Winter Garden/Oakland Land for Sale

Winter Garden/Oakland Land for Sale

Welcome to the picturesque region of Winter Garden and Oakland, Florida, where charming small-town vibes meet the vibrant pulse of modern living. Nestled just west of Orlando, this enchanting area is renowned for its stunning landscapes, rich history, and an array of outdoor activities that make it a delightful place to call home.

Winter Garden boasts a delightful downtown area, complete with historic buildings, boutique shops, and a variety of dining options that cater to every palate. The West Orange Trail, a scenic 22-mile-long path, meanders through lush greenery, offering residents a perfect setting for biking, walking, or jogging. Just a short drive away, Oakland enchants with its serene neighborhoods, historic homes, and beautiful parks, creating a peaceful retreat for families and nature lovers alike.

For those looking to invest in their future, we are excited to present prime land for sale in this thriving community. Whether you envision a cozy family home, a charming vacation retreat, or an investment property, the possibilities are endless in Winter Garden and Oakland. With a growing population and a robust real estate market, this region offers not only a beautiful setting but also a promising opportunity for appreciation.

Imagine waking up to the warm Florida sun, exploring local farmers' markets, or enjoying a weekend at the nearby lakes. With a perfect blend of community spirit and modern conveniences, Winter Garden and Oakland are ready to welcome you home. Don't miss your chance to be part of this vibrant community – your dream property awaits!

Newest Winter Garden/Oakland Land for Sale

$695,000
Johns Cove 43/104 SubDv. ⋅ 34787 Zip Code
Don't miss this rare opportunity to own over half an acre of waterfront property on beautiful Johns Lake! This is the last available lot in Johns Cove, an exclusive gated community of just 69 custom homes. Build your dream home and private boat dock and enjoy everything lakefront living has to offer-fishing, boating, jet-skiing, water skiing, and incredible sunrises from your backyard. Johns Cove is ideally located near charming Historic Downtown Winter Garden, the West Orange Trail, A-rated schools, world-famous theme parks, major shopping, dining, and Orlando international Airport. A true gem offering space, privacy, and lifestyle. Schedule your private viewing today- an opportunity like this won't last long!

906 Johns Point Drive, Oakland
$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
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