Winter Garden/Oakland Homes with No Deed Restriction Community Extras

Winter Garden/Oakland Homes with No Deed Restriction Community Extras

Welcome to the enchanting region of Winter Garden and Oakland, Florida, where the charm of small-town living meets the vibrancy of modern amenities. Nestled just a short drive from the bustling heart of Orlando, this picturesque area offers a unique blend of scenic landscapes, rich history, and a welcoming community spirit.

Winter Garden is renowned for its historic downtown, where brick-paved streets are lined with boutique shops, delightful cafes, and the iconic Winter Garden Theatre. Enjoy leisurely strolls through lush parks or take a scenic bike ride along the West Orange Trail, which meanders through the area’s stunning natural beauty. Oakland, with its tranquil lakes and serene surroundings, complements Winter Garden perfectly, providing a peaceful retreat for those seeking a quieter lifestyle.

For those looking for a home that embodies both freedom and community, our Homes with No Deed Restriction are a perfect fit. These properties allow homeowners the flexibility to truly make their space their own, whether it’s through landscaping, outdoor hobbies, or personalizing their home. Imagine having the freedom to park your RV or boat right at your doorstep, or create the garden of your dreams without restrictive covenants.

With a rich array of recreational activities, a strong sense of community, and the convenience of nearby urban attractions, Winter Garden and Oakland are ideal for families, retirees, and everyone in between. Come discover the charm of this region and find your perfect home where you can enjoy both comfort and the freedom to live life on your terms!

Newest Winter Garden/Oakland Homes with No Deed Restriction Community Extras

$910,000
5 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code
LUXURY LIVING IN THE HEART OF WINTER GARDEN! Welcome to an impressive residence offering approximately 3,619 square feet of beautifully designed living space with 5 bedrooms and 4 bathrooms. Built in 2016, this spacious home delivers the exceptional combination of elegance, comfort, and functionality. From the moment you arrive, the home's commanding presence sets the tone for what awaits inside. The expansive floor plan provides generous spaces for both everyday living and entertaining, while five well-proportioned bedrooms and exceptional flexibility for family, guests, a private home office, fitness room, or additional living space. With four bathrooms and multiple gathering areas, the residence is ideally suited for those who appreciate space without sacrificing comfort or privacy. The heart of the home provides an inviting setting where family and friends can gather, while the thoughtful layout creates a natural flow between living, dining, and entertaining areas. The generous interior proportions provide endless possibilities to personalize the residence and create a lifestyle tailored to its next owner. Located in highly desirable Winter Garden, this property combines residential tranquility with convenient access to the area's outstanding shopping, dining, entertainment, recreation, major roadways, and everything Central Florida has available. Enjoy the lifestyle and charm that have made Winter Garden one of the Orlando area's most sought-after destinations. A remarkable opportunity to own a substantial 5-bedroom residence in one of Central Florida's premier communities. Whether enjoying quiet evenings at home, entertaining family and friends, or taking advantage of the exceptional Winter Garden lifestyle, offers the space, location, and presence to truly feel like home. Schedule your private showing and experience this exceptional property for yourself!

5620 Mangrove Cove Avenue, Winter Garden
$899,000
3 Beds ⋅ 4 Baths ⋅ Del Webb Oasis SubDv. ⋅ 34787 Zip Code
Step into the Renown, a new construction, single-story home situated on a corner homesite near a cul de sac offering 3 spacious bedrooms, 3 beautifully appointed full bathrooms, a powder room, and an open flex room. The open-concept layout seamlessly connects the gourmet kitchen, café, and gathering room, creating an airy atmosphere. The many windows and zero corner sliding glass door leading to the covered lanai bathe the entire space in natural light, elevating the overall feeling of openness. The heart of the home is the chef-inspired kitchen, where white cabinetry with wood uppers meets luxurious quartz countertops. Thoughtfully designed features like soft-close drawers, easy-reach corner cabinets, double roll-out trays, and a waste basket drawer make the kitchen as functional as it is beautiful. Whirlpool stainless steel appliances—including a built-in natural gas cooktop—ensure you have everything you need for both everyday meals and special occasions. The kitchen flows effortlessly into the café and gathering room, where a zero-corner sliding glass door leads to the covered lanai, making this home ideal for seamless indoor-outdoor living. Retreat to the luxurious owner’s suite, a serene sanctuary with two spacious walk-in closets and a spa-like en suite bathroom. Dual vanity sinks, a frameless glass enclosed shower, garden tub, an enclosed toilet, and a linen closet complete the tranquil space. For added convenience, one of the walk-in closets connects to the laundry room which is outfitted with built-in cabinetry, a utility sink trimmed in quartz, and a storage closet. The two additional spare bedrooms, each with their own attached bathroom and walk-in closets, along with the open flex room and powder room, provide ample space for family and guests. Designer-curated finishes elevate every corner of this home, including pendant pre-wire and under cabinet lighting in the kitchen, brushed nickel hardware and plumbing fixtures, and 8’ Cheyenne style interior doors. Enjoy the convenience of modern living with a smart thermostat and doorbell, and LED downlighting. Schedule a tour today!

15000 Canopy Cover Drive, Winter Garden
$824,900
5 Beds ⋅ 4 Baths ⋅ Carriage Pointe A-I & L SubDv. ⋅ 34787 Zip Code
Welcome to a home where thoughtful design, elevated finishes, and effortless Florida living come together. This exceptional 5-bedroom, 3.5-bath residence offers an impressive blend of space, functionality, and custom detail, complete with a bonus room, private office, formal dining room, spacious living room, and a stunning great room that truly serves as the heart of the home. Primary bedroom is located on the first floor offering a split floor plan and privacy. This is a smoke free, pet free home. Interior laundry room with utility sink. The great room seamlessly opens to the expansive kitchen, featuring generous cabinetry, abundant storage, and a comfortable eat-in space designed for everyday gatherings. Custom built-ins, an electric fireplace surrounded by beautiful stone, and ceiling speakers create an inviting atmosphere for both relaxing and entertaining. Throughout the home, Pottery Barn curtain rods, crown molding, upgraded lighting, and an abundance of closet and storage space showcase the attention to detail. Fresh interior paint adds a crisp, move-in-ready feel, while the custom-built office provides an ideal space for working from home. Upstairs, an upgraded wrought-iron staircase creates a striking architectural focal point while adding a sophisticated touch to the home's aesthetic. The versatile bonus room offers additional space for a media room, playroom, fitness area, or second living space—the possibilities are endless. Step outside through the double-sided sliders to your own private retreat. The screened and covered lanai overlooks a sparkling saltwater pool with a sheer-fall water feature, creating the perfect setting for Florida afternoons and beautiful sunsets to top off the evening entertaining possibilities. The outdoor living area is thoughtfully pre-wired for television and equipped for speaker connectivity, making it easy to create the ultimate outdoor entertainment space. The home also delivers an impressive list of functional upgrades, including a kitchen faucet reverse osmosis system, water softener, whole-house surge protector, newer water heater (2024) ,new exterior paint (2026) new windows (2022-23), and a new HVAC (1/26) system with a damper system and remote-control capability thermostat. A spacious 3-car garage and elegant paver driveway provide both convenience and curb appeal. A transferable termite bond (Massey) adds another layer of confidence for the next homeowner. Located within a gated community, residents enjoy added peace of mind along with an outstanding selection of amenities, including a playground, tennis and pickleball courts, soccer field, and picnic area. Beyond the community, Winter Garden offers an exceptional lifestyle with an abundance of dining, shopping, entertainment, and recreation options. Convenient access to 429, the Florida Turnpike, OIA 33 miles, and 535 makes commuting throughout Central Florida a breeze.

2202 Redmark Lane, Winter Garden
$1,085,669
5 Beds ⋅ 4 Baths ⋅ Osprey Ranch SubDv. ⋅ 34787 Zip Code
Under Construction. .

12528 Gold Honeysuckle Street, Winter Garden
$475,000
3 Beds ⋅ 3 Baths ⋅ Hickory Hammock Ph 1c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome Home to 15163 Orange Harvest Drive! YOUR oportunity to live in this incredible neighborhood, is HERE! Move-in ready and beautifully maintained, this townhome offers 3 bedrooms, 2.5 baths, and a bright, open layout perfect for modern living. A paver driveway and charming stucco exterior with mature landscaping set the tone before you even step inside. The main level features a spacious open-concept living and dining area with tile flooring throughout. Sliding glass doors lead out to a private patio, offering a peaceful spot to unwind while overlooking green common space. The kitchen is a standout, showcasing rich espresso cabinetry, gleaming granite countertops, a designer mosaic tile backsplash, stainless steel appliances, and a large island with pendant lighting — ideal for entertaining or casual family meals. Upstairs, the generously sized primary suite includes plush carpet and an en-suite bath with dual sinks, a walk-in shower, and a linen closet. A second full bath serves the additional bedrooms with a dual-sink vanity and a tub/shower combo, and a convenient half bath is located on the main level for guests. As part of a sought-after community, residents enjoy resort-style amenities including a sparkling community pool, tennis courts, a playground, and scenic lakefront views — all just minutes from Winter Garden's shops, dining, and amazing schools. Don't miss your chance to own this stylish, low-maintenance townhome in one of Winter Garden's most desirable communities!

15613 Orange Harvest Loop, Winter Garden
$359,999
3 Beds ⋅ 3 Baths ⋅ Orchard SubDv. ⋅ 34787 Zip Code
Some photos are Virtually Staged. WELCOME to a HOME that truly stands out in THE ORCHARD, a desirable GATED COMMUNITY in WINTER GARDEN! This beautifully updated 3-BEDROOM, 2.5-BATHROOM TOWNHOME is perfectly positioned with NO REAR NEIGHBORS and a BEAUTIFUL OPEN GREEN SPACE BEHIND THE HOME, offering a peaceful and private setting. From the moment you arrive, the inviting PRIVATE ENTRYWAY and spacious ATTACHED 2-CAR GARAGE set the tone for the comfort and convenience this home offers. Step inside to discover NO CARPET ON THE FIRST FLOOR, UPDATED LAMINATE FLOORING, and numerous recent updates throughout. The home features NEW LIGHT FIXTURES AND CEILING FANS (2026), NEW FAUCETS (2026), and NEW CARPET UPSTAIRS (2026). Major systems have also been thoughtfully updated, including a NEW HVAC SYSTEM (2025) and ROOF (2020). The WASHER AND DRYER (2024) add even more value and convenience. The open-concept main living area seamlessly connects the living room, dining area, and kitchen, creating a warm and welcoming space for both everyday living and entertaining. The kitchen features GRANITE COUNTERTOPS, STAINLESS STEEL APPLIANCES, ABUNDANT CABINETRY, a LARGE WALK-IN PANTRY, and a BREAKFAST BAR WITH PENDANT LIGHTING. A versatile FLEX ROOM just off the main living area provides endless possibilities and can easily serve as a HOME OFFICE, PLAYROOM, EXERCISE ROOM, OR ADDITIONAL SITTING AREA. A convenient HALF BATH WITH UPDATED FIXTURES, large storage closet, and direct access to the garage complete the first floor. A DEDICATED LAUNDRY AREA adds even more convenience to the home’s thoughtful design. From the dining area, sliding glass doors open to the PEACEFUL BACKYARD SETTING, where you can relax and enjoy the expansive green space and the added privacy of NO REAR NEIGHBORS. Upstairs, the NEW CARPET INSTALLED IN 2026 continues into the spacious loft, currently used as an office and complemented by additional cabinetry. The generous PRIMARY SUITE features a MASSIVE WALK-IN CLOSET WITH A WINDOW and a private ensuite bathroom offering DUAL SINKS, a STANDING SHOWER, SEPARATE JETTED SOAKING TUB, and PRIVATE WATER CLOSET. Two additional bedrooms are thoughtfully located on the opposite side of the primary suite and share a full bathroom featuring a TUB AND SHOWER COMBINATION. The HOA COVERS THE EXTERIOR OF THE HOME, LAWN MAINTENANCE, AND COMMON AREAS, providing added convenience and peace of mind. Residents of THE ORCHARD enjoy GATED SECURITY, a TRANQUIL COMMUNITY POOL, and PLAYGROUND, all in a prime WINTER GARDEN LOCATION just minutes from shopping, dining, top-rated schools, and the charm of DOWNTOWN WINTER GARDEN. TASTEFULLY UPDATED, WELL-MAINTAINED, AND MOVE-IN READY, this townhome offers an exceptional combination of STYLE, COMFORT, PRIVACY, AND CONVENIENCE, with many of the major updates already completed for you. Come see why you will love calling THE ORCHARD HOME!

242 Winter Nellis Circle, Winter Garden
$699,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1a SubDv. ⋅ 34787 Zip Code
Experience refined Florida living in this impeccably maintained single-story 4BD/3BA residence set on an oversized corner lot in the prestigious Waterleigh community. Thoughtfully designed interiors blend elegance with comfort, highlighted by rich finishes, abundant natural light, and a seamless open layout. The gourmet kitchen showcases espresso cabinetry, granite surfaces, a striking center island, modern lighting, stylish backsplash, and a spacious pantry — all appliances included. The primary suite offers a serene retreat with luxury vinyl plank flooring, tray ceiling, quartz dual vanities, a soaking tub, glass-enclosed shower, and an expansive walk-in closet. Step outside to a private oasis featuring a covered screened lanai, brick patio, and a fully fenced yard ideal for quiet relaxation or elevated entertaining. Additional enhancements include a Ring security system, upgraded blinds, garage storage systems, and specialty garage flooring. Just a short stroll from a resident-exclusive clubhouse with a zero-entry pool, fishing pier, lake views, and sand volleyball. Waterleigh’s resort-style amenities elevate daily living with three pools, two fitness centers, tennis and basketball courts, mini golf, splash pad, dog parks, and scenic trails. HOA includes lawn care, irrigation, and tree maintenance. Located near top-rated schools, a nearby fire station, golf, and evening Disney fireworks views, this smoke-free, pet-free home delivers luxury, convenience, and lifestyle in one of Winter Garden’s most coveted communities.

8711 Eden Cove Drive, Winter Garden
$435,000
8 Beds ⋅ 3 Baths ⋅ Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
8 bedrooms. 3 full baths. Approximately 1,750 SF. Just blocks from Plant Street. Space and location set this property apart. Offering 8 bedrooms and 3 full baths across approximately 1,750 SF, the home sits on a 9,431 SF fully fenced lot—a combination of interior space and land increasingly difficult to find this close to Historic Downtown Winter Garden. Built in 1925 and sold as-is, the home presents an opportunity to update and personalize to your own vision. The flexible room count provides options for bedrooms, guest space, home offices, or additional living needs, while the generous 75' x 125' lot leaves plenty of outdoor space to create a garden, entertaining area, or backyard retreat. No HOA, city utilities, and R-2 zoning add to the property's flexibility and long-term appeal. Location is the part that cannot be renovated. Enjoy being just blocks from Plant Street, the Saturday farmers market, restaurants, cafés, shops, entertainment, and the West Orange Trail, with Lake Apopka, SR-429, and Florida's Turnpike conveniently nearby. Currently income producing, the property offers the flexibility to maintain its existing rental use or be delivered vacant upon request. 8 Bedrooms. 3 Full Baths. Approx. 1,750 SF. 0.22 Acres. 9,431 SF Lot. 75' x 125'. No HOA. Bring your vision and make the space your own in a location that's increasingly difficult to replicate. Schedule your private showing today.

208 3rd Street, Winter Garden
$849,988
4 Beds ⋅ 3 Baths ⋅ Lake Cove Pointe 46/58 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to this beautifully maintained custom home located in the gated community of Lake Cove Pointe, within the Winter Garden Golf Cart District. Conveniently located just minutes from Historic Downtown Winter Garden, this home offers easy access to dining, shopping, theater, entertainment, and local avente. A paver driveway and path lead to the charming front porch and welcoming entry. Inside, this nearly 2, 400-square-foot home features 4 bedrooms, 3 full baths, and a spacious three-way split floor plan designed for comfort and privacy. The main living areas feature attractive wood-look ceramic tile, with carpet in the family room and bedrooms. The well-appointed kitchen offers white cabinetry, beautiful countertops, and glass-pane display cabinets for added character and storage. The spacious Owner's Suite includes custom closets, a comfortable sitting area, and French doors leading to the screened-in patio. The Owner's Bath features a large shower and freestanding soaking tub. Enjoy Florida outdoor living from the screened-in patio, complete with a convenient wet bar and sink, making it an ideal space for entertaining or relaxing. The property also offers an immaculate two-car garage with new epoxy flooring, plus a separate third golf cart garage/workshop combination, providing excellent flexibility for golf cart storage, hobbies, or additional workspace. Recent updates include a 2019 roof, 2019 A/C, a Rheem 60-gallon hybrid water heater installed approximately nine months ago, and lifetime garage door springs! installed last summer. Located in a desirable gated community and close to Historic Downtown Winter Garden, this well-maintained home combines a thoughtful floor plan, attractive updates, excellent garage space, and convenient access to all that Winter Garden has to offer.

427 Tierra Verde Lane, Winter Garden
$795,000
5 Beds ⋅ 4 Baths ⋅ Wintermere Pointe SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully renovated residence offering an additional den, approximately 3,197 square feet of comfortable living space, and a two-car garage. Set on an oversized 0.29-acre lot in the gated Wintermere Pointe community, this home blends generous living areas with thoughtful, contemporary upgrades. Inside, you’re greeted by a bright, open layout finished with fresh neutral colors, crown molding, updated lighting, and attractive flooring throughout the main living areas. The floor plan provides multiple spaces for entertaining, dining, working from home, or simply relaxing. The completely redesigned kitchen serves as the heart of the home, featuring:Extensive shaker-style cabinetry, Dramatic stone countertops, Classic subway-tile backsplash, Under-cabinet lighting, Stainless-steel appliances, Double wall ovens, Contemporary range hood, Oversized waterfall island with abundant workspace and storage, built-in window seat with additional cabinetry, Separate beverage area with wine storage and beverage refrigerators. The kitchen opens naturally to the expansive living and dining areas, creating an inviting atmosphere for everyday living and gatherings. Large windows and sliding glass doors bring in natural light and offer easy access to the outdoor living space and spacious backyard. The first-floor den provides a versatile area that can serve as a home office, study, media room, or guest retreat. With five bedrooms and four bathrooms, the home offers comfortable accommodations and a layout designed for both privacy and flexibility. The upstairs layout includes a spacious bonus area that can easily be converted into a movie theater room. With existing built-in cabinetry and space for a refrigerator or beverage center, it’s an ideal setup for a private entertainment space, gaming room, or family media lounge. This home is located in one of Winter Garden’s highly regarded school zones, serving: Lake Whitney Elementary School, SunRidge Middle School, West Orange High School. Families appreciate the strong academic reputation and convenient proximity to these schools. This area is Prime Winter Garden Location. Just minutes from Winter Garden Village, shopping, dining, entertainment, and major roadways—including SR 429, Florida’s Turnpike, and SR 408—this move-in-ready home offers space, style, and accessibility in one of Winter Garden’s established gated communities. Schedule Your Private Showing Come experience the comfort, upgrades, and welcoming atmosphere of this beautifully updated Winter Garden home.

2157 Wintermere Pointe Drive, Winter Garden
$435,000
Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
9,431 SF. 75' x 125'. R-2. Just blocks from Historic Downtown Winter Garden. A prime infill opportunity offering approximately 0.22 acres in an established area where new construction and redevelopment continue to reshape the surrounding blocks. The fully fenced lot offers R-2 zoning, no HOA, and an existing income-producing home with water and electric utilities already connected. Currently rented by the room, the property generates approximately $1,425 per week / $74,100 annualized gross income at current rents, creating the opportunity to collect income during the holding, planning and permitting period. Delivered occupied or vacant at buyer's election. The R-2 zoning and 9,431 SF lot offer meaningful flexibility for future redevelopment, with the potential for a 3,000+ SF building footprint and a substantial new build, subject to applicable zoning requirements and City approvals. Location completes the picture. Just blocks from Plant Street, the West Orange Trail, Downtown Winter Garden's restaurants, shops, cafés, farmers market and entertainment, with convenient access to Lake Apopka, SR-429 and Florida's Turnpike. 0.22 Acres. 9,431 SF. 75' x 125'. R-2. Utilities Connected. No HOA. $1,425/Week Gross Income. Own the land, collect the income, and plan what comes next. Opportunities like this near Downtown Winter Garden do not stay available long—schedule your private showing today.

208 3rd Street, Winter Garden
$435,000
Twin City Dev Co Sub SubDv. ⋅ 34787 Zip Code
Most Winter Garden listings sell on charm. This one sells on the rent roll. Eight rooms currently rented — seven at $175 weekly and one at $200 — generating $1,425 per week / $74,100 annualized gross income at current rents. In place, occupied, and income producing. The land adds another layer to the opportunity. Situated on approximately 0.22 acres / 9,500+ SF with a 75' x 125' lot, the fully fenced property offers R-2 zoning, no HOA, city water and city sewer, along with ample yard space and future flexibility. Hold the existing income while exploring the property's longer-term expansion or redevelopment potential, subject to applicable zoning requirements and City approvals. The location carries its own value. Just a few blocks from Historic Downtown Winter Garden, Plant Street, the West Orange Trail, shops, restaurants and the farmers market, with SR-429, Florida's Turnpike and Lake Apopka nearby. The surrounding area continues to evolve with renovated properties and new construction. 0.22 Acres. 9,500+ SF Lot. R-2. Eight Rented Rooms. $1,425/Week Gross. Income in place. Land underneath. Future upside ahead. A rare opportunity to own all three near Downtown Winter Garden—schedule your private showing today.

208 3rd Street, Winter Garden
Start Your Search