Winter Garden/Oakland Homes with Maintenance Amenities

Winter Garden/Oakland Homes with Maintenance Amenities

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant area is renowned for its picturesque landscapes, charming historic downtown, and a strong sense of community. With its lush greenery and scenic lakes, Winter Garden is a haven for outdoor enthusiasts, offering numerous parks, walking trails, and recreational activities. The nearby Oakland area boasts a quaint, small-town feel, with beautiful tree-lined streets and a rich history that invites exploration.

One of the standout features of homes in this region is the availability of maintenance amenities. Many properties in Winter Garden and Oakland offer the convenience of maintenance-free living, allowing residents to enjoy their homes without the hassle of upkeep. These amenities often include landscaping services, pool maintenance, and exterior repairs, giving homeowners more time to relish the vibrant lifestyle this area has to offer. Imagine spending your weekends exploring the local farmers' market, dining at charming cafes, or taking leisurely strolls along the West Orange Trail—all while knowing that your home is well taken care of.

Whether you’re seeking a cozy bungalow or a spacious family home, Winter Garden and Oakland provide a diverse selection of properties that cater to various lifestyles. With a blend of modern conveniences and historic charm, this region is the perfect place to call home. Experience the warmth and community spirit of Winter Garden and Oakland, where your dream lifestyle awaits!

Newest Winter Garden/Oakland Homes with Maintenance Amenities

$859,500
5 Beds ⋅ 4 Baths ⋅ Wincey Grvs Ph 2 SubDv. ⋅ 34787 Zip Code
Welcome to your dream home in the highly desirable community of Wincey Groves! This stunning 5-bedroom, 3.5-bath single-family residence, built in 2021, boasts contemporary design and upscale finishes throughout. Enjoy soaring 10-foot ceilings with elegant fascia, and a chef-inspired modern kitchen featuring luxurious quartz countertops and top-of-the-line stainless steel appliances. Experience custom-built cabinetry and exquisite upgraded millwork that add character and style to every room. The spacious primary suite offers generous walk-in closets, a versatile bonus fifth bedroom, perfect for guests or a home office. Step outside to an upgraded back patio and balcony, where you'll find a fully equipped outdoor kitchen with a wine fridge, refrigerator, built-in grill, and a cozy fire pit—ideal for entertaining or relaxing under the stars. Ideally situated just one mile from Hamlin Town Center, you'll have easy access to premier shopping, dining, and entertainment options.

5128 Breezy Acres Street, Winter Garden
$2,860,000
6 Beds ⋅ 6 Baths ⋅ Signature Lks-Pcl 01d Ph 02 SubDv. ⋅ 34787 Zip Code
Virtually Staged. The photo showing Disney fireworks is the only pic that is virtually staged. This beautiful Hancock Lake family friendly home is custom built for maximum lakefront enjoyment including a private covered dock protecting a 20’ +/- boat and 2 jet skis. Motor boat or pontoon around the lake, drop a line in or ski on one of the best skiing lakes in the area. The cul-de-sac lot is 1.29 acres with a BIG fenced yard, manicured gardening beds for your green thumb and plenty of room for outdoor games and pets. The extended screened patio has a sleek outdoor Kitchen with durable Weatherstrong cabinetry, cabana bath and a custom salt pool showcasing a water slide, Fiber optic lighting, solar heated and whimsical Disney characters embedded in the rock’s facade. Relax to lake views, or pull down the projector screen for a movie then watch the Disney’s fireworks nightly over the lake. The home has a freshly painted exterior and interior with crown trim throughout. The Kitchen space is designed for multiple chefs with newer appliances, walk-in pantry, island and informal seating. The first level’s primary suite with patio access was previously a media room complete with surround sound that remains intact. The loft with a balcony overlooking the patio and lake is prepped for entertaining. Two additional ensuites, 3 more bedrooms and a laundry room are also on the upper level. Both A/C Systems, all patio doors, reinforced exterior balcony railings and LR/DR bamboo engineered hardwood flooring are updated. The community offers a wide selection of amenities from boat ramp to pools for residents to enjoy.

7301 Wild Blackberry Trail, Winter Garden
$249,000
2 Beds ⋅ 2 Baths ⋅ Southern Pines Condo SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 2-bedroom, 2-bath first-floor unit with a 1-car garage, located in the highly desirable gated community of Southern Pines in the heart of Winter Garden. Offering the perfect combination of comfort, convenience, and resort-style living, this home is ideal for first-time buyers, downsizers, investors, or anyone seeking a low-maintenance lifestyle. The thoughtfully designed floor plan features spacious living areas, two generously sized bedrooms, and two full bathrooms, all conveniently situated on the first floor for easy access. Enjoy the added value of water, internet, and cable included in the monthly Condo fee, making everyday living both simple and budget-friendly. Southern Pines is known for its outstanding amenities, offering residents a true resort-style experience. Spend your days relaxing by the sparkling pool and hot tub, entertain friends at the BBQ grills and outdoor kitchen, or enjoy the beautifully appointed clubhouse featuring a movie theater, business center, and billiards room. Stay active with the fully equipped fitness center, indoor basketball and racquetball courts, tennis courts, beach volleyball court, and a covered outdoor playground. Additional conveniences include a car wash station and beautifully maintained grounds throughout the community. Ideally located just minutes from Historic Downtown Winter Garden, Winter Garden Village, major highways including SR-429 and the Florida Turnpike, shopping, dining, entertainment, and world-renowned theme parks, this condo offers an unbeatable location with exceptional amenities. Don't miss your opportunity to own a piece of one of Central Florida's most sought-after communities!

405 Southern Pecan Circle Unit 108, Winter Garden
$295,000
2 Beds ⋅ 2 Baths ⋅ Grove Residence & Spa Hotel Condo Ii SubDv. ⋅ 34787 Zip Code
NEWEST TOWER | TOP FLOOR | FOUNTAIN VIEW This is resort-style living at its absolute finest. This Fountain View Palm Unit in Tower 2 — the newest and most beautifully appointed tower in the community — offers the perfect blend of luxury, lifestyle, and income-generating opportunity. Step into a world-class destination that rivals the finest resorts anywhere in the world. With stunning superior views, the most updated and designer-curated décor in the entire property, and access to an unparalleled collection of amenities, this is more than a home — it's a five-star experience every single day. When you're not enjoying it yourself, let your investment work for you. This property sits within a prestigious hotel-managed rental program, meaning a professional, on-site operator handles everything — from bookings and guest services to housekeeping and maintenance. Completely hands-off ownership with income flowing in while the resort does all the heavy lifting. Owners enjoy access to resort amenities including pools, restaurants, spa, fitness facilities, and more — all maintained to the highest hospitality standards. Whether you're seeking a personal escape, a vacation retreat, or a smart investment vehicle, this unit checks every box. Newest tower. Most updated finishes. Superior views. World-class amenities. Professionally managed income potential. Financials available. Opportunities like this are rare — and they don't stay on the market long.

14501 Grove Resort Avenue Unit 2703, Winter Garden
$859,900
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Welcome to 9572 Waterway Passage in the highly sought-after community of Winter Garden! This beautifully move-in ready upgraded D.R. Horton Cresswell floor plan offers the perfect blend of modern style, comfort, and energy efficiency. From the moment you arrive, you'll appreciate the thoughtful enhancements that make this home truly stand out. Inside, laminate flooring flows seamlessly throughout the home, creating a clean, cohesive look with easy maintenance. A stunning geometric accent wall adds a designer touch to the loft and staircase, making a striking first impression. The spacious primary suite has been transformed into a luxurious retreat with a fully customized walk-in closet and a beautifully updated en suite bathroom. The guest bathroom has also been tastefully renovated with contemporary finishes. Step outside to your own private backyard oasis. Enjoy Florida living year-round with a sparkling pool and spa, a fully equipped outdoor kitchen, and built-in Bluetooth speakers—perfect for entertaining family and friends. Privacy bushes and low-maintenance artificial turf create a lush, secluded setting, while permanent exterior lighting enhances both curb appeal and year-round ambiance. Additional highlights include owned solar panels that help improve energy efficiency and reduce utility costs, making this home as practical as it is beautiful. Every detail has been carefully curated, offering move-in-ready luxury in one of Winter Garden's most desirable locations. Don't miss the opportunity to make this exceptional home your own!

9572 Waterway Passage Drive, Winter Garden
$569,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Property in a prime area right behind the Disney parks that lets you enjoy the parks' fireworks. In an excellent community to live in, just 1 block from one of the community pools, and inside are A1+ schools, so don't wait to come see your new home!

15929 Moonlight Bay Street, Winter Garden
$290,000
3 Beds ⋅ 2 Baths ⋅ Southern Pines SubDv. ⋅ 34787 Zip Code
**Click the Virtual Tour Link for 3-D walk-through tour** Welcome home to this well maintained FIRST FLOOR 3-bedroom, 2-bath condominium in Winter Garden, ideally located near shopping, dining, and with easy access to major roadways for trips to the airport and theme parks. This corner unit condo offers convenience to parking and features an open floor plan with spacious living room plus a den - perfect for a home office or flex space. The kitchen includes a breakfast bar, pantry, and convenient laundry room just through the kitchen. The split floor plan provides privacy to the primary suite with walk-in closet, linen closet, and en-suite bathroom. Additional bedrooms also feature walk-in closets and the hallway bathroom has an extended vanity for extra space and storage. Residents of Southern Pines Condos enjoy an exceptional array of amenities such as a pool and spa, outdoor kitchen, clubhouse with theater, office space and billiards, indoor basketball and racquetball courts, fitness center, playroom, covered outdoor playground, tennis and beach volleyball courts, and a car wash station. The gated community's HOA fee includes cable, internet, water, sewer, trash, and exterior maintenance, making for a truly low-maintenance lifestyle. Call for a showing today!

200 Southern Pecan Circle Unit 104, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve SubDv. ⋅ 34787 Zip Code
Luxury Toll Brothers End-Unit Townhome in Lakeshore Preserve! This beautifully maintained CICERO Spanish Colonial floorplan offers an open-concept layout with 10' ceilings, 8' doors, wood-look tile flooring, and abundant natural light. The gourmet kitchen features a center island, 42" cabinets, Diamond white-quartz countertops, stainless steel appliances, natural gas cooking, a large pantry, and a new oversized single-basin sink. The first-floor owner's suite includes a spacious walk-in shower and dual vanities. Upstairs you'll find two generous bedrooms, a loft, and a charming wraparound balcony. A covered walkway connects the home to the attached two-car garage. Recent upgrades include new landscaping, French doors added to the kitchen, water-resistant laminate flooring throughout the upstairs, updated quartz countertops in the kitchen and guest bath, upgraded lighting and staircase chandelier, new refrigerator, washer and dryer, saltwater softener system, patio pavers, and added garage storage. The home has been meticulously maintained with annual HVAC servicing and regular tankless water heater maintenance. Enjoy resort-style living at Lakeshore Preserve with a lakefront clubhouse, fitness center, gathering room, catering kitchen, resort pool, kayaking, and paddleboarding. Ideally located in Horizon West, just minutes from Disney, Universal, shopping, dining, and major retail centers.

8873 Fountain Palm Alley, Winter Garden
$420,000
3 Beds ⋅ 3 Baths ⋅ Summerlake SubDv. ⋅ 34787 Zip Code
Virtually Staged. OBTAINABLE LUXURY IN SUMMERLAKE! This MOVE-IN-READY, Energy Star Certified townhome offers the perfect blend of style, comfort, luxury and convenience with 3 bedrooms, 2.5 baths, a 2-car garage, and 1,738 square feet of thoughtfully designed living space. Recently refreshed with NEW interior PAINT and NEW CARPETING, this home welcomes you from the moment you step onto the covered front porch. Inside, the open-concept floor plan is enhanced by contemporary wood-look tile flooring throughout the first level, creating a warm and inviting atmosphere. The spacious living and dining areas flow seamlessly into the beautifully appointed kitchen featuring granite countertops, rich 42-inch wood cabinetry, stainless steel appliances, a large center island with sink and breakfast bar, walk-in pantry, and a convenient built-in desk workspace. Whether preparing meals or entertaining guests, the open design keeps everyone connected. Step outside to your private, partially fenced courtyard with brick pavers—an ideal setting for morning coffee, outdoor dining, or relaxing after a busy day. The courtyard leads directly to the detached 2-car garage for added convenience. Upstairs, you'll find all three bedrooms, the laundry area, and new carpeting throughout. The spacious primary suite easily accommodates a king-size bed and features a large walk-in closet and an en-suite bath with dual granite vanities, a garden tub, and separate shower. Two additional bedrooms share a full bath with granite countertops. Located in the highly desirable Summerlake community, residents enjoy outstanding resort-style amenities including a community pool, clubhouse with fitness center and recreation room, pickleball/tennis and basketball courts, playgrounds, zip line, parks, dog park, and scenic walking trails. The home is conveniently located near Summerlake Elementary School and a neighborhood park. Summerlake, Hamlin and Horizon schools were all A rated for the 2024/2025 school year!! As an added entertainment bonus, enjoy spectacular nightly Disney fireworks from designated viewing areas throughout the community. Just minutes from Hamlin Town Center, Cinépolis Luxury Cinemas, Orange County National Golf Center & Lodge, shopping, dining, and major roadways. This luxurious, beautifully updated home offers an exceptional opportunity to enjoy one of Horizon West's most sought-after communities. Experience the perfect combination of modern comfort, recent updates, and an outstanding Florida lifestyle. Lawn maintenance is included. Exterior scheduled to be painted!

8150 Red Stopper Lane, Winter Garden
$849,900
4 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to this stunning Toll Brothers Sanibel Spanish Colonial model, where timeless architecture meets modern luxury in the highly sought-after Lakeshore Preserve community. Distinguished by its elegant tile roof and thoughtfully designed floor plan, this exceptional home offers the perfect blend of sophistication, comfort, and functionality. Step inside to discover a massive great room that serves as the heart of the home—an inviting space designed for both everyday living and unforgettable entertaining. The gourmet kitchen is a chef's dream, featuring a natural gas range, quartz counters, oversized center island, abundant cabinetry, and seamless flow into the living and dining areas. Two expansive sliding glass doors, complete with custom blinds, open to a covered and screened lanai, creating the ideal indoor-outdoor living experience for relaxing or hosting guests year-round. The first floor also includes a versatile fourth bedroom or private home office with an adjacent full bathroom, providing flexibility for guests, multigenerational living, or remote work. Upstairs, the luxurious primary suite offers a peaceful retreat with large windows that fill the room with natural light. The spa-inspired primary bath features a soaking tub, separate walk-in shower, dual vanities, and twin walk-in closets. Two additional bedrooms, a spacious loft perfect for a media room or play area, and a convenient second-floor laundry room complete the upper level. Additional upgrades include a tankless water heater and a spacious two-car attached garage with a wireless door opener via remote app and has ample room for vehicles and storage. Living in Lakeshore Preserve means enjoying a low-maintenance lifestyle with HOA dues that include lawn care with annual mulch, internet, and cable. Residents also have access to an impressive collection of resort-style amenities, including a clubhouse, swimming pool, fitness center, playgrounds, sand volleyball courts, dog park, firepit, and kayak launch. Extra wide sidewalks allow for easy activities like running, biking, etc. Close to both Elementary as well as High Schools. Home includes a transferable, structural warranty from Toll Brothers builders (over 2 years left). Experience luxury living, exceptional amenities, and an unbeatable location in one of the area's most desirable communities.

15709 Shorebird Lane, Winter Garden
$169,900
2 Beds ⋅ 2 Baths ⋅ Townhomes Winter Garden SubDv. ⋅ 34787 Zip Code
Priced to sell!! Gorgeous 2 bedrooms-2 bathrooms Corner property condominium in Winter Garden. Open floorplan with a living/dining room combo. Nice size eat in kitchen with kitchen counters for additional seating. All appliances included Refrigerator, stove, dishwater, microwave, washer and dryer. Primary bedroom features private full bathroom 2 assigned parking spots, community swimming pool, exterior maintenance and landscaping are included in the monthly HOA fee. Close to Highway 50, parks, shopping, public transportation and much more.

304 Eron Way Unit 2, Winter Garden
$649,900
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 1c SubDv. ⋅ 34787 Zip Code
Welcome to your private oasis in the highly desirable community of Waterleigh! This rare gem stands out as one of the few homes in the neighborhood to feature its very own private, heated saltwater pool, complete with a spacious covered patio, an impressive newly screened lanai, and the ultimate privacy of no rear neighbors. Boasting one of the most sought-after single-story designs, this open and light-filled home welcomes you with sophisticated new wainscoting architectural details and brand-new, upgraded flooring throughout all four bedrooms. The heart of the home is an incredible gourmet kitchen featuring a massive quartz island illuminated by high-end glass pendant lighting, premium appliances, custom cabinetry, and a stunning backsplash that flows seamlessly into the spacious living and dining areas. Unwind in a luxurious primary suite showcasing elegant tray ceilings and a grand walk-in closet outfitted with a brand-new custom organization system. The upgraded primary bath offers a spa-like experience with granite counters, double sinks, a large shower, and an oversized soaking tub. Every detail has been meticulously enhanced, including a fully renovated laundry room, a pristine epoxy-finished garage floor, sealed and cleaned outdoor pavers, and a freshly repainted exterior. The home is also equipped with permanent outdoor Govee smart lights, allowing you to easily customize your exterior illumination for holidays or everyday ambiance. Located just 15 minutes from Walt Disney World, you can even enjoy the magic of the nightly Disney fireworks right from your own home. Waterleigh offers an unmatched, low-maintenance resort lifestyle where the HOA includes all lawn care, giving you more time to enjoy the two community clubhouses, resort pools, fitness centers, garden, mini-golf, volleyball, and scenic lake viewing docks. Schedule your tour today to experience this highly upgraded, move-in-ready masterpiece!

16131 Hampton Crossing Drive, Winter Garden
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