Winter Park Land for Sale

Winter Park Land for Sale

Winter Park, located in Orange County, Florida, is a charming city known for its natural beauty and vibrant community. Situated just a short drive from downtown Orlando, Winter Park offers a perfect blend of suburban tranquility and urban convenience.

If you are in search of land for sale in Winter Park, you are in luck. This region is home to a variety of available properties, allowing you to build your dream home or invest in real estate opportunities. Whether you are looking for a spacious lot to construct a custom-designed house or a parcel of land for commercial development, Winter Park has options to suit your needs.

One of the key advantages of purchasing land in Winter Park is its prime location. With easy access to major highways and a well-connected public transportation system, commuting to other parts of the state or exploring the surrounding areas is a breeze. Additionally, Winter Park boasts a thriving economy, excellent schools, and a wide range of recreational activities, making it an ideal place to live, work, and play.

The natural beauty of Winter Park is another selling point for land buyers. The city is dotted with picturesque lakes, lush parks, and tree-lined streets, creating a serene and idyllic setting. Whether you prefer boating, fishing, or simply enjoying a leisurely stroll, Winter Park offers ample opportunities to connect with nature.

If you are considering investing in land for sale in Winter Park, now is the perfect time to explore the possibilities. With its desirable location, strong community spirit, and abundant amenities, Winter Park offers a promising future for both residents and investors alike.

Newest Winter Park Land for Sale

1780 Bryan Avenue, Winter Park
$825,000
Lakeview Terrace SubDv. ⋅ 32789 Zip Code
Build your dream home in one of Winter Park’s most desirable locations. This 66.6’ x 127’ homesite at 1780 Bryan Avenue offers a rare opportunity to secure the last remaining lot of three consecutive new construction parcels. Surrounded by newly built luxury residences, the property provides a clean slate for custom design while maintaining strong future value. The lot’s generous dimensions allow for a spacious floor plan, outdoor living areas, and a private backyard retreat. Situated on a quiet, tree-lined street, yet just minutes from Park Avenue, top-rated schools, dining, and shopping, the location strikes the perfect balance between convenience and neighborhood charm. Opportunities like this are increasingly rare in Winter Park—don’t miss your chance to be part of a growing enclave of new construction homes in a highly sought-after area.

1780 Bryan Avenue, Winter Park
1030 Bonita Drive, Winter Park
$1,100,000
Comstock Park SubDv. ⋅ 32789 Zip Code
Exceptional opportunity to build on beautiful Bonita Drive, one of Winter Park’s most picturesque brick-lined streets, with this 0.18-acre (approximately 8,014-square-foot) homesite. Already cleared and ready for new construction, the property offers an ideal setting to create a custom residence tailored to your vision. Ideally positioned just minutes from Park Avenue’s shops and restaurants, Rollins College, the Winter Park Farmers’ Market, leading hospitals and top-rated schools, with convenient access to downtown Orlando, major roadways and area airports. Create your dream home in one of Winter Park’s most desirable residential settings.

1030 Bonita Drive, Winter Park
1399 Aloma Avenue, Winter Park
$575,000
Galloway Place Rep SubDv. ⋅ 32789 Zip Code
Charming 1948 home with Winter Park Chain of Lakes access offers a great opportunity for buyers looking to renovate or explore new construction in an established Winter Park location. Conveniently located near Rollins College, Park Avenue, and Winter Park Hospital, with access to Lake Osceola just a short walk away to launch a paddleboard or canoe. The 3-bedroom, 2-bath character home offers a split floor plan with original hardwood floors, arched doorways, plantation shutters, and a formal living room with a gas fireplace and built-ins. The updated kitchen features Carrara quartz countertops, stainless appliances, and wood cabinetry, and opens to the dining and sunrooms. French doors from the sunroom lead to a covered patio and backyard with mature landscaping, paver walkways, and a tranquil cabana perfect for relaxing. Additional features include an attached one-car garage with washer/dryer, walk-in closets, and a circular driveway for additional parking. Improvements include new PEX water supply lines (2025) and partial drain-line replacement, recent interior painting, and updated bathrooms with a 2019 renovation featuring marble shower and floors. With its original character, thoughtful improvements, and convenient Winter Park location, this home offers an opportunity for its next owner to make it their own.

1399 Aloma Avenue, Winter Park
2036 Via Tuscany, Winter Park
$2,100,000
Tuscania SubDv. ⋅ 32789 Zip Code
**A rare jewel in Winter Park's coveted Vias!** This oversized 0.36-acre lot (112' x 140') has been cleared and is ready for your custom estate home. Set on a charming brick street, it sits among multi-million dollar residences and lakefront estates, just steps from the Winter Park Racquet Club and close to Interlachen Country Club. Enjoy a quick drive to Park Avenue's boutiques and dining and the Winter Park 9 golf course. Zoned for Dommerich Elementary, Maitland Middle, and Winter Park High. Opportunities to build in this sought-after neighborhood are few and far between, so bring your architect and your vision!

2036 Via Tuscany, Winter Park
870 N Phelps Avenue, Winter Park
$850,000
Osceola Or Lakeview Deed SubDv. ⋅ 32789 Zip Code
Bring your vision to life in Winter Park. Situated on N Phelps Avenue, this approximately .24-acre property offers a rare opportunity to build new in an area surrounded by custom homes, luxury residences, and ongoing redevelopment. Offered for its land value, this property is well suited for builders, investors, developers, or anyone ready to create a home designed around their own style and needs. The 75-foot frontage with 140-foot depth provides flexibility for a variety of architectural designs and potential for outdoor living, a pool, and backyard space. With new construction continuing to reshape the surrounding area, 870 N Phelps presents an exciting opportunity to secure a sizable homesite and build from the ground up.

870 N Phelps Avenue, Winter Park
120 Broadview Avenue, Winter Park
$2,400,000
Killarney Estates SubDv. ⋅ 32789 Zip Code
SPECTACULAR OPPORTUNITY ON SCENIC LAKE KILLARNEY! .39 acres: 17,100 sq ft (approx 24,000 sq ft: .55 acres including lakefront & street easement on both corner streets: 95 ft lakefront not included in FAR) Discover a rare opportunity to live on scenic Lake Killarney—a 236-acre, spring-fed private lake with no public access. Nestled along a charming, tree-canopied, lakefront dead-end brick street, this 1947 bungalow offers 1,747 square feet of pure potential, featuring 3 bedrooms, 2 baths, a 2-car garage, and a lovely corner lot. Renovate the existing home or create your dream residence in this tranquil setting, where breathtaking sunsets and peaceful lake views await. Enjoy the convenience of being within walking distance of restaurants and shopping, while having easy access to Interstate 4, Rollins College, and all that Winter Park’s renowned Park Avenue has to offer. THREE Optional OPPORTUNITIES: Option 1 — $1,450,000 155' x 65' property + 65' lakefront. Option 2 — $1,250,000 115' x 65' property + 65' lakefront. Option 3 — $2,250,000 155' x 95' property + 95' lakefront. A truly rare find in a quaint and desirable neighborhood, offering the flexibility to renovate, expand, or build the home you’ve always envisioned. Come experience the tranquility, privacy, and beauty of Lake Killarney. WELCOME HOME!

120 Broadview Avenue, Winter Park
786 W Canton Avenue, Winter Park
$450,000
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! View Virtual tour for a live view of the street.

786 W Canton Avenue, Winter Park
1431 Palm Avenue, Winter Park
$799,999
Lake Knowles Terrace Add 02 SubDv. ⋅ 32789 Zip Code
Welcome to this beautiful lot located in one of Winter Park’s most desirable neighborhoods. This exceptional location presents the perfect opportunity to build your dream home in one of the most sought after school zones Winter Park has to offer. Set along picturesque brick streets shaded by mature trees, the location is hard to beat. It is within walking distance to the beautiful Lake Knowles and Lake Wilbar, just minutes from Park Avenue, the Winter Park YMCA, AdventHealth Winter Park, Rollins College, the Winter Park Chain of Lakes, golf courses, and an abundance of exceptional dining and shopping. Enjoy the chance to create a home tailored to your lifestyle with a perfect blend of classic Winter Park character, beautiful outdoor living, and an unbeatable location.

1431 Palm Avenue, Winter Park
822 Symonds Avenue, Winter Park
$599,999
Capens Add SubDv. ⋅ 32789 Zip Code
Build in the heart of Winter Park. This cleared quarter-acre lot (approx. 10,807 sq ft, 50' x 216') sits on Symonds Avenue on the city's west side. It's just blocks from Hannibal Square, Winter Park Village and Martin Luther King Jr. Park, and minutes from the shops and restaurants of Park Avenue. The lot is ready for your plans. It's cleared, with mature shade trees, a paved street with sidewalk, and public water and sewer available. It's zoned R-2, in Flood Zone X, with no HOA. Builders and buyers have room to create a custom home or an investment project in one of Central Florida's most desirable cities. Land this close to Park Avenue rarely comes available. Buyer to verify zoning, setbacks and permitted uses with the City of Winter Park.

822 Symonds Avenue, Winter Park
2403 Euston Road, Winter Park
$4,299,000
Justamere Camp Rep SubDv. ⋅ 32789 Zip Code
Fly In. Unwind. Build Your Dream on Lake Killarney. Bring your seaplane and envision the lakefront estate of your dreams on one of Winter Park’s rarest offerings. Tucked away on a private peninsula surrounded by multi-million-dollar homes, this extraordinary property spans approximately 432 feet of shoreline along the spring-fed, crystal-clear waters of Lake Killarney. With 1.514 buildable acres across two combined lots (2401 & 2403 Euston Ave), you'll have the space—and the freedom—to design an architectural masterpiece or a serene retreat that blends seamlessly with the natural beauty of this exclusive setting. Lake Killarney is a hidden 234-acre gem, beloved for its tranquility, paddleboarding and watersports, abundant wildlife, and lakeside dining. Locals savor moments like scenic seaplane lunches at Hillstone and cozy evenings around fire pits under starlit skies. With no public access, the lake offers unmatched privacy, and its pristine waters are maintained year-round by a thoughtful system of two drainage wells. Just minutes away, enjoy the vibrant lifestyle Winter Park is known for—Rollins College, Park Avenue, Winter Park Village, Whole Foods, the Farmers Market, and a rich cultural scene are all at your fingertips. Whether you’re dreaming of a peaceful sanctuary or a showstopping entertainer’s paradise, this property offers the ultimate trifecta: land, luxury, and lifestyle.

2403 Euston Road, Winter Park
150 E Reading Way, Winter Park
$1,399,000
Charmont SubDv. ⋅ 32789 Zip Code
A wonderful opportunity to build your dream home on one of Winter Park’s most idyllic streets. Situated on a quaint, one-way brick street with a charming park at its center, this exceptional 12,581-square-foot deep lot offers a rare combination of space, character, and location. Currently featuring a 3-bedroom, 2.5-baths, plus office home with 2,080 square feet, the property offers the flexibility to live in or rent the existing home while you finalize your plans and prepare to build. Ideally located within the highly sought-after “A” school district of Audubon K-8 and Winter Park High School, this property places you just minutes from downtown Orlando, Orlando Health, AdventHealth, and the Dr. Phillips Center for the Performing Arts. Enjoy easy access to the vibrant restaurants and shops along Corrine Drive, as well as the boutiques, dining, and charm of Park Avenue. A rare opportunity to create your ideal Winter Park residence in an extraordinary setting surrounded by convenience, character, and everything this coveted area has to offer.

150 E Reading Way, Winter Park
540 N Pennsylvania Avenue, Winter Park
$3,950,000
Winter Park SubDv. ⋅ 32789 Zip Code
MAJOR PRICE IMPROVEMENT—NOW OFFERED BELOW $4 MILLION! 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 (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 RESIDENTIAL WITH THE MLS #O6436046.

540 N Pennsylvania Avenue, Winter Park
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