Winter Haven Homes with Deed Restrictions Community Extras

Winter Haven Homes with Deed Restrictions Community Extras

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County. Known for its picturesque lakes and vibrant community spirit, Winter Haven is a hidden gem that offers a perfect blend of tranquility and excitement. With over 50 lakes, including the famous Chain of Lakes, residents enjoy a plethora of water activities, from boating to fishing and everything in between. The city is also home to beautiful parks, delightful dining options, and a rich cultural scene, making it an ideal place for families, retirees, and everyone in between.

One of the most appealing aspects of Winter Haven is its diverse array of homes, particularly those situated within deed-restricted communities. These neighborhoods offer a unique lifestyle, ensuring that the community remains well-maintained and aesthetically pleasing. With deed restrictions in place, homeowners can enjoy peace of mind knowing that their investment is protected, and the community's value is upheld.

These communities often provide added amenities such as swimming pools, fitness centers, and walking trails, fostering a sense of belonging and encouraging an active lifestyle. Whether you are looking for a cozy single-family home or a spacious townhome, Winter Haven's deed-restricted communities cater to various preferences and budgets.

Experience the warmth and charm of Winter Haven, where the beauty of nature meets the comforts of home. Discover your perfect property in this vibrant city and embrace a lifestyle filled with community spirit, recreational opportunities, and endless sunshine. Welcome home!

Newest Winter Haven Homes with Deed Restrictions Community Extras

$316,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 4 SubDv. ⋅ 33884 Zip Code
Why wait to build when you can move right in? This 2023-built, 3-bedroom, 2-bath home in VillaMar Phase 4 offers 1,597 square feet and is ready for its next owner! SELLER IS OFFERING $10,000 TOWARD BUYER'S CLOSING COSTS! PLUS, THE 10-YEAR STRUCTURAL BUILDER WARRANTY IS STILL IN EFFECT, offering added peace of mind for the new owner. The open floor plan connects the kitchen, dining, and living areas, making it easy to entertain, host family and friends, or enjoy a night at home. SMART-HOME features include a central control hub, smart front-door lock, Wi-Fi-enabled thermostat, video doorbell, and connected lighting, allowing you to manage select features right from your smart device. Step outside and enjoy the Florida lifestyle without leaving the neighborhood! VillaMar offers resort-style amenities including a community pool, cabana, and playground, with dog parks nearby. The location puts you just minutes from LEGOLAND Florida and Peppa Pig Theme Park, Publix, Walmart, Eagle Ridge Mall, restaurants and shopping along Cypress Gardens Boulevard, and Downtown Winter Haven. US-27, US-17, and Highway 60 are also nearby, providing access to Lakeland, Orlando, and Tampa. WALT DISNEY WORLD is approximately 35 miles away, making weekend trips to the Orlando attractions an easy option. With an established neighborhood and a 2023-built home that's ready now, you can skip the building process, bring your belongings, and start enjoying VillaMar! All information is deemed reliable but is not guaranteed and should be independently verified.

3927 Palazzo Place, Winter Haven
$275,000
3 Beds ⋅ 2 Baths ⋅ Gardens SubDv. ⋅ 33880 Zip Code
Welcome home to this beautifully designed 3 bedroom , 2 bath split plan home located in a desirable gated community! The open layout creates a spacious, inviting feel, with a large kitchen overlooking the living areas - perfect for every day living and entertaining. Step outside to enjoy a large back yard, offering plenty of room for pets, play, gardening or creating your own outdoor oasis. Located in an area convenient to LEGOLAND, major highways shopping, restaraunts, and Central Florida's world-famous theme parks, this home puts everything you need within easy reach. Best of all, there is no CDD, No flood insurance required, and low HOA, making this an attractive opportunity for both homeowners and investors. A gated community, newer roof, paint and carpet, septic pumped in 2025, all makes this one worth seeing!

106 Majestic Gardens Court, Winter Haven
$140,000
2 Beds ⋅ 2 Baths ⋅ Imperial Villas SubDv. ⋅ 33880 Zip Code
Welcome to easy Florida living in desirable Imperial Villas! This well maintained 2 bedroom, 2 bath villa offers a bright, open layout with a comfortable flow. Roof Replaced 2020. The spacious primary suite includes a walkin closet and private bath, and the screened lanai is perfect for morning coffee or relaxing in the evening. Enjoy the heated community pool and a low maintenance lifestyle, with the HOA covering water, sewer, trash, and exterior maintenance. Conveniently located near Lake Howard, shopping, dining, and downtown Winter Haven, this home blends comfort and convenience. Schedule your private showing today.

345 24th Street Nw Unit 1, Winter Haven
$369,900
3 Beds ⋅ 2 Baths ⋅ Hartridge Hills SubDv. ⋅ 33881 Zip Code
Move-In Ready Custom Home in a Gated Community Near the Airport Ideally located for aviation professionals seeking convenient access to the airport or for families looking for a safe, gated community, this beautifully updated custom home offers the perfect blend of comfort, style, and convenience. Built in 1988, this spacious home features an open floor plan with soaring ceilings, stunning exposed wood beams, solid wood doors, and matching wood baseboards that create warmth and character throughout. The split-bedroom layout provides privacy, while the attached two-car garage adds everyday convenience. The recently remodeled interior showcases numerous upgrades, including luxury vinyl plank flooring, fresh interior paint, and updated lighting throughout. The beautifully renovated kitchen features custom wood cabinetry, granite countertops, and a full suite of matching Whirlpool appliances. Both bathrooms have been tastefully updated with new wood vanities, Delta fixtures, Kohler toilets, and stylish tile finishes. The primary bedroom offers the comfort of new carpeting, and the home features smooth ceilings throughout—no popcorn ceilings. Additional highlights include generous laundry room storage, fresh exterior paint, and numerous major improvements for peace of mind. A new roof was installed in March 2026, along with new double-insulated windows, new irrigation, and professional landscaping. Every major update has been completed—simply move in and enjoy. The HOA fee is just $150 per month and includes lawn mowing and fertilization, making it easy to maintain a beautiful yard year-round.

218 Lake Hartridge Drive Nw, Winter Haven
$198,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
Short Sale. CLOSE IN 60 DAYS OR LESS! QUICK and easy HECM Short Sale on this 2 bedroom 2 bath Vienna Square Villa with pond and wooded view. Located next door to the clubhouse! The charming kitchen has upgraded ivory cabinets, and quartz counter tops. The oak floors flow from the kitchen, and great room giving a warm quality finish. The roof was replaced in 2022. Sold strictly AS-IS. No renting for the 1st 2 years of ownership in this charming 55+ community. This home is conveniently located within 10 minutes of restaurants, banks, shopping and Legoland. Vienna Square offers a low-maintenance lifestyle with reasonable fees, in a welcoming setting. Vienna Square is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees include exterior paint, roof replacement, irrigation water, basic yard maintenance, and a Spectrum Internet/TV package. Residents enjoy access to a community pool, fitness center, billiards, movie nights, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

1307 Innsbruck Ct, Winter Haven
$174,900
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Just bring your personal belongings for this fully furnished home. Officially it is 2 bedrooms, 2 bath home however the front room could be converted to a 3 bedroom just add a closet. Wonderful club house, a inground community pool and a pond stocked with fish with a low monthly fee of $65.00/month. 55 plus age requirement of one of the buyers in this community of Garden Grove Oaks. You own your land and you can file homestead making your taxes very low. Kitchen is very user friendly with updated appliances. In fact, the dishwasher and refrigerator are still under warranty. All the carpet was replaced with laminate. This home has a workshop/hobby room in the shed with another storage area and a private back yard screened porch with vinyl windows. Conveniently located to medical facilities, shopping, restaurants and major highways leading to Lake Wales, Haines City, Orlando and Tampa.

6086 Southern Oaks Drive, Winter Haven
$359,900
4 Beds ⋅ 2 Baths ⋅ Residences At Winter Haven SubDv. ⋅ 33880 Zip Code
Move-In Ready! Welcome to The Everglades at Residences at Winter Haven, an exclusive 63-lot semi-custom community offering exceptional craftsmanship, modern design, and a prime central Winter Haven location. This beautifully designed new construction home features 4 bedrooms, 2 bathrooms, a 2-car garage, and 1,905 square feet of thoughtfully designed living space. There is a natural ease to this home, from the open-concept layout to the thoughtfully selected finishes, creating the perfect balance of comfort, style, and functionality. At the heart of the home, the designer kitchen features a stunning full waterfall island, 42-inch cabinets with crown molding and additional storage, stainless steel appliances, and a spacious walk-in pantry. The open living and dining areas flow seamlessly to the covered lanai, making it ideal for both everyday living and entertaining. Premium features throughout the home include: Upgraded 8-foot interior doors Luxury vinyl flooring throughout the main living areas Floor-to-ceiling porcelain tile in the shower and tub surrounds Blinds included on all windows Dedicated laundry room Covered outdoor living space For added convenience and peace of mind, this home also includes a Smart Home Package featuring a Smart Lock, Video Doorbell, Smart Thermostat, and Security Alarm System, along with a 2-10 Home Buyers Warranty. Residents of Residences at Winter Haven enjoy low HOA fees of just $225 per quarter, no CDD fees, and the opportunity to personalize future homes by selecting their lot, floor plan, exterior finishes, interior design package, and upgrade options. Conveniently located near Lake Shipp Elementary School, Westwood Middle School, and Lake Region High School, this community also offers easy access to shopping, dining, healthcare, and major roadways. Offered at $349,900, this exceptional home combines quality craftsmanship, premium finishes, and modern living in one of Winter Haven's most desirable new home communities. Schedule your private showing today!

2145 River Hawk Loop, Winter Haven
$114,995
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to 4063 Rolling Oaks in Winter Haven, located in Oakwood Estates, a desirable co-op 55+ community. This well-maintained 2 bedroom, 2 bathroom home offers a spacious and versatile floor plan featuring a bonus room and a Florida room, providing plenty of space for relaxing, entertaining, hobbies or a home office. Laminate flooring flows throughout the main living areas and bedrooms, while the Florida room features tile flooring. The dining room includes a built-in buffet with display cabinets and additional storage, creating the perfect space for showcasing your favorite pieces and hosting family and friends. The kitchen offers a convenient closet pantry for added storage, and both bedrooms feature generous walk-in closets. Exterior features include window awnings and an attached carport. A BRAND NEW ROOF was put on (08/2026). Oakwood Estates offers an affordable Florida lifestyle with low HOA fees that include water and trash service. Residents can also enjoy many amenities of this lakefront community including; two clubhouses, two swimming pools, an activity center with a pool table, tennis & pickleball courts, a mini golf course and a lake with fishing dock. Don’t miss this opportunity to own a home in a welcoming community conveniently located near shopping, dining, and all the great amenities and attractions Winter Haven is known for.

4063 Rolling Oaks Drive, Winter Haven
$209,900
Osprey Estates SubDv. ⋅ 33884 Zip Code
OSPREY ESTATES IS A SMALL, GATED COMMUNITY LOCATED IN BEAUTIFUL SE WINTER HAVEN, FLORIDA. THE COMMUNITY HAS A TOTAL OF FOUR LOTS--THREE HAVE UPSCALE RESIDENCES AND THIS IS THE LAST ONE AVAILABLE. THE LOT IS .75 ACRE. THIS LOCATION IS CLOSE TO SHOPPING, MULTIPLE RESTAURANTS, LEGOLAND AND BOTH TAMPA AND ORLANDO. HOA REQUIRES A MINIMUM 3,500 SQ FEET OF LIVING AND A MAXIMUM 5,500 SQ FEET OF LIVING--ALSO THE NEW BUILD MUST HAVE A THREE-CAR GARAGE. THERE IS A WELL ON THE PROPERTY FOR IRRIGATION.

Eloise Loop Road, Winter Haven
$149,000
2 Beds ⋅ 2 Baths ⋅ Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B SubDv. ⋅ 33880 Zip Code
This is 55+ living at its best! Fully renovated with high-end finishes, a spotless, move-in-ready interior, and a desirable lakeside setting on the world-famous Winter Haven Chain of Lakes. Welcome to 689 Lake Howard Drive, Unit 213, where thoughtful updates, generous living spaces, and an exceptional waterfront community come together at an attractive price point. Located in The Wellington on the shores of Lake Howard, this impressive 2 bedroom, 2 bath condo feels fresh, modern, and remarkably spacious. The expansive living and dining area features beautiful flooring, crown molding, updated lighting and ceiling fans, and plenty of room for comfortable everyday living and entertaining. Sliding glass doors open to a large enclosed Florida room overlooking the beautifully maintained community grounds, providing even more space to relax and enjoy the Florida lifestyle. The remodeled kitchen is a standout, featuring quartz countertops, abundant white soft-close cabinetry, a farmhouse-style sink, herringbone tile backsplash, under-cabinet lighting, and a complete stainless steel LG appliance package including refrigerator, range, microwave, and dishwasher. Both bathrooms have been beautifully remodeled with quartz-topped vanities and impressive custom tile work. Walk-in showers feature frameless glass enclosures, decorative tile accents, niches, and contemporary finishes. An exceptionally large walk-in closet provides outstanding storage, while an interior laundry closet with included washer and dryer and a large private exterior storage room add everyday convenience. The Wellington offers beautifully landscaped grounds, two pool areas including a heated pool for winter use, clubhouse, shuffleboard, community activities, and a private dock on Lake Howard with access to the Winter Haven Chain of Lakes—perfect for fishing and enjoying life on the water. The condo fee includes basic cable and internet, water, garbage pickup, exterior building maintenance, and grounds maintenance. A private covered parking space is also included. Conveniently located near medical facilities, shopping, restaurants, churches, grocery stores, and charming Downtown Winter Haven. Beautifully remodeled, incredibly spacious, and located in a Chain of Lakes waterfront community—this is 55+ living with the updates already done for you!

689 Lake Howard Drive Nw Unit 213, Winter Haven
$495,000
4 Beds ⋅ 3 Baths ⋅ Hart Lake Hills Ph 01 SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained 4-bedroom, 3-bath pool home located in the highly sought-after gated community of Hart Lake Hills. Offering the perfect blend of comfort, efficiency, and Florida living, this home is designed for both everyday enjoyment and effortless entertaining.Step inside to an open and inviting floor plan featuring a spacious kitchen with stainless steel appliances, a gas range, abundant cabinetry, and plenty of counter space overlooking the main living areas. The generous primary suite provides a relaxing retreat with a well-appointed ensuite bath, while the split-bedroom layout offers added privacy for family and guests. Outside, enjoy the screen-enclosed saltwater pool and expansive lanai overlooking the large, fully fenced backyard. The outdoor space has also been thoughtfully updated with pavers installed on the back deck in 2019, the pool remarcited in 2019, and a new pool pump and salt cells added in 2024. Additional updates and features include a roof installed in 2017, A/C installed in 2019, fresh interior paint in 2020, a whole-home Generac generator, gas hot water heater, and solar panels for added energy efficiency and peace of mind. Perfectly situated near schools, shopping, dining, LEGOLAND Florida Resort, and Highway 27, this home offers convenient access to everything Central Florida has to give while tucked away in one of the area's desirable gated communities. Schedule your private showing today! Solar panel loan must be assumed by buyer.

651 Hart Lake Drive, Winter Haven
$164,800
2 Beds ⋅ 2 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code
Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully maintained, offering peace of mind and comfort from day one! BONUS=2024 Evolution C4PRO golf cart is included! The sales price includes the $11,000 share of ownership in this Co-op Community. The low $145/mo HOA fee includes water, sewer, and lawn mowing. Individual mailbox, community laundry and clothesline available. No pets. No motorcycles. Trucks ok. Located near shopping, entertainment, and health care!

628 Lakeside Ranch Lane, Winter Haven
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