Winter Haven Homes with Private Pool type

Winter Haven Homes with Private Pool type

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County, renowned for its stunning lakes, vibrant community, and a rich tapestry of recreational opportunities. Often referred to as the "Chain of Lakes," Winter Haven boasts over 50 lakes, making it a paradise for water enthusiasts and nature lovers alike. Whether you’re looking to enjoy a leisurely day on the water, explore the beautiful parks, or indulge in the local dining scene, Winter Haven has something for everyone.

One of the standout features of this delightful city is its array of homes with private pools. Imagine stepping into your backyard oasis, where you can unwind and soak up the Florida sun in your very own pool. These homes offer not just a place to live, but a lifestyle filled with relaxation and enjoyment. Picture hosting summer barbecues with friends and family, splashing around in the pool, or simply enjoying a quiet evening under the stars next to your shimmering water feature.

With a variety of architectural styles and price points, Winter Haven’s homes with private pools cater to diverse tastes and budgets. From cozy single-family homes to luxurious estates, you’ll find the perfect sanctuary that complements your lifestyle. The city’s welcoming atmosphere, combined with its stunning landscapes and community spirit, makes it an ideal place to call home.

Explore Winter Haven today and discover the perfect home with a private pool that allows you to embrace the Florida lifestyle to the fullest!

Newest Winter Haven Homes with Private Pool type

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

5 Beds ⋅ 3 Baths ⋅ Hidden Creek SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to this stunning 5-bedroom, 3-bathroom pool residence located in the highly sought-after, gated Hidden Creek community of Winter Haven. Perfectly positioned just minutes from the Polk Parkway and LEGOLAND Florida Resort, and conveniently situated between Lakeland and Winter Haven, this home offers an ideal blend of comfort and unbeatable accessibility. Inside, you will find soaring ceilings, a smart split-floor plan, a dedicated office or bonus room, a large den, and a 2-car garage that delivers ultimate flexibility for modern living, complemented by brand-new carpet replaced in 2025. The beautiful kitchen features granite countertops and a convenient walk-in pantry, while the primary suite serves as a true private retreat featuring a deep soaking tub, separate walk-in shower, dual sinks, a vanity, and a massive walk-in closet. Situated on a generous 0.35-acre lot, the property offers rare privacy, as the home backs up to a preserve with peaceful natural views. The absolute crown jewel of the home is the expansive, screen-enclosed lanai and sparkling saltwater pool with a heated spa, creating an exceptional resort-style outdoor living space masterfully designed for effortless entertaining, relaxing weekend lounging, or simply enjoying the tranquil Florida breeze in total privacy. Schedule your private showing today and discover a rare gem in Winter Haven!

1020 Lena Run Court, Winter Haven

4 Beds ⋅ 3 Baths ⋅ Sun Rdg Village East SubDv. ⋅ 33880 Zip Code

Welcome to this well-maintained Winter Haven pool home, offering over 2,400 sqft of living space on a corner lot. This 4-bedroom, 2.5-bathroom home includes a 3-car garage, wood floors in the kitchen, foyer, and dining room, and spacious rooms with generous closet space. Upstairs, a cozy loft provides the perfect spot to unwind. Step outside to a screened and in-ground pool and spa, surrounded by a large, fenced backyard—ideal for privacy and outdoor enjoyment. The property also includes a rear parking pad with its own side entry, perfect for storing a boat or trailer. If you're looking for an affordable, move-in ready pool home with room to grow—or a strong investment opportunity—this is one you don’t want to miss. The seller is motivated, so schedule your showing today.

5009 Strada Drive, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Acreage SubDv. ⋅ 33880 Zip Code

Welcome home to peaceful country living! Nestled on nearly 2 acres of beautiful pature land and no HOA. This charming 3-bedroom,2-bath farmhouse-style home offers the perfect blend of rustic character and modern comfort. The roof was installed about 5 years ago and the A/C was installed about 4 years ago. The windows have all been updated. Gather with family and friends in the inviting living room, where a cozy fireplace creates the perfect place to relax on cool evenings. The kitchen has updated appliances, farm-style sink and a large pantry. A versatile bonus room provides endless possibilities as a home office, game room, or guest retreat. Need a dedicated workspace? The property also features a separate office, offering privacy and felxibility for remote work, a home business or a creative studio. Step outside and embrace the country lifestyle. Spend warm Florida days cooling off in the above-ground pool with a 16x20 deck. Enjoy the wide-open views, or bring your horses, live-stock or gardening on the spacious pasture. The 2-car garage provides plenty of room for vehicles, tools and outdoor equipment. There is also a 18X18 storage shed with a air-conditioner. Whether you're sipping coffee on the porch at sunrise or watching th sunset over your own piece of the countryside, this property offers the peaceful farmhouse lifestyle you've dreaming of--all while providing the space and freedom to make it your own.

1755 Beth Lane, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Waterside Village SubDv. ⋅ 33880 Zip Code

Virtually Staged. Welcome to Waterside Village, a community of just 48 homes that offers a peaceful setting while keeping you close to everything Winter Haven has. This move-in ready 3-bedroom, 2-bath home offers an open floor plan, spacious kitchen with a large walk-in pantry, and a backyard designed for entertaining. Enjoy the screened-in lanai, pool deck, and above-ground pool with a recently replaced liner, all within a fully fenced yard complete with a storage shed. Conveniently located near shopping, restaurants, grocery stores, and LEGOLAND, you'll love having everything you need just minutes away.

144 Waterside Circle, Winter Haven

5 Beds ⋅ 4 Baths ⋅ Orleans SubDv. ⋅ 33884 Zip Code

Welcome to 3205 La Salle Street, where resort-style outdoor living, an exceptional floor plan, and modern elegance come together in the highly sought-after Orleans community. Built in 2023 by Ryan Homes, this beautifully upgraded Lynn Haven model offers 5 bedrooms, 4 full bathrooms, and 3,021 square feet of thoughtfully designed living space that perfectly balances everyday comfort with effortless entertaining. Situated on a beautifully landscaped corner lot featuring a paver driveway, lush tropical landscaping, and extra green space beyond the backyard, this property offers a setting rarely found in newer construction. The fully privacy-fenced backyard is your own private retreat, complete with a newly added saltwater pool, expansive covered lanai, and additional green space beyond the pool that enhances both privacy and the feeling of having an even larger backyard—perfect for entertaining, pets, or simply enjoying peaceful Florida evenings. Nestled between Lake Eloise and Lake Winterset within the intimate Orleans community of just 42 homesites, residents enjoy low HOA dues, no CDD fees, and select community canal access to Lake Eloise while being less than two miles from Publix, Starbucks, LEGOLAND, shopping, dining, and everyday conveniences. Inside, abundant natural light, soaring ceilings, and an open-concept design create a welcoming atmosphere from the moment you enter. A spacious flex room off the foyer offers endless possibilities as a formal dining room, home office, playroom, or additional living space. The expansive great room seamlessly connects to the chef-inspired kitchen, complete with quartz countertops, stainless steel appliances, a large center island, abundant cabinetry, and a walk-in pantry, creating the ideal gathering space for family and friends. One of this home's standout features is its exceptionally functional floor plan. The first-floor bedroom and adjacent full bathroom provide the perfect private space for guests or multigenerational living. Upstairs, the luxurious primary suite serves as a true retreat with two walk-in closets and a spa-inspired ensuite featuring dual vanities, a walk-in shower with a Roman-style seat, and a private water closet. A secondary upstairs bedroom enjoys the privacy of its own ensuite bathroom, while two additional generously sized bedrooms share a well-appointed guest bath. Completing the second level is an oversized loft, offering endless flexibility as a media room, game room, second family room, or homework space, along with a conveniently located upstairs laundry room. Better than new, this home has already been enhanced with thousands of dollars in premium upgrades, including a saltwater pool, irrigation well, generator-ready wiring, EV charging system wiring, an Ecobee smart thermostat, WiFi-enabled garage door opener, and energy-efficient construction throughout. The roof, HVAC system, water heater, and major kitchen appliances are all approximately two to three years old, providing added peace of mind for years to come. Offering an exceptional combination of luxury, functionality, outdoor living, and one of Winter Haven's most convenient locations, 3205 La Salle Street is truly better than new and ready to welcome its next owners.

3205 La Salle Street, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Deer Lake Terrace Sub SubDv. ⋅ 33881 Zip Code

Welcome to this charming 3-Bedroom, 2-bath home in the heart of Winter Haven! This property offers comfortable living with a functional layout, a welcoming front porch, and a private in-ground pool that's perfect for relaxing or entertaining family and friends. Fully fenced yard. Conveniently located near shopping, dining, schools, and major roadways. DONT miss this opportunity - schedule your showing today!

3334 Avenue J Nw, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Lesnick Park SubDv. ⋅ 33880 Zip Code

Imagine the possibilities! Offering approximately 1,890 square feet of finished living area along with an additional 1,622 square feet of permitted functional space, the property provides approximately 3,512 total square feet, under roof, of combined building area. The expansive open living areas provide endless possibilities—whether you're envisioning an oversized primary suite, game room, home office, music studio, fitness space, or the ultimate man cave or she shed. Unlike many homes with fixed layouts, this property's generous footprint invites you to customize the space to fit your lifestyle. Step outside to enjoy your own private retreat featuring a solar-heated 20' x 40' pool, beautiful paver pool deck, spacious fenced backyard, circular driveway, and no HOA—all in an established neighborhood surrounded by beautiful lakefront homes. A unique 3-car garage configuration provides exceptional flexibility. The oversized 23' x 25' two-car garage includes an adjoining workshop or storage area, while the separate single-car garage with a built-in closet sits adjacent to the utility room, making it ideal for hobbies, storage, a home gym, or recreational equipment. If you've been searching for a home with space, versatility, and room to make it your own, this is one you won't want to miss.

906 Avenue M Se, Winter Haven

1 Beds ⋅ 1 Baths ⋅ The Haven SubDv. ⋅ 33881 Zip Code

Historic charm meets downtown convenience at The Haven. This 1-bedroom, 1-bath condo sits on the 3rd floor of one of Winter Haven's most recognizable former hotels — now reimagined as boutique historic condos just steps from downtown, Lake Howard, restaurants, coffee shops, nightlife, parks, and the popular Saturday Farmers Market. The unit blends vintage character with modern updates: tall ceilings, oversized historic windows, and abundant natural light give the space an airy, elevated feel, with partial views of downtown from the 3rd floor. The kitchen has been fully renovated with granite countertops, brand-new stainless steel appliances, and dual pantry/utility closets — smart, functional storage that's genuinely hard to find in a condo. The primary bedroom comfortably fits a king-sized bed and includes a walk-in closet, while the bathroom has been refreshed with granite counters, a tiled tub surround, and a classic tub/shower combo. Building amenities add real everyday value: secure key-fob entry, elevator access, assigned parking, on-site laundry, additional storage rooms, and a beautifully restored historic lobby that reflects the building's original character. Residents also have access to a private courtyard pool, framed by creeping fig walls, palm trees, and lush landscaping — a peaceful spot to relax or work remotely outdoors. Low-maintenance and move-in ready, this unit suits a range of buyers: first-time homeowners, investors, seasonal residents, or anyone looking for an affordable condo with strong rental potential in a walkable downtown setting. Location is where this property really stands out. You're within walking distance of downtown dining, shopping, entertainment, and lakefront paths along Lake Howard. Winter Haven is home to 50 lakes, including the famous Chain of Lakes, putting boating, fishing, water skiing, and sunset views just minutes away. Everyday essentials are equally close — Publix, Walmart, Aldi, TJ Maxx, and local medical facilities are all nearby, and LEGOLAND Florida Resort is a short drive for weekend fun or extra rental appeal. Affordable, updated, and full of character, this condo at The Haven offers a rare combination: historic charm, modern comfort, and a genuinely walkable downtown lifestyle. Units in this building don't come up often — schedule your showing before this one's gone.

235 6th Street Nw Unit 307, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Winterset Gardens SubDv. ⋅ 33884 Zip Code

Virtually Staged. Rarely does a home this unique come to market! Situated on a spacious .30-acre lot directly across the street from beautiful Lake Winterset, this fully renovated 3-bedroom, 2-bath mid-century modern pool home offers incredible character, modern updates, and NO mandatory HOA or CDD. An optional neighborhood HOA of just $100 per year provides access to the community boat ramp, connecting you to the renowned Winter Haven Chain of 22 Lakes, one of Central Florida's premier destinations for boating, fishing, and watersports. Unlike nearly any other Florida home, this property features an impressive 300+ square foot basement, a rare find that offers endless possibilities as a wine cellar, hobby room, workshop, fitness area, or additional storage. The home's distinctive architectural design is complemented by spectacular views of Lake Winterset from the living and dining rooms, where sliding glass doors open to a charming wraparound front porch—the perfect place to enjoy your morning coffee while taking in the peaceful lake scenery. Upstairs, a spacious bonus room provides flexibility as a potential fourth bedroom, media room, home office, or second living area and includes a private balcony overlooking the front of the property and the lake. The beautifully updated kitchen is designed for both everyday living and entertaining with quartz countertops, a center island, pantry, recessed lighting, tile backsplash, reverse osmosis system, garbage disposal, a window overlooking the screened pool, and a premium 2022 Samsung Bespoke appliance suite. The home's thoughtful split layout places all three spacious bedrooms down a private hallway away from the main living spaces. Wood-look tile flooring flows throughout the main living areas, while luxury vinyl plank flooring extends through the bedrooms, bathrooms, and upstairs bonus room. The spacious primary suite features dual vanities and a beautifully remodeled walk-in shower. Additional conveniences include an indoor laundry closet with the washer and dryer included, and a two-car garage. Step outside to your oversized screened, chlorinated pool complete with a diving board and removable safety fence, creating the perfect backyard retreat for entertaining family and friends year-round. Major improvements provide added peace of mind, including a new roof in 2025, a new pool pump and well pump in 2025, new A/C ductwork and attic insulation in 2025, windows replaced in 2019, A/C replaced in 2019, water heater replaced in 2019, and new appliances installed in 2022. Ideally located just a short drive from Disney, Universal, LEGOLAND, and other Central Florida attractions, this one-of-a-kind home combines timeless mid-century modern architecture, extensive modern updates, a rare basement, beautiful lake views, access to the Winter Haven Chain of Lakes, and a lifestyle that is truly hard to find. Don't miss this rare opportunity to own one of the area's most distinctive homes overlooking beautiful Lake Winterset.

6704 Winterset Gardens Road, Winter Haven

3 Beds ⋅ 2 Baths ⋅ Leisure Shores SubDv. ⋅ 33881 Zip Code

Welcome to this beautifully maintained 3-bedroom, 2-bath home offering approximately 1,627 square feet of comfortable living space in the established Leisure Shores community of Winter Haven. Situated on a spacious 0.22-acre lot, this property is packed with features both inside and out. Step inside to an open floor plan with easy-to-maintain laminate flooring throughout, an updated kitchen featuring granite countertops, newer cabinetry, stainless steel appliances, and plenty of space for everyday living and entertaining. Energy-efficient double-pane windows and an updated sliding glass door help enhance comfort throughout the home. The backyard is designed for enjoying Florida living, complete with a screened lanai, an above-ground pool, a large side deck, and a fully fenced yard that’s perfect for relaxing or hosting family and friends. Need extra space? This property offers multiple detached structures, including a spacious air-conditioned shed that’s ideal for a home office, hobby room, gym, studio, or workshop, plus an additional storage shed for tools and equipment. For those with recreational vehicles or extra toys, you’ll appreciate the dedicated RV parking area with electrical hookup, along with a covered carport for everyday parking. Conveniently located near shopping, dining, schools, and everything Winter Haven has to offer, this home combines comfort, versatility, and outdoor living in one exceptional package. Schedule your private showing today!

2021 Oliver Place, Winter Haven

4 Beds ⋅ 2 Baths ⋅ Mandolin SubDv. ⋅ 33884 Zip Code

Welcome to 233 Mandolin Drive, a spacious four-bedroom, two-bath pool home located in the gated Mandolin community of Winter Haven. The single-story layout features an open living area with vaulted ceilings, abundant natural light and durable hard-surface flooring. The kitchen offers granite countertops, rich wood cabinetry, stainless-steel appliances and a breakfast bar overlooking the adjoining dining area. The primary suite provides a comfortable retreat with a generously sized bedroom, walk-in closet and private bath featuring dual sinks, a soaking tub, separate shower and private water closet. Three additional bedrooms and flexibility for guests, a home office or hobby space, while the indoor laundry room adds everyday convenience. Step outside to an inviting backyard designed for enjoying the Florida lifestyle. The expansive paver deck surrounds a sparkling in-ground pool and raised spa, while the covered patio provides a shaded space for dining, relaxing and entertaining. A pool safety fence, fenced yard, solar panels and attached two-car garage complete the home. Conveniently located near LEGOLAND Florida, shopping, dining, medical facilities and major roadways, this home combines comfortable indoor living with an exceptional outdoor retreat. Schedule your private showing today!

233 Mandolin Drive, Winter Haven

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