Winter Park Real Estate

Winter Park Real Estate

Winter Park is a charming city located in the state of Florida. Situated in Orange County, Winter Park is known for its picturesque beauty, vibrant culture, and rich history. With its tree-lined streets, beautiful lakes, and stunning architecture, Winter Park offers a unique blend of natural and man-made beauty.

One of the highlights of Winter Park is its thriving arts scene. The city is home to several museums, galleries, and theaters, making it a hub for artists and art enthusiasts. The Charles Hosmer Morse Museum of American Art is a must-visit, housing the world's most comprehensive collection of works by Louis Comfort Tiffany.

In addition to its cultural offerings, Winter Park boasts an array of outdoor activities. The city is surrounded by numerous lakes, providing opportunities for boating, fishing, and water sports. The Winter Park Chain of Lakes is particularly popular among locals and visitors alike.

Winter Park is also renowned for its upscale shopping and dining options. Park Avenue, the city's main street, is lined with boutiques, cafes, and restaurants, offering a delightful shopping and dining experience. From high-end fashion to eclectic cuisine, Winter Park caters to a variety of tastes and preferences.

With its excellent schools, safe neighborhoods, and proximity to Orlando, Winter Park is an ideal place to live. Whether you are looking for a peaceful suburban retreat or a vibrant city lifestyle, Winter Park offers the best of both worlds.

Newest Listings in Winter Park

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

3 Beds ⋅ 3 Baths ⋅ Vilasa Twnhms SubDv. ⋅ 32789 Zip Code

Enjoy luxury living and premium sought-after location at Vilasa Homes, the newest construction in Winter Park, FL 32789. Walk to Park Avenue lifestyle, arts and culture- a mini-version of Manhattan’s Central Park, brick streets, historic neighborhoods, area’s hottest restaurants, shopping and the prestigious Rollins College. The finishes for this 2-estory townhome personally selected by one of the nation’s top interior designers. Carefully selected design team of Nasrallah Architectural Group, Ted Maines Interiors and Jordan Builders. Alys Beach inspired incorporating wood accents, architectural stairway, wrought iron and two-story ALL block construction all steps away from downtown Winter Park. Energy-saving features such as Pella double pane windows and extra insulation. Home is prewired for surround sound, cameras, alarm system, etc. Beautifully appointed-engineered wood flooring throughout from Daltile/Mohawk, recessed lights, level 4 wall finishes, 13-foot ceilings on the main floor, and 10-foot ceilings upstairs. This unit has been thoughtfully upgraded with a top modern package worth $40k. Chef’s gourmet kitchen is complete with high-end 18” flat panel cabinetry, 2.5” mitered Quartz countertops, double waterfall Quartz island, Thermador appliances, and beautiful Quartz backsplash. 6 burner Thermador SS gas cooktop, built-in butlers bar in dining room, staircase lighting are all additional upgrades. Spacious primary retreat on second floor with loft area perfect for office, Peloton or game room all wired with internet and electrical. Primary bedroom includes two separate his and hers closets with custom shelving and organizers. Generous closet and storage spaces. Relax in your garden tub and oversized walk-in shower, Quartz countertops, designer tile, Koehler fixtures/bathroom accessories and custom lighting treatments. Two more stately suites that can be used for exercise, office or bedrooms. Automated, remote window coverings. 2-car garages featuring insulated steel garage doors and additional storage. The Swoope townhomes each have an enlarged backyard measuring approx. 40ft x 20ft, including 8ft x 8ft covered patio slab which extends from the sliding doors. Each unit includes privacy fencing and landscaping. Owners maintain own backyard. Convenient and minutes from Hillstones, Whole Foods, Trader Joe's, Park Avenue restaurants and shopping! Top rated-9 hole Winter Park Golf Course, Casa Feliz, Morse Museum, water sports, Rollins, and churches are all a short stroll away.

504 W Swoope Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Woods Unit 01 SubDv. ⋅ 32792 Zip Code

Welcome to turnkey Winter Park living! This beautifully maintained 4-bedroom + office, 2,092 SF pool home features brand-new living room flooring, a roof only 4 years old, newer A/C, NO HOA, and a private in-ground pool. Step inside to a bright, open-concept layout with abundant natural light, granite countertops, modern appliances, generous cabinet space, and a cozy wood-burning fireplace. The spacious primary suite offers pool views, while the oversized enclosed Florida room/lanai creates the perfect setting for entertaining and year-round indoor/outdoor living. Outside, enjoy a fully fenced and landscaped backyard, private pool, irrigation system, attached 2-car garage, and additional parking. Vacant and move-in ready—bring your furniture and start enjoying the Florida lifestyle! Ideally located in the desirable Winter Woods/Lake Howell area, with convenient access to SR-417, I-4, SR-436, Howell Branch Road, Downtown Orlando, Winter Park shopping and dining, UCF, Orlando International Airport, parks, golf courses, and highly regarded Seminole County schools. Pool. No HOA. Major updates. Prime Winter Park location. Move-in ready. This home delivers the space, lifestyle, and convenience today’s buyers are looking for.

2217 Sussex Road, Winter Park

4 Beds ⋅ 3 Baths ⋅ Brookshire Heights 4th Add SubDv. ⋅ 32792 Zip Code

Virtually Staged. Fully renovated from top to bottom, this 4-bedroom, 3-bathroom Winter Park home pairs a bright, light-filled interior with a private pool made for Florida living. Large windows carry natural light through the main living spaces, and the big-ticket items are already done — new roof (2025) and new AC (2025) — so buyers get an established Winter Park address without the deferred maintenance. The kitchen is the centerpiece: gourmet-grade, fully renovated, with quartz countertops and new appliances built for someone who actually cooks. New flooring runs throughout the home, with tile in all three bathrooms for a clean, easy-care finish. Out back, a screened lanai opens onto the pool — shade and bug-free comfort for morning coffee or evening swims, with the pool itself as the yard’s focal point.

618 Blairshire Circle, Winter Park

Ethel Park SubDv. ⋅ 32789 Zip Code

An outstanding opportunity to acquire a generously sized homesite in the highly desirable Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, Winter Park

2 Beds ⋅ 1 Baths ⋅ Ethel Park SubDv. ⋅ 32789 Zip Code

An outstanding opportunity to acquire a generously sized homesite in the highly desirable City of Winter Park area. Measuring approximately 75' x 154', this 11,555-square-foot lot offers excellent potential for a custom luxury residence. This property is being offered for its land value, presenting an ideal opportunity for a builder, developer, investor, or buyer looking to create a custom home tailored to today's luxury lifestyle. The Winter Park area hosts a remarkable collection of luxury homes, custom estates, and continued new development, making this an attractive location for those seeking to build in an established and highly desirable market. With its generous lot dimensions and surrounding luxury development, this property provides an excellent canvas for your next custom-home project.

447 N Phelps Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Eastbrook Sub Unit 16 SubDv. ⋅ 32792 Zip Code

VIRTUALLY STAGED! EXCEPTIONAL POOL HOME IN EASTBROOK! Welcome to Conifer Avenue, where pride of ownership, and an unbeatable Winter Park-area location come together beautifully. This impressive pool home offers an outstanding opportunity to own a well-maintained residence in the highly sought-after Eastbrook community. This FOUR BEDROOM 2 Bath home offers almost 2200 square feet! Split bedroom plan PLUS 21 x 12 office/bonus room; formal living, dining & family rooms;2024 NEW HVAC-POOL PUMP 2025-ROOF 2019-zoned for excellent Seminole County Schools! Oversized 20 x 22 two car garage with additional storage space. Extras include: updated windows; all appliances including washer & dryer; quaint front porch. Call for your private showing! Step outside and discover your own private retreat! Multiple sets of sliding glass doors open to the large screened-in lanai, sparkling swimming pool, and expansive pool deck, creating an exceptional indoor-outdoor living and entertaining space. The nearly quarter-acre lot is fully fenced, offering plenty of room for pets, play, gardening, and outdoor enjoyment. The oversized two-car garage provides generous parking and an abundance of storage options. This is truly an entertainer's dream home—whether you're hosting friends around the pool, enjoying a quiet evening outdoors, or simply relaxing in your own private backyard oasis. And then there's the LOCATION! LOCATION! LOCATION! Convenient access to I-4 and SR 417 makes traveling throughout Central Florida a breeze, with easy access toward Orlando's attractions, Disney, the beaches, shopping, dining, and entertainment. Enjoy being close to the charm of Historic Downtown Winter Park and Park Avenue, including its fabulous restaurants, boutique shopping, cultural attractions, and popular weekly Farmers Market. SunRail is also conveniently nearby, providing another great transportation option throughout Central Florida.

2301 Conifer Avenue, Winter Park

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

Capens Add SubDv. ⋅ 32789 Zip Code

HIGH & DRY | PRIME WINTER PARK LOCATION | BUILD YOUR DREAM HOME Rarely does an opportunity like this become available in the heart of Winter Park! This high-and-dry homesite is ideally situated in a highly desirable area surrounded by beautiful new construction homes, including a newer community of impressive million-dollar residences directly across the street. Located in coveted Old Winter Park/32789, this approximately 96' x 49' lot offers a rare opportunity to create your very own custom home in one of Central Florida’s most sought-after locations. This location offers the finest in Orange County Schools, award winning Winter Park High. Originally home to a residence years ago, this property offers an exciting opportunity to bring your favorite builder and create a home designed specifically for your lifestyle. Imagine building your own one-of-a-kind masterpiece in a neighborhood where new construction and redevelopment are transforming the area while maintaining the character and charm that makes Winter Park so special. LOCATION truly sets this property apart! Bike to Park Avenue or stroll to Winter Park Village, where premier dining, shopping, entertainment, and everyday conveniences are just minutes from your future front door. Enjoy easy access to Hannibal Square, the Park Avenue corridor, U.S. 17-92, I-4, grocery stores, specialty shops, the Winter Park Community Center and Park, Rollins College, and AdventHealth. With new construction continuing to surround the area, this is your chance to secure a piece of Winter Park before available land becomes even harder to find. Zoned R-1A and located within the desirable Winter Park area, this property offers exceptional potential for a custom residence or investment. NO HOA. Bring your imagination, creativity, and builder! If you’ve been searching for that special Winter Park homesite where location, lifestyle, and future value come together, your search may be over. This is the Winter Park sweet spot you’ve been waiting for!

786 W Canton Avenue, Winter Park

3 Beds ⋅ 2 Baths ⋅ Suburban Homes First Add SubDv. ⋅ 32792 Zip Code

Location, location, location! Discover this beautiful, meticulously maintained home in a highly desirable Winter Park neighborhood, conveniently located near excellent schools. Enjoy vinyl flooring throughout—no carpet! The gorgeous, upgraded kitchen features quartz countertops, an oversized island, recessed lighting, and stainless-steel appliances. The beautifully updated bathrooms also feature quartz countertops. Fresh landscaping enhances both the front and backyard. Step outside and enjoy your private swimming pool and fully fenced backyard—the perfect setting for relaxing and entertaining. NO HOA and NO CDD! Conveniently located minutes to UCF, Full Sail, Barry University, Valencia, multiple grocery stores and pharmacies, Winter Park’s scenic Park Avenue, Downtown Orlando, and Orlando International Airport.

4870 Seminole Avenue, Winter Park

4 Beds ⋅ 2 Baths ⋅ Winter Park SubDv. ⋅ 32789 Zip Code

Rare Winter Park redevelopment opportunity on a NEARLY HALF-ACRE CORNER PARCEL JUST MINUTES FROM PARK AVENUE. Newly priced at $3,950,000, this R-3 ZONED (Medium-Density Residential) property offers outstanding redevelopment potential, INCLUDING CAPACITY FOR UP TO SEVEN RESIDENTIAL UNITS. Ideally positioned between Park Avenue and Winter Park Village, the property offers convenient access to renowned dining and shopping, Rollins College, cultural attractions, AdventHealth Winter Park, and major transportation corridors. Three existing residences occupy the site and contribute no value to the offering. Properties of this size and zoning, so close to Park Avenue, are exceptionally rare. THIS PROPERTY IS CROSS-LISTED AS VACANT LAND WITH THE MLS #O6431538.

540 N Pennsylvania Avenue, Winter Park

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

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