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1441 Grove Terrace, Winter Park
$5,950,000
5 Beds ⋅ 6 Baths ⋅ Sylvan Lake Shores SubDv. ⋅ 32789 Zip Code
Under Construction. Exceptional waterfront living meets European-inspired design in this new Vimaro Homes residence on Lake Sylvan. Positioned on an oversized Winter Park lot with 130 feet of water frontage, the home pairs timeless architecture, richly detailed interiors, and expansive outdoor living. Led by a husband-and-wife team originally from Europe, Vimaro Homes brings together her expertise in interior design and his in construction. Their hands-on approach brings a personal commitment to every selection and detail, prioritizing lasting quality, thoughtful design, and craftsmanship over the cost-driven formulas common in investment-built spec homes. A striking façade and tile roof establish an elegant arrival, complemented by a dual-entry driveway featuring a diamond-patterned composition of turf and concrete. An underground three-car garage preserves the architectural approach, while an elevator connects all three levels. Inside, a marble mosaic entry introduces intricate trim work and classic reeded crown molding, establishing the home’s enduring character. The spacious living room features a marble-wrapped fireplace, custom built-ins with LED up-lighting, and expansive sliding doors framing views of the pool and lake. The kitchen pairs marble countertops and custom inset cabinetry with Perrin & Rowe fixtures and Thermador appliances, including a paneled refrigerator. A substantial scullery with a prep kitchen and pantry supports entertaining, while the nearby dining room overlooks the water. The downstairs primary suite offers a private retreat with its own fireplace and an expansive, custom-fitted walk-in closet with a center island. The primary bath features Casablanca marble tile, dual vanities, Perrin & Rowe fixtures, and a spacious walk-in shower. Upstairs, four additional bedrooms each offer an ensuite bath and walk-in closet, alongside a bonus room, laundry room, and terrace. Throughout the home, natural stone, finely crafted cabinetry, and classic architectural details reflect the team’s European influences. Outdoors, a generous lanai with retractable screens and a full summer kitchen extends the living spaces toward Lake Sylvan. A three-tiered deck brings together a pool, spa, and sweeping water views, while expansive green space and a dock complete the waterfront setting. Set on a brick street moments from Park Avenue’s restaurants, boutiques, and cafés, this residence combines Winter Park’s distinctive character with an exceptional lakefront setting. Shaped by the personal vision and craftsmanship of Vimaro Homes, it offers a refined expression of waterfront living.

1441 Grove Terrace, Winter Park

2011 Harmon Avenue, Winter Park
$849,900
4 Beds ⋅ 3 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Under Construction. Welcome to your NEW Home! This residence to-be-built is a rare single story home. This bright open floor-plan features a large great room open to the kitchen. Enjoy dining at the island and plenty of space to entertain, featuring stainless appliances, and an extra large walk-in pantry (6.8 x 7 ft) to meet all your storage needs. The Primary bedroom is located off of the main living with a spacious (10x 6.5 ft) walk in closet. The primary bath features double sinks and a separate shower and soaking tub as well as a private toilet room. All of the secondary bedrooms are generously sized with signifcant built-in closet space. The extra large laundry space gives ample additional storage. 2 Car garage. Summer Kitchen with a grill available to add-on. Don't wait, take this opportunity to make this pre-construction residence you perfect place to call home.

2011 Harmon Avenue, Winter Park

1441 Palm Avenue, Winter Park
$2,449,000
5 Beds ⋅ 5 Baths ⋅ Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Under Construction. In the heart of Winter Park’s coveted Tree Streets, this stunning residence brings together impeccable finishes, a striking architectural presence, and a location that puts so much of daily life within easy reach. Opportunities to find new construction in this established neighborhood are becoming harder to come by, making this home an especially exciting offering. The front façade makes a memorable first impression, with beautiful curb appeal that carries naturally into the interiors. In the spacious living room, a stone-wrapped fireplace anchors the space, complemented by a built-in entertainment center and display shelving with soft LED underlighting. The kitchen is a standout. Calacatta quartz countertops and an intricate mosaic backsplash set an elegant tone, while a full suite of Thermador appliances, including a paneled refrigerator, brings substance to the beautiful design. A spacious pantry keeps everything tucked away, and a wine bar with a dedicated wine refrigerator makes hosting feel effortless. The primary suite offers a lovely sense of retreat. This spacious bedroom is complemented by a beautifully finished bath with marble mosaic tile, a freestanding tub, and a generous walk-in shower with a rain showerhead. An oversized closet adds the kind of everyday luxury that is just as valuable as the finishes themselves. A rare first-floor guest bedroom gives visitors a comfortable place of their own or offers a space for a dedicated office. Upstairs, three additional bedrooms, each with a walk-in closet, surround a loft that offers room for a second living area, movie nights, or a quiet place to unwind. The outdoor living is equally impressive, with a spacious covered lanai and full summer kitchen overlooking the pool and spa, a beautiful setting for dinners or a quiet afternoon at home. Surrounding green space gives the backyard a sense of openness and room to enjoy the Florida sunshine. With Phelps Park and the YMCA moments away, and Park Avenue’s restaurants and boutiques just a golf cart ride from home, the location is every bit as appealing as the residence itself. Beautifully finished and thoughtfully arranged, this is a chance to enjoy the ease of a brand-new home in a neighborhood whose charm has long been established.

1441 Palm Avenue, Winter Park

1825 Chilean Lane, Winter Park
$450,000
5 Beds ⋅ 3 Baths ⋅ Eastbrook Sub Unit 05 SubDv. ⋅ 32792 Zip Code
Welcome to this beautifully renovated pool home featuring a rare and versatile double primary suite layout! Completely renovated in 2024, this 5-bedroom, 3-bathroom home offers 1,636 square feet of stylish, thoughtfully designed living space with modern finishes throughout. Light gray wood-look plank tile flooring and recessed lighting create a bright, cohesive feel. The contemporary kitchen showcases gray shaker-style cabinetry, sleek black granite countertops, a marble-look tile backsplash with black mosaic accents, stainless steel appliances, and a breakfast bar with seating for four. The first primary suite is privately positioned away from the additional bedrooms and features an ensuite bathroom with a marble-look tiled shower, decorative mosaic accents, multiple shower heads including a rain shower, a frameless glass enclosure, and a gray vanity topped with black granite. The second primary suite provides added flexibility for multigenerational living, extended guests, or a private retreat. Step outside to enjoy your own backyard oasis, complete with an in-ground pool, screened lanai, and fully fenced, spacious backyard with plenty of green space for relaxing, entertaining, and outdoor activities. Ideally located approximately 10 minutes from the restaurants and boutiques of Park Avenue, with convenient access to UCF, Full Sail University, Rollins College, major transportation routes, shopping, and dining. Orlando International Airport is approximately 25 minutes away. With its modern renovations, dual primary suites, and inviting outdoor living space, this home offers a unique combination of comfort, flexibility, and convenience! ROOF - 2024 HVAC - 2025 PLUMBING - 2026 ELECTRICAL - 2024

1825 Chilean Lane, Winter Park

345 Beloit Avenue, Winter Park
$1,625,000
3 Beds ⋅ 3 Baths ⋅ Morseland Sub SubDv. ⋅ 32789 Zip Code
Historic Winter Park charm with modern updates, close to N Park Avenue. Set on a picturesque, tree-lined street, this thoughtfully renovated home puts you minutes from Winter Park's restaurants, sidewalk cafés, boutique shops, art galleries, Central Park, and year-round festivals. You get the character of an established historic neighborhood with the comforts of modern living. Set back amid mature landscaping, the home greets you with a charming front porch and an elegant entry with marble floors, arched windows, and beautiful architectural details. Inside, spacious rooms feature rich hardwood floors, crown molding, wainscoting, and plantation shutters. The updated kitchen offers bright cabinetry, stone countertops, a generous island, stainless steel appliances, and a gas range, all opening to a living area with a classic fireplace and custom built-ins. An exceptionally spacious flex room lined with custom cabinetry and shelving works beautifully as a home office, library, or creative studio. The primary suite includes a beautifully remodeled bath with a freestanding soaking tub, oversized glass-enclosed shower, dual vanities, and a customized walk-in closet. Generously sized secondary bedrooms add flexibility for family, guests, or a second workspace. Outside, a private fenced backyard shaded by mature trees features a brick-paver patio made for outdoor dining or quiet relaxation. A rear-access garage adds convenience without disrupting the home's charming streetscape. Timeless character, extensive modern updates, and an exceptional location near the heart of Winter Park. Come enjoy the distinctive lifestyle that makes this community so desirable. Schedule your private showing today.

345 Beloit Avenue, Winter Park

2352 Sun Valley Circle, Winter Park
$280,000
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Welcome to the established and well-maintained community of Cedarwood Village in highly desirable Winter Park! TREE-LINED STREETS lead to this END UNIT, COMPLETELY REMODELED IN 8/2026 and MOVE-IN READY. This 2-bedroom, 2-bath, BLOCK-CONSTRUCTED condominium offers nearly 1,500 square feet of interior living space and includes a versatile LOFT. As you enter the foyer, you’ll immediately appreciate the attention to detail and pride of ownership, with WOOD FLOORS and fresh neutral paint setting the tone for a stylish and inviting interior. The GREAT ROOM is truly the centerpiece of the home, featuring dramatic 2-story VAULTED CEILINGS that create an exceptionally open, voluminous, and luxurious atmosphere. A magnificent corner focal point showcases a cozy WOOD-BURNING FIREPLACE with raised slate tile hearth, while mantle columns extend the full height of the room and frame a soaring vertical mirror that reflects natural light and visually expands the space. TWO SKYLIGHTS further enhance the natural light. From the living area, enjoy serene views of the lanai and lush GREEN SPACE beyond. A stylish WET BAR is tucked into a recessed alcove and beautifully illuminated by warm integrated accent lighting, featuring a POLISHED GRANIT COUNTERTOP and contemporary shaker-style cabinetry—perfect for entertaining. The second-story LOFT provides an incredible overlook into the Great Room below and serves as a highly desirable FLEX SPACE, complete with BLACK WROUGHT-IRON SPINDLE RAILING, modern neutral carpeting, its own SKYLIGHT, and a convenient STORAGE CLOSET. The kitchen features sleek light-gray SHAKER-STYLE CABINETRY, elegant GRANITE COUNTERTOPS, and premium STAINLESS-STEEL APPLIANCES. An oversized peninsula island with deep undermount sink and gooseneck faucet doubles as a breakfast bar for casual dining and entertaining. A charming EAT-IN NOOK overlooks the PRIVATE COURTYARD and provides access through wide sliding glass doors, creating the perfect spot for morning coffee or outdoor dining. For added convenience, the laundry closet, complete with WASHER AND DRYER, is conveniently located within the kitchen. The PRIMARY SUITE offers a peaceful retreat with both WALK-IN and step-in closets, direct lanai access through sliding glass doors, and a beautifully REMODELED ENSUITE BATH accessed through a stylish modern barn door. The bath features a DUAL-SINK VANITY, large walk-in shower with frameless glass door, and private water closet. The spacious SECOND BEDROOM also features a WALK-IN CLOSET and convenient access to the REMODELED HALL BATH, providing privacy for residents while comfortably serving guests. Additional features include a location directly across from green space, 2 DESIGNATED PARKING spaces in front, and a PRIVATE MAILBOX. With LOW HOA DUES, residents enjoy a sparkling community pool, clubhouse, tennis and basketball courts, pickleball, FENCED DOG RUN, and pet walk with waste stations. Monthly fees also include ROOF AND EXTERIOR BUILDING MAINTENANCE, PEST CONTROL, and LANDSCAPING. This ideal Winter Park location is directly across from Casselberry Commons, offering a variety of major retailers, Publix, and fast-food options. Just minutes from Park Avenue, UCF, Rollins College, Full Sail University, shopping, restaurants, entertainment, and medical facilities, this exceptional home combines sophisticated living with convenience in one of Central Florida’s most desirable locations. See video and virtual tour.

2352 Sun Valley Circle, Winter Park

1940 Magnolia Avenue, Winter Park
$1,190,000
4 Beds ⋅ 4 Baths ⋅ Temple Terrace Annex SubDv. ⋅ 32792 Zip Code
New roof fall 2026! Exceptional custom-built estate offering unparalleled security, efficiency and peace of mind on two expansive lots in the heart of Winter Park. This split-plan three-bedroom and 2.5-bath home has over 4,880 total square feet in the main home and 1,944 total square feet in the detached in-law/office unit under roof. Constructed with solid poured concrete block and 1-inch insulation, this remarkable residence was designed to withstand the test of time while delivering modern luxury and comfort. A rare feature, the home includes two reinforced safe rooms built with rebar-reinforced solid poured concrete walls and 12-inch concrete ceilings, along with a built-in, concrete-bolted safe. Additional security enhancements include a full alarm system and security spotlights. Designed for everyday living and entertaining, the property is equipped with a full-house 22-kilowatt generator, a buried 500-gallon propane tank, propane gas range and outdoor grill, two tankless water heaters, whole-house water softening and filtration systems, EV charging capability and energy-efficient construction resulting in remarkably low utility costs. The well-appointed kitchen features a solid wood cabinetry, quartz countertops, a kitchen, butler pantry, coffee bar and laundry room, Verona gas range, Frigidaire Professional French-door refrigerator, KitchenAid dishwasher, convenient under-counter outlets and the kitchen island has lighted shelves. Additional highlights include plantation shutters throughout, wine cellar, climate-controlled storage attic, granite in baths, custom garage cabinetry, epoxy-finished garage floors, hurricane-impact windows in the office/apartment, Pet Turf in the entire backyard with no maintenance necessary and a striking 35-foot flagpole. Combining superior craftsmanship, advanced infrastructure and thoughtful upgrades rarely found in today's market, this extraordinary property presents a unique opportunity to own a one-of-a-kind residence. Total heated square footage includes heated/cooled space to use as garage, workshop, and/or utility room in the detached structure.

1940 Magnolia Avenue, Winter Park

1200 Via Salerno, Winter Park
$5,995,000
5 Beds ⋅ 6 Baths ⋅ Cloister Grove Sub SubDv. ⋅ 32789 Zip Code
Some homes are built, and some are composed. At 1200 Via Salerno, every finish, fixture, & detail was chosen with one goal in mind: a residence that is a pleasure to live in every day and will feel just as right decades from now. Set on nearly half an acre in the highly desirable Vias of Winter Park, this fully renovated, turnkey home is modern European design at its most elegant and understated, with bespoke cabinetry & built-ins in every room and rare natural stone throughout. It offers five bedrooms, five full baths, a half bath, and has been curated with the care of a private collection. A sculptural curved staircase greets you in the foyer, and wood floors carry through the main level. The living room rises beneath vaulted ceilings, centered on a gas fireplace wrapped in Sequoia quartzite, with a wall of sliding glass doors opening to the pool so gatherings drift outdoors without a second thought. In the kitchen, rare leathered Naica quartzite forms the waterfall island, countertops, & backsplash, and custom cabinetry rises floor to ceiling. Appliances include a Wolf gas range with pot filler, Sub-Zero refrigerator, & two Miele dishwashers, plus a prep sink, concealed outlets, & push-to-open, soft-close drawers. To one side, a pantry/butler’s passage with matching cabinetry also houses the laundry. At the front of the home, a bright formal dining room & eat-in area complete the space. Just off the eat-in area, a large turf side courtyard offers a low-maintenance space where kids & pets can play within view of the kitchen. The main-level primary suite features two walk-in closets & a double-sided wood-burning fireplace shared with the private office. The spa-inspired bath showcases leathered Taj Mahal quartzite with integrated dual sinks, an extra-large soaking tub for two, & a walk-in shower, all with Graff fixtures. The office opens to the pool and is outfitted with floor-to-ceiling shelving, cabinetry, & file drawers, versatile enough to become a dressing room. The whiskey lounge with custom wet bar is sized for a game room or second office. A powder room completes the main floor. Upstairs, custom cabinetry lines the loft & hallway, offering storage at every turn. To the left, two bedrooms share an elegant bath with dual sinks and a separate tub & shower, and a single door closes them off creating an optional, private two-bedroom suite. To the right, two additional bedrooms each enjoy an en suite bath. Every bedroom is finished with built-in closets. A separate upstairs wing houses the generously sized media room, with state-of-the-art surround sound & extensive hidden storage. Outdoors, a weathered marble pool deck surrounds the saltwater pool, framed by grounds created by Signature Landscape. The garden pavilion with its own fireplace is one of the home’s most special spaces, joined by a summer kitchen with stone counters & wall, a natural gas grill, & a sink, plus a pool bath. Additional features include a three-car side-entry garage with epoxy floors, EV charger capability, & ample storage, along with Lutron lighting on the main level, Toto toilets throughout, water filtration, natural gas, a whole-home generator, & three Trane HVAC systems. The Winter Park Racquet Club, Interlachen Country Club, the shops & dining of Park Avenue, and the Winter Park 9 golf course are all within walking distance. Refined, move-in ready, and crafted without compromise, 1200 Via Salerno awaits its next owner.

1200 Via Salerno, Winter Park

1735 Demetree Drive, Winter Park
$1,050,000
4 Beds ⋅ 3 Baths ⋅ Waterbridge SubDv. ⋅ 32789 Zip Code
Beautifully maintained Winter Park pool home with a 2026 whole-home repipe, 2019 roof, and 2022 A/C in the desirable Waterbridge neighborhood. Discover the charm of established Winter Park living in this inviting single-story home, situated on a beautifully landscaped 0.36-acre lot in the sought-after 32789 ZIP code. Spacious living areas, abundant natural light, and two inviting fireplaces, including a fireplace in the living room and a distinctive stone fireplace in the primary suite, create a warm and welcoming atmosphere. Step outside to your private swimming pool, surrounded by mature landscaping, offering the perfect setting for relaxing or entertaining. Additional features include a tankless water heater, updated pool equipment, and access to Waterbridge neighborhood tennis courts. An exceptional Winter Park location. Enjoy convenient proximity to AdventHealth Winter Park Hospital, the Winter Park VA Clinic, and Winter Park High School, along with easy access to downtown Winter Park's iconic Park Avenue, renowned restaurants, boutique shopping, Rollins College, Mead Botanical Garden, and downtown Orlando. Combining valuable improvements, single-story convenience, private pool living, and an established neighborhood setting, 1735 Demetree Drive offers the character, comfort, and lifestyle that make Winter Park, Florida, such a desirable place to call home.

1735 Demetree Drive, Winter Park

2330 Westminster Ct., Winter Park
$985,000
5 Beds ⋅ 3 Baths ⋅ Glencoe Sub SubDv. ⋅ 32789 Zip Code
Expect to be impressed by this stunning, renovated 5-bedroom, 3-bathroom home in desirable Winter Park, where modern elegance meets timeless charm. Thoughtfully redesigned from top to bottom, this exceptional residence offers a bright, open feel with multiple living spaces perfect for everyday living and entertaining. The light-filled kitchen features quartz countertops, stainless steel appliances, and a custom backsplash, creating a stylish and functional space for cooking and gathering. Spacious family and game rooms provide plenty of room to relax and entertain, while a sun-filled bonus room offers endless possibilities as a home office, playroom, fitness room, or creative space. Two bedrooms on the first floor provide flexibility for guests, a private office, or multigenerational living. Upstairs, the beautifully redesigned primary suite serves as a private retreat, complete with a gorgeous en-suite bathroom featuring a walk-in shower and soaking tub. Two additional bedrooms and a full bathroom complete the second floor, offering comfortable accommodations and room for everyone. Step outside to enjoy the expansive 0.34-acre lot tucked away on a peaceful cul-de-sac, with plenty of space for outdoor entertaining, play, and relaxation. The oversized detached garage offers 500+ additional square feet of versatile space, ideal for hobbies, projects, a workshop, or extra storage. With no HOA restrictions, you’ll have the freedom to make the property your own. The location is just as impressive, with Lake Killarney just steps away and Park Avenue and Winter Park Village only a short drive away for premier shopping, dining, and entertainment. Convenient access to I-4 makes commuting and exploring Central Florida a breeze. Combining thoughtful renovations, flexible living spaces, an oversized lot, and an unbeatable Winter Park location, this home is a rare opportunity to enjoy the best of Florida living. Schedule your private showing today!

2330 Westminster Ct., Winter Park

1825 Whitehall Drive, Winter Park
$3,195,000
4 Beds ⋅ 6 Baths ⋅ Kenilworth Shores Sec 06 SubDv. ⋅ 32789 Zip Code
1825 Whitehall Drive announces itself in stone. Twin gables of whitewashed stone, a stately brick entry, and striking black-framed windows define its European-inspired architecture in Winter Park’s coveted Kenilworth Shores. Brand-new and awaiting its first owner, this expansive custom residence offers over 4,300 square feet of timeless character and bespoke craftsmanship. Inside, natural light moves across wide-plank engineered white oak floors. Grand entertaining spaces meet intimate rooms. Architectural symmetry defines the great room, where a soaring fluted terrazzo fireplace is framed by custom cabinetry and brass picture lights. Expansive glass opens to the lanai, while a sitting room features a custom bar with brass mesh cabinetry, illuminated shelving, glazed tile, and wine refrigeration. The kitchen is a masterpiece, and you'll know it the moment you walk in. A Taj Mahal quartzite island commands the room, framed by floor-to-ceiling bespoke cabinetry, illuminated reeded glass, and a sculptural fluted hood. Sweeping waterfall edges meet a custom fluted wood base. A 48-inch Viking gas range, double ovens, and separate refrigerator and freezer columns complete the kitchen. Beyond, a windowed butler’s pantry offers quartzite countertops, illuminated shelving, and beverage refrigeration. Opening to the pool, the dining room invites memorable dinners that linger long after the last guest should have left. And then there's the first-floor primary suite—where luxury becomes personal. Vaulted ceilings with stained oak beams bring warmth and architectural character, while the bathroom is a destination in itself. Brass-inlaid marble floors, lilac-veined stone, a quartzite double vanity, and makeup station introduce a spectacular wet room with four rainfall showerheads, two handheld showers, and a sculptural fluted soaking tub. An oversized, fully customized walk-in closet features built-in cabinetry and elegant glass-front displays. Just off the foyer, the library is a room you'll fall in love with. Color-drenched walls, a stained oak-plank ceiling, custom built-ins, and brass-lit shelving create an intimate retreat, enclosed in glass with doors to a secluded side patio. The mudroom, plum-cabinetry laundry, and plaster-inspired powder bath complete the level. Upstairs, a light-filled loft opens to an uncovered terrace with checkerboard stone flooring, made for sunset conversations beneath the stars. Three bedrooms each feature an en-suite bath and custom closet. A jewel-box powder bath and vaulted bonus room, ideal for a cinema or game lounge, complete the level. Outside, a covered lanai with stained tongue-and-groove ceiling features a summer kitchen in whitewashed brick, fluted cabinetry, and leathered granite. French-pattern Talya leathered stone frames the PebbleTec pool, tanning ledge, inset spa, and calming waterfall—a setting made for sunlit afternoons, entertaining, and memorable evenings. Custom-built by Structure Redevelopment, LLC, this residence reflects a passion for distinctive architecture, superior craftsmanship, and uncompromising detail. Among Kenilworth Shores' distinguished residences and lakefront estates, it places you moments from Park Avenue’s restaurants, boutiques, and cafés, Rollins College, and the Chain of Lakes. Schedule your private showing today.

1825 Whitehall Drive, Winter Park

1600 Legion Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Green Oaks Rep SubDv. ⋅ 32789 Zip Code
Long before this home stood gracefully on its prominent corner, it existed as a vision in the mind of master builder Keith D. Field. Conceived as the opposite of a production home, it was crafted with a builder’s eye for structural integrity, thoughtful flow, and a seamless connection between indoors and out. Set on a generous 91-foot wide lot, this custom residence offers 5 bedrooms and a floor plan that feels both substantial and inviting. A wide front veranda sets a timeless tone from the moment you arrive. Dark-framed windows and doors create a striking contrast, while manicured hedges and brick-paved drives enhance the classic curb appeal and highlight the home’s architectural details. Step inside and you immediately sense that this is more than just a beautiful house—it’s a home with a story. At its heart is the reclaimed pine flooring, sourced from a Florida bridge. Rich with character, worn in all the right ways, these floors bring a warmth and authenticity you simply cannot replicate with something new. A long, gracious foyer introduces the main living spaces. To your left, a handsome study/office with a brick fireplace offers an intimate retreat for working. To your right, a formal dining room with garden views comfortably accommodates twelve. A discreet swing door leads to a well-appointed wet bar and large walk-in pantry, which then opens into the expansive kitchen. The kitchen is the true hub of the home, anchored by coffered ceilings, an oversized island, a full suite of high-end appliances, abundant cabinetry, and extensive counter space. A light-filled dinette offers the perfect spot for casual meals. At the center of the home, an oversized great room draws everyone together with its tall brick fireplace, built-in display/bookshelves, and high ceilings that add volume without sacrificing warmth. Two bedrooms are thoughtfully located on the main level, including the primary suite, privately positioned in one of the quietest corners of the home. Filled with soft natural light, accentuating the detailed millwork that runs from floor to ceiling. The primary bath is a retreat in itself, featuring slate flooring, double vanity, claw-foot soaking tub, water closet, walk-in shower with rain head, and a massive custom walk-in closet. The second main-level bedroom functions beautifully as a guest suite or flexible space, with an en-suite bath that also serves as a pool bath, a built-in Murphy bed with integrated cabinetry. A back facing staircase leads to two additional en-suite bedrooms on the second level. At the top of the landing, a large built-in workstation creates an ideal homework or creative zone, and both bedrooms enjoy access to a full-length front balcony. At the back of the home, a separate staircase leads to the fifth bedroom—a wonderfully private suite with dormer windows, angled ceilings with beams, and its own en-suite bath. In addition to a walk-in closet, cleverly designed built-in storage along the walls ensures a place for everything. Off the great room, a covered lanai with tongue-and-groove wood ceiling and brick built-in grilling station creates a comfortable space for year-round relaxation. A 45-foot lap pool is anchored by a striking cabana with fireplace, evoking a resort-inspired setting for long afternoons, evening gatherings, and memorable celebrations. This is a rare opportunity to own a thoughtfully crafted estate where history, craftsmanship, and everyday comfort come together in perfect balance.

1600 Legion Drive, Winter Park

1681 Woodland Avenue, Winter Park
$2,629,000
5 Beds ⋅ 5 Baths ⋅ Comstock Park SubDv. ⋅ 32789 Zip Code
Under Construction. A striking interpretation of Modern Tudor design brings a fresh architectural presence to one of Winter Park’s charming brick streets. Newly built, this stunning residence pairs a distinctive façade with interiors that feel both richly detailed and effortlessly livable. From the marble mosaic foyer to the private poolside retreat, each space offers its own expression of luxury, creating a home with character, warmth, and a beautiful sense of arrival. Beyond the entry, the spacious living area unfolds beneath shiplap ceiling details that lend texture and architectural depth. A statement wall with an electric fireplace anchors the room, establishing an inviting setting for quiet evenings and lively gatherings alike. The kitchen takes center stage with Taj Mahal countertops and a full suite of Thermador appliances. A built-in paneled refrigerator preserves the cabinetry’s seamless appearance, while a spacious walk-in pantry provides ample storage beyond the main kitchen. Positioned downstairs, the primary suite offers a peaceful retreat with a spacious closet and a beautifully composed spa bath featuring dual vanities, a freestanding soaking tub, and a separate shower with a rain showerhead and marble mosaic tile. A second downstairs guest suite adds exceptional versatility, a rare feature for the area, providing comfortable accommodations for visitors or a space for a private office. Providing comfortable accommodations for visitors or an inspiring space for a private office. Upstairs, three additional bedrooms, each with a walk-in closet, offer room for family and guests. A spacious loft introduces another place to gather, unwind, or create a dedicated media or recreation space, while the upstairs laundry room brings convenience to daily routine. Outdoors, a covered lanai with a summer kitchen sets the scene for alfresco dining and entertaining space. Lush landscaping surrounds the pool and spa, creating a beautiful backdrop for entertaining or simply enjoying the Florida lifestyle. Energy efficient doors and windows complete the home’s thoughtful collection of features. The location places neighborhood favorites within easy reach, with Phelps Park and the YMCA just a walk away and Park Avenue’s shops, restaurants, and cafés a short golf cart ride from home. Distinctive in its architecture and generous in its design, this residence offers a compelling opportunity to enjoy brand-new construction amid the established charm of Winter Park.

1681 Woodland Avenue, Winter Park

1751 Glencoe Road, Winter Park
$3,390,000
5 Beds ⋅ 7 Baths ⋅ Forest Hills SubDv. ⋅ 32789 Zip Code
Set along a picturesque brick street in Winter Park’s coveted Lake Sue District, this extraordinary residence delivers the scale, craftsmanship, and thoughtful design rarely found in such a desirable location. Positioned on an expansive homesite with an impressive architectural façade and meticulously curated landscaping, the home makes an unforgettable first impression before revealing an interior designed for both elevated entertaining and everyday living. A dramatic foyer with soaring 22-foot ceilings introduces an exceptional floor plan. To one side, a color-drenched private office is enveloped in custom trim work, while the formal dining room opposite features floor-to-ceiling windows and an elegant coffered ceiling. Beyond, the expansive living room is anchored by a stone-wrapped fireplace and framed by arched built-in shelving with integrated LED lighting. Natural wood beams add warmth and architectural character, creating a space that feels equally refined and inviting. The chef’s kitchen is a statement in both beauty and performance, showcasing custom cabinetry, quartz countertops, a professional Wolf gas range, and an oversized paneled Sub-Zero refrigerator. Overhead beams bring dimension to the space, while the adjoining breakfast nook, with custom built-in bench seating offers a charming setting for casual dining. A generously sized butler’s pantry and laundry room provide exceptional storage and functionality. Privately positioned on the main level, the primary suite opens directly to the covered lanai. Its spa-inspired bath is finished in beautiful marble and features dual vanities with floating mirrors, an expansive wet room with a freestanding soaking tub, and a fully customized wardrobe by award-winning Idelli Closets. Upstairs, a spacious loft creates an additional living area surrounded by four generously proportioned bedroom suites, each complete with a private bath and walk-in closet. A second laundry room adds convenience to the upper level. The outdoor setting rivals a private resort. A magazine-worthy summer kitchen anchors the expansive covered lanai, while retractable screens allow for comfortable year-round entertaining. Beyond, a heated pool and spillover spa are complemented by marble decking and additional green space. Just moments from Lake Sue, Park Avenue, Rollins College, East End Market, and zoned for highly sought-after Audubon Park School, this remarkable residence presents an exceptional opportunity to experience one of Winter Park’s most compelling homes.

1751 Glencoe Road, Winter Park

1407 Broad Wing Lane, Winter Park
$482,000
3 Beds ⋅ 3 Baths ⋅ Enclave At Hawks Crest SubDv. ⋅ 32792 Zip Code
Welcome to The Enclave at Hawks Crest! This 2019-built townhome offers 3 bedrooms, 2.5 baths, and 2,308 sqft of modern, open-concept living. The main level flows from the foyer into a bright living/dining area and an island kitchen with granite-look counters, subway tile backsplash, and a full stainless appliance suite. Wood-look vinyl plank flooring throughout the living areas; carpeted bedrooms upstairs including a primary suite with tray ceiling, dual vanity, and glass-door walk-in shower with large-format tile. A versatile loft adds flexible living space. Step out to the covered lanai with ceiling fan overlooking a wooded view. 2-car garage plus a laundry room with sink and cabinetry. Enjoy resort-style community amenities — clubhouse, pool, playground, and park — minutes from Winter Park shopping and dining. HOA $333/mo. Call and schedule your showing today!

1407 Broad Wing Lane, Winter Park

2613 Lafayette Avenue, Winter Park
$1,699,900
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Under Construction. Nearly complete... be in for the holidays!!!!! Introducing 2613 Lafayette Avenue, a striking new construction residence by LUIH Luxury Homes, bringing warm contemporary design and effortless living to Winter Park. Offering 2,661 square feet, four bedrooms, three-and-a-half baths and a two-car garage, the home pairs a refined architectural presence with light-filled interiors and a highly considered floor plan. At the heart of the home, an expansive open-concept living space brings together the kitchen, dining and family areas for an easy sense of connection. The designer kitchen makes a statement with an oversized island, extensive cabinetry, integrated appliances and sophisticated finishes, while large windows and glass doors invite natural light throughout the main living areas. A first-floor guest suite offers added flexibility for visitors, a private office or multigenerational living. Upstairs, the primary suite is joined by two additional bedrooms, creating a comfortable separation between everyday living and private spaces. The primary retreat features a generous walk-in closet and a spa-inspired bath designed with a soaking tub, dual vanities and an oversized shower. Outside, the covered lanai extends the living space into the backyard, overlooking a private pool and landscaped surroundings, an inviting setting for relaxed afternoons, entertaining and year-round Florida living. With its soft neutral palette, natural textures, modern detailing and thoughtfully connected spaces, 2613 Lafayette Avenue offers a fresh take on new construction in Winter Park, sophisticated without feeling overly formal and designed for the way people live today. Ideally situated near the area’s dining, shopping, parks and everyday conveniences, the residence pairs the ease of new construction with the lifestyle and sense of place that make Winter Park so desirable.

2613 Lafayette Avenue, Winter Park

112 Bell Place, Winter Park
$575,000
3 Beds ⋅ 2 Baths ⋅ Eastgate Sub SubDv. ⋅ 32792 Zip Code
Welcome to 112 Bell Place, a spacious 3-bedroom, 2-bath home offering 2,253 square feet in an established Winter Park neighborhood. Tucked away on a quiet cul-de-sac with a large lot and minimal through traffic, this home offers a great opportunity for buyers looking to move right in and make updates over time, or for an investor looking for a property with great bones and plenty of potential. Inside, you’ll find generous living spaces including a living room with laminate wood flooring and vaulted ceiling, plus a large family room featuring a brick accent wall. The kitchen offers solid wood cabinetry, cooktop, oven and microwave with plenty of opportunity to update and make it your own. All three bedrooms feature built-in closets, while the primary suite includes wood-look laminate flooring and a private bath with shower. The guest bath offers a tub and tile flooring. Additional features include a one-car garage, exterior laundry area, and a hall closet already plumbed for a washer and dryer should the new owner prefer to bring the laundry indoors. With its spacious floor plan, large lot and solid foundation for future improvements, this home has so much potential. Conveniently located in Winter Park and currently zoned for Lakemont Elementary, Maitland Middle and Winter Park High School, this is a great opportunity to get into a sought-after area and add your own style over time. Move in now, renovate at your own pace, and make this Winter Park home your own! Buyer to independently verify school zoning.

112 Bell Place, Winter Park

2322 Woodcrest Drive, Winter Park
$650,000
4 Beds ⋅ 2 Baths ⋅ Kenilworth Estates 1st Add SubDv. ⋅ 32792 Zip Code
Set on a quiet, landscaped, quarter-acre lot, this 4-bedroom, 2-bath POOL HOME offers a rare combination of privacy, space and neighborhood charm - all within the Kenilworth Shores neighborhood of Winter Park. Step inside to find an open and inviting great room filled with natural light and framed by sliding doors overlooking the pool and backyard. At the center of the home, the fully remodeled kitchen features shaker-style cabinetry with a built-in pantry, granite countertops, stainless steel appliances and a large breakfast bar with plenty of space for casual dining and entertaining. Step outside to the screened porch and pool, creating a wonderful extension of the living space for year-round Florida living. The landscaped yard includes an irrigation system and plenty of outdoor space. The primary suite features a walk-in closet and fully updated ensuite bathroom showcasing a beautiful granite topped vanity, updated fixtures and new shower. The renovated hall bath features a granite topped vanity with dual sinks, tile and fixtures. Major updates include a BRAND NEW HVAC system installed in 2026, NEWER ROOF and water heater, insulated DOUBLE PANE WINDOWS, and a new septic drainage field in 2024. The oversized two-car garage and large driveway provide plenty of parking and storage. The location puts you close to so much of what makes Winter Park desirable. WINTER PARK HIGH SCHOOL is within walking distance, with Brookshire Elementary and Glenridge Middle also nearby. Park Avenue is a 10 minute drive, while Baldwin Park and the Lake Baldwin trail and dog park are a five minute walk from the home. Enjoy easy access to Full Sail University, UCF, Valencia College, major transportation routes and Orlando International Airport. With its extensive updates, private pool and convenient Winter Park location, this home is truly move-in ready—schedule your private showing today and come see everything 2322 Woodcrest Drive has to offer!

2322 Woodcrest Drive, Winter Park

2823 Parkland Circle, Winter Park
$3,250,000
5 Beds ⋅ 6 Baths ⋅ Lake Forest Park SubDv. ⋅ 32789 Zip Code
JUST COMPLETED NEW CONTRUCTION in the heart of Winter Park. Tucked away on a quiet cut-de-sac in an established neighborhood surrounded by beautiful newer residences, this nearly 4,500 square-foot home pairs thoughtful design with exceptional indoor-outdoor living. An impressive entry foyer sets the tone for a residence filled with designer details and and a floor plan featuring five en-suite bedrooms, six full baths, and the convenience of two laundry rooms to serve each floor. At the heart of the home, the chef's kitchen is appointed with Thermador appliances and designed for every day living and entertaining. Expansive living spaces are anchored by an indoor fireplace, and flow seamlessly to the covered lanai, where a second fireplace, fully equipped outdoor kitchen and private pool create an exceptional setting for year-round Florida living. Outdoor lush tropical landscaping and striking gas lanterns give the home a distinctive sense of arrival and timeless curb appeal. An oversized garage provides generous space for vehicles and storage, while integrated smart-home features including cameras, alarm, smart switches, and speakers with Sonos, bring modern convenience throughout. Zoned for sought-after Audubon Park School and Winter Park High School.

2823 Parkland Circle, Winter Park

513 Dunraven Drive, Winter Park
$1,950,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 03 SubDv. ⋅ 32792 Zip Code
Under Construction. Anticipated for completion in January 2027, this new-construction luxury home in Winter Park's Kenilworth Shores neighborhood offers five bedrooms, 4.5 baths and a thoughtfully designed floor plan with a first-floor primary suite. Located at 513 Dunraven Drive, the residence combines timeless architecture, refined finishes and indoor-outdoor living in an established Winter Park setting. The open-concept main level features engineered hardwood flooring, spacious living and dining areas, and a kitchen appointed with quartz countertops, a large center island, walk-in pantry and premium Thermador appliances, including a paneled refrigerator, gas cooktop and microwave-oven combination. The first-floor primary suite includes an en-suite bath and expansive walk-in closet, while a second main-level bedroom and full bath provide flexibility for guests or a home office. Upstairs, three additional bedrooms, two full baths, a spacious loft and dedicated laundry room complete the floor plan. Outdoor living centers around a covered lanai with tongue-and-groove ceiling detailing, summer kitchen and private saltwater pool and spa. A welcoming front porch with matching architectural accents, mudroom and electric vehicle charger add comfort and convenience. The Kenilworth Shores location places residents near some of Winter Park's most popular outdoor destinations, including the Cady Way Trail and nearby parks, with opportunities for walking, cycling, golf and recreation. Shopping and dining are easily accessible in Baldwin Park Village Center and along Winter Park's renowned Park Avenue, while everyday conveniences and AdventHealth Winter Park are also nearby. This location offers a balance of neighborhood tranquility and convenient access to the amenities that define the Winter Park lifestyle.

513 Dunraven Drive, Winter Park

266 N Ranger Boulevard, Winter Park
$724,900
4 Beds ⋅ 3 Baths ⋅ Winter Park Pines SubDv. ⋅ 32792 Zip Code
FULLY RENOVATED Winter Park Pines Home with Mother-in-Law Suite, NO HOA & Prime Location! Welcome to this beautifully transformed Winter Park Pines residence, where modern design, thoughtful upgrades, and flexible living spaces come together in one exceptional home. Ideally located adjacent to the Cady Way Trail, with NO HOA, this property offers the lifestyle and convenience of Winter Park with the flexibility today’s buyers are looking for. Upon entering, you’re greeted by a dramatic custom charcoal accent wall with geometric detailing, creating a distinctive architectural focal point and setting the tone for the home’s contemporary design. Inside, the open and inviting floor plan features Luxury Vinyl Plank flooring throughout, recessed LED lighting, all-new interior doors, and a stylish LED fireplace that adds warmth and ambiance to the main living area. The completely renovated kitchen is designed for both everyday living and entertaining, featuring new Shaker-style cabinetry, Quartz countertops, a large center island, luxury backsplash, stainless-steel appliances, and a dedicated coffee bar with wine refrigerator. The open layout provides an ideal gathering space for family and guests. The home also features a private Mother-in-Law Suite with its own entry and outside walkway, offering exceptional flexibility for extended family, overnight guests, a home office, or a private living area. The suite includes its own beautifully renovated bathroom with a rain shower, enclosed by a ceiling-to-threshold glass pane, and an illuminated LED mirror. The primary suite bathroom has been upgraded to a luxurious, contemporary retreat, featuring a smart toilet, dual vanities, illuminated LED mirror, and an executive-style stand-up rain shower. The shower incorporates a thoughtfully designed inclined floor that directs water into a rectangular drain, along with a striking floor-to-ceiling glass enclosure, creating a clean, open, and refined feel without the need for a traditional shower curtain. Additional major improvements include a new Carrier HVAC system, tankless water heater, updated double-pane windows, complete re-plumbing, re-wiring with an updated electrical panel, and a new roof installed 7/17/2023. Step outside and enjoy the home’s inviting outdoor spaces, including a covered front porch with dusk lighting, screened rear porch, spacious backyard, and oversized driveway. A series of cement slab walkways, separated by polished, large river stones, leads from the garage to the front door, with matching paths continuing along the rear of the home. Solar security lighting and decorative LED lighting add both functionality and evening ambiance. Ideally situated in Winter Park Pines and directly adjacent to the Cady Way Trail, the home offers convenient access to major roadways, hospitals, golf courses, colleges, shopping, dining, and highly regarded private schools—all within a short drive. With an extensive renovation, three beautifully updated bathrooms, a private Mother-in-Law Suite, modern kitchen, tankless water heater, new roof, updated electrical and plumbing, NO HOA, and an outstanding Winter Park location, this home offers a rare combination of style, functionality, and convenience. Come experience the renovation, thoughtful details, and flexible floor plan in person. Schedule your private showing today!

266 N Ranger Boulevard, Winter Park

1951 Winter Park Road, Winter Park
$1,949,000
4 Beds ⋅ 4 Baths ⋅ Charmont SubDv. ⋅ 32789 Zip Code
Resort-style living just minutes from Park Avenue and the Audubon Park Garden District. Built in 2014 by Clarkson Concepts and set along the brick-paved streets of historic Charmont, the home is wrapped in mature landscaping and full privacy fencing, so the backyard pool, spa and outdoor kitchen feel completely secluded. Inside, wide hardwood floors and walls of glass doors open the main living spaces to the porches and lanai, filling the home with natural light. At its center, the kitchen is built for gathering, with an oversized island seating six, double wall ovens, a walk-in pantry and a separate coffee and wine bar. Just off the kitchen and family room, a convenient hall to the garage connects a half bath and an oversized laundry room with a large utility sink, two generous banks of cabinetry and a built-in bench, plumbed for a second refrigerator, making it an ideal drop zone, overflow pantry or entertaining station. The main-level primary suite is a true retreat with a custom walk-in closet and a spa bath with a freestanding soaking tub and generous shower with dual shower heads. A wide stairwell under an oversized picture window leads to an unexpectedly spacious and bright loft that is fully an additional living room plus a comfortable office space. The three upstairs bedrooms are served by two pristine, nearly new conditioned bathrooms, including one jack-and-jill bath. You will want to spend all of your time in the private backyard oasis! A covered lanai with outdoor kitchen, bar seating and ceiling fans overlooks the paver pool deck, sparkling pool with raised spa and fire bowls. Out back, the west-facing yard opens to a backdrop of towering canopy trees, where breezes drift through the branches and no neighboring homes look directly in. At sunset, the sky glows through a soft filter of leaves, keeping the lanai shaded, comfortable and beautiful right through the golden hour. Just half a mile from Audubon Park K-8, with Lake Baldwin Park, Mead Botanical Garden, East End Market, Baldwin Park Village and downtown Winter Park's shops and restaurants all close by, and about 4 miles to downtown Orlando and 20 minutes to Orlando International Airport.

1951 Winter Park Road, Winter Park

100 S Virginia Avenue Unit 201, Winter Park
$1,450,000
3 Beds ⋅ 3 Baths ⋅ Winter Park Residential SubDv. ⋅ 32789 Zip Code
Discover luxury and effortless living in this exquisite single-story, second-floor residence at the highly sought-after Douglas Grand in the heart of Winter Park. This spacious three-bedroom, three-bath condominium beautifully balances sophisticated entertaining with everyday comfort, offering an inviting open floor plan filled with natural light, elegant crown molding, and stunning French Oak hardwood flooring. The gourmet kitchen is a true chef’s retreat, featuring a generous island with stunning quartz countertops, custom wood cabinetry, top-of-the-line Sub-Zero, Wolf, and Bosch appliances, and a spacious walk-in pantry. The serene primary suite offers a luxurious escape with an indulgent soaking tub, dual vanities with granite countertops, and two expansive walk-in closets. The second bedroom features a private ensuite bath and generous walk-in closet, while the third bedroom offers excellent flexibility and convenient access to a full bath. Thoughtful updates and amenities include a spacious utility room with a LG washer and dryer, updated light fixtures throughout, Roman shade window treatments, color-changing recessed lighting, Google smart carbon monoxide/fire detectors, Nest thermostats, and a 81-gallon water heater installed in December 2023. One of the residence’s most desirable features is the private entry directly from the secure, gated garage, with two reserved parking spaces conveniently located just outside your front door. Ideally situated in the heart of Winter Park, Douglas Grand places you moments from Park Avenue, the Winter Park Farmers’ Market, Rollins College, Hannibal Square, the Winter Park 9-hole golf course, Winter Park Tennis Center, and Winter Park Village. Experience the best of Winter Park with the comfort, privacy, and convenience of elevated condominium living at Douglas Grand.

100 S Virginia Avenue Unit 201, Winter Park

532 Langholm Drive, Winter Park
$2,990,000
5 Beds ⋅ 5 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32789 Zip Code
Under Construction. Commanding attention with its striking architecture and exceptional presence, this brand-new Winter Park residence unfolds across an expansive 11,000-square-foot homesite in the fast growing Kenilworth Shores neighborhood. Striking curb appeal introduces the home, while a marble mosaic foyer provides an elegant first impression and leads into the expansive great room. At the center of the living space is a dramatic custom entertainment wall featuring illuminated built-in shelving and a sleek electric fireplace. The adjoining dining room is equally impressive, complete with an oversized dry bar, wine refrigerator, and glass-front cabinetry, creating the perfect setting for hosting family and friends. The designer kitchen makes a statement with Taj Mahal countertops, a marble mosaic backsplash, custom cabinetry, and a full suite of Thermador appliances, including a paneled built-in refrigerator. A massive butler’s pantry extends the kitchen’s functionality with abundant storage and preparation space, a second microwave and oven, and an additional dishwasher, making entertaining effortless. The downstairs primary suite offers a private retreat accented by warm wood beams and separate his-and-hers closets. Its jaw-dropping spa-inspired bathroom is wrapped in 12-by-24-inch marble tile and features dual vanities, a freestanding soaking tub, and an oversized walk-in shower with LED-illuminated niches. A dedicated home office is also located on the main level, providing a quiet and refined space for working from home. Upstairs, a massive bonus room creates a flexible second living area ideal for movie nights, a game room, or a children’s retreat. Four additional spacious bedrooms offer comfort and privacy for family and guests, while an upper-level balcony provides another inviting place to unwind. The outdoor living spaces are designed to take full advantage of the oversized lot. A large covered lanai with a complete summer kitchen overlooks the resort-style pool and spa, all framed by an elegant marble deck. Beyond the pool, the expansive backyard offers valuable green space for recreation, entertaining, or relaxation. Additional highlights include a complete impact-rated window and door package for added efficiency and peace of mind. Perfectly positioned near Cady Way Park, AdventHealth Winter Park, and just a golf-cart ride from Park Avenue, this extraordinary new residence presents a rare opportunity to experience uncompromising luxury, exceptional space, and the very best of the Winter Park lifestyle.

532 Langholm Drive, Winter Park

5303 Pine Lily Circle, Winter Park
$659,000
3 Beds ⋅ 2 Baths ⋅ Sanctuary At Aloma SubDv. ⋅ 32792 Zip Code
POOL HOME IN WINTER PARK! Beautifully maintained 2015-built one-story in the quiet, gated community of Sanctuary at Aloma, offering 2,265 sq ft with 3 spacious bedrooms, a dedicated den/flex/home office, and a separate formal dining room, all on one level with no stairs. The open-concept great room flows into a light-filled kitchen featuring a large center island, stone countertops, a sleek backsplash, and abundant cabinetry, perfect for entertaining. The private primary suite is a true retreat with a separate soaking tub and shower plus plenty of storage. Secondary bedrooms are well sized with great closet space. Step outside to your screen-enclosed in-ground pool, added in 2020, with a covered sitting area and a fully fenced, beautifully landscaped backyard, privacy rarely found at this price point. Additional features include tile and laminate flooring, an owned security system, an attached 2-car garage, public water and sewer, and excellent curb appeal with stucco exterior and carriage-style garage door. Low quarterly HOA and NO CDD. Minutes from SR-417 at Aloma Ave, placing UCF, Research Park, Oviedo, and downtown Orlando within an easy commute. Close to Winter Park Village, historic Park Avenue, Full Sail, Rollins College, and Orlando International Airport. All information deemed reliable but not guaranteed; buyer and buyer's agent to verify all measurements and features. Schedule your private showing today!

5303 Pine Lily Circle, Winter Park

533 Country Club Drive, Winter Park
$1,599,000
4 Beds ⋅ 4 Baths ⋅ Lake Killarney Shores SubDv. ⋅ 32789 Zip Code
Welcome to 533 Country Club Drive, a beautifully designed custom residence where timeless coastal style meets effortless Florida living. Located in the Lake Killarney Shores community, this 4-bedroom, 3.5-bath pool home offers 2,942 square feet of thoughtfully designed living space, along with exclusive access to the neighborhood’s private boat ramp and dock on Lake Killarney just across the street. Inside, soaring 10-foot ceilings, 8-foot solid doors, wood flooring and designer lighting create a bright, refined atmosphere. The inviting living room is centered around a natural gas fireplace and opens seamlessly to the pool and covered rear lanai, creating an exceptional indoor-outdoor setting for everyday living and entertaining. The gourmet kitchen impresses with 42-inch designer cabinetry, quartz countertops, tile backsplash, farmhouse sink and an oversized quartz island with generous seating. A premium Viking stainless steel appliance package includes a gas range and hood, French-door refrigerator and dishwasher, complemented by a microwave drawer. The highly desirable dual-primary-suite layout provides exceptional comfort and flexibility. The first floor offers a private bedroom with an ensuite bath, providing convenient accommodations for guests or extended stays. Upstairs, the main primary retreat features wood flooring, an oversized custom closet and a spa-inspired ensuite bath with a combined soaking tub and shower wet area. Two additional bedrooms and a spacious loft complete the second level, offering flexible space for relaxing, entertaining or working from home. Step outside to a private oasis featuring a 10-by-25-foot POOL with a sun shelf, travertine coping and a paver deck. The covered rear lanai includes a SUMMER KITCHEN equipped with a Napoleon gas grill, vented hood, granite countertops, beverage cooler and storage—perfectly designed for year-round dining, entertaining and relaxing by the pool. Recent improvements include custom window treatments throughout, upgraded office and closet installations, privacy and heat-resistant window tinting, an infrared/UV HVAC enhancement, epoxy garage floor and under-stair storage. Additional features include zoned air conditioning with Nest thermostats, a Rinnai tankless gas water heater, Low-E windows, recessed LED lighting, a metal front porch roof and pavers extending across the driveway, walkway, porch and lanai. Enjoy the best of the Winter Park lifestyle with outstanding shopping, dining and entertainment nearby. Winter Park Village is just moments away, while the boutiques, sidewalk cafés, celebrated restaurants and cultural attractions of Park Avenue are also within easy reach. Convenient access to Fairbanks Avenue, US 17-92 and I-4 provides an easy connection to Downtown Orlando, Maitland and destinations throughout Central Florida. This exceptional home brings together custom craftsmanship, beautiful finishes, an enviable lakeside setting and one of Winter Park’s most desirable locations. Schedule your private showing today and experience the custom craftsmanship, lakeside lifestyle and exceptional Winter Park location of 533 Country Club Drive.

533 Country Club Drive, Winter Park

555 E Lake Sue Avenue, Winter Park
$2,095,000
4 Beds ⋅ 4 Baths ⋅ Lake Virgina Shores SubDv. ⋅ 32789 Zip Code
Welcome to the Timberlane Shores area, one of Winter Park's most desirable and established neighborhoods. This beautifully updated home sits on over a third of an acre with deeded access to Lake Virginia. Impeccably maintained, the 4-bedroom, 4-bath home offers 3,776 square feet of heated living space, including an office and sunroom. Inside, a welcoming foyer opens to a traditional floor plan with large formal living and dining rooms on either side. Straight ahead, the spacious family room with fireplace flows into the kitchen, where new quartz countertops and backsplash, upgraded appliances, and gorgeous travertine floors make this a true chef's kitchen. Beyond the kitchen, a light and bright sunroom looks out over the inviting pool and patio with outdoor kitchen. The downstairs office could easily be converted to a first-floor bedroom with an adjacent full bath. Upstairs, you'll find a large primary suite and three additional bedrooms. One of the home's most inviting features is the expansive upper balcony stretching the length of the house and overlooking the pool, perfect for entertaining or enjoying a quiet evening outdoors. Recent updates include a newly renovated kitchen, 2017 roof, and newly reimagined landscaping. Zoned for Audubon Park K-8 and Winter Park High School, and close to Winter Park's historic restaurant and shopping district, this is the perfect location to enjoy everything the area has to offer.

555 E Lake Sue Avenue, Winter Park

1517 Harmon Avenue, Winter Park
$1,049,000
4 Beds ⋅ 4 Baths ⋅ Lawndale SubDv. ⋅ 32789 Zip Code
Some houses impress you. This one welcomes you. A fully remodeled Victorian in Winter Park, reimagined from top to bottom and minutes from Park Avenue shopping and dining. The kitchen is the heart of it all, wrapped in Calacatta Viola quartz with a full height backsplash, cabinet lighting that glows after dark, and all new Bosch appliances. The open first floor flows naturally from kitchen to dining to living, anchored by a fireplace made for slow evenings, and new engineered hardwood flooring runs throughout the entire house. All 3.5 baths are completely redone with marble floors, designer tile, and brass fixtures, including a first floor half bath with wall paneling and a one of a kind vanity that stops people mid tour. This remodel went beyond the pretty parts. A brand new roof covers the entire house and detached garage, all outlets and switches were replaced throughout, and the plumbing was redone for the kitchen and all bathrooms. The water heater is new, and the laundry room has a new stacked washer and dryer too. You move in and live, nothing to fix, nothing to update. Upstairs and down, every bedroom is spacious and has custom built in closet systems, and the stairway shows off custom oak newels and handrails with black metal balusters. Outside, the charm continues with a herringbone brick-tile front porch, balconies and back porch made for morning coffee, fresh paint inside and out, new landscaping, a new paver driveway, and a detached two car garage with a newly stained concrete floor. This is not a quick flip. Every finish was chosen with intention, and every detail was completed with care. 4 bedrooms, 3.5 baths, 2,135 sq ft of living space on a 7,151 sq ft lot, in one of Winter Park's most loved pockets. This is a home you will feel from the first moment you walk in.

1517 Harmon Avenue, Winter Park

1803 Barker Drive, Winter Park
$2,190,000
4 Beds ⋅ 3 Baths ⋅ South Lakemont Shores SubDv. ⋅ 32789 Zip Code
A rare opportunity awaits to own a slice of paradise on Lake Spier in beautiful Winter Park! Set on over two acres and surrounded by mature landscaping, this stunning property offers a secluded setting that feels worlds away, while world-class dining and shopping, trails and parks, and the vibrant Village Center of renowned Baldwin Park are just moments from your door. Inside, you'll find luxury finishes and appliances, expansive hurricane-impact windows, all-new HVAC and a whole-house water filtration system, along with double master suites with vaulted ceilings and distinctive architectural details throughout. Step outside, where 158 feet of lakeshore and your private dock invite you to enjoy the water at its best, from boating and waterskiing to beautiful sunrises and sunsets on the water. With approximately 3,400 square feet, four bedrooms, three baths, a detached garage/workshop and no HOA, this is a truly unique offering in one of Winter Park's most desirable locations.

1803 Barker Drive, Winter Park

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