Winter Haven Homes with Private Pool type

Winter Haven Homes with Private Pool type

Welcome to Winter Haven, Florida – a charming city nestled in Polk County that perfectly blends small-town warmth with vibrant community spirit. Known as the "Chain of Lakes," Winter Haven boasts a stunning array of lakes and waterways, making it a paradise for outdoor enthusiasts and water lovers alike. With a rich history, diverse cultural scene, and an array of recreational activities, this city offers something for everyone.

If you're considering a move to Winter Haven, you’ll find a variety of homes that cater to your lifestyle needs. Among the most sought-after properties are those featuring private pools, providing a perfect oasis for relaxation and entertainment. Imagine stepping outside to your own tranquil retreat, where you can bask in the Florida sunshine, host summer barbecues, or simply unwind after a long day.

Homes with private pools in Winter Haven come in various styles and sizes, from cozy single-family residences to more expansive luxury estates. Many of these properties are strategically located near the city’s beautiful lakes, parks, and recreational facilities, ensuring that you can enjoy both the serenity of your backyard and the excitement of outdoor adventures.

In addition to its natural beauty, Winter Haven offers excellent schools, a thriving downtown area with shops and restaurants, and a strong sense of community. Whether you’re looking to raise a family, retire in peace, or enjoy a vibrant social life, Winter Haven is the perfect place to call home. Dive into the dream of owning a home with a private pool in this picturesque city – your slice of paradise awaits!

Newest Winter Haven Homes with Private Pool type

$595,000
4 Beds ⋅ 4 Baths ⋅ East View Pkwy SubDv. ⋅ 33881 Zip Code
Virtually Staged. Mediterranean-Style Estate with Private Casita, Pool, Covered 2-Car Garage, Spacious Workshop & NO HOA in Winter Haven. Welcome to a truly unique Mediterranean-style estate offering over 4,100 square feet of living space, exceptional versatility, and the freedom of no HOA. This spacious property features a main residence plus a private casita, creating an ideal setup for multi-generational living, extended family, guests, a private home office, or flexible additional living space. Inside, you'll find generous living areas, beautiful architectural details, and plenty of room for both everyday living and entertaining. Recent improvements include a NEW ROOF and NEW AC, offering added peace of mind for the next owner. Step outside to your own private Florida retreat featuring a screened pool and spacious outdoor living areas, perfect for relaxing, entertaining, and enjoying Florida living year-round. The property also features a covered 2-car garage and an ample workshop, providing excellent space for vehicles, hobbies, projects, tools, storage, or recreational equipment. Need even more room for your toys? With no HOA and ample parking for boats, RVs, and recreational vehicles, this property offers the space, flexibility, and freedom that can be difficult to find. Conveniently located near Winter Haven's famous Chain of Lakes, you'll be close to boating, fishing, recreation, shopping, dining, and everything the area has to offer. Whether you're searching for a family estate, multi-generational home, private guest accommodations, a home with income potential, or simply a distinctive property with plenty of space and privacy, this home offers endless possibilities. Can't tour in person? Virtual tours are also available! Contact us today to schedule your private showing or virtual tour and experience everything this exceptional Winter Haven property has to offer.

815 Lake Jessie Drive, Winter Haven
$224,900
3 Beds ⋅ 1 Baths ⋅ 33880 Zip Code
Bring your vision and make this 3-bedroom, 1-bath home your own! This property needs some TLC but offers great potential, with several important updates already completed. Features include original hardwood floors, an inviting screened-in pool, and sliding glass doors that open directly to the pool area—perfect for enjoying Florida living. The home also offers a convenient inside laundry room complete with a washer and dryer and a spacious 25’ x 8’ enclosed front porch complete with ceiling fans, providing additional flexible living or entertaining space. Outside, you’ll find a large fenced yard with plenty of room to enjoy the outdoors. Major updates include a new roof in 2026, New pool pump in 2026, A/C replaced in 2025, and updated windows and glass sliding doors. With the big-ticket items already addressed, this home is ready for someone to add their personal touches and bring out its full potential. The home also has a Brinks home security system. Don’t miss this opportunity to create your own Florida home with a pool and a large fenced yard!

1325 Lake Shipp Dr N, Winter Haven
$350,000
3 Beds ⋅ 2 Baths ⋅ Homewood Sub SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to 117 Homewood Drive in Winter Haven! Situated on a spacious .36-ACRE LOT, this 3-bedroom, 2-bath home offers 1,762 square feet of heated and cooled living space, a versatile BONUS ROOM, screened-in POOL, FENCED backyard, and plenty of space for indoor and outdoor living. Inside, the family room features a wood-burning FIREPLACE, while the kitchen is equipped with new stainless-steel appliances. The bonus room provides additional flexibility for a home office, hobby room, playroom, or additional living space. Step outside to enjoy the screened-in pool, outdoor kitchen area, and recently RESURFACED back patio—an inviting setup for entertaining or enjoying Florida's year-round outdoor lifestyle. The fenced backyard also features a 5-year-old STORAGE SHED with a roll-up door and electrical access, providing convenient space for storage, equipment, or projects. Numerous recent improvements add to the home's appeal, including a NEW ROOF in 2023, A/C replaced in 2024, NEW WATER HEATER, NEW POOL PUMP & MOTOR, new stainless steel kitchen appliances, a resurfaced back patio in 2026, and an updated garage with TESLA charger that conveys. With .36 acres, a screened pool, bonus room, outdoor entertaining space, fenced yard, and substantial storage, this home offers plenty of versatility. Conveniently located with easy access to the Polk Parkway, shopping, dining, and other Winter Haven amenities. Schedule your private showing and experience all that 117 Homewood Drive has to offer!

117 Homewood Drive, Winter Haven
$340,000
3 Beds ⋅ 2 Baths ⋅ Summit East Ph 02 SubDv. ⋅ 33884 Zip Code
Beautifully maintained 3-bedroom, 2-bath pool home in a quiet Winter Haven community with a low HOA of $260/year. This home offers extensive upgrades, modern finishes, and a bright, open layout designed for comfortable living. Major improvements include a new roof (2020), new AC (2020), tankless water heater (2021), updated windows (2018), Culligan water system (2016), and a new pool pump and filter (2025). The kitchen features granite countertops, stainless steel appliances, a breakfast bar, and excellent natural light. The bathrooms also include granite counters, updated fixtures, and a large tub in the primary suite. Paradise Walk in tub (2020) in second bathroom. Enjoy Florida living with a saltwater fiberglass pool, screened enclosure, covered patio, fenced yard and irrigation system. Interior highlights include multiple flex spaces, neutral paint, updated ceiling fans, clean flooring, and move-in ready condition. Located close to shopping, dining, medical facilities, Legoland, and major highways, this home offers strong value with thoughtful upgrades and excellent maintenance. Schedule your private showing today.

7002 Summit Circle, Winter Haven
$725,000
5 Beds ⋅ 3 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to Waterford Oaks, where timeless architectural details and upgraded finishes set this home apart. Beautifully manicured landscaping and a paver driveway lead to an impressive 5-bedroom, 3-bath pool home with nearly 3,000 square feet of living space and an oversized 3-car garage. Decorative glass double entry doors open to a beautifully detailed interior featuring soaring ceilings, extensive crown molding, substantial millwork, architectural columns and arches, plantation shutters and elegant formal living and dining spaces. Thoughtful details continue throughout the home, creating a level of character and craftsmanship rarely found in newer construction. A versatile fifth bedroom at the front of the home also provides an ideal private office or den. At the center of the home, the kitchen combines function with elevated finishes, including granite countertops, rich wood cabinetry, upgraded KitchenAid appliances, a large breakfast bar and walk-in pantry. The kitchen flows into the spacious family room, where recessed lighting and expansive views toward the pool create a comfortable yet refined gathering space. A three-way split bedroom plan provides exceptional privacy. The primary suite is privately positioned in its own wing and features a spacious bath with dual granite-topped vanities, a soaking tub, separate walk-in shower and generous storage. On the opposite side of the home, a separate bedroom and adjacent full bath create an excellent option for guests or in-law accommodations, while two additional bedrooms and another full bath occupy their own private wing. The home's attention to detail carries outdoors to an expansive covered lanai and screened pool, creating a true extension of the living space with room for outdoor dining, entertaining and relaxing year-round. Mature landscaping adds privacy to the backyard setting. Located within gated Waterford Oaks, residents also enjoy community boat ramp and dock access to Lake Winterset and the Winter Haven Chain of Lakes. The combination of architectural detailing, upgraded finishes, a flexible three-way split floor plan, private pool, oversized 3-car garage and Chain of Lakes access makes this a distinctive opportunity in Winter Haven.

9504 Waterford Oaks Boulevard, Winter Haven
$700,000
3 Beds ⋅ 4 Baths ⋅ Acreage SubDv. ⋅ 33880 Zip Code
Welcome to your own private piece of Florida! This unique property offers nearly 5 acres of space, privacy, and endless possibilities with **NO HOA**. Nestled away from the hustle and bustle, this property provides the room and freedom to enjoy a more private, country-style lifestyle while still being conveniently located near everything Winter Haven has to offer. The property features a spacious 3-bedroom, 2.5 bath home plus a detached shed that is currently being used as a she shed. With nearly 5 acres, there is plenty of room for outdoor activities, pets, gardening, recreational equipment, or simply enjoying the peace and privacy of your surroundings. The Pool area also features an outdoor half bath for convenience! Enjoy easy access to Winter Haven's famous **Chain of Lakes**, offering boating, fishing, kayaking and scenic water activities. You're also conveniently located near **LEGOLAND Florida Resort, Peppa Pig Theme Park, SEA LIFE Florida, downtown Winter Haven, local parks, shopping and dining**. For nature lovers, nearby attractions include scenic lakefront parks and trails, while **Bok Tower Gardens** is just a short drive away in Lake Wales. Winter Haven's central location also provides convenient access to the greater Central Florida area, including Orlando and Tampa. If you've been searching for acreage, privacy, flexibility and no HOA while remaining close to Central Florida attractions, this property offers a rare opportunity to enjoy it all.

281 Gerber Dairy Road, Winter Haven
$430,000
4 Beds ⋅ 2 Baths ⋅ Lake Winterset Acres Unit #2 SubDv. ⋅ 33884 Zip Code
A Dream come true in Winter Haven! This beautiful 4-bedroom, 2-bath home checks all the boxes: NO HOA, a private pool, and a spacious backyard. Enjoy comfortable indoor living and plenty of outdoor space to relax and entertain. Conveniently located in the Cypress Gardens area near LEGOLAND Florida, shopping, dining, and everyday conveniences. A wonderful combination of space, freedom, location, and Florida lifestyle. Schedule your private showing today!

9 Winterset Dr, Winter Haven
$419,000
3 Beds ⋅ 3 Baths ⋅ Lake Lucerne Ph 1 SubDv. ⋅ 33881 Zip Code
Discover your own private Florida retreat in this stunning 3-bedroom, 2.5-bathroom pool home, built in 2018 and offering over 2,600 square feet of living space on a spacious, nearly quarter-acre lot in Winter Haven, Florida! Designed for comfort, entertaining, and everyday living, this beautiful two-story residence features an expansive floor plan with a generously sized primary suite, an oversized walk-in closet, and a huge upstairs loft offering endless possibilities for a home office, media room, game room, or additional living area. The heart of the home is the spacious kitchen, featuring elegant quartz countertops, a large center island, abundant cabinetry, and plenty of room for preparing meals and gathering with guests. Step outside into your very own backyard paradise! Enjoy a gorgeous screened-in private swimming pool surrounded by an elegant travertine pool deck, all within a fully fenced backyard offering privacy and plenty of outdoor space. Whether you're hosting weekend gatherings, relaxing poolside, or enjoying Florida's year-round sunshine, this outdoor retreat is designed to impress. Additional highlights include a two-car garage, an extended driveway providing ample parking, and access to a community swimming pool. Located in the desirable Lake Lucerne community, this home offers convenient access to US Highway 27, Interstate 4, shopping, dining, and everyday essentials. Enjoy the attractions of Central Florida, including LEGOLAND Florida Resort, Winter Haven's famous Chain of Lakes, nearby parks, and the restaurants and entertainment of Downtown Winter Haven. The location also provides convenient connections to Haines City, Davenport, and the greater Orlando area. Why settle for an ordinary home when you can enjoy your own private pool, an oversized primary suite, generous living space, and an exceptional Central Florida location? Schedule your private showing today and experience everything this Winter Haven pool home has to offer!

119 Sunfish Drive, Winter Haven
$750,000
5 Beds ⋅ 4 Baths ⋅ Waterford Oaks SubDv. ⋅ 33884 Zip Code
Welcome to an exceptional 5-bedroom, 3.5 bathroom estate in the highly desirable gated community of Waterford Oaks in Winter Haven, This distinctive home offers a 2023 ROOF; NEW EXTERIOR PAINT; and a ONE YEAR HOME WARRANTY offered by the seller, along with lake access, resort-style outdoor living, flexible living spaces, and exceptional parking. A standout feature is community access to LAKE WINTERSET and the Winter Haven Chain of Lakes. A community boat ramp and dock on Lake Winterset are just a short distance away, offering convenient access for boating, fishing, and water recreation. Situated on a beautifully landscaped corner lot, the property features mature landscaping and elegant architectural details. The property offers exceptional parking with an elegant CIRCULAR DRIVEWAY and a separate SIDE ENTRY DRIVEWAY leading to the three-car garage, providing abundant space for guests, vehicles, and recreational equipment. Inside, the spacious floor plan showcases original hardwood floors, high ceilings, multiple tray ceilings, crown molding, custom built-ins, recessed lighting, and abundant natural light. The living room features custom built-in shelving surrounding an electric fireplace, while the adjoining family room offers a custom entertainment center, built-in shelving, and large windows overlooking the screened outdoor living area. The gourmet kitchen is a true centerpiece of the home, featuring custom wood cabinetry, GRANITE COUNTERTOPS, a substantial CENTER ISLAND with prep sink, built-in appliances, gas range with decorative backsplash and pot-filler faucet, abundant counter space, and generous storage. The kitchen overlooks the pool area and connects easily to the entertaining spaces. A spacious BUTLER'S CHAMBER provides additional cabinetry, workspace, storage, and a convenient laundry area. The luxurious primary suite offers a private retreat with a tray ceiling, accent lighting, large windows, plush carpeting, and a walk-in closet. The en-suite bathroom features dual vanities, tile flooring, a deep soaking tub beneath an arched window, and a spacious walk-in shower. One additional bedroom is currently used as a dedicated pool table/billiards room, offering flexibility as a recreation space or bedroom. Upstairs, an expansive TV room or potential mother-in-law suite provides additional privacy and versatility with a microwave, refrigerator, sink, 1/2 bathroom, and walk-in closet currently used as a small office. The outdoor living space is truly one of the home's major highlights, featuring a screened-in lanai, large pool with a swim-out area, OUTDOOR KITCHEN, barbecue area with NEW BARBECUE GRILL, and spacious brick-paver pool deck. The pool enclosure was rescreened last year, creating an inviting setting for swimming, dining, relaxing, and entertaining. Additional highlights include two tankless water heaters, with one serving the primary bedroom and the other serving the remainder of the home; a private well supplying irrigation for the property and adjacent vacant land which is also available for purchase. Conveniently located near shopping, dining, major roadways, local lakes, LEGOLAND Florida, and other Central Florida attractions, this distinctive estate combines Lake Winterset access, a resort-style saltwater pool, outdoor kitchen, gourmet kitchen, three-car side-entry garage, exceptional parking, multiple entertainment spaces, flexible upstairs living, and significant recent improvements.

9513 Waterford Oaks Boulevard, Winter Haven
$379,900
4 Beds ⋅ 3 Baths ⋅ College Estates SubDv. ⋅ 33881 Zip Code
Virtually Staged. COMPLETELY RENOVATED 4-BEDROOM POOL HOME WITH NO HOA, OVERSIZED .42-ACRE LOT, DETACHED GARAGE/WORKSHOP AND A BRAND-NEW ROOF! Designed for entertaining inside and out, this move-in-ready 4-bedroom, 2.5-bath home offers 2,189 sq. ft. of heated living space and 2,818 total sq. ft. under roof, with no rear neighbors and an incredible backyard retreat. The transformation starts at the curb with a BRAND-NEW ROOF, fresh sod, updated landscaping and freshly painted exterior. Step inside to a bright, updated interior featuring luxury vinyl plank flooring throughout, fresh paint, abundant natural light, new lighting fixtures, updated hardware and new ceiling fans. At the heart of the home is a completely renovated kitchen featuring solid-surface countertops, brand-new cabinetry and stainless steel appliances. With plenty of workspace and an inviting layout, the kitchen flows naturally into the home's living areas, creating an ideal setting for everyday living and entertaining. The spacious primary suite features a beautifully renovated en-suite bathroom with dual sinks and a tiled walk-in shower. The guest bathroom has also been completely remodeled and includes a dual-sink vanity. Need even more space? A versatile bonus room with its own mini-split air-conditioning system, half bath and separate closet creates the perfect game room, home office, guest retreat, media room or additional living space. An air-conditioned breezeway leads to an oversized indoor laundry room offering even more storage and functionality. Now step outside to the feature that truly sets this home apart—YOUR OWN PRIVATE BACKYARD OASIS! The fully refurbished swimming pool features a refreshed finish, all-new pool equipment and new surrounding decking, creating a fantastic setting for Florida outdoor living. An attached covered outdoor pavilion provides the perfect shaded space for grilling, dining and entertaining, plus an additional storage room. The oversized, fully fenced .42-acre backyard offers plenty of room for pets, play and outdoor activities, while NO REAR NEIGHBORS adds to the sense of privacy. Double-gate access leads to a detached two-car garage/workshop, providing outstanding space for vehicles, hobbies, tools, equipment or additional storage. A BRAND-NEW SEPTIC TANK AND DRAINFIELD adds another significant recent improvement. With a NEW ROOF, RENOVATED KITCHEN AND BATHROOMS, REFURBISHED POOL, NO HOA, oversized fenced lot, detached garage/workshop, stainless steel appliances, luxury vinyl plank flooring, flexible home-office space and extensive updates throughout, this property checks the boxes today's buyers are searching for. Schedule your private showing and experience this move-in-ready Florida pool home for yourself!

822 17th Terrace Ne, Winter Haven
$598,000
5 Beds ⋅ 3 Baths ⋅ Hidden Creek SubDv. ⋅ 33880 Zip Code
Virtually Staged. Welcome to 1020 Lena Run Court, where space, privacy, and Florida living come together inside the gated Hidden Creek community. Offering 3,068 square feet of living space, this spacious Winter Haven pool home provides the room and flexibility today’s households are looking for, with multiple gathering spaces, a screened pool with a fully fenced back yard, a dedicated home office, and a versatile 5th bedroom/den/playroom without a closet. One of the home’s standout features is the large kitchen offering generous counter space, abundant cabinetry, and plant of room for cooking, gathering, and entertaining. The kitchens open connection to the main living area flows right out the back door to a screened saltwater pool and spa with a covered outdoor space overlooking preserve land and no rear neighbors. Enjoy peaceful mornings by the pool, frequent sightings of local birds and wildlife, and a natural backdrop that creates a tucked-away feel, yes still close to everyday conveniences. Whether hosting weekend gatherings, enjoying an evening swim, or simply relaxing with your morning coffee, this outdoor space was made for enjoying the Florida lifestyle. Inside, the generous split floor plan offers space to spread out without sacrificing connection. The spacious primary suite creates a comfortable retreat, while additional bedrooms and flexible living areas provide options for family, guests, working from home, a playroom, or multigenerational living. Conveniently located in Winter Haven just minutes from the Polk Parkway, 1020 Lena Run Court offers easy access to both Winter Haven and Lakeland, including dining, shopping, medical facilities, LEGOLAND Florida, the Chain of Lakes, and Central Florida recreation. Move-in ready and beautifully maintained. If you’ve been searching for a spacious pool home in Winter Haven with easy access to Lakeland, 1020 Lena Run Court deserves to be experienced in person. Schedule your private showing today.

1020 Lena Run Court, Winter Haven
$1,200,000
3 Beds ⋅ 2 Baths ⋅ N/A SubDv. ⋅ 33884 Zip Code
Welcome to your slice of heaven in Winter Haven! Situated on just over 6.5 acres you will find this charming 3/2/2 Cassidy custom pool home surrounded by green meadows and mature oak trees. 4401 Chambliss Rd. offers space, freedom, and a lifestyle you simply won’t find inside typical neighborhoods. This expansive homestead provides room for horses, chickens, gardens, equipment, and future additions, all thanks to the no-HOA flexibility that lets you live the way you choose. There is a refreshing pool perfect for Florida summers and is surrounded by mature trees and wide-open land that create exceptional privacy. A large pond sits quietly among huge cypress trees on the property, adding a peaceful backdrop without dominating the landscape. Acreage of this size is almost unheard of in Winter Haven, making this a standout opportunity for anyone seeking space, seclusion, and the freedom to have a true country retreat while staying close to town conveniences. Updates include: HVAC 2018, Roof 2024, Water Heater 2018. 2 large sheds and large RV/Boat shed.

4401 Chambliss Road, Winter Haven
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