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5303 Pine Lily Circle, Winter Park
$654,000
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

4260 Bear Gully Road, Winter Park
$585,000
4 Beds ⋅ 4 Baths ⋅ Bear Gully Forest SubDv. ⋅ 32792 Zip Code
RENOVATED 4 BED / 3.5 BATH ON AN OVERSIZED 0.57-ACRE LOT | GOURMET KITCHEN | SCREENED LANAI | FENCED YARD | ROOF 2018 | FLOOD ZONE X | LOW HOA. Welcome to 4260 Bear Gully Road, a move-in-ready two-story home on nearly 25,000 sq ft of land, with space for a pool, garden or play area (buyer to verify). The gourmet kitchen was fully remodeled two years ago with upscale cabinetry and modern appliances, and luxury vinyl flooring gives the home a clean, low-maintenance look. The primary suite is on the first floor with a walk-in closet, and four bedrooms and three and a half baths give everyone room for family, guests or a home office. Ceiling fans, a two-car garage with opener, and concrete block and stucco construction add comfort and peace of mind. Relax on the screened lanai overlooking the large fenced backyard. Near Publix-anchored shopping and dining on Aloma Avenue, AdventHealth Winter Park, the Cross Seminole Trail and SR 417, with Winter Park Village and Park Avenue a short drive away. Seminole County schools: Eastbrook Elementary, Tuskawilla Middle and Lake Howell High (buyer to verify). Seller has a recent third-party home inspection report on file, available to buyers upon request. Buyers are encouraged to conduct their own inspections during the inspection period. Schedule your showing today!

4260 Bear Gully Road, Winter Park

2463 Grand Teton Circle Unit 2463, Winter Park
$249,000
3 Beds ⋅ 3 Baths ⋅ Cedarwood Village 1 SubDv. ⋅ 32792 Zip Code
Virtually Staged. Don't miss this incredible opportunity in one of Winter Park's most desirable locations! This spacious 2-story condo offers over 1,700 square feet of living space, featuring an open floor plan that's perfect for everyday living and entertaining. A dedicated office space adds flexibility for remote work or a home study a rare find at this price point. While the home could use some updating, the bones and layout make this a fantastic canvas to add your personal touch and build instant equity. Currently occupied by a great tenant, this property is a perfect turnkey opportunity for investors looking to add a cash-flowing asset to their portfolio, or for buyers ready to move in once the lease ends on June 2027. With its unbeatable location near Winter Parks shopping, dining, and entertainment, this is the kind of opportunity that won't last long at $249,000. Don't miss this and make your appointment today!

2463 Grand Teton Circle Unit 2463, Winter Park

662 Granville Drive, Winter Park
$3,495,000
5 Beds ⋅ 6 Baths ⋅ Park Grove SubDv. ⋅ 32789 Zip Code
Timeless elegance meets effortless modern living in this exceptional five-bedroom, 5.5-bath residence in Park Grove, one of Winter Park's most coveted neighborhoods. Designed for gracious living and sophisticated entertaining, the home features formal living and dining spaces alongside an expansive open-concept family room and gourmet kitchen. The first floor offers a serene primary suite, a private guest suite and a dedicated office, while the second level provides three generously sized guest suites, a versatile bonus room and a second laundry room. Retractable accordion doors extend the living space outdoors, creating a seamless connection between the sophisticated interiors and outdoor living areas. Outside you will find retractable screens along the porch area along with a putting green conveniently located beside the pool. Rich hardwood floors, custom trim and molding and exceptional interior finishes add warmth and refinement throughout. The gourmet kitchen is beautifully appointed with solid wood cabinetry, quartz countertops and premium appliances. Ideally situated in Park Grove, this distinguished residence offers the rare combination of privacy, luxury and navigability, just moments from Park Avenue, the Winter Park Village and the Winter Park Golf course.

662 Granville Drive, Winter Park

1166 Palmer Avenue, Winter Park
$5,500,000
5 Beds ⋅ 7 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. PRE-CONSTRUCTION: Introducing an exceptional new construction residence by Nautilus Homes, ideally positioned in the heart of Winter Park near Lake Osceola, with convenient side access from Via Bella. This remarkable five-bedroom, five-full bath and two half bath residence brings together Organic Modern architecture with Contemporary West influences, combining clean architectural lines with natural stone, warm wood elements, expansive glass, and organic textures throughout. Step through the entrance into a dramatic grand foyer, where expansive glass and architectural floating stairs immediately introduce the home's modern design. Natural materials and thoughtfully selected organic elements transition seamlessly from the exterior into the interior, creating warmth and continuity throughout the residence. Beyond the foyer, the home opens into an impressive great room, where expansive glass fills the space with natural light and creates a strong connection to the outdoor living areas. A sleek linear electric fireplace serves as an architectural focal point, complementing the clean lines and warm organic materials found throughout the home. At the heart of the residence is a thoughtfully designed chef's kitchen featuring top-of-the-line appliances sub Zero and Wolf and a dramatic double-island configuration, providing exceptional space for preparation, casual dining, and entertaining. Just beyond the kitchen, a thoughtfully designed combination mudroom and pantry provides additional storage and everyday functionality while maintaining the home's clean, luxurious aesthetic. An impressive wine storage wall adds another distinctive element to the main entertaining spaces. The primary suite is designed as a private retreat, complete with the added convenience of a dedicated laundry room positioned just off the primary suite. An extensive architectural lighting package and integrated smart-home technology further enhance the home's combination of luxury, functionality, and modern living. A dedicated entertainment room provides an additional space for gathering and relaxing, while the second floor offers additional bedroom accommodations and a versatile bonus room, ideal for a media lounge, game room, home office, or secondary entertainment space. The home's indoor living spaces transition naturally to one of its signature features—an impressive 42-foot-long lanai designed for year-round Florida living. Anchored by a gas fireplace, this expansive covered outdoor space creates an exceptional setting for entertaining, dining with automatic drop screens for relaxing while extending the home's Organic Modern design into the outdoors. Completing the residence with a perfect size pool/spa with ample yard space. A three-car garage configuration, including a separate detached one car garage. Depending on final dimensions and equipment specifications, the detached one-car garage may potentially accommodate a vehicle lift for additional automobile storage, creating an attractive feature for the automotive enthusiast or collector. Winter Park is renowned for its upscale retail, high-end dining, and vibrant culinary community, offering an exceptional blend of luxury and lifestyle. Just minutes away, enjoy the boutiques, restaurants, cafés, and charm of Park Avenue, along with convenient access to two nearby golf courses, making this an ideal location for experiencing the best of Winter Park living.

1166 Palmer Avenue, Winter Park

1271 Palmer Avenue, Winter Park
$2,125,000
4 Beds ⋅ 5 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Set on a generous corner lot, this stunning single-story pool home in Winter Park has been beautifully remodeled and offers the kind of effortless, one-level living that's genuinely hard to find. Step through the foyer and the floor plan flows naturally into the gourmet kitchen, through the open family and living spaces, past a flexible home office/den, and out to the backyard, where multiple exits blur the line between indoor and outdoor living. The kitchen is anchored by a substantial island with breakfast bar seating, while a Thermador natural gas cooktop takes center stage, complemented by stainless steel appliances, solid wood cabinetry, a wine refrigerator, and granite countertops — a space equally suited to quiet mornings or full-scale entertaining. The home offers 4 bedrooms, 4.5 bathrooms, and a home office/bonus room, thoughtfully organized in a triple split plan that frames the open-concept gathering areas. Three bedrooms enjoy private en-suite baths, the fourth sits directly beside the hall bath, and the office/bonus room is adjacent to the guest half bath — everyone has a bathroom of their own. The primary suite offers its own private retreat, complete with a luxurious en-suite bath and a spacious walk-in closet appointed with custom built-ins. Outside, a custom inground pool and spacious patio are framed by mature hedges for true backyard privacy, while natural gas fuels an outdoor firepit for evenings well past sunset. Recent updates include outdoor perimeter lighting, a rear fence, privacy hedges, and irrigation. All of this sits on a 0.34-acre lot, with a gracious circular drive off Palmer Avenue for guests and a separate garage and driveway entrance off Temple Drive for everyday comings and goings. A paver path connects the home to its 2-car detached garage, with ample additional parking between the front circular drive and rear driveway — perfect for year-round entertaining. Just moments from Phelps Park, the Winter Park Racquet Club, and the historic beauty of Kraft Azalea Garden, with the shops, restaurants, and farmer's market of Park Avenue close at hand — this is single-story Winter Park living at its very best.

1271 Palmer Avenue, Winter Park

2119 Howard Drive, Winter Park
$3,195,000
5 Beds ⋅ 6 Baths ⋅ Timberlane SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. A striking new custom residence by FG Schaub Custom Homes, located at 2119 Howard Drive in Winter Park. This exceptional 5-bedroom, 5.5-bath home offers 4,139 square feet of beautifully appointed living space, thoughtfully designed for elevated everyday living and effortless entertaining. The dramatic two-story stone entry creates a memorable first impression, complemented by crisp stucco, dark Anderson windows, and warm, refined finishes. The handcrafted iron front door makes a statement of its own, featuring innovative electronic glass that transitions from clear to frosted at the touch of a button, offering both architectural impact and privacy. Inside, an expansive open-concept floor plan showcases soaring ceilings, abundant natural light, and seamless connections between the main living spaces. The great room is enhanced by beautifully custom coffered ceilings, adding architectural dimension and a sophisticated sense of scale while creating an inviting atmosphere for both intimate gatherings and entertaining on a larger scale. The first-floor primary suite offers a luxurious escape, featuring a spacious walk-in closet and spa-inspired bathroom designed to provide a serene retreat at the end of the day. Also on the first floor, a private guest suite with en-suite bathroom provides an ideal space for overnight guests or extended family. Three additional bedrooms and bathrooms are located on the second floor, offering exceptional flexibility for family, guests, a gym, or a home office. At the heart of the home, the gourmet kitchen combines sophisticated design with everyday functionality, featuring a large quartz island, custom cabinetry, and premium Wolf and Sub-Zero appliances. The open-concept layout allows the kitchen to flow effortlessly into the surrounding living and entertaining spaces. Designed for the quintessential Florida lifestyle, the expansive outdoor living area known as the “Transitional Room” features electric roll-away screens, a mini split, and a fully equipped summer kitchen. The adjoining pool and spa create the perfect setting for poolside afternoons, al fresco dining, and memorable evenings with family and friends. Additional highlights include an oversized two-car garage with EV charger, spray foam insulation throughout the home for energy efficiency, designer-curated finishes, and a fully fenced yard with thoughtfully designed landscaping and lighting to further enhance the home’s outdoor ambiance.

2119 Howard Drive, Winter Park

618 Blairshire Circle, Winter Park
$875,000
4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code
Virtually Staged. FULLY RENOVATED 4-BEDROOM, 3-BATH POOL HOME IN THE HEART OF WINTER PARK! this beautifully updated home sits on a spacious 9,915-square-foot lot surrounded by mature trees and charming streets. Thoughtfully renovated from top to bottom, this move-in-ready property offers modern finishes, major system upgrades, and the Florida lifestyle you've been looking for! Step inside to discover a bright, inviting interior featuring NEW FLOORING THROUGHOUT, NEW WINDOWS, AND FRESH INTERIOR AND EXTERIOR PAINT. The completely remodeled kitchen showcases NEW CABINETRY, NEW APPLIANCES, AND UPDATED FINISHES, creating a stylish and functional space for everyday living and entertaining. Enjoy added peace of mind with a NEW ROOF (2025), NEW AC SYSTEM (2025), AND NEW WATER HEATER.Step outside to your private backyard retreat featuring a FULLY RESURFACED POOL and a spacious, fenced yard perfect for relaxing, entertaining, and enjoying Florida's beautiful weather year-round. The property also features a 2-CAR GARAGE AND AN OVERSIZED DRIVEWAY, providing plenty of additional parking. Washer and dryer are included! Ideally located just minutes from **CADY WAY TRAIL, PARK AVENUE, ROLLINS COLLEGE, AND WINTER PARK PINES GOLF CLUB, with convenient access to shopping, dining, parks, and major roadways. Zoned for Brookshire Elementary, Glenridge Middle, and Winter Park High School. Enjoy the charm of an established Winter Park neighborhood with the convenience of a fully updated home. ALL THE MAJOR UPDATES HAVE BEEN DONE—JUST MOVE IN AND ENJOY! Some photos have been virtually staged.

618 Blairshire Circle, Winter Park

913 Moss Lane, Winter Park
$900,000
3 Beds ⋅ 2 Baths ⋅ Maitland Shores First Add SubDv. ⋅ 32789 Zip Code
913 Moss Lane is in the Vias of Winter Park, on a tree-lined street in Maitland Shores. Neighborhood access to the Winter Park chain of lakes is a block away. Winter Park Racquet Club is a short walk. Park Avenue is a short drive. The home is zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. The house is a 1953 split-level with 3 bedrooms, 2 baths, about 1,887 square feet, and a two-car garage. The main floor has the living room, dining area, kitchen, and Florida room. The bedrooms are upstairs. The 2023 renovation added new flooring, interior and exterior paint, a kitchen with white cabinetry, stone counters, and stainless appliances, and an updated bath with a walk-in glass shower. The backyard is fenced and has a patio. There is no homeowners association. This is a renovated three-bedroom in the Vias. See it for the street, the schools, and the lakes.

913 Moss Lane, Winter Park

2383 Sun Valley Circle Unit 2383, Winter Park
$234,900
2 Beds ⋅ 2 Baths ⋅ Cedarwood Village SubDv. ⋅ 32792 Zip Code
Don't miss your opportunity on this super clean 2 bed 2 bath Winter Park condo! Updated kitchen with White shaker cabinets, granite counters complete with all the appliances including washer and dryer. Formal dining room and family room with vaulted ceilings, skylights, along with a wet bar and cabinetry complimented by a centerpiece wood burning fireplace. Master bedroom features hardwood flooring along with updated vanity with granite counters along with a separate tub and shower. Secondary bedroom has laminate flooring along with updated vanity and granite countertops. Ceramic tile throughout the rest of the home as there is no carpet. French doors leading out to the oversized screen enclosed covered patio overlooking lush landscaping with no direct rear neighbor.  2 assigned parking spaces directly in front of the unit.There is also a small courtyard just outside the kitchen. Community features a recently remodeled pool, clubhouse and tennis courts. Winter Park location benefits include easy access to Full Sail University, UCF, Valencia College, Park Avenue filled with famous restaurants and boutique shopping.

2383 Sun Valley Circle Unit 2383, Winter Park

2410 Sherbrooke Road, Winter Park
$769,000
4 Beds ⋅ 3 Baths ⋅ Sherbrooke SubDv. ⋅ 32792 Zip Code
Welcome to 2410 Sherbrooke Rd in Winter Park! This spacious single-story home offers 2,141 sq ft of living space with 4 bedrooms, 2.5 bathrooms, and an attached two-car garage, all in a convenient location within walking distance of Winter Park High School. 10 minutes to Full Sail University, Rollins College, or Downtown Winter Park. Step inside to find generous living and family spaces filled with natural light, beautiful hardwood flooring, and a flexible layout designed for both everyday living and entertaining. The upgraded kitchen features granite countertops, abundant wood cabinetry, stainless steel appliances, recessed lighting, a center island, and a breakfast bar overlooking the family room. The spacious primary suite features new vinyl flooring and an updated en-suite bathroom with dual vanities and a large walk-in shower. Three additional bedrooms provide plenty of flexibility for guests, home office space, or other needs. An additional full bathroom, half bath, and dedicated laundry room complete the interior. French doors lead to the screened patio, offering a comfortable space for outdoor dining and relaxing. Beyond the patio is an exceptionally large backyard surrounded by mature trees and landscaping, with plenty of room for gardening, recreation, entertaining, or creating your own outdoor retreat. Major improvements include a ROOF REPLACED IN 2022 and A/C REPLACED IN 2022, giving the next owner added peace of mind. With its upgraded kitchen and bathrooms, spacious floor plan, beautiful flooring, huge backyard, screened patio, two-car garage, and recently replaced major systems, this Winter Park home offers an outstanding combination of space, comfort, and location. Schedule your private showing today and discover everything this home has to offer!

2410 Sherbrooke Road, Winter Park

825 Palmer Avenue, Winter Park
$5,195,900
5 Beds ⋅ 7 Baths ⋅ J Kronenberger Sub SubDv. ⋅ 32789 Zip Code
Pre-Construction. To be built. A rare convergence of timeless French Country architecture, brand-new custom construction, and coveted access to the Winter Park Chain of Lakes. Thoughtfully designed and being built by FG Schaub Custom Homes, this exceptional property offers the character of a timeless estate with the amenities and craftsmanship expected in a luxury new construction home. The residence will feature five bedrooms, a dedicated office, five full bathrooms, and two half bathrooms, with beautifully appointed living spaces designed for both refined entertaining and comfortable everyday living. The striking exterior showcases classic French Country influences, stone accents, decorative brick detailing, crisp stucco, expansive windows, and multiple gabled rooflines, creating an elegant and welcoming architectural presence. Outdoor living is equally impressive, with a private pool and spa, covered outdoor living area with roll away screens, and a full summer kitchen creating a resort-style retreat. A brand-new private boathouse, included with the property, is positioned directly on the canal and provides access to the Winter Park Chain of Lakes, offering the opportunity to enjoy boating, water sports, fishing, and so much more. Final plans, specifications and finishes are subject to change.

825 Palmer Avenue, Winter Park

1773 Walnut Avenue, 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

2622 Lake Howell Lane, Winter Park
$3,400,000
4 Beds ⋅ 3 Baths ⋅ Acreage & Unrec SubDv. ⋅ 32792 Zip Code
Welcome to an extraordinary private lakefront retreat in Winter Park, where expansive grounds, exceptional amenities, and breathtaking Lake Howell views come together in one special property. Set behind a private gated entrance on approximately 4.3 total acres, with roughly half of the property consisting of dry land and the balance extending into Lake Howell, this remarkable estate offers a rare combination of privacy, space, and direct lake access, yet remains just minutes from the charm of Park Avenue, Interlachen Country Club, shopping, dining, and everything Winter Park has to offer. Lake Howell provides a spectacular backdrop for everyday living and entertaining, with opportunities for boating, fishing, water sports, sunset cruises, and unforgettable days on the water. The property features its own private boat ramp, boathouse, and boat dock, making lake life exceptionally convenient. The grounds are designed for both grand entertaining and relaxed family living. A massive detached barn offers an incredible flexible space for private events, parties, gatherings, game nights, or simply creating your own ultimate entertainment venue. Fully air conditioned and featuring high ceilings, the barn provides room for additional vehicles, RVs, boats, recreational equipment, and more. It also includes a private gym and bathroom, making it a versatile addition to the property. For RV enthusiasts, the property features a full 50 amp RV hookup with water and sewer hookups. The property is Agriculture zoned and allows horses. A separate four-car detached garage with workshop provides substantial storage and workspace. A generator adds convenience and peace of mind. The expansive fenced grounds offer plenty of room for family, pets, recreation, and outdoor activities, including a large playset and a firepit with comfortable seating—the perfect setting for cool evenings, roasting marshmallows, sharing stories, and making memories together. The recently updated pool area is designed to feel like your own private resort. Enjoy the covered lanai, outdoor kitchen, pool, and stunning lake views, along with a gas fireplace that creates an inviting atmosphere for evening entertaining. The outdoor kitchen is a chef’s dream, making it easy to host everything from casual family gatherings to unforgettable waterfront celebrations. Inside, the home was thoughtfully renovated in 2016 and offers just over 3,377 square feet under air, with approximately 7,758 total square feet. Beautiful wood flooring, tile, and carpeted bedrooms create a comfortable blend of style and functionality. The Florida room provides the perfect place to relax, take in the lake views, and enjoy the natural beauty surrounding the home. The upgraded kitchen features stainless steel appliances and a Thermador range, while the spacious executive office provides an ideal work-from-home environment or private study. The residence offers four bedrooms and three bathrooms, providing generous accommodations for family and guests. With multiple indoor and outdoor gathering spaces, extraordinary storage, recreational amenities, and direct access to Lake Howell, this property is much more than a home—it is a private lifestyle estate. Whether you're looking for a peaceful waterfront sanctuary, a place to entertain on a grand scale, a family compound, or simply a rare piece of Winter Park property with exceptional lake access, this property delivers an unparalleled opportunity.

2622 Lake Howell Lane, Winter Park

698 N New York Avenue, Winter Park
$5,995,000
5 Beds ⋅ 6 Baths ⋅ Greens/Pk SubDv. ⋅ 32789 Zip Code
Brand new 2026 custom residence in the heart of downtown Winter Park, just completed and showcasing elevated finishes thoughtfully curated by FG Schaub Construction & SOCO Interiors. Positioned across from the seventh green of the Winter Park 9 Golf Course, this exceptional five-bedroom, five-and-one-half-bath home includes a dedicated office, plus upstairs lounge in offering an extraordinary combination of sophisticated design, exceptional craftsmanship, and an unparalleled location. A striking front entry, framed by steel & glass doors open to a dramatic two-story foyer, where a floating glass-railed staircase sets the tone for the home’s contemporary aesthetic. The front-corner office features expansive windows overlooking the Winter Park 9 Golf Course. The overall living design is an open-concept floor plan that creates effortless connectivity between the living, dining areas and kitchen. Designed for the discerning chef, the kitchen features Wolf and Sub-Zero appliances, including a six-burner gas range, integrated refrigeration, wine storage, a generous waterfall island with seating, and a spacious walk-in pantry. The adjacent living areas are anchored by a custom wet bar with ice maker and two wine towers, an linear electric fireplace, and a wall of disappearing glass sliders that seamlessly connect the interior to a fully enclosed 600+ square-foot, air-conditioned lanai outfitted with a complete summer kitchen. The expansive indoor/outdoor lanai provides an exceptional setting for year-round entertaining that opens up via three additional sets of glass panel doors or automatic screens to the pool and outdoor oasis. The 633sf lanai has its own dedicated HVAC system however, is NOT included in the home’s primary heated & cooled living area square footage of 5,096sf. Privately positioned on the first floor, the luxurious primary suite features a wall of glass with direct access to the outdoor living area and an outdoor shower. The spa-inspired primary bath includes a freestanding soaking tub, glass-enclosed shower, generous size custom walk-in closet, and private sauna. Transition upstairs by either elegant staircase or elevator a spacious lounge area/loft and three additional bedroom suites, each offering a walk-in closet and ensuite bath. A versatile flex room with dedicated bath and a walk-in closet can easily serve as a fifth bedroom. A full hall bath and second-level laundry room (note: there is also a first-level laundry rm) provide additional convenience. Outside, a heated saltwater pool and spa, three pool side fire bowl features, outdoor private shower, and meticulously landscaped grounds create a sanctuary to relax and unwind... An exceptional opportunity to experience refined urban living in one of Winter Park’s most coveted settings, with the tranquility of a golf course backdrop to being in the downtown Park Avenue corridor. Stroll to renowned boutiques, award-winning restaurants, sidewalk cafés, Central Park, the Saturday Farmers Market, art museums, The Alfond Inn, and the many cherished events and traditions that make downtown Winter Park living so special!

698 N New York Avenue, Winter Park

436 N Wymore Road, Winter Park
$1,350,000
Killarney Circle SubDv. ⋅ 32789 Zip Code
Prime Winter Park commercial office building with visibility of monument signage from 1-4 East bound traffic and Ideally situated on Wymore Road. This 2018 built one story office building offers Low-maintenance ownership, with approximately 3021 total square feet, creating a professional office environment with flexible layout options for investors or owner-users. The property features 10 parking spaces includes one handicap with public street parking option located in 32789. Both suites have separate entrances, with access door in between, both with reception areas, open air built-in workspaces. Each suite has its own kitchen and bathroom facilities. Building has 6 total private offices, ( 4 & 2) providing convenience for both administrative and operational functions. Well-constructed, high ceilings, attractive flooring, 2 conference rooms with high-end lighting fixtures, window treatments. Both suites are leased, generating $9,678.60 per month with the tenants' paying utilities, alarm, housekeeping, building taxes, and insurance. One of the tenants' leases (1736 Sq foot suite) expires September 1, 2029 (rental income increases every year) The other suite (1285 sq ft) lease is owner occupied and available for rent immediately or owners are willing to stay up for up to seven months based on new owners' situation. This property offers an excellent opportunity for an owner-occupant of one suite while obtaining rental income. The property manager is the listing RE Agent/seller who will provide a smooth transition upon closing. This property is a prime opportunity for businesses seeking a high-quality, move-in-ready or flex space in one of the area's most accessible commercial corridors.

436 N Wymore Road, Winter Park

200 S Interlachen Avenue Unit 350, Winter Park
$2,350,000
3 Beds ⋅ 4 Baths ⋅ Versailles Winter Park Condo SubDv. ⋅ 32789 Zip Code
Welcome to The Versailles of Winter Park, an extraordinary opportunity to own one of only seven exclusive private residences in one of Winter Park's most coveted luxury communities, nestled just steps from the world-renowned Park Avenue and adjacent to the prestigious Alfond Inn & Spa. This magnificent third-floor residence offers 3,110 square feet of impeccably designed one-level living, oak hardwood floors throughout, elegant crown molding, and an abundance of natural light pouring through French doors set the tone for refined sophistication. Entertain effortlessly in the grand living area with a sprawling balcony adorned with Chicago brick and stone railing. Kitchen includes wood cabinet, granite, Monogram refrigerator, convection oven and microwave. The versatile split-bedroom floor plan ensures ultimate privacy, with the lavish primary suite accessed through double doors, walk-in closet, private balcony access, and an opulent spa bath featuring dual vanities, a soaking tub, walk-in shower. A designated office with wall-to-wall built-ins, a formal dining room accommodating up to twelve guests, a private two-car garage, and meticulously maintained landscaping. The Versailles of Winter Park is the ultimate expression of luxury living offering an unparalleled lifestyle just moments from the finest dining, boutique shopping, art festivals, and cultural events that makes Winter Park one of Florida's most desirable destinations.

200 S Interlachen Avenue Unit 350, Winter Park

2275 Island Run, Winter Park
$279,999
3 Beds ⋅ 2 Baths ⋅ Windward Square Sec 3 SubDv. ⋅ 32792 Zip Code
Great opportunity in the established Windward Square community of Winter Park! This END-UNIT home offers 3 bedrooms, 2 full bathrooms and approximately 1,467 square feet of living space, with added privacy and plenty of potential. ROOF REPLACED IN 2017! 10K seller contribution for the floor. The home is ready for some TLC and personal updates, giving the next owner the opportunity to renovate and make it their own. The spacious living and dining areas gives a functional layout, while the large screened porch provides additional space to relax, entertain, and enjoy Florida living. Being located at the end provides additional privacy and a more open feel compared with interior units. The community offers amenities including a swimming pool and tennis courts. Conveniently located near shopping, dining and major roadways, with easy access to Winter Park, Orlando and surrounding areas. Whether you’re looking for a primary residence or an investment opportunity, this property offers great potential and an excellent opportunity to add value through your own improvements. Bring your vision and make this home your own!

2275 Island Run, Winter Park

508 Brechin Drive, Winter Park
$579,000
3 Beds ⋅ 2 Baths ⋅ Kenilworth Shores Sec 01 SubDv. ⋅ 32792 Zip Code
Renovated and move-in ready, this updated Winter Park home offers a fresh, modern interior. The brand-new kitchen features new cabinetry, quartz countertops and all new appliances, while both bathrooms have been fully renovated with new finishes and fixtures. New luxury vinyl plank flooring runs throughout the home, complemented by fresh interior paint. The roof was replaced in April 2022, providing added peace of mind for today's buyer. With 3 bedrooms, 2 bathrooms and approximately 1,785 square feet of living space, this home offers a comfortable and functional floor plan in an established Winter Park location. The spacious yard offers plenty of room for outdoor enjoyment and the opportunity to create your own ideal landscaping. Enjoy easy access to Cady Way Park and the Cady Way Trail, perfect for walking, biking and recreation. Just minutes from the restaurants, shopping and charm of Park Avenue, as well as the popular Baldwin Park area. Conveniently located near AdventHealth Winter Park and numerous dining, shopping and recreational options. Agent owned property.

508 Brechin Drive, Winter Park

500 N Pennsylvania Avenue Unit G, Winter Park
$349,500
2 Beds ⋅ 1 Baths ⋅ Village Condos SubDv. ⋅ 32789 Zip Code
Virtually Staged. LOCATION, LOCATION, LOCATION in Winter Park!!! **Rare opportunity to own in the highly desired Downtown of Winter Park for under $350,000!** Enjoy the highly desired downtown Winter Park lifestyle with Park Avenue’s boutiques, restaurants, cafés, arts and culture, Rollins College, the Winter Park Train station, Casa Feliz, seasonal festivals and community events all just a short walk from your front door. This charming 2-bedroom, 1-bath condo offers an inviting open-concept living and dining area, along with a kitchen featuring granite countertops and convenient counter seating. Condo is highlighted with beautiful plantation shutters. Located within a charming, intimate condominium community, it offers a wonderful combination of comfort, location and low-maintenance living, all within an area known for its highly regarded Winter Park-area schools. Whether you’re searching for a primary residence, a second home, a great option for downsizing, or an investment property, this is your opportunity to own a piece of one of Central Florida’s most desirable cities. Imagine strolling to dinner on Park Avenue, meeting friends for coffee, walking to Rollins College, enjoying the beauty and history of Casa Feliz, browsing the shops, attending an art festival or catching the train — all without worrying about finding a parking space. Simply walk out your front door and enjoy the incredible lifestyle that makes Winter Park such a special place to call home. **Opportunities to own downtown Winter Park real estate at this price point are rare. Don’t miss your chance — schedule your private showing today before this one is sold. A location and lifestyle like this won’t last long!**

500 N Pennsylvania Avenue Unit G, Winter Park

3020 Nicholson Drive, Winter Park
$470,000
4 Beds ⋅ 2 Baths ⋅ Wrenwood Unit 3 3rd Add SubDv. ⋅ 32792 Zip Code
UPDATED 4-BEDROOM POOL HOME IN WINTER PARK WITH NO HOA! Welcome to 3020 Nicholson Drive, a beautifully updated 4-bedroom, 2-bath home with a private pool, 2-car garage, and NO HOA, tucked into the established Wrenwood neighborhood of Winter Park. From the thoughtfully updated interior to the backyard designed for Florida living, this home offers the space, flexibility, and location you've been looking for. Step inside to a bright and inviting interior featuring new LVP flooring throughout, a split-bedroom floor plan, and multiple living and dining spaces that provide plenty of room to spread out, gather, and entertain. The kitchen features abundant cabinetry and counter space, stone countertops, a built-in oven and cooktop, and a window overlooking the backyard. Custom epoxy flooring in the kitchen and entry adds durability and a unique finishing touch. The primary suite is one of the home's standout spaces, featuring a beautifully remodeled bathroom with a double vanity and an oversized glass-enclosed shower, along with a custom-built closet with shelving and organization designed to maximize storage and functionality. But the backyard may be where you'll want to spend most of your time. Step outside to a private in-ground pool, covered screened patio, fenced backyard, and an expanded pool deck with additional pavers, creating multiple spaces to lounge, entertain, dine outdoors, or simply enjoy the Florida sunshine. There's even green space beyond the pool, giving the backyard a more open feel than you might expect from a pool home. The home also offers important improvements already completed for you, including a roof replaced in 2019, re-pipe completed in 2013, and HVAC system replaced in 2018/2019. A professionally installed security system and security cameras add another layer of functionality. The location ties it all together. Situated in Winter Park's Wrenwood neighborhood, 3020 Nicholson Drive puts you within easy reach of some of Central Florida's favorite destinations, including Park Avenue, Winter Park Village, and Baldwin Park, with shopping, dining, entertainment, and everyday conveniences nearby. Convenient access to SR 436 and the 408 also makes it easy to reach Downtown Orlando and destinations throughout Central Florida.

3020 Nicholson Drive, Winter Park

1850 Bryan Avenue, Winter Park
$699,000
3 Beds ⋅ 2 Baths ⋅ Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Tucked beneath mature oak trees, 1850 Bryan Avenue is a well-maintained home offering comfortable single-story living in Winter Park. Natural light and warm wood floors flow through the inviting living and dining spaces, while a flexible bonus room is well suited for a home office, den or creative space. The kitchen features wood cabinetry and ample counter space. The spacious primary suite offers a private retreat. Additional features include an indoor laundry room and an attached two-car garage. Outside, the fenced yard provides a peaceful setting for gardening, entertaining or relaxing beneath the trees. With shopping, dining, parks and other Winter Park amenities nearby, this home brings together character, comfort and a desirable location.

1850 Bryan Avenue, Winter Park

702 Via Bella, Winter Park
$4,090,000
4 Beds ⋅ 6 Baths ⋅ Palmer Ave Lakeside Prop SubDv. ⋅ 32789 Zip Code
Completed in 2025 by Floridian Custom Homes, this distinguished English cottage-inspired residence brings refined character, thoughtful design, and exceptional craftsmanship to one of Winter Park’s coveted residential corridors. Encompassing 3,720 square feet, the four-bedroom, five-and-one-half-bath home blends sophisticated interiors with contemporary systems and inviting spaces designed for both everyday living and entertaining. "OPTION TO PURCHASE HOME TURN-KEY": Owner has just finished a ~ $500,000 complete furnishings install thru Brianna Michelle Interior Design! A solid mahogany front door opens to interiors defined by Botticino limestone flooring with a distinctive textured finish, bespoke millwork, and generous gathering spaces. Coffered ceilings and recessed WAC lighting add architectural dimension, while insulated casement windows fill the home with natural light. The expansive central living area flows seamlessly into the dining space and beautifully appointed kitchen, featuring custom cabinetry by Grit & Grain, leathered Taj Mahal quartzite countertops, and a remarkable collection of professional-grade appliances, including a 43-inch La Cornue gas range with McGurken hood, Thermador refrigerator and freezer columns, and Bosch dishwasher. A generously sized walk-in pantry continues the custom cabinetry and quartzite finishes while incorporating dual refrigeration drawers and a dedicated ice maker. The adjacent mudroom is outfitted with substantial hardwood built-ins, providing exceptional organization and storage. The first-floor primary suite occupies a private wing and showcases wide-plank European white oak flooring by Forrest Accents, a customized walk-in closet, and an elegant spa-inspired bath. Natural stone countertops, Rohl polished nickel fixtures, marble flooring and shower surfaces, and a frameless glass enclosure create a polished yet inviting retreat. Throughout the home, solid-core doors are complemented by Emtek hardware. Positioned near the front entry, the library offers a sophisticated setting for work or quiet reflection, with matching oak flooring and custom casement windows. A solid wood staircase ascends to a second living area with an adjoining lounge or flex space. Three additional bedroom suites provide private accommodations, each with en-suite baths featuring porcelain flooring, frameless glass showers, brushed quartz and dolomite vanities, designer lighting, and integrated closet systems. Modern infrastructure includes CAT-5/6 wiring, Sonos-integrated speakers, Lutron RA-3 smart lighting controls, and pre-wiring for home security with digital camera ports strategically located at key entry points. Multiple access points from the primary suite and kitchen wing extend to a beautifully enclosed outdoor environment framed by mature landscaping designed by Signature Landscape. A Roman-inspired cabana with soaring ceilings and exposed beams serves as the centerpiece for outdoor entertaining. The fully tiled saltwater pool, representing a $50,000 upgrade, features therapy jets, LED-lit bubblers, a dual-skimmer system, Jandy heat-pump automation, and a Paramount self-cleaning system. Minutes to vibrant shopping, restaurants, sidewalk cafes of Park Avenue, and all that downtown Winter Park has to offer.

702 Via Bella, Winter Park

222 Lewfield Circle, Winter Park
$189,900
2 Beds ⋅ 2 Baths ⋅ Stratford A Winter Park Condo SubDv. ⋅ 32792 Zip Code
One or more photos was virtually staged. This 2 Bedroom, 2 Bath, 953 SF Winter Park condo in the amazing Stratford community offers a comfortable, functional floor plan complemented by fresh interior paint, updated flooring, and a 2026 HVAC system. The spacious living area features a ceiling fan and sliding glass doors that bring in natural light and open to a covered balcony, creating an easy extension of the indoor living space. The adjacent dining area provides flexibility for everyday meals or additional living space. The kitchen features wood cabinetry, generous counter space, tile flooring, and stainless steel refrigerator, while an in-unit laundry closet adds everyday convenience. Bedrooms feature updated flooring, neutral finishes, ceiling fans, and ample natural light. A large walk-in closet with extensive shelving and storage helps keep everything organized, while the bathroom includes a tiled walk-in shower and vanity storage. Freshly touched up throughout and offering a practical layout with comfortable living spaces, this Winter Park condo is ready for its next chapter.

222 Lewfield Circle, Winter Park

276 Detmar Drive, Winter Park
$3,600,000
4 Beds ⋅ 5 Baths ⋅ Detmar Terrace Winter Park SubDv. ⋅ 32789 Zip Code
Tucked away in the heart of Winter Park, this custom-built residence seamlessly blends modern luxury with the comfort of everyday living. Thoughtfully designed with exceptional attention to detail, the home offers clean, contemporary interiors balanced by beautiful architectural elements, and abundant natural light. The main level offers two bedrooms and three full bathrooms, including a primary suite with a versatile bonus room behind French doors—perfect for a private office, gym, or additional bedroom. The ensuite features two walk-in closets, a double sink vanity, a large rainfall shower, and a soaking tub. The open-concept floorplan features a beautifully appointed kitchen with high-end appliances and custom cabinetry, flowing seamlessly with the dining area and the spacious living room, where a gas fireplace creates a welcoming gathering space. Architectural light wood ceiling beams, plantation shutters, and expansive glass sliders frame beautiful views of the outdoor living area. Upstairs, two additional bedrooms each feature private ensuite baths and balconies, complemented by a kitchenette and additional living space. This flexible layout is ideal for multigenerational living, guests, live-in staff, or simply creating a private retreat within the home. Designed for effortless indoor-outdoor living, the entire downstairs opens to a private backyard oasis featuring a sparkling saltwater pool, lush bamboo backdrop, summer kitchen, gas fireplace, and outdoor shower. The covered lanai is equipped with automatic screens, creating an inviting and comfortable space to enjoy the outdoors year-round. Beyond its sophisticated design, the home offers exceptional functionality, including an oversized two-car garage pre-wired for EV charging, whole-home surround sound, hurricane-impact windows, a whole-house Generac generator, indoor built-in sprinkler system, dual laundry rooms, and enhanced insulation for exceptional peace and quiet. The entire first floor is completely wheelchair accessible. Tastefully furnished and offered with all furnishings, this exceptional residence presents a rare combination of refined design, thoughtful functionality, and classic Winter Park charm. Ideally located just one mile from Park Avenue and minutes from Winter Park’s renowned restaurants, shops, hospitals, schools, and scenic Lake Osceola, this is a home designed for both elevated living and everyday comfort.

276 Detmar Drive, Winter Park

7605 Aloma Pines Court, Winter Park
$349,000
3 Beds ⋅ 3 Baths ⋅ Aloma Trails SubDv. ⋅ 32792 Zip Code
Virtually Staged! Amazing Townhome! GATED Community of Aloma Trails Townhomes in a great Winter Park location, 3 bedroom, 2.5 bathroom with features of spacious living and comfortability. This stunning Townhome has Ceramic Tile flooring throughout the first floor leads to a kitchen with all the upgrades including SS appliances. 42” Cabinets, upgraded granite countertops and backsplash, and an island with plenty of seating along with a carpet in the second floor and all bedrooms. The master suite is outfitted with large Walk-In closet, glass-enclosed shower with dual sinks, and oversized cabinets. The two additional bedrooms share a second full bath and there is a half bath on the main floor convenient for guests. Separated interior laundry closet provides convenience and comfort. A nice big Car Garage and driveway, which will easily suit for multiple vehicles as necessary. This community comes with hassle-free lawn care, and well-maintained common areas and a BEAUTIFUL location. The fitness enthusiast will enjoy the Crunch Fitness facility just across the community and, the CADY WAY trail and the CROSS SEMINOLE trail- all just steps away from your front door. Walmart, Costco and Publix are almost 3 min driving distance. Close to Park Ave in Winter Park, SR 417, UCF, Fulsail University, and just 40 minutes to the Beach! Add in top notch Seminole County Schools. You don't need to look any further for your Dream Home! Schedule your viewing today! Note: Some of the pictures are showing the virtual staging of the unit and the furnitures/decorative items are not included to the listing.

7605 Aloma Pines Court, Winter Park

900 Carver Street, Winter Park
$659,000
3 Beds ⋅ 3 Baths ⋅ Magnolia Gardens Sub SubDv. ⋅ 32789 Zip Code
Completely Renovated | Move-In Ready | Single-Story Living. A comprehensive renovation brings modern finishes and functionality to this Winter Park home, with a redesigned kitchen that opens to the main living area. The kitchen features 42-inch shaker cabinetry, Calacatta quartz countertops, stainless steel appliances, a center island, and pantry storage. Luxury vinyl flooring extends through the main living areas, complemented by recessed LED lighting and updated fixtures. A complete interior renovation and landscaping updates were completed in 2026, complementing major improvements from 2019, including a new roof, HVAC system, and double-pane windows. The three-bedroom, three-bathroom layout includes two spacious en-suite bedrooms, with all bathrooms completely remodeled. Additional features include an interior laundry closet and a fully fenced backyard. Outside, paver walkways, manicured lawns, and refreshed landscaping complement the home's updated exterior. Located in Magnolia Gardens with no HOA, the property offers convenient access to Park Avenue's restaurants, boutiques, and farmers market, as well as Lake Lily, Maitland City Centre, and I-4.

900 Carver Street, Winter Park

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