Winter Haven Homes with Pool View

Winter Haven Homes with Pool View

Welcome to Winter Haven, Florida, a picturesque city nestled in the heart of Polk County, renowned for its stunning lakes and vibrant community spirit. With a rich history and a plethora of recreational opportunities, Winter Haven is the perfect place to call home. Known as the "Chain of Lakes City," it boasts over 50 lakes, offering residents and visitors alike a stunning backdrop of natural beauty and outdoor adventure.

One of the most sought-after features in Winter Haven real estate is homes with pool views. Imagine waking up each morning to the serene sight of shimmering water and lush landscaping right from your bedroom window. These properties not only provide a tranquil oasis but also create an ideal setting for relaxation and entertainment. Whether you're hosting summer barbecues or enjoying a quiet evening under the stars, a home with a pool view enhances your lifestyle in this charming city.

In addition to its beautiful homes, Winter Haven is home to a vibrant downtown area filled with unique shops, delightful restaurants, and cultural attractions. Families will appreciate the excellent schools and community events that foster a sense of belonging. With year-round sunshine, residents can enjoy outdoor activities like boating, fishing, and hiking, making it a haven for nature lovers.

If you're looking for a place that combines the tranquility of lakeside living with the excitement of a growing community, Winter Haven is the perfect destination. Explore our selection of homes with pool views today, and discover your dream oasis in this enchanting Florida city!

Newest Winter Haven Homes with Pool View

$699,000
4 Beds 3 Baths Hart Lake Hills Ph 01 SubDv. 33884 Zip Code
From the moment you enter, it is immediately apparent this is not your typical lakefront home. Elevated sightlines extend across the pool to the tranquil waters of Hart Lake, creating a dramatic first impression and an almost infinity-edge style of living. Situated on approximately half an acre in the gated SE Winter Haven community of Hart Lake Hills, this immaculate custom residence offers 4 bedrooms, 3 baths and over 2,500 SF of refined living space with a level of finish and customization rarely found at this price point. Designed for upscale everyday living and impressive entertaining, the home showcases gorgeous travertine and wood flooring, substantial millwork, designer lighting, custom tile and stonework, granite surfaces and distinctive architectural details throughout. Statement fixtures incorporating sculptural, crystal and glass elements add another layer of sophistication. The open, triple-split bedroom floor plan includes a spacious family room, formal dining, office/den, kitchen with dinette and inside laundry. The family room captures panoramic lake views through expansive glass doors opening to the pool and features a custom wood TV wall accented with natural-edge detailing. The kitchen offers quartz countertops, stainless appliances, custom wood cabinetry, breakfast bar and a light-filled dinette overlooking the pool and lake. The adjoining dining room is illuminated by a dramatic faceted glass chandelier, while the office/den room provides flexibility as an office, study or additional sitting room. The primary suite features wood flooring, a large walk-in closet with built-ins and an extraordinary spa-inspired bath. Travertine and stone surround a floating-edge soaking tub with black stone deck, dramatic underlighting and sleek linear fireplace. An oversized open shower features multiple body sprays, handheld fixture and rainfall shower, complemented by floating cabinetry, granite-topped vanity, designer lighting and a private water closet. Three generously sized guest bedrooms are privately positioned away from the primary suite with excellent closet space and access to beautifully customized guest baths. The third bath also serves the pool and features a glass-enclosed MrSteam steam shower. Outside, wide steps transition from the elevated interior to an expansive screened outdoor living area where the saltwater pool appears visually connected to Hart Lake beyond. A large covered lanai with travertine flooring offers room for dining and lounging, while generous deck space provides plenty of room for entertaining and enjoying the Florida sunshine. Hart Lake offers opportunities for fishing, boating and enjoying the natural waterfront setting. Additional features include double-pane windows, insulated sliding doors, central vacuum, irrigation well, 2019 roof, 2020 A/C and a pool enclosure refurbished in 2024 with new screening, doors and screws. All this and centrally located between Tampa and Orlando, approximately 10 minutes from shopping, dining and medical facilities, and within walking distance of Chain of Lakes Elementary.

644 Hart Lake Drive, Winter Haven

$144,900
2 Beds 2 Baths Lakeridge Condo SubDv. 33881 Zip Code
**LARGE 2 BEDROOM - 2 BATH CONDO - NEW LISTING IN CENTRAL FLORIDA**- AGE 55+, GATED COMMUNITY (however, a slightly younger age may be approved). This up-to-date condo provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Florida. NEW ENERGY-EFFICIENT WINDOWS THROUGHOUT. The monthly fee INCLUDES: water, sewer, trash, fiber optic cable package with Choice HD, digital video recorder & fiber optic internet w/ 1 gig speed, & use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated secured entrances, covered assigned parking space, social events & activities. This well-appointed, move-in-ready condo has a large, bright kitchen w/ lots of cabinets, a tile backsplash, flush-mount LED ceiling lighting, plenty of counter space, all appliances & a pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional FL/bonus area & storage closet. The 16' x 14 ' primary bedroom easily accommodates a king-size bed & has a walk-in closet with a decorative barn door. The beautiful remodeled primary bathroom has an extra-wide door for easy direct access & includes a walk-in shower with a large format designer wall tile, & a comfort-height vanity with a vessel sink. The 2nd bedroom is convenient to the hall bath, which has a tub/shower combination & comfort-height vanity. The WASHER & DRYER are included in the sale. The Flooring throughout is either wood-look luxury vinyl or tile, NO CARPETING. Custom window shades are in place and are included in the sale. An extra assigned storage bin is located on the same floor. Enjoy beautiful views of Spring Lake and the evening sunsets from most rooms. Shopping, medical, hospital, places of worship, groceries, restaurants & bus line are very close by. COVERED ASSIGNED PARKING SPACE. SharePoint electric car charger on site for owners! Measurements are approximate. Information is believed to be accurate but not guaranteed. NON-SMOKING COMPLEX THAT IS WELL MAINTAINED & MANAGED. FURNITURE IS NEGOTIABLE. Make this your full-time or winter home!

1776 6th Street Nw Unit 308, Winter Haven

$119,000
2 Beds 2 Baths Lakeridge Condo SubDv. 33881 Zip Code
Virtually Staged. Virtually staged bedroom. CENTRAL FLORIDA LAKE VIEW CONDO- THIS IS THE ONLY GATED 55+ CONDOMINIUM COMPLEX IN WINTER HAVEN. (Slightly younger buyer could possibly get approved.) NEW ENERGY-EFFICIENT WINDOWS IN THIS IMMACULATE, MOVE-IN READY 2 BEDROOM 2 BATH CONDO. WATER HEATER is 2025 & CENTRAL AIR CONDITIONER is a 2020. The kitchen is larger than most condo kitchens & the unit has a total of 1,347 sq. ft. of living area. MONTHLY FEE INCLUDES-WATER, SEWER, CABLE, FIBER OPTIC INTERNET, TRASH REMOVAL, CONDO RESERVES & use of recreational facilities- HEATED POOL, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. All appliances & washer/dryer are included. The 26'x14' great room adjoins the additional FL/bonus room with large storage closet. The 16X14 foot master bedroom easily accommodates a king-size bed & has a walk-in closet & en-suite bathroom with walk-in shower. The 2nd bedroom includes a space-saving drop-down Murphy bed. The 2nd bathroom has a tub/shower combination. The linen closet is near the washer & dryer for convenience. Lakeridge is close to shopping, places of worship, groceries, restaurants, medical offices & hospital. Extra assigned storage on the same floor. Social activities available, if you wish to participate. Lakeridge is well-maintained, well-managed & passed inspections & studies with flying colors. Electric car charger on site for owners use. YOU ONLY HAVE TO PAY FOR YOUR ELECTRICITY HERE, AS EVERYTHING ELSE IS INCLUDED IN THE MONTHLY FEE. ONE SMALL PET MAY BE APPROVED. NON SMOKING PROPERTY. Quick Closing is available. Information believed to be accurate but not guaranteed. Measurements are approximate.

1776 6th Street Nw Unit 409, Winter Haven

$1,399,900
4 Beds 3 Baths Magnolia Shores SubDv. 33881 Zip Code
Welcome to your own private lakefront retreat on 1.23 acres along Lake Hamilton with NO HOA! This stunning 4-bedroom, 3-bath home offers an exceptional combination of luxury, entertaining space, and the ultimate Florida waterfront lifestyle. Bring your boat and jet skis and enjoy the convenience of a private dock featuring an electric covered boat lift and built-in fishing bench. The outdoor living space is truly spectacular! Step through the French doors to a sparkling saltwater PebbleTec pool featuring iridescent tile, fiber-optic lighting, a swim-up bar, fountains, and a roof-line waterfall. The propane-heated pool is surrounded by an expansive travertine deck, while the nearby gas fire pit with custom-cushioned seating creates the perfect setting for evening gatherings. Propane-connected tiki torches add a tropical ambiance, and a hidden sump pump provides worry-free drainage after storms. Entertaining is effortless with the outdoor kitchen, complete with a new grill and refrigerated drawers. The fenced backyard extends halfway to the lake, providing plenty of room for pets to play. Professional Florida-native landscaping, enhances the lush, resort-like setting. Inside, the beautifully designed chef's kitchen features quartz countertops, a copper farmhouse sink, paneled refrigerator, trash compactor, and spacious butler's pantry with a full-size refrigerator and abundant storage. The open floor plan includes a dedicated buffet area with dual wine refrigerators adjacent to the dining space—perfect for hosting family and friends. Nine-foot ceilings, crown molding, porcelain tile, shiplap accents, custom lighting, and a central vacuum system add comfort and sophistication throughout. The luxurious primary suite offers direct access to the pool deck, with a convenient open-air shower just outside. The ensuite features dual vanities and a walk-in shower with dual shower heads. The expansive walk-in closet includes a center island, custom shelving, heated towel rack, and an extra-large Liberty Safe. The home underwent a complete rebuild in 2017, so all features are 2017 or newer. Recent improvements include a new roof (2025), new pool pump (2025), a new 12x24 storage shed (2025) and new irrigation system (2025). The irrigation water comes from the lake so it doesn’t affect your water bill. Additional features include a split-bedroom floor plan, with two guest bedrooms sharing a Jack-and-Jill bath; hurricane shutters; a whole-home Generac generator; and TVs in every room, including the back porch. The spacious 3-car garage features tiled flooring, storage, a workshop, and an industrial ice maker. A pavered circular driveway provides ample parking, plus an additional parking pad with room for an RV. From the custom interior and exterior lighting to the custom painting, bamboo chair rail, and travertine exterior accents, every detail has been thoughtfully designed. The home is also pre-wired for ADT security at the front and rear doors and garage service door. Boating, fishing, entertaining, relaxing, and resort-style living—all in one exceptional Lake Hamilton property with no HOA!

3640 Crump Road, Winter Haven

$430,000
3 Beds 2 Baths Overlook Estates SubDv. 33884 Zip Code
This property went under contract fast and it's back on the market, no fault of the owner. If you missed it the first time, here's your second chance! Welcome to the beautiful neighborhood of Overlook Estates. This 3 bedroom 2 bath + bonus room is waiting for its new owner/s to make it their own. This home is completely vacant which makes it that much easier to envision your own life here. When you first arrive you will notice the beautiful curb appeal this home offers. Upon entering you will be greeted by the stunning entrance. This home is bright and spacious with high ceilings and beautiful wood beams giving it character right off the bat. The kitchen was completely remodeled in 2022. It has floor to ceiling cabinets giving you plenty of space for storage. Use the large island with a built in cook top or move it over to a more formal dining room. Either way this home is the perfect place for entertaining. You can access the lanai/salt water pool from the primary bedroom, kitchen, living room, and even the full guest bath. The open floor plan allows for friends and family to gather while still having plenty of space to spread out. The primary bedroom with ensuite bath and walk in closet as well as that access to the lanai. The primary bathroom has a walk in shower, garden tub, dual vanity and also includes a walk in closet as well as a linen closet. The two additional bedrooms as well as a full bath are located on the opposite side of the house. A fourth room allows for the perfect office space or even a room to host your guests. This home has been wonderfully updated while still holding onto its charm and character. Schedule your showing today!

280 Santa Rosa Drive, Winter Haven

$880,000
2 Beds 3 Baths Lake Eloise Sub SubDv. 33884 Zip Code
Major Price Reduction .....Welcome to an exceptional and truly distinctive lakefront estate with a private pool, defined by architectural artistry, refined character, and timeless Spanish-Mediterranean elegance. This 2-bedroom, 3-bath residence offers more than 3,700 square feet under roof, providing expansive, thoughtfully designed interiors ideal for both entertaining and serene everyday living. From the moment you enter, you are welcomed by an atmosphere of bespoke craftsmanship and enduring design. Exquisite brick archways, rich warm wood detailing, and three elegant wood-burning fireplaces establish a setting that is both inviting and unmistakably unique. The kitchen continues this elevated architectural story, showcasing custom extensive cabinetry, stone countertops, premium stainless steel appliances, and a dramatic brick-arched passage that serves as a striking focal point. Thoughtfully designed to capture the essence of the Florida lifestyle, the home opens to a private resort-style swimming pool set against a peaceful lakefront backdrop, creating an extraordinary environment for relaxation, refined entertaining, and sweeping waterfront views. Seamless indoor-outdoor transitions enhance the sense of openness throughout, making the residence equally suited as a distinguished full-time home or an exclusive private lakefront retreat. With its authentic Spanish-Mediterranean influence, handcrafted brick detailing, multiple fireplaces, resort-style pool, and premier waterfront location, a rare opportunity to own a residence of true individuality and lasting appeal—one that cannot be replicated. Schedule your private showing and experience the elegance and exclusivity of this remarkable lakefront offering.

1019 W Lake Eloise Terrace, Winter Haven

$299,000
3 Beds 2 Baths Saxon Myers Rep Ph 2 SubDv. 33881 Zip Code
Affordable pool home with NO HOA in the heart of Winter Haven! Welcome to 133 Rebecca Drive NE, a move-in-ready 3 bedroom, 2 bath home offering a private screened saltwater pool, important updates, comfortable living spaces, and an impressive combination of features and value. If you've been searching for an affordable Central Florida home where you can enjoy the Florida pool lifestyle right in your own backyard, this one deserves a closer look. Inside, the spacious main living area features attractive porcelain tile flooring, a vaulted ceiling, and a gas fireplace, creating a comfortable gathering space for everyday living and entertaining. The adjoining dining area provides direct access to the pool and outdoor living area, while the kitchen features clean white cabinetry, beautiful granite countertops, plenty of storage, and a full suite of included appliances. The desirable split-bedroom layout includes two comfortably sized guest bedrooms and a spacious primary suite with an en-suite bath and generously sized walk-in closet. Both bathrooms have been updated, including a beautifully renovated primary bath with a custom walk-in shower. Step outside and imagine weekends filled with pool time, grilling on the back deck, entertaining friends and family, and enjoying the Florida sunshine. The large screened outdoor living area features a private saltwater pool, plenty of deck space for lounging, dining, and grilling, plus a covered area where you can relax in the shade. Start the morning with coffee by the pool, spend a sunny afternoon in the water, then fire up the grill for dinner and enjoy a warm Florida evening at home. This is the kind of outdoor space that makes it easy to enjoy everything the Florida lifestyle is all about. Beyond the pool enclosure, the fully fenced backyard provides additional usable yard space with plenty of potential for landscaping, a vegetable garden, or your own collection of Florida fruit trees. An included storage shed provides convenient space for lawn and gardening equipment while keeping the two-car garage free for vehicles and additional storage. Major improvements include a NEW A/C system in 2025, all new double-pane windows and sliding glass door in 2021, a 2017 roof, newer front door, rain gutters and low utility bills. Best of all, there is NO HOA! Located in the heart of Winter Haven, you're convenient to downtown Winter Haven, Polk State College, shopping, dining, medical facilities, and recreation. Winter Haven's central location between Tampa and Orlando also puts theme parks, international airports, beaches, professional sports, and some of Central Florida's best entertainment within reach.

133 Rebecca Drive Ne, Winter Haven

$144,000
2 Beds 2 Baths Wellington Pt 01 Bldgs 01 02 & Wellington Pt 02 B SubDv. 33880 Zip Code
Virtually Staged. Completely remodeled 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

$749,000
3 Beds 4 Baths Cypresswood Palma Ceia SubDv. 33884 Zip Code
Meticulously maintained and beautifully remodeled, this exceptional Palma Ceia residence in Cypresswood offers pond frontage, three private en-suite bedrooms, a dedicated office, a heated swimming pool, and incredible golf course views. The pavered driveway and walkways, manicured flower gardens, and a 2022 black metal roof set the stage for the impressive interior. Elevated ceilings, crown molding, waterproof Pergo flooring, stone counters, and plantation shutters are just a few of the home’s stunning features. At the heart of the home is a spacious great room featuring a natural gas fireplace with shiplap façade. Triple sliding glass doors, with new screens, create a seamless indoor-outdoor flow to the covered lanai and pool area while showcasing the outdoor views. The updated kitchen features quartz counters, an island with a prep sink and filtered water, a Kohler workstation sink, breakfast bar, stainless appliances, double ovens, gas range, Bosch dishwasher, and a spacious dinette overlooking the pool. A private office provides the perfect setting for working from home. Designed to give everyone their own space, the home offers three bedrooms with en-suite bathrooms. The primary suite includes pool access, a tray ceiling, two walk-in closets with built-in shelving, and a gorgeous remodeled bathroom featuring a six-foot freestanding soaking tub, glass-enclosed walk-in shower, dual vanities, and a water closet. The second bedroom includes an equally impressive en-suite bath with custom tile flooring, a granite counter, tub, and separate walk-in shower. Located at the rear of the home, the third en-suite bedroom is ideal for visiting guests and can be closed off with a pocket door for added privacy. Its bathroom offers a granite counter with dual sinks, a tub and shower combo, and a linen closet. An additional linen closet is located in the guest-wing hallway. The interior laundry room provides a closet pantry, storage closet, and convenient half bathroom. Florida living takes center stage outdoors with a screen-enclosed heated pool, expansive covered lanai, and a separate screened area for sunning. The peaceful setting overlooks the pond and third hole of the golf course, where a variety of birds and wildlife can be enjoyed daily. Meticulously designed gardens, window planter boxes and a pavered sitting area near the pond—ideal for a fire pit—complete this private outdoor oasis. The two-car garage features an epoxy floor, utility sink, storage closets, and overhead storage racks. Additional improvements and features include a 2026 installed gas water heater, a 26-gauge standing seam metal roof (2022) with a 40-year warranty, dual-zone air conditioning (2020), irrigation on separate meter, plantation shutters throughout, remote-controlled lanai lighting, pool safety fence, Ring cameras, rain gutters, and more. Located within the guarded Cypresswood community, this remarkable home combines thoughtful updates, exceptional care, abundant privacy, and a truly beautiful golf course and waterfront setting. Cypresswood Golf & Country Club features an 18-hole championship golf course, driving range, pro shop, jr. olympic pool, tennis & pickleball courts, an event venue, a sports pub and more. Located just minutes from shopping, medical facilities and downtown Winter Haven. Centrally located between Tampa and Orlando with easy commutes to airports and beaches. Come see what this magnificent home and community in Central FL has to offer!

4040 Palma Ceia Circle, Winter Haven

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