Winter Garden/Oakland Homes with Special Community Restrictions Community Features

Winter Garden/Oakland Homes with Special Community Restrictions Community Features

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 west of Orlando, this vibrant area is renowned for its picturesque landscapes, historic downtown, and a strong sense of community. With lush parks, scenic lakes, and a rich agricultural heritage, Winter Garden offers an idyllic setting for families, retirees, and everyone in between.

One of the standout features of this region is the diverse selection of homes available, particularly those within communities that come with special restrictions. These thoughtfully designed neighborhoods cater to a variety of lifestyles, ensuring that residents enjoy a harmonious living environment. Many of these communities prioritize safety, aesthetics, and a sense of belonging, making them perfect for those seeking a close-knit atmosphere.

Residents can take advantage of community amenities such as sparkling pools, fitness centers, and playgrounds, promoting an active lifestyle and fostering connections among neighbors. Additionally, many of these homes are strategically located near top-rated schools, shopping centers, and recreational facilities, providing easy access to everything you need.

Whether you're drawn to the historical charm of Winter Garden's downtown or the serene beauty of Oakland's natural surroundings, this region offers a wealth of opportunities for relaxation and recreation. Discover your dream home in one of these special communities and experience the warm, welcoming spirit of Winter Garden and Oakland—where community and comfort come together beautifully.

Newest Winter Garden/Oakland Homes with Special Community Restrictions Community Features

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code

Discover a high-value investment opportunity at The Grove Resort & Water Park, one of Orlando’s most successful condo-hotel destinations just minutes from Walt Disney World. This fully furnished 2-bedroom, 2-bath unit offers a spacious layout, modern finishes, and a private balcony that enhances guest appeal and repeat bookings. Designed for both personal enjoyment and strong rental performance, this property delivers year-round demand driven by Orlando’s booming tourism market and The Grove’s exceptional amenities. Guests enjoy multiple pools, private cabanas, a full water park with surf simulator and lazy river, onsite restaurants, spa, fitness center, arcade, lake activities, and daily entertainment—premium features that consistently boost occupancy and revenue. Investors benefit from a turnkey, professionally managed short-term rental program, ensuring seamless operations, high visibility, and stable returns. The resort’s reputation, location, and amenity package create a powerful combination of passive income potential and long-term appreciation. Whether expanding your portfolio or securing a reliable income-producing asset, this unit offers a strategic opportunity in one of Central Florida’s strongest hospitality markets.

14501 Grove Resort Avenue Unit 2135, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo 3 SubDv. ⋅ 34787 Zip Code

Experience the ultimate vacation lifestyle and investment opportunity at Grove Resort & Spa Orlando! This beautifully appointed 2-bedroom, 2-bath condo-hotel offers approximately 1,265 square feet of thoughtfully designed living space with an open-concept layout, stone countertops, stainless steel appliances, walk-in closet, in-unit laundry, private balcony, and elevator access. Fully furnished and turnkey, this residence is ideal as a personal vacation retreat or income-producing property within one of Central Florida's premier resort destinations. Owners and guests enjoy world-class amenities including Surfari Water Park with FlowRider® surf simulator, lazy river, multiple resort pools, private cabanas, waterslides, fitness center, full-service spa, lake activities on Lake Austin, on-site restaurants and bars, arcade, concierge services, 24-hour gated security, and complimentary transportation to Walt Disney World®. Located just minutes from Disney, Flamingo Crossings, shopping, dining, golf, and Orlando's world-famous attractions, this exceptional resort property delivers the perfect blend of luxury, convenience, and unforgettable Florida living.

14501 Grove Resort Avenue Unit 3303, Winter Garden

2 Beds ⋅ 2 Baths ⋅ Del Webb Oasis Phase 2 SubDv. ⋅ 34787 Zip Code

Welcome to this ELEGANTLY UPGRADED and nearly new 2-bedroom, 2-bath residence in the highly sought-after Del Webb Oasis of Winter Garden, a GUARD-GATED 55+ community where resort-style living meets everyday sophistication. Perfectly situated on one of ONLY TWO PREMIUM HOMESITES of its kind within the community, this exceptional property enjoys a truly rare distinction: an EXCLUSIVE SIDE EASEMENT that creates exceptional privacy, expanded green space, and a level of openness rarely found in community living, with no immediate neighbor on one side and convenient proximity to the clubhouse area. From the moment you arrive, the home impresses with its REFINED CURB APPEAL, lush landscaping, and a spacious 2-car garage enhanced with CUSTOM STORAGE SOLUTIONS. Inside, a bright OPEN-CONCEPT LAYOUT welcomes you with abundant natural light and meticulous attention to detail throughout every space. The Kitchen is a TRUE SHOWPIECE, equipped with premium stainless steel appliances, a GAS COOKTOP, BUILT-IN OVEN, a CUSTOM BUILT-IN PANTRY WITH PULL-OUT DRAWERS, generous cabinetry, and stone countertops, all seamlessly flowing into the living and dining areas. The Living Room has been elevated with an INTEGRATED SURROUND SOUND SYSTEM, creating the perfect setting for daily enjoyment and entertaining. The Primary Suite is a private retreat featuring a CUSTOM-DESIGNED WALK-IN CLOSET SYSTEM and a well-appointed en-suite bath with dual vanities, generous storage, and a walk-in shower. An additional SECONDARY BEDROOM provides comfortable accommodations for family or guests, while the DEDICATED DEN, enhanced with UPGRADED HIGH BASEBOARDS and RECESSED LIGHTING, offers the flexibility of a home office, hobby room, or formal sitting area. CUSTOM CLOSET SYSTEMS throughout ensure every space is as functional as it is beautiful. Step outside to where this property truly STANDS APART. The expansive SCREENED-IN LANAI opens to an EXTENDED OUTDOOR DECK and a fully appointed BUILT-IN OUTDOOR KITCHEN (BBQ Area), all framed by CUSTOM OUTDOOR LIGHTING, creating an exceptional outdoor retreat designed for year-round Florida living. Additional highlights include a WHOLE-HOME WATER FILTRATION AND SOFTENER SYSTEM, FRESH INTERIOR PAINT throughout, and additional RECESSED LIGHTING both inside and outside that elevates the home's ambiance day and night. Residents of Del Webb Oasis enjoy RESORT-STYLE AMENITIES, including a 12,000 SF clubhouse with coffee bar, lounge, and wine lockers, a sparkling pool, state-of-the-art fitness center, tennis courts, and a vibrant social calendar, along with included cable and internet, fostering the active and connected lifestyle that Del Webb is famous for. IDEALLY LOCATED in Winter Garden, you are just minutes from the charm of HISTORIC DOWNTOWN WINTER GARDEN, known for boutique shops, dining, and a weekly farmers market. Enjoy outdoor recreation along the WEST ORANGE TRAIL, or take a short drive to WORLD-CLASS ATTRACTIONS including Walt Disney World Resort and Universal Studios. Convenient access to FL-429 and major roadways makes it easy to enjoy the very best of Central Florida. This exceptional residence offers a RARE OPPORTUNITY to enjoy elevated, low-maintenance living on one of the community's most coveted homesites, where every upgrade has been thoughtfully chosen and every detail meticulously executed. Homes of this caliber and setting are a TRUE RARITY in Del Webb Oasis. Now is the time, don't miss your chance to call this home.

15139 Canopy Cover Drive, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Johns Landing SubDv. ⋅ 34787 Zip Code

Welcome to this exceptional pool home located in the sought-after gated lakefront community of Johns Landing. Situated on an oversized 13,000+ square-foot corner lot with a mostly fenced backyard, this spacious home offers over 3,000 square feet of thoughtfully designed living space. Featuring 4 bedrooms, 4 full bathrooms, a dedicated office, media room, and spacious loft, this home provides the perfect balance of comfort and functionality for today’s lifestyle. The open-concept floor plan is highlighted by soaring ceilings, abundant natural light, and a gourmet kitchen that seamlessly connects to the main living and dining areas, making it ideal for both everyday living and entertaining. The first-floor primary suite serves as a private retreat, complete with dual vanities, separate his-and-her walk-in closets, and a spacious en-suite bath. Upstairs layout is Bedroom/Full bath, loft and Large media room that could be 5th bedroom. Downstairs features 3 bedrooms and 3 full bathrooms. Step outside to your screened lanai and sparkling private pool, where you can enjoy Florida’s beautiful weather year-round. The expansive backyard offers plenty of space for outdoor entertaining, while the three-car garage provides ample room for vehicles and storage. Residents of Johns Landing enjoy exclusive amenities including a private boat ramp and community dock, playground, tennis and pickleball courts, basketball court, and access to beautiful Johns Lake. Ideally located just minutes from historic downtown Winter Garden, the West Orange Trail, Costco, shopping, dining, and major highways, this home offers the perfect combination of luxury, convenience, and an active Florida lifestyle. Recent updates include a new roof (2019) and two HVAC systems (2019 and 2017), providing added peace of mind for years to come. *Sold As-is . Bring your design ideas! *Seller offers a $10,000-$20,000 credit for updates or buyer's closing costs.*

710 Regina Circle, Oakland

3 Beds ⋅ 3 Baths ⋅ Orchard Hills Ph 4 SubDv. ⋅ 34787 Zip Code

Investor opportunity in the highly desirable Orchard Hills community of Winter Garden. This well-maintained two-story townhome offers 3 bedrooms, 2.5 bathrooms, and approximately 1,712 square feet of living space with an open-concept layout, spacious family room, and private balcony overlooking peaceful tree and wooded views. The kitchen is equipped with modern appliances including built-in oven, cooktop, microwave, dishwasher, disposal, refrigerator, and electric water heater. Residents enjoy access to resort-style community amenities including a pool, fitness center, playground, park, sidewalks, and beautifully maintained common areas. Conveniently located near Winter Garden Village, Hamlin shopping and dining, top-rated schools, and quick access to SR-429, this property offers a combination of location, lifestyle, and investment potential in one of Central Florida’s most sought-after communities. The property is currently tenant-occupied. Current tenant is paying: $2325 per month until 2/28/27.

5686 Cypress Hill Road, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Storey Grove Ph 1b-2 SubDv. ⋅ 34787 Zip Code

Welcome to this exceptional 5-bedroom, 3-bath residence offering luxury, comfort, and unbeatable location. SITUATED ON A PRIVATE CONSERVATION LOT WITH NO REAR NEIGHBORS, this home features a stunning saltwater pool, spacious screened lanai, and a fully fenced backyard designed for relaxation and entertaining. Enjoy nightly DISNEY FIREWORKS and beautiful SUNSET VIEWS right from your own backyard. Inside, you’ll find elegant upgrades including luxury vinyl plank flooring with a warm oak finish, high-end details, and custom woodwork throughout. The thoughtful layout includes a private downstairs office, a first-floor guest suite with full bath, and a large upstairs bonus room offering flexible living space for any lifestyle. A three-car garage provides ample parking and storage. Located in a highly sought-after community with resort-style amenities—pool, clubhouse, fitness center, playgrounds, dog park, and walking trails. Zoned for top-rated Water Spring schools, including walking distance to Water Spring Elementary and proximity to Horizon West High School. Just minutes from Disney, SR-429, Flamingo Crossings, dining, and shopping. Enjoy low-maintenance living with HOA-provided landscaping services, including the front yard, side yards, and the expansive grounds extending to the rear property line. Only the landscaping surrounding the pool area is the homeowner's responsibility.

10264 Love Story Street, Winter Garden

5 Beds ⋅ 4 Baths ⋅ Sunset Lakes SubDv. ⋅ 34787 Zip Code

Experience luxury living in this gorgeous home in the highly sought after Sunset Lakes community in Winter Garden. This FULLY-REMODELED, 5-bedroom, 4-bath POOL/SPA home sits on a SERENE POND and offers 3,389 sq. ft. of beautifully designed living space on OVER HALF AN ACRE, complete with a three-car side entry garage. Four of the 5 bedrooms are conveniently located on the first floor (including the Primary Bedroom), with the 5th Bedroom, a full bath and a bonus loft located on the second level. Inside, the home features designer ENGINEERED HARDWOOD FLOORING throughout the main living areas and the downstairs primary suite. The CHEF'S KITCHEN is a showpiece, boasting THREE SLABS OF PERMIUM CALCUTTA QUARTZ, an ITALIAN MARBLE BACKSPLASH, 60-inch DOUBLE-STACKED ALL WOOD SHAKER CABINTRY, a handy FOOD PREP ISLAND, a BREAKFAST BAR and TOP-OF-THE-LINE SAMSUNG APPLIANCES! The family room features AUTOMATIC ROLLER SHADES and is open to the kitchen and features Cathedral ceilings, a huge picture window and French Doors to the inviting lanai and sparkling pool. The primary suite is a retreat of its own, offering a FULLY-RENOVATED, SPA-INSPIRED bathroom with floor to ceiling CALCUTTA TILE, a frameless glass shower, a freestanding soaking tub, tall custom cabinetry with WHITE EXOTIC CARERRA QUARTZ COUNTERS and a massive walk-in closet! Architectural details elevate every room, including Plantation Shutters, multiple sets of French Doors, tray ceilings, volume and cathedral ceilings, extensive crown molding, transom windows, recessed lighting, bead boarding and elegant custom millwork. Step outside to a stunning outdoor oasis. The completely remodeled pool and spa area is surrounded by 2100 sq. ft. of travertine decking that extends across the covered lanai and additional outside patio space—perfect for entertaining! The lanai ceiling is finished with tongue and groove wood planks, adding warmth and sophistication. Other major upgrades include NEW DOUBLE-PANE, THERMAL WINDOWS (2023), a 2019 ROOF a 2019 AC SYSTEM and rain gutters. The extended brick paver driveway and matching walkway enhance curb appeal, while the well-fed irrigation system coupled with the well water (filtered by the whole house WATER SOFTENER) help keep utility costs low. Note: The wooden planter at the back of the pool and the retaining wall at the back of the lot needs some work and conveys 'AS IS.' All of this is just 5 minutes from the 429, offering quick access to Orlando and surrounding areas. Downtown Winter Garden & Winter Garden Village are also nearby as well as numerous championship golf courses for all your shopping, dining and recreational needs! Nearby top-rated schools are just another plus! Call for your showing today if you want to be the lucky one to snag this one-of-a-kind home before someone else does!

13536 Sunset Lakes Circle, Winter Garden

5 Beds ⋅ 7 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code

Within the gated community of Canopy Oaks in Winter Garden, Parade of Homes award-winning Delray model by renowned builder A.R. Bailey Homes combines timeless architecture with curated upgrades rarely found in today’s market. Within an intimate enclave of only 49 homesites, this meticulously maintained home offers over 4,000 square feet of flexible multigenerational living, entertaining spaces and seamless indoor-outdoor Florida living. Ideally just minutes from Historic Downtown Winter Garden, Winter Garden Village, Orlando Health, the Roper YMCA, shopping, dining, recreation and major roadways including Florida’s Turnpike, SR 429, SR 408 and Interstate 4. A paver driveway, concrete tile roof, stone-accented exterior, wood-look garage doors, three-car garage and grand solid wood double-entry doors create a striking first impression. Inside, 10-foot ceilings in the great room, architectural details, abundant natural light, elegant finishes, and wood-look porcelain tile flooring throughout the first floor create a sophisticated yet welcoming atmosphere. The chef’s kitchen serves as the heart of the home, designed for everyday living and entertaining. Highlights include a natural gas cooktop with exterior vent, built-in wall oven, upgraded appliances, pot filler, oversized center island, 42-inch cabinetry with crown molding, under-cabinet lighting, designer tile backsplash and an expansive walk-in pantry overlooking the coffered-ceiling great room. A gated wine cellar adds a distinctive feature rarely found at this price point. The luxurious first-floor primary suite was designed as a spa-inspired retreat, featuring a beautifully appointed primary bath with premium finishes, dual vanities, an oversized walk-in shower, freestanding soaking tub and a spacious walk-in closet. A separate first-floor en-suite bedroom provides flexibility for guests, extended family, multigenerational living or a private home office. Upstairs, a second primary suite is complemented by two additional en-suite bedrooms, a spacious loft, guest powder bath and covered balcony, providing privacy and versatility for family and guests. Designed to embrace Florida’s indoor-outdoor lifestyle, dramatic corner-opening glass doors and expansive stacking sliders open to the covered lanai with a motorized retractable screen, creating effortless entertaining year-round. The backyard, accented by a stucco privacy wall, offers ample space for a custom pool, outdoor kitchen and additional outdoor living areas. The three-car garage provides generous space for vehicles, golf carts, storage and recreational equipment. Additional highlights include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, decorative iron stair railings, mudroom, reading nook and generous storage throughout. Residents of Canopy Oaks enjoy scenic recreational trails, a community playground and an exceptional Winter Garden location near shopping, dining, healthcare, recreation and everyday conveniences. Offering five en-suite bedrooms, seven baths, dual primary suites, a spa-inspired first-floor primary suite, wood-look porcelain tile throughout the first floor, a three-car garage, natural gas, award-winning design and an exceptional location within Canopy Oaks, this beautifully maintained residence presents an outstanding opportunity to experience refined Winter Garden living. Also available for lease (MLS #O6416527).

706 Canopy Estates Drive, Winter Garden

5 Beds ⋅ 3 Baths ⋅ Stoneybrook West Un 06 SubDv. ⋅ 34787 Zip Code

WOW!!! OVER $60,000 RECENT PRICE REDUCTION!! BRAND NEW AC SYSTEM INSTALLED LAST WEEK (7/2/26) Experience refined Florida living in this beautifully enhanced home located within a highly desirable golf course community. The property offers both style and peace of mind with a roof replaced just five years ago and a recently sealed and painted exterior. Inside, the home is designed for both comfort and entertainment, featuring an immersive surround sound system throughout the main level and an impressive dedicated theater/bonus space. Every detail has been curated to elevate everyday living. Step outside to your own private retreat—an exceptional backyard showcasing a custom pool and spa with a striking grotto feature, creating the perfect setting for relaxing or entertaining guests year-round. Residents enjoy access to an array of resort-style amenities, including a clubhouse with dining, fitness center, tennis and basketball courts, beach volleyball, playgrounds, and an expansive community pool. Ideally situated just minutes from world-renowned attractions like Walt Disney World, with convenient access to major expressways and premier shopping and dining destinations nearby, this home offers the perfect balance of luxury, location, and lifestyle. One or more photo(s) have been virtually staged. PLEASE REMOVE SHOES BEFORE ENTERING THE HOME!

13412 Fox Glove Street, Winter Garden

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