Winter Garden/Oakland Homes with Park Amenities

Winter Garden/Oakland Homes with Park Amenities

Welcome to the picturesque region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This charming area is a perfect blend of small-town warmth and modern convenience, making it an ideal place for families, retirees, and everyone in between. With its lush landscapes, vibrant downtown, and rich history, Winter Garden and Oakland offer a lifestyle that is both relaxed and engaging.

One of the standout features of this region is its commitment to outdoor living and community amenities. Homes in Winter Garden and Oakland often come with access to beautiful park amenities, providing residents with a plethora of recreational options right at their doorstep. Imagine waking up to the sight of manicured parks, playgrounds, and walking trails, perfect for morning jogs or leisurely strolls with family and friends. The area boasts several parks, including the popular Newton Park and the scenic Lake Apopka, where you can enjoy picnics, fishing, and breathtaking sunsets.

In addition to the natural beauty, Winter Garden's historic downtown is a vibrant hub filled with unique shops, delightful eateries, and a bustling farmers market. The community hosts numerous events throughout the year, fostering a strong sense of connection among residents.

Whether you’re looking for a cozy single-family home or a spacious abode with modern features, the real estate options in Winter Garden and Oakland cater to diverse preferences. Embrace the charm of this enchanting region, where homes with park amenities create a perfect backdrop for a fulfilling lifestyle. Welcome home!

Newest Winter Garden/Oakland Homes with Park Amenities

$1,249,990
5 Beds ⋅ 4 Baths ⋅ Twinwaters SubDv. ⋅ 34787 Zip Code
Virtually Staged. Modern architecture. Total effortlessness. This five-bedroom residence is a masterclass in high-end finish designs, featuring high ceilings, iron-rod accents, and a dramatic, gallery-inspired aesthetic. At its heart, a chef-caliber kitchen serves as the ultimate hub for refined entertaining. Step into a home where luxury meets thoughtful innovation. This sprawling corner-lot property, crafted by the renowned Meritage Homes, is a rare find that perfectly balances grand proportions with everyday comfort. Boasting five spacious bedrooms, four full baths, and two half baths, the layout is designed for those who love to host and move freely through their space. The heart of the home is an expansive, sun-drenched open floor plan that flows effortlessly toward your own private oasis. Step outside to find a beautiful screened-in pool area, ideal for afternoon swims or evening gatherings without the worry of the elements. What truly sets this residence apart is the commitment to quality and efficiency. Protected by a timeless tile roof, the home features high-energy windows and spray-foam attic insulation, keeping the interior crisp and cool while keeping utility costs in check. The oversized three-car garage even comes equipped with a Tesla charger, ready for your electric vehicle. From the numerous high-end upgrades found throughout the interior to the curb appeal of its prominent corner position, every detail has been considered. This is more than just a house; it’s a modern, energy-efficient sanctuary built for a sophisticated lifestyle. The experience extends to a private pool house, complete with a game room and a theater-style loft. Outside, the pool anchors an at home retreat. This is luxury without the logistics. Your residency is entirely turnkey and ready for you to move in.

1734 Amsel Falls Park Terrace, Winter Garden
$565,000
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Luxurious upgraded TOLL BROTHERS Townhome located in coveted Lakeshore Preserve! As you enter this Immaculate 3-bedroom, 2.5-bathroom townhouse the living area offers a bright spacious open floor plan with 10' ceilings and upgraded kitchen area perfect for entertaining or simply bringing out your inner chef! The large center island provides plenty of space for multiple people to enjoy and an additional generous sized counter invites guests to join all activities centered in the kitchen. Featuring 42" upgraded cabinets, stainless steel appliances and a natural gas range, the area has sliding glass doors that open up to the private patio so that enjoying the outdoors becomes effortless. Outside, a covered walkway leads to the 2-car garage located across the beautifully paved patio. Moving upstairs, the primary bedroom is a tranquil retreat with a generous sized walk-in closet and an ensuite bathroom with dual sinks and at private water closet. From the relaxing bedroom you can enjoy beautiful sunsets in the evening without leaving the comfort of your home. Located on the other side of the second floor are two comfortable bedrooms that share a spacious bathroom across the hall. In addition, the home offers a whole house water filtration system, tankless water heater and above head storage racks in the garage. If you are ready to enjoy resort style living, Lakeshore Preserve also offers plenty of activities with a beautiful clubhouse with fitness center, outdoor community pool and playgrounds nestled along the shores of Panther Lake. Whether you enjoy going for a stroll along one of the walkways or grabbing a seat in one of the beautifully landscaped park areas, you are sure to find a quiet place with views. Best of all, your HOA dues cover not only all the amenities, but also exterior maintenance of your townhome, exterior painting, roof cleaning, and basic cable and internet. This well-maintained townhome in Horizon West is close to top rated schools, Disney attractions, shopping, dining, and has easy access to HWY 429.

8932 Bismarck Palm Drive, Winter Garden
$1,030,000
4 Beds ⋅ 4 Baths ⋅ Cypress Reserve Ph 1 SubDv. ⋅ 34787 Zip Code
Welcome to luxury living at its finest! Perfectly positioned on the largest homesite in the community, this exceptional 4 bedroom home, fully equipped with oversized loft and theatre/bonus room, sits on a premium 1/3-acre oversized lot with tranquil green space views, offering both privacy and room to enjoy Florida living. From the moment you arrive, you’ll be impressed by the freshly painted exterior, upgraded landscaping, elegant stone accents, and expansive paver driveway. Inside, thoughtful upgrades and quality craftsmanship are showcased throughout, including 8-foot interior doors, crown molding, custom window casings and sills, upgraded wood flooring, premium carpeting, and designer tray ceilings in both the dining room and the luxurious owner’s suite. The heart of the home is the stunning gourmet kitchen, featuring upgraded cabinetry, a California-style countertop, a vented exterior range hood, motion-activated faucet, and abundant space for entertaining and everyday living. The spacious owner’s retreat provides a peaceful escape with its elegant tray ceiling and spa-like atmosphere, while the open-concept layout is designed for both comfort and entertaining. This home is full of valuable efficiency upgrades, including a radiant barrier roof for exceptionally low energy costs, gutters, and numerous quality enhancements that provide peace of mind for years to come. This is a rare opportunity to own one of the community’s most desirable homesites, combining luxury finishes, energy efficiency, and an unbeatable oversized lot with beautiful green space views. A truly exceptional home, with LOW HOA and A RATED SCHOOL-ZONES that is as impressive inside as it is out. Schedule your showing today!

13852 Jomatt Loop, 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
$775,000
5 Beds ⋅ 4 Baths ⋅ Lakeview Pointe At Horizon West SubDv. ⋅ 34787 Zip Code
WELCOME TO LAKEVIEW POINTE AT HORIZON WEST! This 5-bedroom, 4-full-bath Pulte Creekview floorplan offers a flexible two-story layout with a downstairs primary suite, upstairs loft, flex room, 3-car garage, and a fully fenced corner-lot backyard. Hardwood flooring extends throughout the first floor, complemented by tray ceilings in the foyer and primary suite, plantation shutters, neutral interior paint, and updated lighting in the flex space and breakfast nook. The open kitchen, café, and family room create a central gathering space, featuring 42-inch maple cabinetry with crown molding and hardware, granite countertops, an oversized island with breakfast bar seating, built-in wall oven and microwave, corner walk-in pantry, and extended cabinetry along the breakfast nook for additional storage. Glass sliders with a remote-controlled window treatment open to the covered, extended screened brick-paver patio overlooking the private fenced yard. The downstairs primary suite includes a tray ceiling, oversized walk-in closet, dual-sink granite vanity, glass-enclosed tiled walk-in shower, and private water closet. Three additional bedrooms are located downstairs, including one adjacent to a full bath with dual-sink granite vanity, while two bedrooms share another full bath. Upstairs, a loft, storage room, fifth bedroom with extensive closet space, and a fourth full bath provide versatile space for guests, work, hobbies, or media use. Recent improvements include interior and exterior paint, two new AC systems installed in 2025, ceiling fans, bathroom mirrors, front door hardware, epoxy-finished garage floor, and overhead garage storage racks. Kitchen appliances, washer, and dryer convey. A transferable Choice Home Warranty is included through May 2027, subject to warranty terms. Lakeview Pointe HOA includes lawn care, irrigation, community pool, fitness center, playground, and additional community amenities. Convenient Horizon West location near Hamlin shopping and dining, SR-429, Winter Garden Village, Walt Disney World Resort, and major Central Florida attractions.

7052 Enchanted Lake Drive, Winter Garden
$500,000
3 Beds ⋅ 2 Baths ⋅ Waterleigh Ph 3b 3c & 3d SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained Laurel floor plan, featuring fresh professional exterior paint (2026), 3 bedrooms, 2 bathrooms, and an open-concept layout thoughtfully designed for comfortable everyday living and effortless entertaining. The spacious kitchen serves as the heart of the home, featuring stainless steel appliances, a breakfast bar, a walk-in pantry, and an adjoining dining area that flows seamlessly into the living room. Elegant ceramic tile extends throughout the main living areas, while the abundant natural light create a bright, inviting atmosphere. The private primary suite offers a generous walk-in closet and an ensuite bath with dual vanities and a large walk-in shower. Two additional bedrooms are thoughtfully positioned toward the front of the home, providing flexibility for guests, a home office, or hobbies. Enjoy Florida living year-round on the private brick-paver patio, with additional upgrades including an epoxy-coated garage floor, overhead storage racks, seamless gutters, upgraded front elevation with brick accents, and a rear-entry garage for enhanced curb appeal. Located in the Waterleigh master-planned community, residents enjoy resort-style amenities including multiple pools, fitness centers, walking trails, parks, playgrounds, sports courts, community gardens, and scenic lakes. Conveniently located near Horizon West, Hamlin Town Center, New Publix, shopping, dining, major roadways, Walt Disney World, and everything Winter Garden has to offer. Don't miss the opportunity to own this move-in-ready home in one of Central Florida's most desirable communities.

16802 Oakboro Street, Winter Garden
$815,000
3 Beds ⋅ 4 Baths ⋅ Watermark Ph 1b SubDv. ⋅ 34787 Zip Code
WELCOME HOME to this spacious 3 bedroom / 2 full & 2 half bathroom property, located in the desirable Horizon West area of Winter Garden. Conveniently located within the Watermark community, just one mile east of the 429 and a short drive to all major theme parks, shopping and dining. Built in 2016 by Meritage Homes, this Alcott model offers over 2500sqft with a large bonus room / half bath as well as an oversized living room. Expansive backyard that contains a covered outdoor space, complete with summer kitchen and hot tub, under warranty until Feb/2027. Step into the fully fenced backyard onto the private putting green with tropical landscaping. SunPower 2KW 6-Panel solar system that is owned outright. Large 2-car garage with sealed floor, overhead storage and 50 Amp Heavy Duty EV Charging Port. Original owner who has meticulously cared for this low maintenance and energy efficient property. A/C unit replaced in Sept/2024 with 10 Year warranty. Screen enclosure structure and roof under 10 Year warranty. This property is a move-in ready gem, and will not last long. Schedule your showing today!

14681 Seton Creek Boulevard, Winter Garden
$589,000
4 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to your Newbury model home! This Dream Finders Home is a 4-bedroom, 3-bathroom that offers 2,083 square feet! This PREMIUM CORNER LOT next to conservation area and Lake View from primary suite. This home has a beautifully upgraded living space in a desirable area of Winter Garden. The neighborhood of Serenade at Ovation offers Elevation C which is the upgraded elevation with a more desirable curb appeal that includes stone veneer. The heart of the home features a modern kitchen with upgraded cabinets, backsplash tile and stylish light fixtures extending into the breakfast nook. This lot is near the conservation area and lake view from primary suite window. Throughout the house, you'll find upgraded light fixtures and enhanced lighting in the living room, creating a warm and inviting atmosphere. Tile throughout the 1st floor was a BUILDER UPGRADE! This primary bathroom boasts upgraded faucets, tile, and cabinets! The wood grain adorns the staircase instead of traditional carpet for an elegant touch. Every window is dressed in upgraded wood blinds as a BUILDER UPGRADE, and fresh upgraded paint brightens all interior rooms. Practical upgrades include an enhanced sink and cabinet in the laundry room; plus, extra light sockets strategically placed in the living room and additional prewiring in the upstairs bonus room for your convenience. Upgraded utility sink and cabinets in laundry room on the 2nd floor. This thoughtfully upgraded home combines comfort, style, and functionality in a prime location. The attention to detail in every room, from the kitchen upgrades to the enhanced lighting throughout, creates a move-in ready property that's perfect for modern living. This neighborhood offers excellent connectivity with nearby transportation options and shopping conveniences. The proximity to quality educational facilities, including Horizon High School just minutes away, adds to the home's appeal. The area provides easy access to recreational opportunities, with Disney Theme parks and entertainment venues within a short drive. Brand New Publix, Miller's Alehouse in shopping plaza nearby. Enjoy Winter Garden's local history and charm! Bonus: includes high-speed fiber optic internet!. Home is currently rented through 10/31/2026 current rental rate is $3,000.00.

13043 Serene Glade Road, Winter Garden
$729,000
4 Beds ⋅ 4 Baths ⋅ Waterleigh Ph 2b SubDv. ⋅ 34787 Zip Code
Designed for comfortable everyday living and easy gatherings, this inviting Waterleigh home pairs a flexible two-story layout with fresh interior finishes and thoughtfully connected living spaces. Brand-new interior paint creates a bright, polished backdrop throughout, while decorative wainscoting and chair rail added in 2021 bring character to the main living areas. Just off the foyer, a versatile flex room can serve as a home office, formal dining room, playroom, hobby space, or additional sitting area based on your needs. Wood-look tile extends across the first floor, where wide archways create an easy flow between the kitchen, casual dining area, and family room. The kitchen is anchored by a large island with seating and features white cabinetry, stainless steel appliances, a blue glass-tile backsplash, generous counter space, a walk-in pantry, and a cabinet-lined serving area. The refrigerator was replaced in July 2024, and the microwave was replaced in November 2023. The first-floor primary suite offers a comfortable retreat with a tray ceiling, multiple windows, and an en suite bath featuring dual vanities, a soaking tub, separate shower, and an exceptionally large walk-in closet. Upstairs, one secondary bedroom includes its own full bath, while two additional bedrooms share another full bathroom with dual sinks. The oversized loft provides adaptable space for media, recreation, work, or hobbies. A dedicated laundry room, powder bath, built-in drop zone cabinetry, and attached two-car garage add everyday convenience. Wi-Fi-enabled features include the refrigerator, washer, dryer, microwave, thermostat, garage door openers, Ring device, and two smoke detectors. The exterior was painted in August 2025, and the covered front porch, covered rear lanai, and grassy backyard provide additional space to relax outdoors. Waterleigh residents have access to amenities throughout every phase of the community, including four resort-style pools, three fitness centers, tennis courts, sand volleyball, mini-golf, multiple playgrounds, pavilions, and walking paths. Lawn maintenance is included with the HOA, allowing more time to enjoy the neighborhood and its convenient Horizon West location near SR-429, shopping, dining, and Central Florida attractions.

9561 Waterway Passage Drive, Winter Garden
$875,000
5 Beds ⋅ 4 Baths ⋅ West Lake Hancock Estates SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 5-bedroom, 3-bath home with a dedicated office, offering the perfect blend of elegance, comfort, and functionality in the highly desirable Overlook at Hamlin community of Winter Garden. Thoughtfully designed for today's lifestyle, this spacious floor plan features a sought-after first-floor primary suite, providing a private retreat with convenience and flexibility. From the moment you enter, you'll appreciate the pride of ownership evident throughout. Gorgeous wood flooring flows through the main living areas, complemented by brand-new carpet and fresh interior paint for a truly move-in-ready feel. The dedicated office is ideal for working from home, studying, or creating a quiet flex space. The heart of the home is the open-concept living area, where a beautiful gas fireplace creates a warm and inviting focal point. The spacious kitchen overlooks the family room and dining area, making it easy to entertain while staying connected with family and guests. Step outside to one of the home's standout features—an oversized covered lanai and an expansive screened enclosure that extends your living space outdoors. Whether you're enjoying your morning coffee, dining al fresco, or hosting gatherings, this incredible outdoor retreat is designed for year-round Florida living. Upstairs, you'll find generously sized secondary bedrooms that provide plenty of space for family and guests, while the thoughtful layout offers privacy and versatility for every stage of life. Located in the sought-after Hamlin area, residents enjoy exceptional resort-style amenities, including a private community boat ramp with access to Lake Hancock, a lakeside clubhouse, fitness center, community pool, playgrounds, parks, walking trails, and waterfront recreation. Just minutes from Hamlin Town Center, Walt Disney World, shopping, dining, entertainment, top-rated schools, and major highways, this location offers unmatched convenience and an exceptional lifestyle. With fresh interior paint, gorgeous wood floors, new carpet, a first-floor primary suite, dedicated office, gas fireplace, and an incredible screened outdoor living space, this meticulously maintained home is truly move-in ready and offers everything today's buyers are looking for.

7773 Minutemen Loop, Winter Garden
$720,000
4 Beds ⋅ 4 Baths ⋅ Harvest At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. What's Special: South Facing Lot | Gourmet Kitchen | Large Kitchen Island. New Construction - November Completion! Welcome to the Ozark at 15997 Honey Harvest Street in Harvest at Ovation! This thoughtfully designed floor plan offers a spacious and functional layout centered around an open-concept gathering room, dining area, and kitchen, creating the perfect space for everyday living and entertaining. Tile flooring throughout the main living areas enhances both style and durability, while elegant tray ceilings add architectural detail and a sense of openness. The private primary suite is tucked away at the rear of the home and features a luxurious bath and large walk-in closet. Three additional bedrooms provide comfortable accommodations for family and guests, including one with a private en-suite. A versatile tandem garage offers extra storage or hobby space, while the expansive extended covered lanai seamlessly extends the living area outdoors. Complete with an outdoor kitchen rough-in, the lanai is ideal for hosting gatherings, dining al fresco, or simply enjoying the Florida lifestyle year-round. Visit Harvest at Ovation in Winter Garden to enjoy one of the final new-construction opportunities in Horizon West. This charming community offers access to planned amenities including a pool and cabana, a Butterfly Garden, a Nature Play Space, a dog park, and walking trails—all in a highly coveted location. Additional Highlights Include: pocket sliding doors at Great Room, 8' interior doors, additional sink at bathroom two, pre-plumb for laundry sink, quartz countertops, pendant lighting at kitchen island, laundry cabinets, and whole house blinds. Virtually staged photos are for representative purposes only. MLS#O6425653

15997 Honey Harvest Street, Winter Garden
$715,000
4 Beds ⋅ 3 Baths ⋅ Waterleigh Ph 4b & 4c SubDv. ⋅ 34787 Zip Code
Virtually Staged. Experience the highly sought-after KENTON FLOOR PLAN in the award-winning WATERLEIGH community, just MINUTES FROM DISNEY! Ideally situated on a QUIET CUL-DE-SAC with NO THROUGH TRAFFIC, this beautifully upgraded 4 BEDROOM, 3 BATHROOM home offers WOOD-LOOK TILE throughout the main living areas and LUXURY VINYL PLANK upstairs. A welcoming foyer with TRAY CEILING opens to a versatile FLEX ROOM, perfect for a home office or formal dining room. The OPEN-CONCEPT design centers around a stunning GOURMET KITCHEN featuring 42" UPGRADED SHAKER CABINETS WITH CROWN MOLDING, QUARTZ COUNTERTOPS, UPGRADED TILE BACKSPLASH, 7' ISLAND, STAINLESS STEEL APPLIANCES, VENT HOOD, WALL OVEN & MICROWAVE COMBO, 5-BURNER COOKTOP, OVERSIZED SINGLE-BASIN SINK, WALK-IN PANTRY, plus a built-in COFFEE BAR/DROP ZONE. The spacious family room overlooks the covered lanai and backyard. A FIRST-FLOOR BEDROOM & FULL BATH provide the perfect guest or multigenerational suite. Upstairs, the PRIMARY SUITE features a TRAY CEILING, spa-inspired bath with GARDEN TUB, GLASS-ENCLOSED SHOWER, DUAL QUARTZ VANITIES, and an OVERSIZED WALK-IN CLOSET. A large LOFT offers the perfect space for a media room or playroom. Bedrooms 3 and 4 share a bath with DOUBLE SINKS, while the oversized laundry room includes a UTILITY SINK, WASHER & DRYER. Additional upgrades include BLOCK-ON-BLOCK CONSTRUCTION, WHOLE-HOUSE WATER FILTRATION, REVERSE OSMOSIS SYSTEM, UPGRADED LIGHTING & FANS, VIDEO DOORBELL, LOW-E DOUBLE-PANE WINDOWS, R-30 INSULATION, and RECLAIMED WATER IRRIGATION for outstanding energy efficiency. Enjoy MAINTENANCE-FREE LIVING with lawn care included and access to 4 RESORT-STYLE POOLS, 3 CLUBHOUSES, FITNESS CENTERS, TENNIS COURTS, FISHING PIER, PLAYGROUNDS, PARKS, WALKING TRAILS, and more. WATER SPRING ELEMENTARY and WATER SPRING MIDDLE SCHOOL are just a SHORT WALK AWAY, making everyday routines incredibly convenient. Zoned for HORIZON HIGH SCHOOL and ideally located near shopping, dining, Disney, and with easy access to 429, 417 & 408, this home offers the perfect blend of luxury, convenience, and lifestyle.

11031 Jackson Cove, Winter Garden
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