Winter Garden/Oakland Homes with Special Community Restrictions Community Features

Winter Garden/Oakland Homes with Special Community Restrictions Community Features

Welcome to Winter Garden and Oakland, two charming communities nestled in the heart of Central Florida. Known for their picturesque landscapes, friendly neighborhoods, and rich history, these areas offer a delightful blend of suburban tranquility and vibrant local culture.

Winter Garden, with its historic downtown district, is a treasure trove of quaint shops, delightful eateries, and scenic parks. The West Orange Trail, a popular destination for cyclists and joggers, winds through the area, providing residents with beautiful views of nature and a perfect spot for outdoor activities. Just a stone's throw away, the charming town of Oakland boasts a serene atmosphere, complete with lovely oak trees and a close-knit community feel.

For those considering a home in this beautiful region, it’s important to note that many properties come with special community restrictions. These restrictions are designed to maintain the integrity and aesthetics of the neighborhoods, ensuring that the community remains a welcoming and attractive place to live. Features such as gated access, well-maintained landscaping, and designated common areas are common, providing residents with a sense of security and pride in their surroundings.

Whether you're drawn to the historical charm of Winter Garden or the peaceful ambiance of Oakland, these communities offer a unique lifestyle that perfectly balances modern conveniences with natural beauty. Experience the best of Florida living in a home that not only meets your needs but also aligns with the values of a vibrant community. Welcome home!

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

$205,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort And Spa Hotel Condominium 22019039615 SubDv. ⋅ 34787 Zip Code
The lowest-priced 3-bedroom/3-bath on a higher floor at The Grove Resort & Water Park! This 5th-floor corner unit is the largest "Sable" model in the community, offering 1,544 sq ft with an open living/dining/kitchen area, a separate in-unit utility/laundry room, and a screened balcony. The kitchen features stainless steel appliances and granite counters. The primary suite includes an extra sitting area/solarium with direct balcony access, a bath with double sinks, a separate shower and soaking tub, and a large walk-in closet with a safe. Each bedroom includes a flat-screen TV. This condo-hotel offers an in-house hotel rental program that generates income to offset the cost of ownership — an ideal opportunity to own an Orlando/Disney-area vacation home just 6 miles from Walt Disney World. Resort amenities are exceptional. Surfari Water Park features the FlowRider Double Surf Simulator (one of only a few double units in the U.S.), dual water slides, a 695-foot lazy river, a zero-entry pool, and a kids' activities pool. The Springs Pools offer three full-sized pools, an oversized hot tub, a splash area, and private cabanas. Lake Austin provides catch-and-release fishing, watersports, and a lakeside pier overlooking the nature preserve. Additional amenities include a 24-hour fitness center, Flip Flop's Fun Center with a glow-in-the-dark indoor mini golf course and arcade, and a Kids' Activity Center. Dining options abound: The Springs Bar & Grill for relaxed poolside dining, Longboard Bar & Grill overlooking the FlowRider, Alfresco Market for outdoor cafe seating, and DYVE at The Terraces above the upscale pool area. The resort also offers daily transportation to Walt Disney World, Universal Orlando, and SeaWorld, plus complimentary resort-wide Wi-Fi. A rare chance to own a turnkey resort residence in one of the Orlando area's premier destinations.

14501 Grove Resort Avenue Unit 2542, Winter Garden
$489,000
3 Beds ⋅ 2 Baths ⋅ Black Lake Park Ph 01 SubDv. ⋅ 34787 Zip Code
WELCOME HOME TO BLACK LAKE PARK — a gated community where every day feels like a retreat. As you pass through the gates, you're welcomed by the community's stunning 10-acre park, complete with a charming white gazebo and wide-open green space that instantly sets the tone. There's a sense of warmth and connection here that's hard to put into words — you simply feel it. Pulling into the driveway and stepping through the inviting front door, you already know this is more than just a house... it's home.Offering over 1,923 square feet of thoughtfully designed living space, this move-in-ready 3-bedroom, 2-bath home with a 2-car garage has everything you need. Inside, natural light pours through the windows, highlighting the open layout and laminate flooring throughout the main living areas. If you love to cook, gather, and entertain, the remodeled kitchen will absolutely capture your heart, featuring quartz countertops, a glass cooktop, and built-in double ovens. Whether you're hosting a holiday gathering or enjoying a quiet morning coffee, this kitchen truly delivers. Sliders open to the patio — perfect for relaxing evenings or weekend get-togethers.Down the hall, bedrooms 2 and 3 offer comfortable accommodations and share a beautifully appointed guest bath. The primary suite is your private retreat, complete with a spacious walk-in closet, while the en-suite bath features a dual-sink vanity and a walk-in shower — your own personal escape at the end of the day.Living in Black Lake Park means enjoying an array of amenities, including a playground, fitness area, volleyball court, swimming pool, tennis courts, basketball court, pickleball courts, soccer field, private boat ramp and dock, and sidewalks throughout the neighborhood. Imagine ending your day with a walk to the community dock to watch breathtaking sunsets over the water, or enjoying seasonal fireworks lighting up the sky on the 4th of July. The community also hosts memorable events throughout the year, including a Halloween Costume Parade, Christmas caroling and movie night in the park, Easter egg hunts, organized garage sales, and more — creating opportunities to connect and build lasting memories.Location truly completes the package — just minutes from Downtown Winter Garden, Winter Garden Village, and major highways including the 429, the Florida Turnpike, and the 408, and conveniently close to Walt Disney World and other world-class attractions.This is more than a home. It's a lifestyle filled with comfort, connection, and everyday moments that turn into lasting memories.

502 First Cape Coral Dr, Winter Garden
$199,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort SubDv. ⋅ 34787 Zip Code
Located on the second floor of Building 3, closest to the Safari Water Park, this fully furnished, two-bedroom, two-bathroom condo offers fantastic pond views and excellent proximity to resort amenities. This property is perfect for vacation home buyers seeking a true resort experience. Owners will enjoy resort-style living with access to multiple pools, a water park, a full-service spa, on-site restaurants, a state-of-the-art fitness center, and a large game room. For investors, this unit presents a compelling opportunity in Central Florida's booming tourism market. Located just minutes from Walt Disney World, Universal Studios, SeaWorld, upscale shopping, and diverse dining, this property promises strong rental potential and the flexibility to generate income while serving as a personal escape.

14501 Grove Resort Avenue Unit 3215, Winter Garden
$239,000
3 Beds ⋅ 3 Baths ⋅ Grove Resort & Spa SubDv. ⋅ 34787 Zip Code
Exceptional opportunity to own a spacious top-floor 3-bedroom, 3-bathroom condo at The Grove Resort & Water Park, just minutes from Walt Disney World! This fully furnished 1,544 sq. ft. “Sable” floor plan offers an ideal combination of personal vacation use and income-producing potential through The Grove’s professionally managed hotel rental program. Located on the 7th and top floor of Building 1, the condo features a spacious split-bedroom layout, three full bathrooms, a well-equipped kitchen with granite countertops, comfortable living and dining areas, and a screened balcony with elevated views. The Grove delivers the complete Orlando resort experience with Surfari Water Park featuring water slides, a lazy river, splash areas and private cabanas, multiple onsite dining options, a full-service spa, fitness center, arcade, and a 20-acre activity lake offering fishing and water activities. When you're not enjoying the condo yourself, the turnkey rental program provides professional management for vacation rentals. Whether you're looking for your own Orlando getaway or a furnished vacation rental investment near Disney, this top-floor 3-bedroom residence offers an outstanding opportunity at one of Central Florida's most amenity-rich resort destinations.

14501 Grove Resort Ave Unit 1707, Winter Garden
$280,500
3 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to Southern Pines, one of Winter Garden's most desirable gated condominium communities. This spacious second floor 3 bedroom, 2 bathroom condo offers approximately 1,453 square feet of comfortable living space with an open, functional layout that is perfect for everyday living, working from home, or entertaining family and friends. The unit offers luxury vinyl flooring, the kitchen overlooks the living and dining areas, creating a bright and inviting gathering space, while the split bedroom floor plan provides added privacy for the primary suite. The generous primary bedroom features a walk in closet, and the two additional bedrooms offer excellent space for guests, family, or a home office. Southern Pines is known for its outstanding amenities, including a resort style pool and spa, clubhouse with a gaming area and a movie room, fitness center, indoor basketball and racquetball courts, tennis courts, playground, picnic and barbecue area, and beautifully maintained grounds. The monthly condominium fee also covers valuable services including water, sewer, trash, cable, internet, exterior maintenance, grounds maintenance, and security, making ownership both convenient and low maintenance. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major shopping and dining, the West Orange Trail, SR 429, the Florida Turnpike, Highway 50, and world famous attractions such as #Disney and #Universal, this home offers an exceptional combination of location, lifestyle, and value. Whether you are looking for your primary residence, a second home, or an investment opportunity, this move in ready condo is one you will not want to miss. Schedule your private showing today and discover everything Southern Pines has to offer.

142 Southern Pecan Circle Unit 204, Winter Garden
$244,900
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
$215,000
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
$699,000
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
$875,000
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
$999,900
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
$1,225,000
5 Beds ⋅ 7 Baths ⋅ Canopy Oaks Ph 1 SubDv. ⋅ 34787 Zip Code
An exceptional opportunity to own an award-winning luxury home in Canopy Oaks, an intimate gated community in Winter Garden, Florida. Located at 706 Canopy Estates Drive, this Parade of Homes award-winning Delray model by A.R. Bailey Homes offers five en-suite bedrooms, seven baths, dual primary suites, a three-car garage and more than 4,000 square feet of thoughtfully designed living space. Inside, 10-foot ceilings, abundant natural light and wood-look porcelain tile complement an open, flexible floor plan designed for everyday living and entertaining. The gourmet kitchen features a natural gas cooktop with exterior vent, built-in wall oven, upgraded appliances, pot filler, oversized island, 42-inch cabinetry, walk-in pantry and designer finishes overlooking the coffered-ceiling great room. A gated wine cellar adds a distinctive touch. The first-floor primary suite features a spa-inspired bath with dual vanities, oversized shower, freestanding soaking tub and walk-in closet. A separate first-floor en-suite bedroom offers flexibility for guests, extended family or a home office. Upstairs, a second primary suite, two additional en-suite bedrooms, spacious loft, powder bath and covered balcony provide additional privacy and versatile living space. Designed for Florida indoor-outdoor living, corner-opening glass doors and expansive stacking sliders connect the interior to a covered lanai with a motorized retractable screen. The private backyard offers ample room for a custom pool and outdoor kitchen. Additional features include dual tankless water heaters, dual HVAC systems with zoned climate control, motorized roller shades, a mudroom and abundant storage. Residents of Canopy Oaks enjoy recreational trails and a community playground, just minutes from Historic Downtown Winter Garden, Winter Garden Village, Orlando Health, the Roper YMCA, Florida's Turnpike, SR 429 and other major Central Florida roadways. Combining award-winning design, five en-suite bedrooms, dual primary suites and an exceptional Winter Garden location, this beautifully maintained residence offers a distinctive opportunity in one of the area's desirable gated communities. Also available for lease (MLS #O6416527).

706 Canopy Estates Drive, Winter Garden
$829,900
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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