Winter Garden/Oakland Land for Sale

Winter Garden/Oakland Land for Sale

Welcome to the enchanting region of Winter Garden and Oakland, Florida—a hidden gem that beautifully blends small-town charm with modern conveniences. Nestled just a short drive from the bustling city of Orlando, this picturesque area is renowned for its lush landscapes, vibrant community, and rich history. With its scenic parks, charming downtown filled with boutique shops, and a thriving farmers market, Winter Garden offers a delightful lifestyle for families, retirees, and everyone in between.

The serene lakes and nature trails surrounding Winter Garden and Oakland invite outdoor enthusiasts to explore their beauty. Whether you're biking along the West Orange Trail or enjoying a leisurely afternoon at Lake Apopka, the area's natural allure is simply irresistible. The friendly neighborhoods, complete with excellent schools and community events, foster a welcoming atmosphere that makes residents feel right at home.

For those looking to invest in their future, there is an exciting opportunity to purchase land for sale in this dynamic region. Imagine building your dream home amidst the stunning Florida landscape, where you can enjoy the perfect blend of tranquility and accessibility. With a range of available lots, you can choose the ideal location that suits your lifestyle—whether it’s a spacious property with room for a garden or a cozy spot near the heart of downtown.

Don’t miss out on the chance to be part of this thriving community. Explore the land for sale in Winter Garden and Oakland today, and take the first step toward creating your own piece of paradise in sunny Florida!

Newest Winter Garden/Oakland Land for Sale

$1,195,000
Briley Farm Ph 1b SubDv. ⋅ 34787 Zip Code
Discover an exceptional opportunity to build a custom lakefront residence on Lot 45 in Briley Farm Phase 1B. Located at 552 Walker Street in Oakland, this approximately 0.82-acre homesite offers beautiful Lake Apopka views, direct lake frontage and generous space to create a personalized retreat exclusively with Element Home Builders. With no predetermined floor plan, buyers can collaborate with Element to create a custom design subject to applicable approvals. Briley Farm offers a peaceful setting near downtown Winter Garden, the West Orange Trail, shopping, dining and major roadways. Public water, public sewer, electricity and natural gas are available within the community. The list price is for the homesite only and does not include home construction. The purchaser must build with Element Home Builders; outside builders are not permitted.

552 Walker Street, Oakland
$299,900
34787 Zip Code
1 acre of beautiful mature trees with a mixture of oaks and Cypress towards the lakefront. Utilities on site. Located on a spring fed lake. Ok for boats, skis, etc. Great school district. Ag zoning , ADU allowed (2nd dwelling with restrictions) , paved road with easy access to commute. This is your slice of paradise you've been waiting for. Bring your own builder with NO HOA!!!

Arrowhead Boulevard, Winter Garden
$595,000
Briley Farm Ph 1b SubDv. ⋅ 34787 Zip Code
Build your custom residence on Lot 21 in Briley Farm Phase 1B, a thoughtfully designed community in Oakland, Florida. Located at 523 Walker Street, this approximately 0.52-acre interior homesite offers the opportunity to create a custom home exclusively with Element Home Builders, with no predetermined floor plan. Enjoy a desirable location near charming downtown Winter Garden, the West Orange Trail, shopping, dining and major roadways. Public water, public sewer, electricity and natural gas are available within the community. The list price is for the homesite only and does not include home construction. Home designs, architectural plans and improvements are subject to Element Home Builders, community and governmental approvals. Buyer and buyer’s agent are responsible for independently verifying acreage, dimensions, utilities, taxes, HOA information, building requirements and restrictions.

523 Walker Street, Oakland
$299,000
Arrowhead Lakes SubDv. ⋅ 34787 Zip Code
Opportunity to own a ready to build spring fed lakefront land. 11 minutes to Disney World. 14 minutes to Orange County National Golf Center and Lodge.A2 zoning. A+ schools. No HOA. Established neighborhood. Well, Septic, Electricity, Fishing Dock, Boat Ramp, Concrete Seawall and Deck, Shed, Private Gate are all ready and permitted. All you need is the Architectural and Engineering plans. Farmland Rural District, which allows for agricultural uses, single-family homes, and modular dwellings.

17101 Arrowhead Boulevard, Winter Garden
$639,000
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
$449,000
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
$449,900
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
$195,000
34787 Zip Code
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
$305,000
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
$200,000
34787 Zip Code
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
$299,000
34787 Zip Code
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
$550,000
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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