. There is also neighborhood access to Lake Maitland. Enjoy easy access to Park Avenue, Winter Park Racquet Club and more. Schedule your private showing today.

914 Moss Lane, Winter Park
$2,750,000
4 Beds ⋅ 5 Baths ⋅ Tuscany Terrace SubDv. ⋅ 32789 Zip Code
One or more photo(s) has been virtually staged. Gorgeous Alys-Rosemary Beach-style coastal residence in the sought-after Vias neighborhood near the WPRC and ICC. Built in 2020, nothing was overlooked with many custom finishes and thoughtful designer details that are captivating from the moment you walk through the front entry. A masterfully, well-designed open floor plan with soaring ceilings (decorative accent beams), along with quality expansive windows and glass doors flooding the home with natural light. Elegant living areas for various seating groups, including a bar area, living area, additional dining and gathering room all transition from inside to outside with a seamless flow that allows for comfortable casual Florida living and entertainment. The fabulous chef's kitchen offers a 6-burner gas range, two built-in ovens, an expansive “4-person” bar stool island in addition to a wonderful breakfast nook with pool views. The secluded primary suite includes another fireplace, separate walk-in closets, a lavish bath with private botanical garden, and French doors with peaceful views of the pool. The recently added den/home office complements the first floor flawlessly and can also be utilized as a secondary bedroom (includes a built-in with Murphy bed system) and en-suite bath. This home lives primarily as a one-level residence, having only 2 secondary bedrooms upstairs and they are more than generous in size as well. When making your way outside the main residence, there is a wonderful, detached pool cabana that features a wall of folding glass Casablanca-style accordion doors that bring the outdoors in. The cabana is equipped with a wet bar and a full bath, great for guests/in-laws, an art/yoga studio, separate home office, and much more. The outdoor area is truly an enjoyable private oasis including 7 perimeter gas lanterns. Enjoy Florida days and nights on the covered lanai with wet bar and in the picturesque pool and tranquil private backyard amenities. There is a climate-controlled detached two-car garage “carriage house” that is easily accessible to the main residence via a covered breezeway. There is also a parking area and wraparound front/side yard lawn encompassed by a podocarpus hedge and a private linear dog run or lawn with turf grass that completes the grounds. The Vias is an unsurpassed Winter Park neighborhood, just a few minutes away from downtown Winter Park/Park Avenue, A-rated schools, Winter Park Racquet Club, Interlachen Country Club and much more. Bedroom Closet Type: Walk-in Closet (Primary Bedroom).

1254 Via Estrella, Winter Park
$1,775,000
4 Beds ⋅ 4 Baths ⋅ Fontainebleau SubDv. ⋅ 32789 Zip Code
Meticulously maintained four bedroom, four bath home nestled on a quiet Winter Park street ready for immediate move in. Custom built in 2015 by FG Schaub, this home looks and feels brand new, and offers an open floor plan - perfect for entertaining or easy/comfortable living. The spacious kitchen showcases custom wood cabinets, a large breakfast bar/island with loads of storage, and overlooks the great room and dining room. The kitchen easily flows to the great room with a wall of built-ins for more storage and display, along with an under-counter beverage cooler. Two sets of French doors open out to the covered lanai with retractable screens which allow for climate control and seamless indoor/outdoor living. Enjoy cool evenings with the built-in fire pit, or a morning coffee listening to the water fountain. The private primary suite offers a large bath with separate vanities and a walk-in shower, and a very large walk-in closet. A secondary bedroom with walk-in closet is also on the first floor - which can be used as a guest suite or an office. A huge pantry room and laundry room off the two-car garage and mudroom/desk area finish off the first floor. The second floor features two bedrooms, each with en-suite baths and a 32 x 14 bonus room, which could easily be converted to a smaller bonus room and a fifth bedroom. Additional upgrades include a tankless water heater, a whole home water filtration system, and a water softener. Located in a premier neighborhood, minutes to Park Avenue and easy access to major roadways and highly-rated Winter Park schools.

1531 Place Picardy, Winter Park
$1,400,000
3 Beds ⋅ 4 Baths ⋅ Perle Du Lac SubDv. ⋅ 32789 Zip Code
This is your opportunity to live the ultimate lock-and-leave lifestyle and have the lakefront living that makes Winter Park so special. Perle Du Lac is a gorgeous condominium community situated on the shores of Lake Virginia. Unit 203 is a spectacular 3-bedroom, 3.5-bath split-bedroom home with a breathtaking pool and lake views. A completely remodeled kitchen by S&W Kitchens (December 2022) offers custom cabinetry, Cambria quartz countertops, new GE Profile gas range/oven plus a built-in oven, and under-counter wine fridge. The spacious living room has beautiful Brazilian Cherry wood floors and a wall of sliding glass doors that open to the patio and showcases the amazing views of the pool, grounds and Lake Virginia. The private primary suite has French doors to the patio, a remodeled bath (2021) with dual sinks plus a vanity, a large glass-enclosed shower, and a walk-in closet. The secondary bedroom has an ensuite bath, and the third bedroom, currently used as an office has a custom built-in desk, cabinetry/shelves and a Murphy bed which conveys with the home. All bathrooms were remodeled in 2021. This unit also offers a separate climate-controlled storage room within the building, secured underground parking garage with 2 designated parking spaces, a picturesque community pool, and a deeded covered boat slip with motorized lift. Close to restaurants and shopping on Park Avenue, the Alfond Inn, Rollins College, the WP Farmers Market, and much more.

662 Osceola Avenue Unit 203, Winter Park
$1,400,000
3 Beds ⋅ 4 Baths ⋅ Winter Park Rev SubDv. ⋅ 32789 Zip Code
Beautifully appointed "Italian Villa" style home in the heart of Winter Park. Just a few blocks from Rollins College and Winter Park's famed Park Avenue where you will find high-end shops and plenty of fabulous restaurants. This is as close as you can get to a "lock-and-leave" residence and still have the privacy of a detached single-family home. Built by a custom home builder for their personal residence, no expense was spared to create wonderful living spaces perfect for entertaining friends and family or enjoying the Winter Park lifestyle peacefully. As you enter the foyer you are greeted with a flex room to your left that can be utilized for dining, office, exercise or whatever your lifestyle desires. Interior features include stone flooring, high ceilings, extensive detail in the millwork, custom built-ins, and open floor plan. The living areas are light and bright with tons of natural light and views of the private backyard. The chef's kitchen boasts Carrara marble countertops, custom cabinets, Sub-Zero refrigeration, a double oven Wolf gas range, and a window-framed banquette eat-in area. All 3 bedrooms are en-suite with walk-in closets and the primary bathroom has a marble enveloped soaking tub and separate glass shower, and dual marble vanities. Another primary suite features is the "Juliette" balcony overlooking the pool area. The bonus space upstairs is perfect for additional TV area, study, or office space. Other interior details include gorgeous hardwood and tile floors upstairs, designer lighting throughout, high-end fixtures and hardware, and multiple-zone audio. The tropical backyard pool area has complete privacy, a lagoon-style pool, maintenance-free artificial turf, and "award-winning" landscaping installed and maintained by Signature. This home has been designed to take advantage of every inch of space. Perfectly located with easy access to all the Central Florida amenities and top-rated Winter Park schools.

621 Huntington Avenue, Winter Park
$1,690,000
4 Beds ⋅ 6 Baths ⋅ Winter Park Village SubDv. ⋅ 32789 Zip Code
Welcome to this beautiful home in Winter Park neighborhood. This beautiful home is built for entertaining. The spacious home offers a little over 4,600 square feet of living space. The first floor offers a large open floor plan with incredible view into tour outdoor oasis. The kitchen features a 6-burner range with grill and double oven, large Electrolux fridge and freezer, microwave drawer, wine fridge, upper and lower cabinets with under cabinet lighting. An ample living room, with wall-to-wall custom solid wood built-ins and wired in speakers. Full panel sliding doors which flow into the outdoor retreat featuring a full Paradise Grills outdoor kitchen built for grill masters and hibachi lovers. Full bar service set up, wired in music with lights to play to the beat or perhaps colors for the holiday seasons. The large 30 foot pool equipped with solar heated pool system, beautiful glass tiled firewall and jetted fountains. Pool storage, pool bath and outdoor shower. The opulent primary suite gives you enough room for a California king bed, large walk in closet and spa like bathroom with his and her vanities. Upstairs you will find a large loft with a huge bonus room and 3 large bedrooms each with en-suite bathrooms.

1411 Border Drive, Winter Park
$2,150,000
5 Beds ⋅ 5 Baths ⋅ Virginia Heights SubDv. ⋅ 32789 Zip Code
In the highly sought-after Virginia Heights Historic District with Lake Virginia access, an updated residence combines modern luxuries and timeless charm sitting on nearly a third of an acre and surrounded by a live oak tree canopy. This home offers a blend of original architectural elements and contemporary features. The new solid wood custom door opens to a warm living room space with a fireplace. A newly updated dining room features Schumacher wall covering, custom window treatments and a stylish chandelier that compliments the new designer lighting selected throughout the home. The owners have added a professionally designed butler’s pantry offering the ideal space for staging parties or more intimate gatherings and tastings. Whimsical Thibaut wall covering mixes with sleek dark countertops and space for cases of your favorite varietals. The updated kitchen includes solid surface countertops, a gas range, abundant storage and casual countertop dining space. Off the kitchen is the recently added utility mudroom with plenty of space for a home office and additional storage for a busy household. The open plan includes the kitchen, casual dining and the family room in a shared space. The owners have also added built-in benches, an additional fireplace and warm lighting to make the family room a cozy space for gatherings. Flexible space for an office or playroom as well as a full bath completes the first floor. The second floor includes a newly renovated primary suite with an expansive closet and a new primary bath. All of the baths throughout the home have been updated to match the renovations of this home. Three additional bedrooms and two additional baths finish this second story. The spacious screened lanai off the family room opens up to a saltwater pool and heated spa added in 2021. The poolside ambiance is further enhanced by the detached 400-square-foot guest house, which stands as an independent structure outside the main square footage, ideal for a guest house or owner’s workshop or studio. The owners have construction plans available that show the potential to turn this space into a gym, entertaining area and guest space. Throughout the meticulous renovations, great care has been taken to preserve the age and historic significance of the home, ensuring it seamlessly integrates into its distinguished surroundings. This Winter Park gem invites discerning homeowners to experience the union of heritage and contemporary living. Don't miss the opportunity to own a piece of history with this extraordinary residence in Winter Park.

1470 Glencoe Road, Winter Park
$1,295,000
2 Beds ⋅ 2 Baths ⋅ Alabama Condo SubDv. ⋅ 32789 Zip Code
A spectacular two-bedroom, two-bath home available in the historic Alabama Condominiums. Located on the second floor with breathtaking views of Lake Maitland on the Winter Park Chain of Lakes and the beautiful grounds of The Alabama. Recently renovated with updated bathrooms, and a new kitchen which includes gorgeous cabinets, stone counters and stainless steel appliances. The living/great room offers a wall of built-ins, and gorgeous wood floors. The Florida room showcases seven large windows which allow for plenty of light to fill the home, and gives amazing views of the lake. The Alabama is a Winter Park icon with a community pool, a clubhouse with a full kitchen and a fitness room, a community dock on Lake Maitland, and boat slips. Currently there is a boat slip available with no wait list. Fee is $2,500/year. This unit offers an additional storage space and one assigned covered parking space. Enjoy scenic sunsets from the adirondack chairs on the lawn or at the dock. Lakefront living without the maintenance. Luxury living with the lock and leave lifestyle.

1602 Alabama Drive Unit 203, Winter Park