Winter Garden Homes with Deed Restrictions Community Extras

Winter Garden Homes with Deed Restrictions Community Extras

Winter Garden, located in Orange County, Florida, is a charming city that offers a perfect blend of small-town charm and modern amenities. With its rich history, beautiful landscapes, and a strong sense of community, Winter Garden has become a sought-after destination for homebuyers.

Nestled in the heart of the Sunshine State, Winter Garden enjoys a warm and pleasant climate year-round, making it an ideal place to live for those who enjoy outdoor activities. The city boasts numerous parks, trails, and lakes, providing ample opportunities for hiking, biking, boating, and fishing. The West Orange Trail, a popular 22-mile paved trail, runs through Winter Garden, offering residents a scenic route for walking, jogging, or cycling.

Winter Garden is known for its historic downtown area, which is filled with quaint shops, restaurants, and entertainment options. Residents can explore the local farmers market, attend live performances at the Garden Theatre, or simply relax at one of the many outdoor cafes. The city also hosts various festivals and events throughout the year, including the Winter Garden Music Fest and the Winter Garden Art Festival.

For those seeking a community with deed restrictions, Winter Garden offers a variety of options. These communities provide additional amenities and services, such as gated entrances, clubhouse facilities, swimming pools, and maintenance services. These extras ensure a comfortable and convenient lifestyle for residents, allowing them to focus on enjoying their homes and the surrounding community.

Whether you're looking for a peaceful retreat or an active lifestyle, Winter Garden has something to offer everyone. With its picturesque landscapes, friendly atmosphere, and desirable deed-restricted communities, Winter Garden is a city that truly captures the essence of Florida living.

Newest Winter Garden Homes with Deed Restrictions Community Extras

$889,900
4 Beds ⋅ 3 Baths ⋅ Oakland Parkb-3 SubDv. ⋅ 34787 Zip Code
A rare opportunity in highly sought-after Oakland Park—this beautifully furnished, turnkey home offers **4 spacious bedrooms, 3 full bathrooms, including a first-floor bedroom and full bath ideal for guests, extended family, or an in-law arrangement**, plus the exceptional Winter Garden lifestyle buyers are looking for. Tall ceilings, 8-foot doors, elegant architectural details, high-end décor, and thoughtfully designed living spaces create an elevated yet comfortable feel throughout. The showpiece kitchen is truly the heart of the home, featuring premium quartz countertops, a 5-burner gas range, stainless steel hood, striking designer backsplash, and spacious walk-in pantry. The spa-inspired primary suite offers an expansive private bathroom and generous walk-in closet, creating the perfect retreat. And for a little extra personality, the home even has its very own “Harry Potter” closet! Enjoy Florida living from the inviting screened front porch, complete with a porch swing perfect for morning coffee, an afternoon book, or relaxing at the end of the day. The back patio and fenced yard provide another comfortable setting for entertaining, outdoor dining, or simply enjoying the beautiful Florida weather. An expansive 3-car garage offers exceptional space and storage. Offered fully furnished with beautiful, high-end furnishings and décor, this home is truly turnkey—just bring your suitcase and start enjoying the lifestyle. Located near highly regarded schools and just moments from the West Orange Trail, walk, bike, take your golf cart, or drive to charming Downtown Winter Garden, the Farmers Market, restaurants, shopping, and entertainment. Move in before the holidays and experience everything this incredible community has to offer, including festive neighborhood traditions and upcoming celebrations such as the golf cart parade, fall festival, and more. An exceptional opportunity to own a remarkably equipped home in one of the area’s most desirable communities at an amazing value.

226 Hammock Preserve Loop, Oakland
$649,900
4 Beds ⋅ 3 Baths ⋅ Horizon Isle SubDv. ⋅ 34787 Zip Code
WALK ON IN AND CALL IT HOME! Welcome to this beautiful, almost-new K. Hovnanian home, where thoughtful design, spacious living, and stylish upgrades come together beautifully. As you enter, you’re greeted by a welcoming foyer. To the right are two generously sized bedrooms and a full bathroom. Continue down the hall and discover a functional nook that’s perfect for a home office, study area, or homework station. With its own charming barn door, this space can easily be closed off for added privacy. Just to the right, French barn doors open to a versatile flex space that can be used as an office, formal dining room, or even a fourth bedroom—whatever best suits your lifestyle. Step into the spacious great room and prepare to be impressed! Gorgeous exposed beams create a warm and inviting atmosphere, while the chef-inspired kitchen is the true centerpiece. Featuring ample counter space, a beautiful white farmhouse sink, built-in oven, freestanding oven, stylish range hood, and stunning backsplash, this kitchen is both functional and beautifully appointed. The oversized primary suite offers a peaceful retreat, with a spacious bedroom and a luxurious ensuite bathroom designed with comfort in mind. Enjoy a large walk-in shower, freestanding soaking tub, dual vanities, and an enormous walk-in closet. This thoughtfully designed home also features a generously sized laundry room and mudroom, an oversized garage, and a beautiful lot with a fully fenced backyard—perfect for entertaining, relaxing, or enjoying time outdoors. And the location is just as impressive! Zoned for highly desirable schools and conveniently located near the 429, Turnpike, and 408, with easy access to Disney, shopping, dining, and so much more. With its spacious layout, beautiful finishes, and fantastic location, this home is sure to impress. Schedule your private showing today before this one is SOLD!

13184 Dendy Way, Winter Garden
$749,000
4 Beds ⋅ 3 Baths ⋅ Westfield Lakes SubDv. ⋅ 34787 Zip Code
Welcome home to this stunning pool home with a beautiful water view in desirable Westfield Lakes! Offering 2,335 square feet in a triple-split design, this home features a screened pool overlooking the water and an impressive list of recent improvements, including roof (2023), AC (2019), water heater (2023), whole-home repipe (2021), pool resurfacing and new tile (2020), repainted kitchen cabinets (2026) and fully remodeled bathrooms. Enjoy the Florida lifestyle from your screened pool and lanai, whether starting the day with coffee by the water, taking an afternoon swim or entertaining family and friends. Westfield Lakes is known for its mature tree-lined streets, beautifully landscaped entrances and welcoming neighborhood atmosphere. Residents enjoy Lake Beulah with two fishing docks, scenic ponds with lighted fountains, tennis and pickleball courts, and two playgrounds. The neighborhood is also home to abundant wildlife, including sandhill cranes, herons, egrets, bald eagles and owls. With the Roper YMCA, Southwest Aquatics and two dog parks nearby, this home offers a wonderful combination of space, recreation and convenience. A screened pool, peaceful water view, major updates and plenty of space all in beautiful Westfield Lakes.

12021 Windstone Street, Winter Garden
$724,999
4 Beds ⋅ 4 Baths ⋅ Waterside/Johns Lk-Ph 2a SubDv. ⋅ 34787 Zip Code
FORMER BUILDER MODEL HOME - and it shows. When a builder builds their own model, they hold nothing back, and this 4-bedroom, 3.5-bath, 2,958 sq ft home in Waterside on John's Lake is the proof: Upgrades everywhere! Gourmet kitchen with stacked cabinets, 8-foot doors throughout, recessed lighting, wood panel on ceiling, a whole-home speaker system, plus so much more! A finish package that is nearly impossible to replicate today. The open kitchen-living-dining space was designed to entertain. The kitchen is finished wall to wall with stacked upper cabinets plus crown molding, lighted glass-front uppers, quartz countertop, double built-in ovens, gas cooktop, decorative tile backsplash and an oversized island with seating. A butler's pantry and a fully built-out walk-in pantry with its own seating area keep everything in place, and the laundry room is also finished with custom cabinetry, a sink and extra countertop space. Across the room, a floor-to-ceiling stacked-stone wall anchors the living area, with an electric fireplace and the TV and entertainment system built right in, framed by lighted shelving and cabinets. A dedicated study sits off the dining room with its own work island, wall-to-wall shelving and a wood-planked ceiling. A first-floor bedroom with an en-suite bath makes an ideal guest or in-law suite, plus a powder bath for visitors. Upstairs, the primary suite features a wood beam ceiling and a walk-in closet outfitted with a custom shelving system. The primary bath is built around an oversized walk-in glass shower spanning an entire wall, with dual vanities opposite. Two additional bedrooms, a full bath, and a generous loft with a built-in media center complete the second level. Bidets in the baths. Engineered hardwood in the loft and primary bedroom, wood-look tile downstairs. Outside, a screened lanai with a tongue-and-groove wood ceiling opens to a private paver courtyard. The 2-car garage is already fitted with a NEMA 14-50 EV charging outlet, providing extra storage and parking for your Tesla or other electric car. Best of all: NO FRONT NEIGHBORS. The community pool and amenity center sit directly across the street with plenty of guest parking, and there are water views of John's Lake from the front of the home. Waterside on John's Lake offers something most communities do not: a true lap pool with lane markers for training and distance swimming, plus a separate leisure pool. Add a playground, fitness center, clubhouse and oak-canopied trails with picnic and grill areas leading to a lakefront pier for an evening walk or a little fishing. Minutes from Winter Garden Village, Hamlin and SR-429, with downtown Winter Garden's Plant Street, farmers market and the West Orange Trail just up the road - and Disney a short drive away. Model homes are built to sell a neighborhood. Here is your chance to own one - schedule your private showing today.

16924 Tradewind Point, Winter Garden
$795,000
5 Beds ⋅ 4 Baths ⋅ Lakeshore Preserve Ph 1 SubDv. ⋅ 34787 Zip Code
Luxury living in the ENZO Model townhome located in Lakeshore Preserve, a Toll Brothers community surrounded by million-dollar homes in Winter Garden. This spacious executive style townhome offers 5 bedrooms, 4 bathrooms, and over 3,100 square feet of living space, including a private 1-bedroom apartment with kitchenette above the garage and its own private entrance perfect for guests, multigenerational living, or a student retreat. Built in 2017, this home features an open concept layout, Wolf gas cooktop, two gas tankless water heaters, whole home water softener, and two A/C systems with Nest thermostats. Recent updates include luxury vinyl flooring throughout the downstairs, all new carpet installed upstairs and in all bedrooms, and plantation shutters, adding both style and functionality. The home has also been upgraded with over $20,000 in custom closet systems, providing exceptional storage, organization, and convenience throughout. Enjoy the extended wrap around front porch, private courtyard, and even views of Disney fireworks and space launches from the front of the home. Lakeshore Preserve offers resort style amenities including a lakefront clubhouse, fitness center, pool, lake access, kayak launch, volleyball court, firepit, and dog park. Conveniently located near Disney, Hamlin shopping and dining, Flamingo Crossings, Orlando Health, and top rated schools. HOA includes exterior maintenance, cable, internet, and community amenities. A rare opportunity to own a luxury townhome in one of Winter Garden’s most desirable communities.

8866 Bismarck Palm Drive, Winter Garden
$180,000
2 Beds ⋅ 2 Baths ⋅ Grove Resort & Spa Hotel Condominium SubDv. ⋅ 34787 Zip Code
Own your piece of the Orlando vacation market at The Grove Resort & Water Park! Located on the 4th floor of Building 3, near the water park, this fully furnished 2-bedroom, 2-bath condo offers the perfect combination of a personal vacation retreat and investment opportunity. The Grove is a Walt Disney World Good Neighbor Hotel located just minutes from the parks, with complimentary shuttle service to Walt Disney World. Owners and guests enjoy resort-style amenities including Surfari Water Park with a lazy river, water slides and FlowRider surf simulator, multiple pools, spa, fitness center, mini golf, arcade, and on-site restaurants and bars. With an on-site rental management program and a prime location near Central Florida’s top attractions, this turnkey condo offers an easy, hands-off ownership opportunity while giving you your own place to enjoy when visiting Orlando.

14501 Grove Resort Avenue Unit 3403, Winter Garden
$879,999
4 Beds ⋅ 3 Baths ⋅ Waterleigh SubDv. ⋅ 34787 Zip Code
Virtually Staged. Welcome to Waterleigh! This beautiful 2023-built, 4-bedroom, 3-bath home sits on a spacious lot with a peaceful natural lake view from the backyard. Featuring an open-concept layout, modern kitchen, versatile loft, and private owner’s suite. Enjoy resort-style pools, clubhouses, fitness centers, tennis courts, trails, and playgrounds. Publix is conveniently located at the community entrance, with schools, shopping, dining, SR-429, and Walt Disney World nearby. Enjoy space, views, convenience, and the best of the Horizon West lifestyle

17882 Adrift Road, Winter Garden
$490,000
4 Beds ⋅ 3 Baths ⋅ Westhaven/Ovation SubDv. ⋅ 34787 Zip Code
Almost New & Move-In Ready! Built in 2024, this beautifully maintained corner-unit townhome offers the perfect combination of modern style, comfort, and functionality. Featuring 4 full bedrooms and 3 full bathrooms, the thoughtfully designed floor plan includes a convenient first-floor bedroom, ideal for a home office, guest suite, or private bedroom. The home showcases upgraded tile flooring throughout the main living areas and stylish granite countertops, creating a clean and contemporary feel. The spacious kitchen comes fully equipped with stainless steel appliances, including refrigerator, microwave, and dishwasher, plus a washer and dryer for added convenience. Enjoy Florida living from the screened-in back porch, perfect for relaxing or entertaining while enjoying the outdoors. A private 2-car garage located at the rear of the home provides secure parking and additional storage. Residents enjoy an impressive selection of community amenities, including a resort-style pool, fitness center, gathering area, playground, and community mailbox. With its desirable corner-unit location, modern finishes, flexible first-floor bedroom, and excellent amenities, this almost-new townhome is an exceptional opportunity for both homeowners and investors. Come see why this beautiful 2024 townhome is the perfect place to call home!

14075 Lochend Way, Winter Garden
$475,000
3 Beds ⋅ 2 Baths ⋅ Crown Point Springs SubDv. ⋅ 34787 Zip Code
Live in Winter Garden’s Golf Cart District! This charming 3 bed, 2 bath home with an office/den in one of Winter Garden’s most desirable communities, Crown Point Springs. This home has an open floor plan with split bedrooms, an enclosed patio, fenced yard, inside laundry room and a two-car attached garage. The foyer will welcome you into the home with the formal dining on your left and the French door enclosed office/den on your right (currently being used as a game/theatre room. You will love the ceramic tile floors in the formal dining and family rooms. Walk further into the heart of the home - the kitchen, that features painted cabinets and counters, a new stainless steel stove, dishwasher and fridge. The breakfast nook overlooks the yard. The kitchen is open to the family room that has a brick front wood burning fireplace. A French door leads to the enclosed patio – what a great space to enjoy your morning coffee or relax after a long day! The spacious yard is fenced in and there’s plenty of room for a pool. The owner’s suite is off the kitchen and features and en-suite bath with an updated “adult height” vanity with two sinks, a glass enclosed shower and a walk-in closet. The guest bedrooms are on the other side of the home and share the guest bath that features an updated “adult height” one sink vanity and a tub/shower combo. This home has been lovingly maintained! Additional updates include a new roof (2026), new garage door, new fan in the family room, interior paint, cabinets for additional storage in the laundry room and the washer & dryer are included! This home has leased solar panels that the Buyer will have to take over, making the electricity bill low. Community is located minutes away from downtown Winter Garden, half a mile from the West Orange Trail, close to Chapin Station where you can enjoy picnic areas, playground, a tennis and basketball court. Crown Point Springs is also close to Newton Park where you’ll find a boardwalk, boat ramp, grills, picnic tables and playground, etc. Take your golf cart to Plant Street’s restaurants, boutiques, theater, festivals, and the popular Saturday farmer’s market. Close to top-rated schools, Winter Garden Village, AdventHealth, Publix, 429, and the Florida Turnpike. Don't miss this chance to own a home in one of Central Florida’s most desirable communities. Schedule your showing today!

1553 Spring Ridge Circle, Winter Garden
$510,000
3 Beds ⋅ 3 Baths ⋅ Summerlake Pd Ph 1b-A Rep SubDv. ⋅ 34787 Zip Code
Welcome home to this freshly painted, charming Craftsman- inspired residence offering 2193 square feet of thoughtfully designed living space in one of Winter Garden's most desirable communities! This beautifully maintained home features 3 spacious bedrooms, 2 1/2 baths and a versatile loft/bonus room- perfect for a home office, media room or play area. The heart of the home is the open-concept kitchen overlooking the dining and family room, complete with an EXTRAORDINARY walk-in pantry that provides exceptional storage. Tile flooring flows throughout the main living areas, while the primary suite features warm hardwood flooring. Upstairs, the loft and secondary bedrooms are finished with comfortable Berber carpet. Step outside to relax or entertain on the screened lanai, offering the perfect space to enjoy Florida's beautiful weather year-round. Residents enjoy outstanding community amenities, including a resort-style pool, clubhouse, tennis courts, zip line and a dog park. Summerlake also appreciates access to TOP-RATED "A" schools. Conveniently located with easy access to Disney, Universal, Sea World, shopping, dining, major highways and all that Central Florida has to offer, this home truly combines comfort, convenience and an exceptional lifestyle!

7921 Iceland Gull Street, Winter Garden
$730,000
4 Beds ⋅ 3 Baths ⋅ Wintermere Harbor Ph 02 48 21 SubDv. ⋅ 34787 Zip Code
Welcome home to this one-story pool home situated on an oversized lot that overlooks a pond! ***NEW WINDOWS, NEW COMMODES, 2022 ROOF, 2020 SMART POOL*** Tucked into the back of this gated community, this spacious oasis is ready for its next owners. One of Florida's most popular floor plans features a formal living space at the entrance of the home, casual living space in the middle of the home, the primary suite privately on one side of the home, and the 3 secondary bedrooms on the other side of the home. Choose to repurpose the "formal living space" into whatever your wants and needs may be, or use them as the formal living room and formal dining room as the builder intended. The primary suite has an extension included and is ready to be used as yet another flex space. French doors open from this extension right onto the covered outdoor living space. The primary bathroom boasts a soaking tub, dual vanities, and 2 custom closets. The casual living space is open and inviting with the kitchen, large dining nook, and family room, and lots of natural light brightens this space up even more by way of a wall of sliding glass doors that lead to the outdoor living space, another door with a window that also leads to the outdoor living space, and a set of bay windows in the dining nook. Bedrooms 2 and 3 are located down a hallway off of the casual living space and have a full bathroom they share. The 4th bedroom is in the back of the home with its own bathroom. Step out back to the screened in patio which holds a gorgeous pool with a sun shelf and waterfall, covered portion, and extension under the screen for total and full enjoyment opportunities! Continue outside of the screen enclosure to the fully fenced in backyard that overlooks a pond. Whether looking for peace and serenity or fun and activity, this home has a solution to it all! Inquire today to for a private viewing to see if this gem will become your next home!

2039 Harbor Cove Way, Winter Garden
$814,990
4 Beds ⋅ 3 Baths ⋅ Lake Star At Ovation SubDv. ⋅ 34787 Zip Code
Under Construction. Welcome to this stunning new construction home at Lake Star At Ovation in Winter Garden, FL. Built by M/I Homes, this 2-story home offers 2,753 square feet of thoughtfully designed living space with 4 bedrooms and 3 bathrooms. Step inside to discover an open-concept living space that creates a seamless flow between the main gathering areas, perfect for everyday living and entertaining. The quality of design is evident throughout, with carefully selected finishes and a well-planned floorplan that maximizes both comfort and functionality. The owner's bedroom features a spa-inspired en-suite bathroom and a large walk-in closet, providing a relaxing retreat at the end of each day. 3 additional bedrooms offer generous space for family, guests, or a home office. The spacious loft open to below and makes a great secondary family room or gaming area. A covered lanai extends your living area outdoors, ideal for enjoying Florida's beautiful weather year-round. This home is situated within a well-established neighborhood with convenient proximity to parks and recreational areas, making it an ideal setting for active lifestyles and families. The neighborhood offers a welcoming atmosphere with access to green spaces where residents can enjoy the outdoors.

17425 Water Hemlock Road, Winter Garden
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