Winter Garden/Oakland Homes with Fence Restrictions Amenities

Winter Garden/Oakland Homes with Fence Restrictions Amenities

Welcome to the enchanting region of Winter Garden and Oakland, nestled in the heart of Orange County, Florida. This vibrant community is a delightful blend of small-town charm and modern conveniences, making it an ideal location for families, retirees, and anyone seeking a serene lifestyle with easy access to urban amenities.

Winter Garden is renowned for its picturesque downtown area, where historic buildings house trendy shops, delightful eateries, and lively farmers' markets. The scenic West Orange Trail winds through the region, offering residents the perfect opportunity for outdoor activities such as biking, jogging, and leisurely strolls. The area's lush landscapes and beautiful parks, including the popular Lake Apopka, provide a tranquil escape from the hustle and bustle of city life.

When it comes to real estate, Winter Garden and Oakland offer a variety of homes that cater to diverse tastes and lifestyles. Many properties in this region come with fence restrictions, ensuring a cohesive and aesthetically pleasing neighborhood environment. These restrictions often encourage homeowners to maintain their yards and gardens beautifully, contributing to the overall charm of the area.

In addition to the stunning homes, residents enjoy a wealth of amenities, including top-rated schools, recreational facilities, and community events that foster a close-knit atmosphere. Whether you’re looking for a cozy single-family home or a spacious property, Winter Garden and Oakland provide a welcoming community that feels like home. Experience the magic of this charming region, where every day feels like a vacation!

Newest Winter Garden/Oakland Homes with Fence Restrictions Amenities

$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
$295,000
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
$930,000
5 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 3 SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained 5-bedroom, 3.5-bath home with a spacious 3-car garage, offering the perfect blend of comfort, style, energy efficiency, and location. From the moment you step inside, you’ll appreciate the soaring ceilings, open living spaces, and thoughtful upgrades throughout. The custom stone fireplace, bring an inviting ambiance to those cozy evenings or when entertaining guests year round. At the heart of the home is the gourmet kitchen, featuring granite countertops, built-in appliances, abundant cabinetry, and plenty of space for cooking and entertaining. The adjoining living area is highlighted by a built-in fireplace, creating a warm and inviting focal point for family gatherings. One of the home’s standout features is the fully owned solar system, helping keep monthly electric costs exceptionally low—averaging approximately $33 per month. The exterior has been recently painted, adding fresh curb appeal. Step outside to the expansive backyard designed with possibilities in mind. The generous outdoor space offers ample room to add a pool whilst still leaving plenty of space for a dedicated grilling and outdoor dining area. Whether you're hosting summer barbecues, family gatherings or relaxing with friends, the spacious yard provides the ideal setting for creating your own private outdoor retreat. The modern floor plan offers five bedrooms and 3.5 bathrooms, providing flexibility for families, guests, or a home office, along with a generous 3-car garage for vehicles and additional storage. Ideally located in one of Winter Garden’s most desirable communities, this home is zoned for highly rated schools and offers convenient access to Walt Disney World, SR-429, downtown Orlando, and Orlando International Airport (MCO), making commuting, travel, shopping, dining, and entertainment easily accessible. If you’re looking for a move-in-ready home with premium features, exceptional energy savings, generous living space, and an outstanding location, this home is ready to welcome you.

5079 Palmetto Park Drive, Winter Garden
$559,000
3 Beds ⋅ 3 Baths ⋅ Waterleigh Phase 3bcd SubDv. ⋅ 34787 Zip Code
Welcome to this beautifully maintained home in the master-planned community of Waterleigh community of Horizon West in Winter Garden. This popular Bellake floor plan offers over 2,200 square feet of beautifully maintained living space. Rare concrete block construction on both the first and second floors, thoughtful updates by the current owner, and a functional open-concept layout make this home stand out from the moment you arrive. As you step inside, you're welcomed by a versatile flex room to the left, perfect for a home office, playroom, or formal sitting area, while the updated half bath with a new vanity and light fixture is conveniently located to the right. Continue into the spacious great room that flows seamlessly into the kitchen, creating an inviting space for everyday living and entertaining. The kitchen features stainless steel Whirlpool appliances, granite countertops, a large center island with additional cabinet storage, ample cabinetry, a dedicated dining area, and overlooks the main living space. Select areas of fresh interior paint, refreshed tile flooring, updated lighting, and a new ceiling fan add to the home's clean, well-cared-for feel. Just beyond the kitchen, a mudroom provides access to the attached two-car garage. Additional storage can be found beneath the staircase. Upstairs you'll find all three bedrooms, two full bathrooms, the laundry room, and an additional storage closet. The spacious primary suite features a beautifully remodeled en-suite bathroom with a walk-in shower finished in timeless subway tile, contrasting dark grout, sleek matte black fixtures, and a custom-designed walk-in closet. The secondary bedrooms share a full bathroom with a dual-sink vanity. Sliding glass doors off the great room open to the covered, screened lanai with paver flooring overlooking the side and backyard. The security system, security cameras, washer, and dryer all convey. Enjoy Waterleigh's resort-style amenities including four pools, four parks, two fitness centers, tennis courts, beach volleyball, putt-putt golf, walking trails, a fishing pier, and a beautiful clubhouse, while the HOA maintains the lawn and shrubs. Minutes from Hamlin Town Center, Publix, SR 429, Disney, and the shores of Hickory Nut Lake, you'll even enjoy Disney fireworks from your driveway. Schedule your private showing today!

15741 Fountain Springs Road, Winter Garden
$1,099,000
6 Beds ⋅ 5 Baths ⋅ Cypress Reserve Ph 2 SubDv. ⋅ 34787 Zip Code
Experience luxury living in this exceptional 6-bedroom, 5-bathroom residence located in the highly sought-after Cypress Reserve community of Winter Garden. Perfectly positioned on a premium homesite with no rear neighbors, this impressive home offers exceptional privacy, tranquil conservation views, and a versatile floor plan designed for today’s lifestyle. The open-concept design showcases beautifully appointed living spaces throughout both floors, making it ideal for multigenerational living or hosting extended family and guests. A dramatic second-floor loft overlooks the main living area, creating an open and inviting atmosphere while providing additional living space. Upstairs also features a second primary suite, three additional spacious bedrooms, a dedicated theater/media room, and a flex room that serves perfectly as a home office, den, or playroom. At the heart of the home is a chef-inspired gourmet kitchen designed to impress, featuring stainless steel appliances, a gas cooktop, double wall ovens, quartz countertops, and an oversized center island with an undermount sink, generous seating, and double-sided cabinetry that provides exceptional storage for both everyday living and entertaining. Motorized shades throughout the main living area add a touch of sophistication and everyday convenience. The spacious family room opens effortlessly to the outdoor living space through triple pocket sliding glass doors, creating a seamless indoor-outdoor lifestyle. Relax year-round on the screened lanai overlooking peaceful conservation views or entertain with ease around the sparkling pool and fully equipped outdoor kitchen featuring a Paradise Grill, built-in sink, and refrigerator. Luxurious owner's suite is a private retreat featuring a spa-inspired bath with dual vanities, a relaxing garden tub, a zero-entry walk-in shower with seamless glass enclosure, and double-door entry to an expansive custom-designed walk-in closet that is sure to impress. A private hallway just off the main living area leads to a spacious guest suite with direct access to the pool, along with a generously sized laundry room for added convenience. Upstairs, you'll find a second primary suite, three additional bedrooms, an expansive loft, a dedicated theater/media room, and a versatile flex room—offering abundant space for family, guests, a home office, fitness room, or additional living area. Additional highlights include a three-car tandem garage offering abundant storage and ample room for a home gym, workshop, or hobby space. LOCATED just minutes from Downtown Winter Garden, the award-winning Winter Garden Farmers Market, Winter Garden Village, shopping, dining, top-rated schools, and major roadways including State Road 429 and Florida’s Turnpike, this exceptional home offers the perfect blend of luxury, comfort, convenience, and location *** This is a rare opportunity to own one of Cypress Reserve’s premier residences and experience the very best of the Winter Garden and true Florida lifestyle. ***

14067 Jomatt Loop, Winter Garden
$585,000
3 Beds ⋅ 3 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Stunning Luxury Townhome in Highly Sought-After Lakeshore Community! Welcome to this beautifully appointed 3-bedroom, 2.5-bath townhome offering a PRIVATE POOL (salt-water and heated), modern elegance, thoughtful design, and exceptional comfort in the heart of Horizon West. Located in the prestigious Lakeshore by Toll Brothers community, this residence showcases upscale finishes (Restoration Hardware fixtures), abundant natural light, and a spacious open-concept layout perfect for both everyday living and entertaining. Step inside to discover a bright and inviting living space, gourmet kitchen with premium cabinetry and top-of-the-line stainless-steel appliances, and a dining area that flows seamlessly to your private outdoor retreat. Upstairs, the luxurious owner’s suite features a spa-inspired bath with soaking tub, separate shower and generous customized walk-in closet, accompanied by two additional well-sized bedrooms and a stylish full bath. A convenient 2-car garage adds practicality and storage. Other features include whole house water filtration system, built-in speakers, custom woodwork, Haiku fans, upgraded sliding doors to patio with recently resealed pavers. Lakeshore offers resort-style amenities including a sparkling pool, clubhouse, fitness center, playgrounds, and scenic walking paths—plus you’re just minutes from top-rated schools, shopping, dining, Disney, and all the excitement of Hamlin and the Horizon West lifestyle. This is refined townhome living at its best—move-in ready and waiting for you. The HOA fee includes all amenities plus yard maintenance, exterior painting and pressure washing, roof replacement, irrigation water, 1 gig internet and basic cable.

8937 Lakeshore Pointe Drive, Winter Garden
$949,999
5 Beds ⋅ 4 Baths ⋅ Orchard Hills Ph 1 SubDv. ⋅ 34787 Zip Code
Virtually Staged. Beautifully maintained 5-bedroom, 3.5-bath home with over 4,000 square feet in the highly sought-after Orchard Hills community. Situated on a spacious corner lot, this home offers an ideal floor plan with the primary suite on the first floor and expansive living spaces designed for both everyday living and entertaining. The gourmet kitchen features stainless steel appliances, double wall ovens, an oversized center island, abundant cabinetry, a butler’s pantry, and a large walk-in pantry, all overlooking the open family room and screened lanai. This home is loaded with valuable upgrades, including a SOLAR energy system that helps keep electric costs exceptionally low, with most monthly electric bills averaging around just $33. Additional improvements include a HYBRID energy-efficient water heater, a Pelican whole-house WATER FILTRATION system, and CUSTOM his-and-hers walk-in closets in the primary suite. There is NO CARPET throughout the home, with luxury vinyl plank flooring covering the entire second floor for a modern, low-maintenance finish. The spacious first-floor primary suite offers a private retreat with dual custom walk-in closets and an elegant en-suite bath featuring dual vanities, a makeup station, an oversized walk-in shower, and a soaking tub. Upstairs, you’ll find four additional bedrooms, two full bathrooms, a large loft, and a separate bonus/media room, providing flexible space for family, guests, or working from home. The back yard is fully fenced and plenty of room for a pool. Residents of Orchard Hills enjoy resort-style amenities including a community pool, fitness center, clubhouse, playground, dog park, and walking trails with the pool and clubhouse being a couple of minutes walk. The home is zoned for highly rated schools and is conveniently located just minutes from Walt Disney World, the rapidly growing Hamlin Town Center, shopping, dining, and entertainment. With easy access to SR 429, the Florida Turnpike, and SR 408, commuting is simple, and Orlando International Airport is within easy reach. Combining energy efficiency, extensive upgrades, generous living space, and an exceptional location, this home is truly move-in ready.

14301 White Moss Way, Winter Garden
$524,990
3 Beds ⋅ 3 Baths ⋅ Serenade At Ovation SubDv. ⋅ 34787 Zip Code
Major Price Improvement!! Take advantage of the 4.99% interest rate if you close by the end of July 2026!!! Welcome to Serenade at Ovation, one of Winter Garden's most desirable new home communities, where modern design meets an unbeatable Central Florida lifestyle. This completed brand-new Cooper floor plan offers 2,078 square feet of thoughtfully designed living space with 3 bedrooms, 2.5 baths, a versatile loft, and a 2-car garage, all perfectly positioned with the front of the home overlooking peaceful conservation views. The open-concept layout is ideal for both everyday living and entertaining. At the heart of the home, the gourmet kitchen showcases beautiful quartz countertops, elegant linen cabinetry, and abundant workspace while seamlessly connecting to the spacious dining and living areas. Stunning level-three natural wood-look plank tile flooring flows throughout the first floor, creating warmth, durability, and timeless appeal. Upstairs, the spacious primary suite serves as a private retreat featuring a large walk-in closet, dual-sink vanity, and oversized walk-in shower. Two additional bedrooms, a full bath, and a flexible loft provide plenty of space for a home office, media room, playroom, or additional gathering area. Modern finishes, energy-efficient construction, and thoughtful design details throughout make this home truly move-in ready. Residents of Serenade at Ovation enjoy an exceptional location in the heart of Winter Garden, one of Central Florida's fastest-growing and most sought-after communities. Just minutes away, Historic Downtown Winter Garden offers charming brick-lined streets, boutique shopping, farmers markets, live entertainment, and an impressive selection of local restaurants, cafés, breweries, and outdoor dining options. Nearby Winter Garden Village provides convenient access to popular retailers, grocery stores, fitness centers, and everyday conveniences. Outdoor enthusiasts will appreciate close proximity to the award-winning West Orange Trail, numerous parks, lakes, golf courses, and recreational opportunities throughout the area. Families and professionals alike will enjoy the community's convenient access to major roadways including State Road 429, Florida's Turnpike, State Road 535, and Interstate 4, providing quick connections to Downtown Orlando, Disney, Orlando International Airport, and the region's major employment centers, entertainment destinations, and attractions. Experience the perfect combination of contemporary living, natural surroundings, and unmatched convenience in this exceptional new home at Serenade at Ovation.

13023 Tranquil Water Alley, 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
$910,510
6 Beds ⋅ 4 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
Virtually Staged. Under Construction. Pre Design Center Pricing Sample Image Welcome to this beautifully designed newer-construction home in the highly sought-after Hamlin Meadows community of Winter Garden, this spacious residence offers modern finishes, an open-concept layout, and a prime location just minutes from Hamlin Town Center, shopping, dining, top-rated schools, and major highways. Inside, you’ll find a bright and inviting floor plan featuring a large kitchen with upgraded cabinetry, stainless steel appliances, stone countertops, and an oversized island overlooking the main living and dining areas — perfect for entertaining. Pricing does not include design selections; you have the opportunity to customize the home to fit your taste

17350 Wild Daisy Drive, Winter Garden
$823,309
6 Beds ⋅ 5 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
Virtually Staged. Pre-Construction. To be built. SAMPLE IMAGES The Anna Maria with Bonus with 6 Bedrooms floorplan is a thoughtfully designed home featuring four bedrooms and two and a half bathrooms on the 1st floor and 2 additional bedrooms and 2 baths on the 2nd floor, along with a bonus room perfect for comfortable family living. The open-concept layout highlights a spacious great room that flows seamlessly into the kitchen and dining area, making it ideal for gatherings and relaxation. The primary bedroom offers privacy with a well-appointed ensuite and a large walk-in closet. Additionally, the home includes a covered patio for outdoor enjoyment and a convenient two-car garage

17139 Ingram Bluff Drive, Winter Garden
$721,820
4 Beds ⋅ 3 Baths ⋅ Hamlin Meadows At Hamlin SubDv. ⋅ 34787 Zip Code
Virtually Staged. Under Construction. Sample Images The Anna Maria floor plan is a beautifully designed one-story home offering four bedrooms and two and a half bathrooms, thoughtfully arranged for comfortable everyday living. The open-concept layout features a spacious great room that flows effortlessly into the kitchen and dining area, creating an inviting space for entertaining or relaxing at home. The private primary suite includes a well-appointed ensuite bath and a generous walk-in closet. A covered patio extends the living space outdoors, while the two-car garage adds convenience and functionality. With 2,235 square feet of well-designed living space, the Anna Maria delivers both style and practicality.

17127 Ingram Bluff Drive, Winter Garden
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