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$2,475,000
3 Beds 3 Baths Phillips Circle Rep SubDv. 32789 Zip Code
Quintessential Winter Park Lakefront Living with your own covered boatslip! You must see this Stunning Lakefront Penthouse Residence overlooking Lake Osceola and just two blocks from Park Avenue. Residence 1-5 is located on the quiet, private NE corner of the Whispering Water complex, and it offers the largest floor plan within Whispering Waters at 2,316 sq. ft. under A/C (plus two step-out balconies). This light-filled residence offers an open floor plan and raised ceiling heights. From the moment you enter, you are drawn to the breathtaking lake views and understated elegance of this spacious home. The lakefront great room includes a large living area with adjacent bar and dining areas. The living area opens to the kitchen allowing the lake view to be enjoyed in all main living areas. The kitchen has been updated with white wood cabinetry, a built-in stainless Bosch oven, Bosch glass induction cooktop, Bosch microwave, Subzero refrigerator with two freezer drawers and two additional built-in refrigerator drawers. The custom mirrored backsplash adds a luxury feel, and the flexible center console provides additional work space. The primary suite offers a large walk-in closet and en-suite bathroom with a large walk-in shower, custom floating vanity and elegant fixtures. Bedroom #2 includes two closets and is directly across the hall from a large full bathroom with tub/shower. The 3rd bedroom is currently configured as a large Family Room and includes built-in cabinetry, a private door to the South hallway, two closets and an adjacent alcove ideal for office space. In the photos you'll see a floor plan virtually depicting bedroom #3 with a wall and doorway to the main hallway and living areas. Bathroom #3 is just across the hall and features a large walk-in shower. Wait, there's more! Residence 1-5 includes your own covered boat slip (#1). The entire residence features new seagrass floor covering in all the main living areas. This neutral, organic flooring makes for the perfect contemporary, elegant foundation for your furnishings and for showing off your own custom carpets and rugs. Additional features include plantation shutters throughout, additional storage closet in the garage, and a designated parking space in the gated under-building garage. Residents enjoy a community pool, gated underground parking with elevator access, and an unbeatable location just steps from Park Avenue’s shops, restaurants, museums, and seasonal events. Residence 1-5 is the jewel of Whispering Waters. This home provides the very finest of Lakefront "lock and Leave" living in the heart of Winter Park. All measurements are approximate and Buyer to verify all dimensions. Please see attached Disclosures and Governing Documents.

311 E Morse Boulevard Unit 1-5, Winter Park

$2,725,000
5 Beds 5 Baths Conwill Estates SubDv. 32789 Zip Code
Under Construction. Set within Winter Park’s highly sought-after Tree Streets, this exceptional new home delivers a sophisticated blend of architectural presence, refined interiors, and effortless indoor-outdoor living. A striking façade creates an unforgettable first impression, while a marble mosaic entry introduces the artistry and attention to detail found throughout the home. The main living space is designed to feel both impressive and inviting, centered around a dramatic electric fireplace wrapped in fluted stone. Expansive sliding glass doors fill the room with natural light and create a seamless connection to the outdoor entertaining areas. Open to the living room, the chef’s kitchen is a true statement, pairing richly veined Calacatta Gioia countertops with custom cabinetry, a built-in refrigerator, and a full suite of Thermador appliances. A generous walk-in pantry provides abundant storage and preparation space while maintaining the kitchen’s clean, elevated aesthetic.The first-floor primary suite offers a private retreat with vaulted ceilings and direct access to the backyard. Its spa-inspired bathroom is a sanctuary of beautifully selected marble tile and a serene, sophisticated color palette. A freestanding soaking tub, oversized walk-in shower, dual vanities, and thoughtfully curated finishes create an atmosphere reminiscent of a luxury resort. Also located on the main level is a versatile secondary bedroom that could serve beautifully as a private home office or guest suite, along with a well-appointed powder bath and a combined laundry and mudroom designed for everyday convenience. Upstairs, three additional guest suites provide comfort and privacy, while a spacious loft offers flexibility as a second living room, media space, or playroom. A second laundry room adds another layer of functionality to the thoughtfully planned layout. Outside, the home continues to impress with a covered lanai and full summer kitchen, creating the perfect setting for year-round entertaining. A marble pool deck surrounds the sparkling pool and spa, while the spacious backyard offers room to relax, gather, and enjoy the Central Florida lifestyle in complete comfort. The location is what really sets this home apart. New construction opportunities are becoming increasingly rare within the up-and-coming Tree Streets, making this residence an especially compelling offering. Just a short walk from the Winter Park YMCA, Phelps Park, and Interlachen Country Club, the home places recreation and everyday conveniences close at hand. Hop on your golf cart and arrive to Park Avenue's boutiques, cafes, and restaurants within minutes. A home of this caliber in such a coveted location is a rare find and it won’t remain available for long.

1773 Walnut Avenue, Winter Park

$5,999,990
4 Beds 5 Baths Maitland Shores First Add SubDv. 32789 Zip Code
Virtually Staged. AN ARCHITECTURAL STATEMENT IN ONE OF WINTER PARK'S MOST COVETED LOCATIONS. Set on a prominent corner lot within exclusive Via Tuscany, this extraordinary new-construction residence by Developer & Builder Group represents far more than exceptional modern design. Its distinction lies equally in what you see and in what you don't see, the extraordinary level of construction, engineering, materials, and craftsmanship behind every detail. Built with reinforced concrete, steel, and iron framing and incorporating exceptionally high construction specifications, the residence was created with an uncompromising commitment to structural integrity, durability, and long-term quality. From its substantial structural components to its impact-resistant glass and carefully sourced materials, the home reflects a philosophy rarely found in residential construction: build beautifully, but build exceptionally well. Offering approximately 4,636 square feet of heated living space and 5,260 total square feet, the residence features 4 bedrooms, 4.5 bathrooms, a private pool, and an attached two-car garage. Expansive floor-to-ceiling impact-resistant Techno Glass walls define the architecture, bringing abundant natural light into the interiors while creating a striking connection between indoor and outdoor living. At the center of the home is a dramatic 16-foot custom Costa One-Tree solid steel installation a true architectural work of art and one of the many elements created specifically for this residence. The same uncompromising approach continues throughout the interiors. Imported Italian porcelain flooring, sophisticated lighting fixtures imported from Greece, and carefully selected European finishes elevate every space. The gourmet kitchen features one-inch-thick Italian quartz countertops, imported Italian cabinetry, an extended entertaining island, premium Wolf appliances, and a Sub-Zero refrigerator. Two luxurious primary suites, one on each level provide exceptional flexibility and privacy, each complemented by a beautifully appointed bath and custom walk-in closet. Private balconies crafted with exquisite boat wood create intimate outdoor retreats, while the private pool completes the home's sophisticated indoor-outdoor lifestyle. The setting is equally exceptional. Via Tuscany offers a coveted Winter Park address near Interlachen Country Club and only minutes from Park Avenue's renowned dining, boutiques, museums, and cultural attractions, with convenient access to Downtown Orlando. This is a residence for the buyer who understands that true luxury is not defined by finishes alone. It is defined by the quality of the materials, the integrity of the construction, the precision of the craftsmanship, and the attention given to what lies behind the walls as much as what is visible within them. RESILIENT BY DESIGN. EXCEPTIONAL BY CONSTRUCTION. REFINED IN EVERY DETAIL.

2661 Via Tuscany, Winter Park

$739,777
4 Beds 2 Baths Lake Waunatta Woods SubDv. 32792 Zip Code
Welcome to Lake Waunatta Woods, where neighbors become family. It is rare to find an exclusive, tight-knit community where neighbors look out for one another, and friendships feel more like family. This charming enclave of homes is a sanctuary of warmth, connection, and tranquility in a well-established Winter Park neighborhood. At the heart of this exceptional community is a beautifully renovated one-story residence, thoughtfully designed and built by its owners with a modern flair. From the moment you arrive, you are greeted by an elegant neutral palette, charming architectural windows and a beautifully pavered driveway leading to the stately four-pane glass front door. Step inside to soaring ceilings, art niches, elegant and an abundance of natural light that creates a warm and inviting atmosphere. To the right of the entry, the formal living room offers versatility and could easily serve as a home office, library, or additional gathering space. The heart of the home is the extraordinary chef's kitchen, beautifully appointed with custom Dovetail Gray cabinetry, oak cabinetry accented with ebony pulls, stacked white subway tile backsplash, farmhouse sink, wine cooler, state-of-the-art appliance package and a spectacular 10-foot island topped with luxurious white quartzite accented by subtle veining. This stunning kitchen flows effortlessly into the family room, creating an ideal space for everyday living and entertaining. Luxury plank flooring, neutral earth tones, and a dramatic wood-burning fireplace surrounded by natural floor-to-ceiling stone add warmth and character, while the abundance of natural light brings the beauty of the outdoors inside. The primary suite is a private retreat styled in a calming ivory palette, with wood floors, beautifully dressed windows and double doors opening directly to the poolside. The primary bath offers a distinctive custom vanity with a charming wooden treasure-chest design and a luxurious walk-in shower finished with stacked white subway tile, sitting bench and multiple shower heads for the ultimate in comfort and relaxation. Each bedroom is thoughtfully equipped with a California Closet system. Two additional generously sized bedrooms and a beautifully updated shared bath complete the one-story floor plan, offering flexibility for every lifestyle. This home has been lovingly maintained and thoughtfully refreshed, with major systems and improvements recently completed, including Andersen windows in 2024, roof in 2024, renovated baths in 2023, blown attic insulation in 2023, water heater in 2025, pool resurfacing in 2021, new salt system in 2026, and a Trane variable-speed air-conditioning system with UV light purification. The fully fenced PVC backyard provides a private setting surrounded by peaceful wooded views and beautifully landscaped grounds featuring Blue Bamboo, Foxtail trees, flower beds, and decorative river rock. Step outside to your own private backyard retreat, complete with a sparkling saltwater swimming pool and generous space for outdoor entertaining, relaxing, and enjoying the Florida lifestyle. A separate detached office/den adds exceptional versatility, featuring electricity, soundproofing and internet connectivity, making it ideal for a private home office, gym, playroom, studio, or creative space. The European-style pergola is equipped with power for lighting and a unique roof and gutter removal system and was thoughtfully designed for outdoor living space.

4039 Cool Water Court, Winter Park

$3,265,000
5 Beds 6 Baths Green Oaks Rep 02 SubDv. 32789 Zip Code
One of the most coveted neighborhoods in all of Winter Park, this exceptional custom-built residence offers a rare combination of timeless design, modern sophistication, and an unbeatable location. Completed in 2017 and first sold in 2018, this 5-bedroom, 5.5-bath home has been meticulously maintained by its original owner and enhanced with high-end designer finishes. Much of the interior was thoughtfully reimagined by renowned designer Ted Maines, resulting in a sophisticated yet timeless aesthetic throughout. Perfectly positioned on a prime oversized corner lot, this remarkable residence blends transitional architecture with modern elegance. Expansive sliding glass doors fill the open-concept living spaces with natural light while creating a seamless connection between the indoors and outdoors. The main living area flows effortlessly from the formal living room and spacious dining area into the gourmet kitchen, complete with custom cabinetry, Carrara marble surfaces, and premium Sub-Zero and Wolf appliances. A refined yet inviting family room with a fireplace provides the perfect setting for everyday living and entertaining. The private first-floor primary suite offers direct access to the lanai and heated saltwater pool and is complemented by a spa-inspired bath with a steam shower and custom his-and-her walk-in closets. A secondary ground-floor bedroom provides exceptional flexibility for guests, multigenerational living, or a private home office. Upstairs, a spacious loft with a custom dry bar leads to a versatile media room. Three additional en-suite bedrooms complete the second level. Recent enhancements include a whole-house generator supported by a 250-gallon buried propane tank, new pool solar equipment, a newly added semi-circular driveway that enhances both curb appeal and functionality, two newer A/C units, and a new 2026 A/C system featuring re-engineered, high-efficiency ductwork designed to provide optimal climate control throughout the home. The outdoor living space is equally impressive, featuring a heated saltwater pool and spa with a cascading waterfall, elegant stone decking, an outdoor shower, ambient lighting, and a covered summer kitchen—perfect for year-round entertaining. A rare three-car garage completes this exceptional property. All of this is just moments from the shops, dining, parks, and unmistakable charm of downtown Winter Park

1761 Legion Drive, Winter Park

$1,949,500
3 Beds 4 Baths Sylvan Lake Shores SubDv. 32789 Zip Code
Experience a rare expression of design-forward lakefront living on Lake Sylvan in the heart of Old Winter Park. Fully remodeled through a comprehensive, down-to-the-studs transformation, virtually every major component is new—giving this approximately 2,400-square-foot residence the quality, systems and finishes of a modern custom home. Framed by mature live oaks and sweeping 180-degree water views, the home combines refined craftsmanship and extraordinary lakefront serenity with warm European Contemporary architecture influenced by Belgian design and Organic Modern principles. Expansive, minimalist-profile windows frame the water from nearly every principal living space, while a dramatic 12-foot sliding glass wall connects the open living area to approximately 1,500 square feet of additional outdoor living. Multiple terraces, an integrated outdoor kitchen and beautifully landscaped surroundings create an exceptional setting for waterfront entertaining or quiet mornings beneath the oak canopy. Inside, natural wood, matte black accents, architectural lighting and tactile materials establish a cohesive, warm and inviting aesthetic. Custom white oak wall panels made in Spain, hand-cut white oak beams and architectural transitions, a textured brick feature wall, built-in Sonos audio and a dedicated entertaining bar reflect the attention given to every detail. The European-inspired kitchen features full-height cabinetry incorporating materials imported from Portugal, extensive integrated pantry storage, a Thermador appliance suite with a 36-inch range and griddle, and a Miele steam oven. Positioned at the heart of the living area, the kitchen creates an effortless setting for everyday life and entertaining, always with the lake close at hand. Each of the home’s three bedrooms includes a private en-suite full bath, with an additional powder room serving the common areas. A flexible lake-view office—currently used as a fitness and sauna studio—offers an inspiring setting for work, wellness or creative pursuits. The primary suite opens through nearly eight feet of accordion-style glass doors to a private rooftop terrace, inviting morning coffee, yoga, sunbathing or evening movies beneath the sky. Beyond its architectural design, the comprehensive transformation includes a new roof and roof components, electrical wiring, plumbing and piping, four-zone HVAC system, windows, stucco, drywall, flooring, kitchen and bathrooms. The result combines the character, proportions and established setting of an Old Winter Park home with the quality, efficiency and peace of mind expected from a modern custom residence. Turnkey, distinctive and intimately connected to the water, this exceptional home brings together architectural vision, modern livability and the coveted Winter Park lifestyle on the shores of Lake Sylvan.

1420 Aloma Avenue, Winter Park

$1,995,000
4 Beds 4 Baths Tantum Add SubDv. 32789 Zip Code
Truly a rare Winter Park offering. Perfectly positioned along the dogleg of the fourth fairway of the historic Winter Park 9-Hole Golf Course, this beautifully renovated four-bedroom, four-bath Mediterranean residence seamlessly blends timeless architectural character with sophisticated modern living. Rich in charm and thoughtfully updated throughout, the home welcomes you with an elegant living room featuring a gas fireplace, classic built-in shelving and abundant natural light. At the heart of the home is a stunning chef's kitchen, complete with custom floor-to-ceiling cabinetry, premium Thermador appliances, a charming breakfast nook and an inviting bar with wine refrigeration that flows effortlessly into the formal dining room, ideal for entertaining. A distinguished first-floor office offers an exceptional work-from-home environment, showcasing a breathtaking custom wall of built-in shelving, cabinetry and an integrated desk. This versatile space also serves beautifully as a library or den. Upstairs, all four bedrooms provide privacy and comfort. The luxurious primary suite features two separate closets, a spacious spa-inspired bath with a soaking tub overlooking the golf course and a private covered balcony perfect for enjoying peaceful morning coffee or evening sunsets. A generously sized secondary suite offers exceptional flexibility with its own custom walk-in closet, en suite bath and private rear staircase, making it ideal for guests, multigenerational living or a secluded retreat. Two additional bedrooms and a well-appointed full bath complete the second level. Updated features include smart house lighting, cabinet and shelving accent lighting, custom built-ins and much more. Designed to embrace Florida's indoor-outdoor lifestyle, the home offers a screened porch accessible from both the dining room and breakfast nook, creating an inviting space for year-round entertaining. Two additional open patios provide the perfect setting to relax while enjoying picturesque golf course views and the tranquil surroundings. Perhaps the home's greatest luxury is its exceptional location. Just steps from the boutiques, acclaimed restaurants, sidewalk cafés and vibrant atmosphere of Park Avenue, this residence offers an unmatched Winter Park lifestyle. Convenient access to downtown Orlando, major hospitals, world-renowned attractions and both Orlando International and Orlando Executive airports makes everyday living as effortless as it is elegant. This is a rare opportunity to own a beautifully updated Mediterranean home in one of Winter Park's most coveted and locations.

922 N Pennsylvania Avenue, Winter Park

$2,569,999
5 Beds 5 Baths Orange Grove Sub SubDv. 32789 Zip Code
Under Construction. Experience the very best of Winter Park living with this stunning new construction home, where sophisticated design, luxury finishes, and an incredible location come together on a quiet tree-lined street. Ideally positioned just a short golf cart ride from Park Avenue, the YMCA, and Interlachen Country Club, this home offers the perfect combination of privacy, convenience, and refined Winter Park living. From the moment you step inside, an impressive foyer greets you, showcasing intricate marble mosaic tile that sets the tone for the craftsmanship found throughout. The open-concept floor plan flows effortlessly into the main living spaces, where the spacious living room serves as the centerpiece of the home with elegant archways, custom shelving with LED underlighting, warm wood beam accents, and a stunning stone-wrapped fireplace creating the perfect balance of sophistication and comfort. Designed for both everyday living and entertaining, the dining room features a beautiful dry bar complete with a wine refrigerator, while the chef’s kitchen is truly the heart of the home. Outfitted with Calacatta quartz countertops, a paneled built-in refrigerator, a full suite of Thermador appliances, and a spacious walk-in pantry, every detail has been thoughtfully selected to deliver both style and functionality. The first-floor primary suite provides a private retreat with generous proportions and a spa-inspired bathroom featuring marble mosaic tile, dual vanities, a freestanding soaking tub, an expansive walk-in shower, and a large walk-in closet. A rare additional first-floor guest suite adds incredible flexibility for family and visitors. Upstairs, the home continues to impress with a spacious loft, a conveniently located laundry room, and three additional bedrooms, offering plenty of room for everyone. Step outside and experience your personal outdoor oasis with a spacious covered lanai featuring a full summer kitchen overlooking the sparkling pool and spa. The oversized backyard provides an abundance of green space, creating the perfect setting for relaxing, entertaining, or enjoying time with family. Additional highlights include impact-rated windows and doors, premium finishes throughout, and an unbeatable location surrounded by some of Winter Park’s most desirable amenities. This is a rare opportunity to own a brand-new home combining thoughtful design, exceptional craftsmanship, and one of Central Florida’s most sought-after lifestyles.

1754 Taylor Avenue, Winter Park

$2,549,000
5 Beds 5 Baths Lake Knowles Terrace Add 02 SubDv. 32789 Zip Code
Under Construction. Nestled along a quiet street in Winter Park’s coveted Tree Streets, this stunning coastal farmhouse new build delivers the perfect combination of timeless architecture, luxury finishes, and an unbeatable location. From the moment you arrive, the home captivates with its warm and inviting facade, charming architectural details, and exceptional curb appeal. Step inside to an impressive open layout where natural light, designer finishes, and meticulous craftsmanship set the tone. The spacious living room serves as the heart of the home, showcasing a sleek electric fireplace, custom built-in bookshelves with LED accent lighting, and expansive pocketed glass sliding doors that create a seamless connection to the outdoor living space. The chef’s kitchen is a true centerpiece, beautifully appointed with Taj Mahal countertops, custom cabinetry with LED underlighting, a premium Thermador appliance package, and a hidden walk-in pantry that blends functionality with luxury. Flowing effortlessly from the kitchen, the dining area offers the perfect setting for hosting, complete with a custom dry bar, additional cabinetry, and a dedicated wine fridge. Designed with a highly desirable layout rarely found in Winter Park, the first-floor features both the primary suite and an additional guest suite. The primary retreat offers generous proportions, beautiful natural light, and private sliders opening directly to its own lanai. The spa-inspired bathroom provides a true escape with marble mosaic flooring, dual vanities, and an elegant wet room featuring a spacious walk-in shower and freestanding soaking tub. Completing the suite is an expansive walk-in closet with its own stackable washer and dryer for ultimate convenience. Upstairs, a spacious loft creates an additional living area accompanied by a full laundry room and three generously sized bedrooms, providing flexibility for family, guests, or additional workspace. Step outside and experience Florida living at its finest. The covered lanai is designed for year-round enjoyment with a fully equipped summer kitchen overlooking the sparkling pool and spa, along with additional green space perfect for relaxing or entertaining. Located in the heart of Winter Park’s iconic Tree Streets, this residence offers one of the area’s most desirable lifestyles. Enjoy the ability to walk to Phelps Park while being just minutes from the Winter Park YMCA, Park Avenue’s renowned shopping and dining, and everything that makes this community one of Central Florida’s most sought-after destinations. Don’t miss this rare opportunity to own a brand-new construction residence in Winter Park’s highly coveted Tree Streets!

1823 Sunset Drive, Winter Park

$5,600,000
5 Beds 6 Baths Maitland Shores First Add SubDv. 32789 Zip Code
This elegant transitional French Provincial residence was the feature home in the Orlando Museum of Art's 2022 "mystery home tour" and is located on a large, elevated corner lot in a quiet and secluded area in the Via’s of Winter Park. This residence has been significantly enhanced inside and out by the current owner. The home features 5,200 square feet of living space and 800+ square feet of outdoor space with 5 bedrooms, 5 bathrooms ensuite, 1 half bathroom, 3 car garage, pool, patio 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 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 slate roof/swooped decorative copper roof with chimney caps, complete chimney rebuild, nine iron French doors, white oak tongue and grove hardwood floors, renovated master bath and two ensuite baths, two new HVAC home units and a new garage mini-split air conditioner. 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. One or more rooms virtually staged

2228 Azalea Place, Winter Park

$1,399,000
3 Beds 3 Baths Vilasa Twnhms SubDv. 32789 Zip Code
Steps from Park Avenue, this architecturally stunning Vilasa townhome blends modern luxury with the timeless elegance of Winter Park living. Designed by Nasrallah Architectural Group, Ted Maines Interiors, and Jordan Builders, the residence showcases an Alys Beach–inspired aesthetic with warm wood accents, wrought iron detailing, and two story block construction for enduring quality. Inside, sophistication is evident throughout: 13' ceilings on the main level and 10' upstairs, level four wall finishes, all wood flooring, Pella double pane windows, and curated designer lighting create a refined atmosphere. The chef’s kitchen is a centerpiece with high end flat panel cabinetry, quartz surfaces, Thermador appliances, and an expansive quartz waterfall island overlooking lush greenery. A private in unit elevator provides effortless access to the second floor, enhancing convenience and accessibility. The primary retreat offers a serene escape with a loft for office or wellness space, a spa caliber bath with soaking tub and oversized shower, and generous closet options. Two additional bedrooms with designer finishes complete the second level, ideal for guests, office, or fitness space. Outdoor living is exceptional with an expansive 40' x 20' private fenced in backyard and covered patio extending from the sliding glass doors — a rare feature in Winter Park townhomes. A 2-car garage with insulated doors completes the residence. Moments from Winter Park’s finest dining, boutiques, museums, lakes, Hannibal Square, and Rollins College, this home offers a rare opportunity to live at the center of it all — wrapped in luxury, design, and timeless style.

512 W Swoope Avenue, Winter Park

$1,049,900
5 Beds 5 Baths Lake Florence Preserve SubDv. 32792 Zip Code
Located in an intimate gated community of just 28 homes and minutes from Downtown Winter Park, this exceptional former K. Hovnanian model home features over $200,000 in builder and custom upgrades. Ideally located just 2 miles from Target and Costco, near the 417, and next to highly regarded private schools including Trinity Preparatory School, this home offers luxury and convenience in an unbeatable location. The stunning Michelson floorplan features an open-concept design with beautiful wood-look tile flooring, a private office, formal dining room, built-in speakers, and designer finishes throughout. The gourmet kitchen showcases quartz countertops, 42” cabinetry, stainless steel appliances, gas cooktop, oversized island, butler’s pantry with wine fridge, and a custom walk-in pantry. Massive 12-foot triple sliding doors open to a resort-style backyard with a pool, custom fire pit, pergola seating, and pre-wire for a gas grill. The first floor includes a private guest suite with pool access, full bath, mudroom, half bath, and oversized three-car tandem garage with overhead storage. Upstairs features an expansive loft and bonus room, spacious bedrooms with walk-in closets, Jack-and-Jill bath, additional full bath, large laundry room, and a luxurious owner’s retreat with tray ceilings, coffee bar, spa-inspired bath, oversized shower, and enormous walk-in closet. Residents also enjoy a private community dock for kayaking, paddleboarding, or sunset views. Additional highlights include a brand-new A/C and countless high-end finishes. TAX SAVINGS! Buyers who qualify for Florida Homestead may also benefit from a proposed 2026 constitutional amendment that could increase the homestead exemption to $150,000 in 2027 and $250,000 in 2028 on non-school property taxes if approved by voters. Buyers should verify eligibility and potential savings with the Seminole County Property Appraiser. A rare combination of luxury, location, privacy, and potential tax benefits—this meticulously maintained home is a must-see!

1448 Lake Florence Way, Winter Park

$3,150,000
3 Beds 5 Baths South Interlachen Place SubDv. 32789 Zip Code
Virtually Staged. Welcome to South Interlachen Place, an exceptional luxury townhome ideally positioned in the heart of downtown Winter Park. Just steps from Park Avenue, this sophisticated residence offers an unparalleled lifestyle defined by elegance, convenience, and access to the area’s finest dining, shopping, and cultural experiences. Thoughtfully designed with 3 bedrooms, 3 full bathrooms, and 2 half baths, this nearly brand-new residence is filled with natural light and refined architectural details throughout. Extensive upgrades include new roof, new exterior doors, new windows, new HVAC systems, new tankless water heater, new private elevator, and more—all with included warranties for added peace of mind and long-term value. A private front patio and double glass entry doors set the tone for the home’s elevated design. Inside, expansive floor-to-ceiling windows, an interior atrium, and skylights create a bright, airy ambiance throughout the main living spaces. The open-concept living and dining areas are ideal for both intimate gatherings and grand entertaining. At the heart of the home, the chef’s kitchen is a true statement of style and function, appointed with premium appliances including a Wolf gas cooktop and Sub-Zero refrigerator. A stunning quartz waterfall island anchors the space, while a dedicated bar and coffee station—complete with a Sub-Zero wine refrigerator and dual beverage drawers—adds a layer of sophistication for effortless entertaining. The second level is a private sanctuary, dedicated to the luxurious primary suite. The spa-inspired bath features dual vanities, a freestanding soaking tub, and an expansive walk-in shower, complemented by a generous custom closet. A refined loft with built-in cabinetry offers a flexible space for a home office or lounge, enhanced by a mini built-in Sub-Zero refrigerator for added comfort and convenience. On the third level, two well-appointed guest suites each feature en-suite baths, with one offering access to a serene open-air atrium—bringing a unique architectural element and tranquil outdoor connection into the home. Seamlessly blending luxury and functionality, the residence is equipped with Lutron lighting and a new private interior elevator providing effortless access from the secure garage to every level, including the rooftop. The crown jewel of this home is the private rooftop terrace, an extraordinary urban retreat designed for elevated living. Complete with a full outdoor kitchen, BBQ, beverage refrigerator, half bath, and fireplace, this space offers multiple lounge and dining areas—perfect for entertaining under the stars or enjoying quiet evenings above the city. Additional features include a secure private garage with storage, guest parking, and the added benefit of a concierge service included in the HOA fee, enhancing convenience and elevating the overall lifestyle experience. This is a rare opportunity to own a truly exceptional, move-in-ready luxury townhome in one of Winter Park’s most coveted locations—where design, quality, and lifestyle converge.

125 S Interlachen Avenue Unit 2, Winter Park

$989,500
1 Beds 2 Baths Village Winterset Inc SubDv. 32789 Zip Code
Winterset is celebrated for its boutique scale, mature landscaping, and timeless Winter Park character. Residents enjoy glimpses of Lake Osceola, tranquil surroundings beneath stately oaks, and the privilege of living in a community where privacy and exclusivity are paramount. This fully remodeled Penthouse Suite's location is unmatched—one block to Park Avenue, offering effortless access to fine dining, boutique shopping, the Morse Museum, Rollins College, and the scenic Chain of Lakes. Whether you’re downsizing, escaping winter months or seeking a refined second home, this residence delivers the perfect blend of luxury, simplicity, and prestige. Designed for comfort and ease, the home welcomes you with a bright, open living space enhanced by crown molding, warm natural light, and a seamless flow ideal for both quiet escapes and intimate entertaining. The primary suite features a generous walk-in closet, while the kitchen offers modern functionality with quality appliances and thoughtful storage. This unit offers its own washer/dryer combo unit, large exterior storage closet, assigned parking space under canopy and extra open parking spaces. Please note rentals are not allowed and no pets except for Service Animals.

269 E Canton Avenue Unit 269, Winter Park

$172,000
2 Beds 2 Baths Hidden Oaks Condo Ph 7 SubDv. 32792 Zip Code
Welcome to this beautifully maintained 2-bedroom, 1.5-bathroom townhouse-style condominium located in the desirable Hidden Oaks Condominium community. This charming unit features a spacious living and dining area with tile flooring throughout the first floor, along with a well-appointed kitchen, breakfast nook, and convenient indoor laundry room. The home has been freshly updated with new interior paint and new blinds throughout, and all appliances are included for added convenience. Step through the sliding glass doors off the kitchen to enjoy a private fenced patio, complete with an additional exterior storage room — perfect for extra storage space or outdoor essentials. Upstairs, you’ll find comfortable carpet flooring throughout, including a generously sized primary bedroom with a large closet, as well as a spacious guest bedroom with ample closet space. Residents of Hidden Oaks Condominium enjoy access to excellent community amenities, including a sparkling community pool and a fenced playground area. The monthly HOA fee includes water and trash services. Ideally located near Full Sail University, University of Central Florida, and Valencia College, with convenient access to shopping, dining, Downtown Orlando, Downtown Winter Park, FL-408, and FL-417. This move-in ready home offers comfort, convenience, and an excellent location. Schedule your private showing today — this opportunity won’t last long!

3243 Forest Oaks Court Unit 117, Winter Park

$1,599,000
5 Beds 4 Baths Fremar SubDv. 32789 Zip Code
Situated in the heart of Winter Park, this custom-built Mediterranean-style estate offers an exquisite living experience that marries timeless architecture with modern innovation. A dramatic grand foyer introduces a residence where every finish has been meticulously curated, from Turkish travertine stone and rich wood flooring to Brizo hardware in Brilliance Polished Gold. At the heart of the home, the chef’s kitchen blends elegance and function with gleaming stainless steel appliances, crisp white cabinetry, granite countertops, and a well-appointed Butler’s pantry with a dedicated bar, creating a sophisticated setting for effortless entertaining. Integrated smart features further elevate daily living, including an intercom system for seamless communication, electronic blackout curtains for instant privacy and ambiance, and thoughtful, layered lighting throughout. The magazine-worthy primary bath—featured in Florida Home—feels like a private spa retreat, with floor-to-ceiling back-lit mirrors, a self-cleaning smart toilet with bidet, a custom Barclay soaking tub with black matte exterior, and Calcutta gold marble countertops and backsplash. These luxe finishes are anchored by an oversized chevron pattern tile by Crossville in Ice White, a throwback diamond-pattern shower floor, and a sculptural Kuzco LED chandelier that completes the space with dramatic flair. Expansive living areas open to resort-inspired outdoor spaces where a heated saltwater pool and spa, private mini-golf green, and a summer kitchen with tongue-and-groove wood ceiling create a true indoor-outdoor sanctuary. Velux solar-powered skylights with acoustic rain sensors that automatically close at the first sign of rain, a Mosquito NIX misting system, comprehensive surveillance, and electronic private gated access provide both comfort and peace of mind. Natural gas service and a dedicated hook-up for a whole-house generator underscore the home’s emphasis on performance and preparedness. Crafted for those who expect uncompromising quality, this Winter Park residence is more than a home—it is a refined sanctuary where architectural presence, rich materiality, and thoughtful technology converge in one coveted address.

1864 Grinnell Terrace, Winter Park

$205,000
3 Beds 3 Baths Hidden Oaks Condo Ph 03 SubDv. 32792 Zip Code
Welcome to Unit 46 at Hidden Oaks, a townhome-style condo nestled in one of Winter Park's most convenient and well-established communities. Ideal for first-time buyers, down-sizers, or investors looking for location and lifestyle in one. The floor plan offers three bedrooms upstairs with two full bathrooms, plus a half bath on the main level — perfect for guests and everyday living. Two reserved parking spots included. The HOA covers the community pool, water, trash, grounds maintenance, and structural upkeep, making this a truly low-maintenance lifestyle. Pets welcome. Hidden Oaks lives up to its name with lush, mature landscaping throughout. Unbeatable location — minutes from Full Sail University, UCF, and Valencia College, with easy access to major Central Florida employers. Downtown Winter Park's dining, shopping, and Park Avenue charm are all within reach. Properties in this community move quickly — schedule your showing today.

3371 River View Way Unit 46, Winter Park

$1,595,000
4 Beds 2 Baths Virginia Heights Rep SubDv. 32789 Zip Code
A distinctive offering where design, location and performative upgrades come together seamlessly. One of the original modern homes in Winter Park, this iconic residence has been thoughtfully reimagined through a designer-led renovation that emphasizes clean lines, natural light, easy maintenance and high durability. The result is a bright, refined space that balances architectural character with modern comfort. A flexible two-level layout offers main living areas on the first floor, complemented by an upper-level studio or retreat space with optional deck access, ideal for today’s lifestyle. Extensively improved with over $260,000 in recent upgrades, the home was enhanced with durability and efficiency in mind. Major improvements include a commercial-grade TPO roofing system with advanced drainage and a 20-year warranty completed in 2024, as well as hurricane-impact aluminum sliders all around with large missile-rated glass and enduring waterproofing. Additional features such as a white reflective roof, whole-house surge protection, updated electrical components, and a new code-compliant deck railing further elevate the home’s long-term value and performance. The outdoor spaces have been equally curated, with mid-century-inspired landscaping designed for beauty and ease of maintenance. Palms, agave and drought-tolerant plantings create a clean, modern aesthetic, while redesigned yard spaces enhance openness and usability. A professionally landscaped east yard, low-maintenance turf on the west side, a five-zone irrigation system, and private well irrigation contribute to a thoughtfully executed exterior environment. An expanded driveway provides ample parking, and outdoor lighting enhances ambiance and function. Just moments from desirable Park Avenue, this architecturally significant modern residence is ideally in one of Winter Park’s sought-after neighborhoods, near Lake Virginia, Rollins College and Winter Park Tennis Center. Set on a quiet, tree-lined corner lot with no through traffic, the home enjoys an elevated position on a natural rise, offering peace of mind with no history of flooding, along with ideal north-facing orientation and beautiful natural light throughout the day.

446 Melrose Avenue, Winter Park

$1,750,000
4 Beds 4 Baths Green Terrace V/140 Lot 3 Blk B SubDv. 32789 Zip Code
Welcome to 1750 Carollee Lane, where timeless charm meets modern luxury. Set on a homesite with desirable southern exposure in the heart of Winter Park, this four-bedroom, 3.5-bath, custom pool and spa residence offers more than 3,200 square feet of thoughtfully updated living space near Park Avenue, the Chain of Lakes and top-rated schools. The fully renovated 2025 kitchen serves as the centerpiece of the home, featuring quartzite countertops, a custom wood hood, Zellige-style backsplash, induction cooktop, oversized workstation sink and an expansive island designed for gathering and entertaining. The first-floor primary suite offers a private retreat with a completely reimagined spa-inspired bath showcasing marble flooring, quartzite surfaces, custom solid wood cabinetry, a freestanding soaking tub and upgraded walk-in shower. Designed for comfort and entertaining, the home also features a dedicated office and an upstairs loft with a custom dry bar and beverage refrigerator. Outdoors, the backyard lives like a private resort-style oasis, complete with a saltwater pool and spa, sun shelf, travertine decking, electronic roll-down screens and a fully equipped outdoor kitchen designed for year-round enjoyment. Lush new backyard landscaping completed in May 2026, including enhanced privacy elements, creates an intimate outdoor setting rarely found this close to the heart of Winter Park. Additional highlights include updated irrigation supported by a private well, a new downstairs HVAC system and a home warranty provided for the buyer at closing. Move-in ready and impeccably maintained, this residence offers refined living in one of Winter Park’s desirable settings.

1750 Carollee Lane, Winter Park

$2,195,000
5 Beds 4 Baths Lugano Terrace SubDv. 32789 Zip Code
Located in highly desirable Lugano Terrace just steps from the shores of Lake Knowles, this stunning all new interiors, 5-bedroom, 3.5-bath brick home effortlessly blends timeless charm with extensive modern updates. Set on a beautifully oversized landscaped lot with a roundabout driveway. Winter Park’s most sought-after neighborhoods adjacent to the Vias, Winter Park Racquet Club and Dommerich Elementary. Inside, wide-plank engineered white pine flooring flows throughout, complementing vaulted ceilings, wood-burning fireplace in the living room, and a spacious open layout ideal for entertaining. The informal dining room overlooks the private backyard and resurfaced PebbleTec pool, while the chef’s kitchen impresses with dual islands, quartz countertops and full-height quartz backsplash, custom hood, Thermador appliances including a 48” six-burner gas range and French door refrigerator. The gorgeous, light filled family room showcases gas fireplace and a built-in bar with wine fridge. The expansive upstairs primary suite is a luxurious retreat, featuring a spa-like bath with a dual-entry shower with Infrared sauna, soaking tub, dual vanities with LED mirrors, expanded closets, and a sitting area. Also upstairs is a flexible loft or library space, an office/nursery with a private balcony, and a bonus exercise room or third closet. Three spacious bedrooms are located downstairs, including a second primary or guest suite with its own en-suite bath and pool access. Notable upgrades include a new roof (2021), PEX plumbing and water heater (2025), updated electrical panels, new propane tank, new AC supply grills and a new second AC system (2025). Additional features include Level 4 smooth drywall, custom trim and moldings, 8’ metal front and double back doors, custom wood interior doors, upgraded light switches and plugs, all-new designer light fixtures ( Regina Andrew, Visual Comfort, etc. ), fireplace surrounds, and custom metal and wood staircase. Black interior and exterior Anderson windows: Dual Pane Low-E Smart Sun Standard Argon Fill Simulated Divided Light (SDL). Outside, enjoy a fully fenced and gated backyard with turf and paver landscaping, updated pool coping, and a covered porch ideal for entertaining, new exterior paint and gas lanterns. The 2-car garage includes custom paneled doors, painted floor and workshop area. Located within walking distance to top-rated Dommerich Elementary, Maitland Middle, and Winter Park High, and just minutes from Park Avenue and the Winter Park Racquet Club and Interlachen Country Club, this home offers exceptional quality, location, and lifestyle. NEW April 2026 Black Steel doors windows with low e-dual pane glass ($150k value!).

1885 Temple Drive, Winter Park