Winter Park Land for Sale

Winter Park Land for Sale

Winter Park, Florida is a picturesque city located in Orange County, just a few miles north of downtown Orlando. Known for its charming tree-lined streets, beautiful lakes, and historic architecture, Winter Park offers a unique blend of natural beauty and cultural attractions.

One of the key features of Winter Park is its abundance of land for sale. Whether you are looking for a residential lot to build your dream home or a commercial plot for a business venture, Winter Park has options to suit every need. With its prime location and thriving real estate market, investing in land in Winter Park can be a smart and lucrative decision.

The land for sale in Winter Park offers a range of opportunities. From small, cozy lots perfect for a single-family home to larger parcels of land suitable for commercial development, there is something for everyone. Many of these properties boast stunning views of the city's lakes or are nestled within established neighborhoods, offering a sense of community and convenience.

Winter Park's land for sale is highly sought after due to its proximity to top-rated schools, trendy shopping districts, and world-class dining options. Additionally, the city's commitment to preserving its historic charm ensures that any development adheres to strict guidelines, resulting in a harmonious blend of old and new.

If you are looking to invest in land in Florida, Winter Park should be at the top of your list. With its idyllic setting, thriving real estate market, and endless possibilities, Winter Park offers a truly unique opportunity to build the life you envision.

Newest Winter Park Land for Sale

$2,100,000
O6434781 MLS
A rare opportunity to own nearly 7 acres on the pristine shores of Private Lake Howell! This exceptional lakefront property offers the perfect setting to build your custom dream home while enjoying the privacy and tranquility of one of Central Florida's premier waterfront locations. Spanning nearly 400 acres, Lake Howell is a skiable lake ideal for boating, water skiing, fishing, kayaking, canoeing, paddleboarding, and endless outdoor recreation. With expansive acreage, breathtaking water views, and ample space to create your own private estate, the possibilities are endless. The value is in the land, making this an incredible opportunity for those seeking a premier homesite in a highly desirable location. Don't miss your chance to own one of the area's rare large-acreage lakefront parcels.

1133 Bella Lago Cove, Winter Park
$1,495,000
O6430223 MLS
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
$4,600,000
O6431538 MLS
Rare Winter Park redevelopment opportunity on a nearly half-acre corner parcel just minutes from Park Avenue. Zoned R-3 (Medium-Density Residential), this parcel offers outstanding residential redevelopment potential, including up to seven residential units. Ideally situated between Park Avenue and Winter Park Village, the property enjoys convenient access to renowned dining, 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. Opportunities of this size and zoning in such close proximity to Park Avenue are exceptionally uncommon.

540 N Pennsylvania Avenue, Winter Park
$249,000
TB8535201 MLS
A rare piece of land in the heart of Winter Park. Short distance to Park Ave. Approved permits for 2000 sqft under AC housing project.

669 W Comstock Avenue, Winter Park
$1,894,000
O6427443 MLS
Fully remodeled! One of the most competitively priced homes featuring over 3,300 SF, in the 32789 zip code, and in the K-8 Audubon Park School District. The K-8 Audubon Park School District is a small pocket, and ranked one of the best district's in the state. Fully remodeled luxury pool homes in the highly sought-after Audubon K-8 and Winter Park school district with over 3,300 square feet of exceptional living space, capped with a brand-new, architecturally stunning tile barrel roof that blends timeless Mediterranean elegance with lasting durability. 2614 Parkland Drive, a fully reimagined luxury residence in the heart of Winter Park. This is your chance to own a showpiece property with over 3,300 SF zoned for the coveted Audubon Park K-8 and Winter Park High School districts. Completely remodeled in late 2022, this home radiates warmth and sophistication. Solid light oak floors, custom railings, and an open-concept flow make entertaining effortless. The chef’s kitchen is a centerpiece; quartz counters, full-height designer tile, and abundant storage bring form and function together. Out back, discover your private resort. A heatable custom pool & spa finished in ultra-rare Caribbean blue tile sets the tone; elevated with two natural-gas fire pits, dramatic waterfalls, porcelain privacy walls, and a built-in grill. Every evening feels like a five-star escape.The first-floor master suite offers direct access to the outdoor oasis, while upstairs features three oversized bedrooms, a loft, and a private patio for sunset views. Brand-new tile roof, dual tankless water heaters, central vacuum, and all-natural gas appliances ensure low-maintenance, worry-free living. This is more than a home it’s a statement. A chance to live where luxury, location, and lifestyle converge.

2614 Parkland Drive, Winter Park
$425,000
O6426549 MLS
A great opportunity to own land in one of Winter Park's most sought-after pockets. This property's true value lies in its prime homesite. You can build your dream home or renovate to suit, all while capturing the location that can't be replicated. Tucked in an established, tree-lined neighborhood minutes from Park Avenue's boutiques and dining, Winter Park's chain of lakes, and easy access to I-4, this address puts you at the center of it all. Zoned for top-rated Winter Park schools, this is the kind of location families compete for. Whether you're an investor, builder, or buyer looking to create something custom, this is a foundation worth building on. Land + location + schools — the trifecta that makes Winter Park real estate hold its value.

1909 Taylor Avenue, Winter Park
$1,750,000
O6424300 MLS
Exceptional opportunity to build on beautiful Lake Sylvan with this 0.37-acre (approximately 16,603-square-foot) lakefront homesite. Offering a picturesque waterfront setting, the property is ideally positioned just minutes from Park Avenue's shops and restaurants, major roadways, leading hospitals and top private schools. Create a custom lakefront residence tailored to your vision in one of Central Florida's most desirable waterfront settings. For buyers seeking inspiration, a separately listed proposed new construction residence designed specifically for this homesite is available for review. See MLS #O6407606 for renderings and conceptual plans illustrating one potential vision for the property.

313L Sylvan Drive, Winter Park
$2,200,000
O6423553 MLS
Exceptional opportunity to build your dream home in one of Winter Park’s most sought-after neighborhoods! This cleared, vacant homesite is ready for construction and offers the perfect canvas to create a custom residence tailored to your vision. Nestled on a quiet street, the property is surrounded by beautiful homes while providing convenient access to Park Avenue’s renowned shopping and dining, Rollins College, top-rated schools, parks, golf courses, and major roadways. Whether you’re a builder, investor, or future homeowner, this is a rare chance to secure a prime piece of land in an established community where new construction opportunities are increasingly limited. Don’t miss the chance to bring your vision to life in the heart of Winter Park!

1415 Grove Terrace, Winter Park
$499,000
A11792799 MLS
Excellent Development opportunity in highly sought after area

3718 N Goldenrod Road, Winter Park
$449,000
O6419256 MLS
Some opportunities don't announce themselves. They show up quietly in Winter Park's most sought-after zip code, waiting for someone who knows exactly what to do with them. This vacant lot inside Waterbridge sits in the 32789 zip code, a rare chance to build the home you've always had in mind, in a neighborhood that has already decided who it is. Waterbridge is a tight-knit, tree-lined enclave where the homes are custom and the neighbors stay. Lots like this do not come available often. The address puts you minutes from Park Avenue's galleries and weekend farmers market, AdventHealth Winter Park, and the employers and services that make this corridor one of Winter Park's most connected. The schools zoned here, Glenridge Middle and Winter Park High, are among the most respected in Orange County and part of why buyers seek out this zip code specifically. Build the primary suite you've never been able to find. Design the kitchen around how you actually cook. Choose the ceiling heights, the materials, the layout. Every decision a resale home will never let you make is yours to make here. A lot in Waterbridge represents something that rarely surfaces: the convergence of a blank canvas and a proven address.

Jessica Court, Winter Park
$1,595,000
O6416144 MLS
Exceptional opportunity in the heart of Winter Park - a truly premier and irreplaceable homesite offering rare scale, privacy, and extraordinary future build potential. The primary value is in the land, presenting an unparalleled canvas for a custom luxury residence, with virtually no comparable vacant land available in the immediate vicinity. Set on a tranquil small lake that provides remarkable serenity and picturesque water views, this property combines peaceful natural surroundings with unbeatable walkability. Ideally positioned just steps from the Racquet Club, moments to Park Avenue's renowned dining, boutiques, and cultural venues, and within easy reach of the Winter Park Chain of Lakes. The location also offers the distinct prestige of residing within the coveted "Vias" of Winter Park, a collection of streets long regarded as one of the city's most established and desirable residential enclaves. Whether envisioned as a modern architectural statement or an elegant estate home, this site delivers the location, setting, and versatility sought by discerning builders, investors, and end users alike - a rare chance to secure one of winter Park's most desirable land offerings in a highly established neighborhood.

1113 Via Del Mar, Winter Park
$1,450,000
O6410178 MLS
STUNNING SUNSET VIEWS OF LAKE KILLARNEY FROM THIS CORNER LOT SITUATED ON A SERENE PRIVATE BRICK DEAD END STREET WITH 65 FEET OF LAKE FRONTAGE. BUILD YOUR LAKEFRONT DREAM HOME AND ADD A BOAT DOCK FOR THIS PRIVATE LAKE EXPERIENCE. THIS IS A RARE FIND IN WINTER PARK. SELLER IS ADDING AN ADDITIONAL 40 X 65 FROM BACK LOT LINE. THIS ADDED LAND BRINGS THE LOT SIZE TO 155 X 65. or 10,075 SF BUILDABLE LOT. LAKEFRONT PORTION OF LOT NOT INCLUDED IN BUILDABLE LOT SO ACTUAL LOT SQUARE FOOTAGE IS CLOSER TO 11,000 SF. CURRENT RESIDENCE ON LOT WAS BUILT IN 1947 AND WOULD NEED TO BE COMPLETELY REMODELED AND RENOVATED. WALKING DISTANCE TO HILLSTONE, TRADER JOE'S, ETC. AND A SHORT DRIVE TO PARK AVE AND ROLLINS COLLEGE.

120 Broadview Avenue, Winter Park
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