Winter Garden/Oakland Land for Sale

Winter Garden/Oakland Land for Sale

**Discover Your Dream Property in Winter Garden and Oakland, Florida**

Nestled in the heart of Central Florida, Winter Garden and its charming neighbor, Oakland, offer a delightful blend of small-town charm and modern conveniences. Known for their picturesque landscapes, vibrant community life, and rich history, these areas are the perfect backdrop for your next investment or dream home.

Winter Garden is renowned for its historic downtown district, where you can stroll along cobblestone streets lined with quaint boutiques, artisanal eateries, and local farmers' markets. The West Orange Trail, a scenic 22-mile-long pathway, invites outdoor enthusiasts to explore the natural beauty of the region, making it ideal for biking, walking, or jogging. Meanwhile, the serene lakes and lush parks in Oakland provide a peaceful retreat, perfect for family picnics or weekend getaways.

For those considering a land investment, Winter Garden and Oakland present an exceptional opportunity. The area boasts a variety of parcels available for sale, ranging from spacious lots perfect for custom home builds to prime commercial sites that promise lucrative returns. With the ongoing growth and development in Central Florida, investing in land here is not just a purchase—it's a step toward a vibrant future.

Whether you envision a tranquil retreat surrounded by nature or a bustling hub of activity, Winter Garden and Oakland have the perfect piece of land waiting for you. Embrace the warmth of the Florida sun and the welcoming spirit of the community—your dream property is just a decision away!

Newest Winter Garden/Oakland Land for Sale

Joe Louis Park First Add SubDv. ⋅ 34787 Zip Code

Vacant buildable lot near Downtown Winter Garden!! 135 feet deep and 50 feet across. Paved street with new sidewalks and lots of new construction on the block. No rear neighbors. Enjoy all that Winter Garden has to offer with dining and shopping. Convienent to SR 429, SR 50, The Florida Turnpike and the 408. This one will not last. Call today for more details.

1690 E Bay Street, Winter Garden

Hickory Lake Estates SubDv. ⋅ 34787 Zip Code

One of the only lakefront lots located in the highly desirable Horizon West area and minutes from Disney. Offering direct water frontage with breathtaking sunset views right from your back yard, this property captures the best of Florida living—peaceful, scenic, and close to everything. Enjoy skiing, kayaking, paddleboarding and fishing from your own backyard on the clear waters of Lake Hickory Nut. This stunning lot provides ample space to design a custom home that maximizes privacy and panoramic vistas. Plans are available for a 4,400SF estate home including ADU for in-laws, multigenerational living or rental for extra income. Situated just minutes from Orange County Country Club with top-rated schools, dining, shopping, and major highways, this location blends natural beauty with everyday convenience. Don't miss this chance to own a piece of paradise in one of the most desirable areas in the U.S. Rare opportunities like this don’t come often. Secure your slice of lakefront paradise and start building the lifestyle you’ve been dreaming of.

9444 Lake Hickory Nut Drive, Winter Garden

Lake Apopka Sound SubDv. ⋅ 34787 Zip Code

Discover the perfect blend of luxury and natural beauty with these stunning lakefront lots in the Lake Apopka Sound subdivision. Set along the shores of scenic Lake Apopka, these spacious homesites offer breathtaking water views, serene sunsets, and access to one of Central Florida’s most picturesque settings. Lake Apopka Sound provides the ideal backdrop for your custom dream home. With close proximity to Winter Garden, Clermont, and major highways, you’ll enjoy both peaceful lakefront living and convenient access to shopping, dining, and entertainment. Don’t miss the opportunity to secure one of these rare waterfront lots and create the lifestyle you’ve always envisioned.

17862 Hither Hills Circle, Winter Garden

Lake Apopka Sound SubDv. ⋅ 34787 Zip Code

Discover the perfect blend of luxury and natural beauty with these stunning lakefront lots in the Lake Apopka Sound subdivision. Set along the shores of scenic Lake Apopka, these spacious homesites offer breathtaking water views, serene sunsets, and access to one of Central Florida’s most picturesque settings. Lake Apopka Sound provides the ideal backdrop for your custom dream home. With close proximity to Winter Garden, Clermont, and major highways, you’ll enjoy both peaceful lakefront living and convenient access to shopping, dining, and entertainment. Don’t miss the opportunity to secure one of these rare waterfront lots and create the lifestyle you’ve always envisioned.

2012 N Old Killarny Street, Winter Garden

Discover the potential of this exceptional 0.54-acre vacant lot in the heart of established Winter Garden. Measuring approximately 120 feet wide by 200 feet deep, this residentially zoned (R-2) property offers an outstanding opportunity to build your dream home or make a smart investment in one of Central Florida's most desirable and rapidly growing communities. Enjoy the freedom of no HOA and the added benefit of being located outside the flood zone. Ideally situated just minutes from Winter Garden Village at Fowler Groves, Historic Downtown Winter Garden, charming parks, museums, unique boutiques, and an array of popular restaurants, AN on going expending 209-acre park that offers a variety of outdoor activities and natural experiences is only few minutes away from this land , the value is growing . This property combines peaceful residential living with convenient access to everyday amenities. Florida's Turnpike is just minutes away, providing easy commuting throughout Central Florida. Whether you're planning to build now or invest for the future, this prime homesite offers endless possibilities. Don't miss your chance to secure this incredible property and schedule your visit and make your offer today!

Avalon Road Unit 53, Winter Garden

Lake Avalon Heights SubDv. ⋅ 34787 Zip Code

Incredible chance to build your dream lake front home. Just under 2 acres on Lake Avalon in the heart of the rural settlement. Zoning allows Livestock and horses ! Incredible views of 184 acre Lake Avalon. BRING YOUR OWN BUILDER. NO BUILDER TIES to this lot, your lot your choice. Sought after schools K-12 and minutes to Windermere Preparatory and Foundation academy campuses. Live the country lifestyle with the 429 expressway and Disney minutes away from your front door. The existing building is just an unfinished shell with multiple out buildings/ workshop has power. New well pump in last year. Septic and power on site too ! This is the perfect canvas for your dream home.

3421 Rex Drive, Winter Garden

Overstreet Crate SubDv. ⋅ 34787 Zip Code

Rare vacant lot in the heart of East Winter Garden — cleared, graded, and ready to build! This 70' x 140' lot (0.23 acres) sits in the coveted Golf Cart District, just minutes from the charm of Downtown Winter Garden, the West Orange Trail, local dining, shops, and the Saturday Farmers Market. Zoned R-2 with ADU approval already in place — a true value-add opportunity for investors, builders, or future homeowners looking to maximize the lot's potential. Approved permits secured and renderings for the single-family home available upon request. Don't sleep on one of the last buildable lots in this rapidly growing, in-demand neighborhood. Opportunities like this in Winter Garden don't last.

441 E Cypress Street, Winter Garden

Lake Highlands 23-22-26 SubDv. ⋅ 34787 Zip Code

Rare opportunity to own 5 acres of highly versatile land near Orlando, Clermont, and Winter Garden, located at 16838 Old Highway 50 in one of Lake County’s rapidly growing corridors. With 300 feet of frontage and already divided into three parcels, this property features agricultural, commercial, and residential zoning, creating endless possibilities for developers, builders, investors, or anyone searching for Orlando land for sale, Clermont development land, Winter Garden acreage, or Central Florida investment property. Positioned in a high-growth area with ongoing expansion and development, the property is ideal for residential development, mixed-use projects, future commercial opportunities, equestrian use, farming, or multi-generational living. There is ample space for animals, horses, barns, stables, workshops, and agricultural operations, offering flexibility for both personal and investment use. As an added bonus, the property includes two manufactured homes. One has been fully remodeled within the last two years with a new kitchen, updated flooring, and extensive renovations completed down to the studs, making it suitable for immediate occupancy or rental income. The second manufactured home is a 4-bedroom, 2-bath residence currently used for storage, but it can easily be converted into a guest home, in-law suite, or additional living space. The property also features a city-converted self-watering system, with additional details available from the listing agent. With flexible zoning, prime frontage, rare acreage, and close proximity to Orlando, Clermont, and Winter Garden growth areas, this is an exceptional opportunity to secure Central Florida land with significant future upside. **This house comes with a REDUCED RATE through the seller's preferred lender. This is a lender-paid rate buydown that reduces the buyer's interest rate and monthly payment.**

16838 Old Highway 50, Winter Garden

PRIME WINTER GARDEN LAND OPPORTUNITY – 0.54 ACRES | R-2 ZONING Located along Avalon Rd in the highly desirable Winter Garden corridor, this 0.54-acre residential parcel offers an excellent opportunity for builders, investors, or end-users looking to secure land in one of Central Florida’s fastest-growing areas. Zoned R-2, the property allows for flexible residential development, ideal for a custom home or income-producing project. With 120 feet of frontage and nearly 200 feet of depth, the lot provides a well-proportioned footprint for efficient site planning and design. Situated in Flood Zone X (no flood insurance required) and with electricity, cable, and high-speed internet available nearby, this parcel presents a straightforward path for future development. The area continues to experience strong growth driven by proximity to major roadways, employment centers, and lifestyle amenities. Enjoy convenient access to the charm and energy of Historic Downtown Winter Garden, as well as major retail and dining at Winter Garden Village. The location also benefits from its connectivity to the greater Orlando market, making it attractive for both resale and rental strategies. Whether you're looking to build, hold, or invest, this parcel offers location, flexibility, and long-term upside in a proven growth market.

Avalon Road, Winter Garden

Developer alert! Secure this rare residential lot that has plans for the construction of FOUR (4) RESIDENTIAL UNITS. Incredible opportunity to secure a multi-family development site complete with fully drafted architectural plans for a 4-unit building. Skip months of initial design work and the associated architectural expenses because these plans are completed and ready for submission to the city for permitting. The property features a flat and clear lot located in a high-demand area with strong rental and resale potential. Ideal project for a builder or investor looking to streamline their timeline and maximize returns. Buyer to verify all utilities, zoning requirements, and city permitting processes. Sold as-is with plans included.

9th Street, Winter Garden

Are you looking for a perfect place to build your dream home? Look no further than this expansive open space, featuring stunning lakefront sunsets over Lake Apopka, one of the largest and most beautiful lakes in Central Florida. This 3.0 acre lot offers breathtaking views of true Florida it's surrounding nature, as well as access to fishing, boating, and wildlife watching. You will enjoy the tranquility and privacy of this lot, while being close to the amenities and attractions of Winter Garden, a charming and historic city with a vibrant downtown, farmers market, and festivals. Winter Garden boasts premier dining, shopping, and top-rated schools. An unparalleled blend of land, location, and lifestyle. Experience true freedom from HOA or CDD fees and restrictions. Don't miss this rare opportunity to own a piece of paradise on Lake Apopka! Bring your own builder and create a custom masterpiece in this highly sough after location, and take advantage of the luxury of expansive open space and the upscale charm of Winter Garden. Sample site plan, with wetland impact, available upon request.

1401 N Fullers Cross Road, Winter Garden

Bray J W F Add 01 SubDv. ⋅ 34787 Zip Code

Prime Vacant Land in the Heart of Downtown Winter Garden. Rare opportunity to own a 16,338 sq. ft. vacant lot perfect to build a custom home, two single family homes or a duplex. in the picturesque downtown Winter Garden area. Just a short walk to Plant Street, this property is ideally situated near the vibrant heart of the city, offering unmatched convenience and charm. This spacious lot provides endless possibilities in one of Central Florida’s most sought-after communities. Downtown Winter Garden is known for its welcoming atmosphere, featuring award-winning restaurants, boutique shops, theaters, local events, and a lively cultural scene. Enjoy walkability, historic character, and modern amenities all in one location. Whether you envision a private residence or an investment opportunity, this property offers an exceptional chance to build in a thriving area.

47 Oak Street, Winter Garden

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