Winter Park Homes for Sale

MLS Number O6269585

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 11,255
• Year Built 2009

Nestled within the exclusive community of Windsong on Lake Berry, this magnificent 1.6-acre gated Mediterranean Estate is a true private oasis. With over 11,000 square feet of living area and a beautifully landscaped lakefront lot, this residence offers an exceptional blend of elegance, charm, and privacy that is rarely found in Winter Park. The home features 7 spacious bedrooms and 9 full and 2 half baths. Entertain in the all-glass conservatory, dedicated theater room with motorized seating, and a fully equipped game room. Modern conveniences throughout including gas-powered generators, an elevator and dumbwaiter. Two above-garage apartments provide ideal accommodations for guests and family. Outdoors, enjoy an expansive covered lanai, infinity edge pool and spa, boat dock with jet ski lift, and a summer kitchen complete with wood burning fireplace, gas grill, refrigerator and icemaker, all overlooking the beautifully landscaped yard and lake. With its own private gated entrance, this home is a one-of-a-kind opportunity to enjoy all of the amenities that Winter Park and Windsong have to offer.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6260493

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 4,564
• Year Built 2024

Introducing a stunning modern European-style home, blending contemporary design with timeless elegance. This property offers luxurious finishes, open-concept living spaces, Located in the heart of Historic Winter Park, Florida, this exceptional property offers top-of-the-line amenities, perfect for those who appreciate Luxury living. Features:o 4,564 sq ft of living space o 4 Bedrooms, 4 Bathrooms, 1 Half Bath o Custom Built CostaRica One Tree Solid Piece - A 16-foot tall, one-of-a-kind steel masterpiece featured prominently in the design o Italian Porcelain Floors throughout o All-Glass Windows with impact-resistant, top-of-the-line glass by Techno Glasso Chef's Kitchen featuring: o Custom 1-inch thick Italian Quartz countertopso Imported Italian cabinetry o Extended island perfect for entertaining o Wolf Appliances and Sub-Zero Refrigerator o Two Master Suites: One on the first level and another upstairs, each with private luxury baths and walk-in custom closets o Private Balconies for each bedroom. HOME IS ALL CONCRETE steel framing !! offering stunning views and tranquility o Corner Lot situated on one of Winter Park's most exclusive streets, Via Tuscany-a private and serene location that offers privacy and charm. This home is perfectly positioned just 6 minutes from Interlachen Country Club, a historic private course where you can enjoy exclusive access to the Winter Park Golf Course-a scenic 9-hole, par-35 walking course established in 1914. Short drive to downtown Orlando, Winter Park offers a serene escape with easy accessibility, Known for its unique blend of charm, history, and cultural offerings, Winter Park is a standout destination in Central Florida.One of its key highlights is the iconic Park Avenue. This vibrant street, lined with cobblestone and historic architecture, features boutique shops, art galleries, upscale restaurants, and cozy cafes. It's a favorite spot for both residents and visitors and serves as the hub for community events like the annual Winter Park Sidewalk Art Festival, which draws artists and attendees from across the country. Cultural attractions further enrich Winter Park's appeal. Rollins College, renowned for its stunning campus, adds depth to the local arts and culture scene with performances, lectures, and art exhibitions. The Charles Hosmer Morse Museum of American Art is another must-see, housing the world's largest collection of works by Louis Comfort Tiffany, including breathtaking stained-glass pieces. Other local art and history museums add to the area's vibrant cultural fabric. For nature enthusiasts, Winter Park offers scenic beauty and outdoor activities. The Chain of Lakes provides opportunities for boat tours, kayaking, and paddle boarding, with the Winter Park Scenic Boat Tour being a favorite way to explore the area's natural charm. Food lovers will also find plenty to enjoy in Winter Park. The town boasts a thriving dining scene, ranging from fine dining establishments to casual eateries serving international cuisine and farm-to-table options. Winter Park effortlessly combines the energy of a cultural hub with the warmth of a tight-knit community, making it an attractive place to visit or call home for individuals and families alike. This home offers the ideal balance of luxury, privacy, and exclusivity in one of Winter Park's most coveted locations. Don't miss out on this exceptional opportunity! schedule your private showing today!!

Listing Courtesy of PV LUXURY GROUP PA

MLS Number O6212012

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 7,916
• Year Built 1996

Custom Waterfront Estate located in the heart of Winter Park with a covered Boat Dock on Lake Maitland - the largest of the Winter Park Chain of Lakes. A timeless Neoclassical Italian home that exudes luxury and sophistication. Built by Charles Clayton. Designed by Marc Michaels. The main house boasts over 7,100 sf with 4 bedrooms, 4 full bathrooms, and 3 half bathrooms. The detached Guest House/In-Law is approx. 500 sf, with 1 bedroom, 1 bathroom, two closets, and a wet bar. The detached Catering Room with half (pool) bath is approx. 350 sf with an additional refrigerator, wall-to-wall built-in storage, and is conveniently attached to one of the two-car garages. Enjoy expansive entertaining areas that seamlessly blend indoor and outdoor spaces, offering a grand setting for lavish gatherings. Outfitted with the finest custom finishes, gourmet chef's kitchen, equipped with top-of-the-line appliances, an oversized island, and large dinette space. Awe-inspiring private courtyard with heated pool and spa, covered porch, outdoor grill, and several separate terraces. Impressive primary suite with office and sitting area has separate his and hers ensuite bathrooms and closets. Stunning two-story closet with office on the second floor and laundry room on first floor. Impressive entertainment/media room with state-of-the-art projector, media equipment and electronic blackout shades. Second story features a spacious loft, 3 bedrooms, 2 full bathrooms, a laundry room and two balconies. Storage is abundant throughout this property. You will find two 2 car garages behind the electronic gated side facing driveway, one garage with a kennel and a Tesla charging station. Experience quintessential Winter Park living in this one-of-a-kind estate that is the epitome of opulence and grandeur. More upgrades than can be mentioned. More architectural detail than can be captured in photographs. This estate is a must see!

Listing Courtesy of IRON VALLEY REAL ESTATE CENTRAL FLORIDA

MLS Number O6268853

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 4,725
• Year Built 2008

Welcome to your dream home in the heart of Winter Park, Florida! Nestled in the prestigious Timberlane Shores neighborhood, this exquisite custom-built residence by Farina & Sons offers the perfect blend of luxury and tranquility. With 4 bedrooms, 3.5 baths, and a generous 4,725 sq ft of living space, this home is an Aurora and Parade of Homes Grand Winner and boasts 130 ft of lakefront frontage on the serene Lake Virginia. As you approach this stunning property, you'll find it situated on a quiet cul-de-sac, ensuring peace and privacy. Step into the backyard oasis, where a lanai with a gas fireplace invites you to unwind and enjoy Florida's beautiful weather. Relax in the hot tub or take a dip in the pool equipped with an Ultraviolet System which ensures the healthiest pool water possible, complete with an outdoor shower. The outdoor home lighting creates an enchanting ambiance, while the boat dock with a covered electronic boat lift offers easy access to water adventures. Experience breathtaking sunrises and sunsets over Rollins and Knowles Chapel from your own piece of paradise. The first floor of this home is designed for both comfort and style. Anderson doors and windows fill the space with natural light, highlighting the wood floors and architectural details like coffered ceilings with wood beams in the open family room. The master suite serves as a private retreat, featuring a spa bathroom, custom closets, and ample storage. Two additional bedrooms, a bathroom, and a half bath provide versatility and convenience. The kitchen is a chef's delight, boasting Caesarstone concrete countertops, a copper hood range, top-of-the-line Subzero and Viking appliances, walk-in pantry. A walk-in bar and wine room enhance the home's functionality, while a Pelican whole house water filtration system and a Kangen Leveluk water purifier ensure the highest quality water. The second floor is perfect for entertaining, offering a spacious area with a bonus room, bar, kitchenette, and an additional bedroom with an en-suite bath. This versatile space is ideal for hosting guests or creating a personal retreat. The city of Winter Park has approved plans to add an enclosed 385 square feet to the second floor, providing potential for additional space. Don't miss the opportunity to own this extraordinary lakefront home in one of Winter Park's most sought-after neighborhoods. Experience luxury living at its finest with unparalleled lakefront views, exceptional amenities and convenience to all the restaurants and shopping that Winter Park has to offer.

Listing Courtesy of HOMEVEST REALTY

MLS Number O6239351

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,264
• Year Built 2024

This gorgeous, new-construction FG Schaub custom home is the epitome of stunning contemporary design by architect, Michael Weinrich. As you enter this sprawling residence, with views of both Lake Sue and Lake Chelton you'll be greeted by exquisite tile work with brass inlays, wood floors, drop down ceiling, crown molding, wainscoting and natural light that pulls the outside living in. The first floor was meticulously designed with your Owner's suite, an additional en suite bedroom with walk in closet, large laundry room with full size washer and dryer and an abundance of cabinet and counter space, an eye catching drop zone, elevator, storage room, kitchen and great room. The kitchen truly is a chef's dream with Quartz countertops, spacious island, custom cabinetry with a satin brass inlay, and modern appliances including Tru refrigerator, freezer, a dual zone 150 bottle wine fridge, 60" Wolfe range with a custom range hood. The custom cabinetry continues into hidden butlers pantry complete with ice maker, microwave drawer, additional sink and Bosch dishwasher. The great room will be your hot spot for entertaining! Located off the kitchen, offering plenty of space for friends and family to gather with easy access to the pool area. Floor to ceiling Anderson windows, bar and an electric fireplace for that added touch of ambiance. Continuing into the Owner's suite you will find more expansive Anderson windows, private access to the outdoor living area, luxurious en-suite bathroom and custom closet. Feast your eyes on the 3x10 large format porcelain tile flooring, dual undermount glass sinks, 24K plated brushed gold fixtures, towel warmer, free standing soaking tub, large walk in shower and private water closet with smart toilet in your Owner's bathroom. And the closet is a feature in itself with lighted LED rods, custom built ins, full length door mirrors and island. Access the second floor via the private elevator or staircase with a glass railing that leads to 3 additional bedrooms, all en-suite with custom tile work and walk in closets with built ins. You'll also find an additional laundry room with a stackable washer and dryer, linen closet, mechanical room and the activity space complete with wet bar and wrap around balcony with a custom glass railing offering sunsets over Lake Sue. Step outside to your own private oasis featuring a sparkling pool with 3 built in stools, sunshelf and spa, fire pit, and cabana with a full summer kitchen, roll away screens, half bathroom and an outdoor shower - ideal for weekend gatherings or relaxing evening meals poolside. Attention to detail carries out to the oversized 3-car garage which features epoxy flooring and a custom LED light design on the ceiling. While a hand crafted iron gate to the front courtyard gives a nod to Winter Parks favorite resident peacocks. A standing seam metal roof and lush landscaping adds the final aesthetic touch on this FG Schaub masterpiece. Welcome home to one of the most exceptional properties on the market!

Listing Courtesy of CORCORAN PREMIER REALTY

MLS Number O6250411

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,072
• Year Built 2008

Gorgeous Winter Park home beautifully curated with designer details and recently featured in June's “Orange Appeal” and was the 2022 Mystery Home Tour selected by Council of 101 for the Orlando Museum of Art. This elegant transitional French Provincial residence is located on a large, elevated corner lot in a quiet and secluded area in the Via's of Winter Park. This designer home has been significantly enhanced inside and out by the current owner and is in “brand new condition.” The home features 5,100 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms, 1 half bathroom, 3 car garage, pool, patio, outdoor shower and professionally landscaped yard and lighting. Upon entry, you are welcomed through the exquisite foyer where you instantly notice the craftsmanship and expert care that went into the custom carpentry and crown molding details throughout. To the left of the foyer is an elegant and intimate parlor with grass cloth wallpaper, a gas vented fireplace and built-in bookshelves. To the right of the foyer is the formal dining room with beautiful hand painted wallpaper and an adjacent butler's pantry. Past the foyer you are led to a spacious and grand formal living room with lacquered walls and 6 new French iron doors that flow out to a covered brick porch and picturesque back yard & pool. Designed with entertainment in mind, the adjoining chef's kitchen includes newly painted custom cabinetry, a Sub-Zero/Wolf appliance package, a grand center island and a walk-in pantry. Built in desk and casual dining area all open to the adjoining beamed ceiling family room with gas vented fireplace and additional French doors that lead to street side patio with new awnings. First floor master retreat overlooks the pool & yard and features 14-foot wood beam vaulted ceilings. The oversized master bath with double custom lacquered vanities made in Palm Beach, mosaic marble shower and a Waterworks free standing tub, brushed brass fixtures, and walk in closet. The second-floor features nine-foot ceilings with four bedrooms (one which was converted to a beautiful women's dressing room) and four ensuite bathrooms, covered balcony adjoining two bedrooms, two built in desks and bookshelves for office/study time and large media room with big screen tv and wet-bar. There are also two laundry rooms, one upstairs and one downstairs. Attic space inside the home and inside the garage. Recent upgrades include new slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine new iron French doors, new ebony-stained oak hardwood floors, lacquered walls, newly renovated master bath and two ensuite baths. This home offers boat access to the Winter Park chain of lakes and is within short distance of the Winter Park Racquet Club. It's also a bike ride away and a short drive to the Interlachen Country Club and Park Avenue shopping and dining district. The property is zoned for Dommerich Elementary, Maitland Middle School, and Winter Park High School.

Listing Courtesy of COMPASS FLORIDA LLC

MLS Number O6263091

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 6,338
• Year Built 2023

Nestled in the esteemed The Vias area and near the WPRC, resides a home signifying the essence of sophistication and luxury. Situated on a secluded street, it occupies an approximately 0.58-acre lot with an expansive backyard landscape that is truly captivating. This exquisite home encompasses five bedrooms and six-and-a-half bathrooms with a four-car garage. An indomitable presence is seen in its immense and grand pivoting iron door which directs you to a double-height foyer and great room separated by a glass-railing catwalk. The property boasts exclusive features like a formal dining room endowed with a glass-encased wine display as well as an intimate den/office safeguarded by private entrance doors. The airy master bedroom is adorned with sliding doors that open up to reveal a private lanai overlooking the pool area; one cannot overlook its distinctively vast his-and-hers walk-in closets complemented by a spa-like luxurious bathroom suite. A state-of-the-art kitchen featuring gold Calacatta Quartz countertops/backsplash matched alongside an oversized walk-in pantry, creating everyday usability flanked with indulgence! Two separate upper and lower level laundry rooms serve this expansive open floor plan a win-win situation for convenience! Adding exceptional charm to this stunning home is a family room equipped with zero corner sliding doors opening up towards the summer kitchen leading onto a large covered patio encased in travertine pavers-- making it your personal haven for enhancing entertainment moods. Venturing upstairs via an elegant Quartz staircase leads you to an additional four en-suite bedrooms (each with walk-in closets). Complementing your leisure needs flawlessly are a comfy lounge space and fun-filled game room with a wet bar setup; creating a direct pathway onto a sprawling balcony exhibiting glass railings overlooking backyards - commanding mesmerizing views of your saltwater gas-heated pool and cozy gas firepit with a seating area for social gatherings! A dedicated full-bath pool with a steam shower. Home gets fully enveloped using high-quality materials fashioned from Large Porcelain format tiles, European tiles, Travertine pavers, and Swiss-origin WPL catering to its strength quotient. Tor uniquely detailed outlook, the property also offers a detached additional building that has been thoughtfully renovated to deliver an extra 600 sq ft of living space - not part of the main house size calculation (6475 sq ft). With 1 bedroom, 1 full bath, a fully functional kitchen circumvented by a living area, and a covered/tiled porch; it makes for a rare addition delivering discernible usefulness. Think creativity! Convert it into a guest house, in-law suite, gym space, professional office setup, or even a hobby room - multiple endless usage options make its possession a valued choice! The home is available now and move-in ready! Get one step closer to owning the realization of your dream dwelling experience!

Listing Courtesy of LA ROSA REALTY HORIZONS LLC

MLS Number O6220284

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 5,500
• Year Built 1967

Pre-Construction. To be built. Welcome to Winter Park lakefront living at its finest. In the heart of Winter Park, this new construction residence promises to be a masterpiece of luxury and modern living. Spanning over 5,500 square feet, this magnificent lakefront residence offers an unparalleled lifestyle with breathtaking panoramic sunset views. Tolaris Homes, an esteemed custom builder in Central Florida with over 45 years of expertise, will guide you from conceptualization to realization of your dream home. Designed to capture the essence of serene lakeside living, the home is ideally positioned to provide scenic vistas of the water and the vibrant hues of the setting sun. As you step onto the expansive balcony, the splendor of this property unfolds. The balcony, designed for relaxation and entertainment, offers a front-row seat to nature's nightly show, where the sky transforms into a canvas of oranges, pinks and purples. Imagine enjoying a glass of wine or hosting a gathering with friends and family, all while soaking in the tranquil beauty of the lake and its surroundings. Inside the home, elegance blends harmoniously with modernity, featuring spacious open-plan living areas that seamlessly transition from one room to the next. High ceilings and large windows ensure natural light illuminates the interior, enhancing the feeling of openness and connection to the outdoors. The thoughtful design includes luxurious finishes and state-of-the-art amenities, catering to every need and desire of its future owners. Experience the ultimate lakefront lifestyle with year-round boating, kayaking and water skiing on your private lake in Florida. Lake Killarney is one of the few lakes in Central Florida where you can land your seaplane on the water. Beyond the walls of this exquisite home, Winter Park offers a vibrant community rich in culture and amenities. From upscale dining and shopping to outdoor activities and renowned schools, this location balances convenience and exclusivity.

Listing Courtesy of PREMIER SOTHEBY'S INTL. REALTY

MLS Number O6255877

• Residential
• Area Winter Park
• Mls Status Active
• Square Feet 4,520
• Year Built 2025

Under Construction. Exquisite new construction residence nestled in the heart of Winter Park, walking distance to Park Ave. This luxurious home boasts over 4,000 square feet of meticulously designed living space, offering an unparalleled blend of elegance and modern sophistication. Upon entering, you are greeted by soaring two-story ceilings that create a grand and inviting atmosphere. The home features 5 spacious bedrooms and 5 1/2 beautifully appointed bathrooms, each showcasing high-end finishes that exemplify luxury living. The gourmet kitchen is a chef's dream, equipped with top-of-the-line appliances and elegant cabinetry, seamlessly flowing into the open-concept living and dining areas, perfect for entertaining guests or enjoying family gatherings. The expansive primary bedroom suite provides a serene retreat with its opulent en-suite bathroom and generous walk-in closet. Step outside to discover a private oasis featuring a large backyard and a sparkling pool, ideal for relaxation and outdoor enjoyment. The detached two-car garage provides ample storage and long driveway provides the luxury of additional off street parking. Experience the epitome of refined living at 1751 Glencoe Road, where every detail has been crafted to perfection.

Listing Courtesy of COMPASS FLORIDA,LLC