Winter Haven Homes with Pool Amenities

Winter Haven Homes with Pool Amenities

Welcome to Winter Haven, a charming city located in Polk County, Florida. Known for its beautiful lakes and warm climate, Winter Haven is a popular destination for those seeking a relaxed lifestyle with plenty of outdoor activities.

In Winter Haven, you can enjoy the luxury of having a home with pool amenities. Imagine coming home to your own private oasis where you can unwind, exercise, and entertain friends and family. Whether you're looking to cool off on a hot summer day or simply enjoy the tranquility of the water, having a pool at your home adds a touch of luxury to your everyday life.

With a variety of homes offering pool amenities in Winter Haven, you can find the perfect property to suit your needs and preferences. From cozy bungalows to spacious estates, there's a wide range of options to choose from. Whether you're a first-time homebuyer or looking to upgrade to a larger property, Winter Haven has something for everyone.

So why wait? Explore the real estate market in Winter Haven today and find your dream home with pool amenities. Experience the best of Florida living in this picturesque city surrounded by natural beauty and modern conveniences.

Newest Winter Haven Homes with Pool Amenities

5365 Hogan Lane, Winter Haven
$574,900
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph 01 SubDv. ⋅ 33884 Zip Code
Discover refined Florida living in Lake Ashton, Central Florida’s premier 55+ active-adult community. Perfectly positioned along a tranquil pond with a beautiful nature preserve beyond, this distinguished three-bedroom, two-bath residence with a private den offers exceptional privacy, sophisticated design, and some of the most captivating views along Hogan Lane. Every room along the back of the home showcases a gorgeous view of the pond and surrounding natural beauty. The home’s striking stone-accented façade, bronze-screened entry, and elegant double glass doors create an impressive arrival. Inside, meticulous care and upscale architectural details are evident throughout, including terraced crown molding, coffered ceilings in the living room and primary bedroom, and five solar tubes that fill the interior with abundant natural light. The beautifully appointed kitchen combines elegance and functionality with rich cabinetry, glass-front display cabinets, a built-in wine rack, polished black granite countertops, and a generous walk-in pantry. The serene primary suite serves as a private retreat, complete with its own sitting room, a beautifully detailed coffered ceiling, and gorgeous views. Both bathrooms feature granite countertops and spacious walk-in showers. The home’s most remarkable feature is its expansive outdoor living space. A magnificent 51' x 13' bronze-screened veranda overlooks the sparkling 7½' x 36' bromine pool, peaceful pond, and lush nature preserve. This exceptional setting offers breathtaking sunrise views, abundant wildlife, and an atmosphere of complete serenity—ideal for elegant entertaining or quiet relaxation. A three-year-old roof provide additional peace of mind. Lake Ashton offers a resort-caliber lifestyle with two championship 18-hole golf courses, a 26,000-square-foot clubhouse, a state-of-the-art health and fitness center, theater, bowling alley, pickleball courts, and an impressive collection of recreational and social amenities. This exceptional residence presents a rare opportunity to enjoy refined waterfront living, natural beauty, and the prestige of one of Central Florida’s most sought-after active-adult communities. Schedule your private showing and experience the finest in Lake Ashton living.

5365 Hogan Lane, Winter Haven
3838 Bedford Avenue, Winter Haven
$429,900
3 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to Traditions at Lake Ruby, Winter Haven’s desirable gated 55+ community, where resort-style amenities, beautiful surroundings, & an active lifestyle come together! This beautifully maintained 3-bedroom, 3-bathroom residence offers an exceptional floor plan featuring TWO BEDROOMS FEATURE PRIVATE EN SUITE BATHROOMS, a THREE-CAR GARAGE, AN OFFICE/FLEX SPACE and picturesque views of a tranquil pond and fountain. From the moment you arrive, you’ll appreciate the home’s inviting curb appeal, freshly painted exterior, and attractive paver driveway. Inside, a spacious, thoughtfully designed floor plan welcomes you with freshly painted interiors, recently replaced flooring, and an abundance of natural light. The ROOF was REPLACED IN 2024 and the HVAC SYSTEM was REPLACED IN 2021, offering added peace of mind. One of the home’s most appealing features is its thoughtfully designed split-bedroom floor plan, with all three bedrooms positioned in separate areas of the home for exceptional privacy. The spacious primary suite offers a peaceful retreat with beautiful pond and fountain views, along with sliding glass doors providing direct access to the screened patio. Imagine stepping outside each morning to enjoy your coffee while overlooking the water! The second bedroom features its own private en suite bathroom, making it ideal for overnight guests, while the third bedroom is conveniently located near a full guest bathroom just outside its door. An additional flex room with double-entry doors provides the perfect space for a home office, hobby room, or private sitting area. Designed with both comfortable everyday living and entertaining in mind, the home features a formal living room, formal dining room, and spacious great room. The beautifully appointed kitchen offers granite countertops, a breakfast bar, stainless steel appliances, and an abundance of attractive cabinetry providing generous storage. An adjoining dinette offers a charming setting for casual dining while enjoying the beautiful water views. Perhaps one of the most captivating features of this home is the picturesque pond and fountain that serve as a stunning backdrop from nearly every main living area. Enjoy these peaceful views from the primary suite, formal living room, formal dining room, kitchen, dinette, and screened patio. Sliding glass doors from the great room and primary suite provide convenient access to the screened outdoor living space, creating a seamless connection between indoor comfort and Florida’s beautiful outdoors. The home’s northeast-facing front exposure allows for lovely natural light throughout the day. Beyond the home itself, Traditions at Lake Ruby offers an exceptional resort-style lifestyle! Residents enjoy a beautiful lakefront clubhouse overlooking Lake Ruby, a heated swimming pool and spa, fitness center, aerobics studio, ballroom, billiards room, library, arts and crafts room, and inviting spaces for community gatherings. Outdoor amenities include tennis, pickleball, bocce ball, and shuffleboard courts, scenic walking paths, a dog park, & access to Lake Ruby. An active social calendar filled with clubs, activities, and community events provides wonderful opportunities to enjoy the lifestyle this neighborhood is known for. Conveniently situated near shopping, restaurants, medical facilities, and everything Winter Haven has to offer, this community provides the perfect balance of peaceful surroundings & everyday convenience.

3838 Bedford Avenue, Winter Haven
1550 11th Street Ne Unit H4, Winter Haven
$100,000
2 Beds ⋅ 2 Baths ⋅ Lake Buckeye Condo SubDv. ⋅ 33881 Zip Code
Virtually Staged. LAKE BUCKEYE CONDO WITH A LAKEFRONT COMMUNITY POOL AND FISHING DOCK. Screened balcony, washer and dryer included, luxury vinyl plank floors and a building roof replaced in 2021. This 2-bedroom, 2-bath end unit offers 1,148 square feet of living space with a split-bedroom floor plan and stainless steel appliances. The open living and dining area has big windows and a ceiling fan, and sliding glass doors lead out to the covered, screened balcony. The galley kitchen has wood cabinets plus a stainless refrigerator, range and dishwasher. A laundry room past the kitchen holds the washer and dryer. The primary suite has a walk-in closet and its own bath with a walk-in shower, while the second bedroom sits on the opposite side of the home next to a full bath with a tub. Outside, the community offers a lakefront pool with a sun deck, a fishing dock, and assigned plus guest parking. The HOA covers exterior maintenance, grounds and the pool, so your weekends stay yours. Polk State College is about a mile away, downtown Winter Haven's restaurants and shops are about 2 miles, and LEGOLAND Florida Resort is less than 7 miles. Picture coffee on the balcony in the morning and evenings at the dock watching the light change over the lake. Buyer to verify all information, including HOA fees and pet and leasing rules.

1550 11th Street Ne Unit H4, Winter Haven
3205 Matthew Place, Winter Haven
$215,390
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This upscale new Summit two-story townhome provides ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3205 Matthew Place, Winter Haven
6485 Peppertree Path Ne, Winter Haven
$159,000
2 Beds ⋅ 2 Baths ⋅ Brookhaven Village First Add SubDv. ⋅ 33881 Zip Code
Enjoy affordable retirement living in this welcoming 55+ community where YOU OWN THE LAND! This spacious 2-bedroom, 2-bath home offers 1,566 square feet of living space with a desirable split-bedroom floor plan. The primary suite features a private bathroom with dual vanities and a walk-in shower. Additional highlights include an inside laundry room, enclosed 12’ x 14’ Florida room, carport with a workshop, Brick Skirting, and a NEW ROOF in 2023! Offered Partially FURNISHED. Carpets Freshly Cleaned. With an incredibly low HOA fee of just $34 per month, residents enjoy access to the community clubhouse, swimming pool, and shuffleboard courts. The community also offers a fenced storage area for RVs, boats, and trailers. Conveniently located near Highway 27, shopping, restaurants, and medical facilities, with Disney attractions approximately an hour away and Florida's beautiful East and West Coast beaches within approximately 1.5–2 hours. Whether you're looking for a seasonal retreat or a full-time Florida residence, this home offers comfort, convenience, and an affordable lifestyle!

6485 Peppertree Path Ne, Winter Haven
3391 Livingston Way, Winter Haven
$215,000
2 Beds ⋅ 2 Baths ⋅ Traditions Ph 1 SubDv. ⋅ 33884 Zip Code
Welcome to your Florida retreat! This beautifully maintained 2-bedroom, 2-bathroom FURNISHED home offers low-maintenance living in a gated Winter Haven community filled with resort-style amenities! Whether you're searching for a full-time residence or seasonal getaway, this home is ready for you to move right in! Enjoy peace of mind with numerous updates, including a roof approximately 5 years old, NEW A/C February 2026, NEW range 2026, refrigerator approximately 2 years old, microwave 1 year old, and carpeting approximately 5 years old. Spend less time maintaining and more time enjoying Florida! The HOA takes care of exterior painting and front landscaping. Additional included services feature cable TV, internet, grounds maintenance, private roads, community pool, recreational facilities, management, and common area taxes. LOVE THE WATER? Enjoy lake access, community boat ramp, boat slips, dock, fishing, and beautiful waterfront areas! Cruise the neighborhood in your golf cart or enjoy the walking paths and sidewalks. Community amenities include a clubhouse, fitness center, swimming pool, tennis courts, dog park, parks, and gated entry! Conveniently located near shopping, dining, medical facilities, and Central Florida attractions. EXCITING PROPERTY TAX NEWS! With Florida's newly approved Amendment 3, establishing Florida residency by December 31, 2026, may qualify eligible homeowners for expanded homestead tax benefits without the new-resident waiting period! Residency and exemption requirements apply. Why spend another winter wishing you were in Florida? This furnished home offers comfort, convenience, and the Florida lifestyle you've been dreaming of! Schedule your private showing TODAY! Buyer approval and community restrictions apply. Verify HOA benefits, amenity availability, and tax eligibility.

3391 Livingston Way, Winter Haven
807 Eagle Pond Drive Unit 807, Winter Haven
$159,000
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Enjoy peaceful pond views from this beautifully situated second story condo in Winter Haven! This inviting unit features wood-look tile flooring, granite kitchen countertops, indoor laundry, and a 2017 HVAC system. Step outside and take in relaxing water views, or enjoy the community amenities that include: A swimming pool, 24-hour guarded security, fitness center, and tennis courts. Centrally located in the heart of Florida, between Tampa and Orlando, this condo offers convenient access to shopping, dining, entertainment, and major attractions. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this condo offers comfortable living and convenient community amenities in a desirable Winter Haven location!

807 Eagle Pond Drive Unit 807, Winter Haven
3099 Captain Jax Way, Winter Haven
$205,090
3 Beds ⋅ 3 Baths ⋅ Serenity At Peace Creek Th SubDv. ⋅ 33884 Zip Code
Under Construction. This new two-story townhome offers ample space to live and grow with a total of three bedrooms. The first level features a spacious and flexible open-concept layout shared between the kitchen, dining room and family room, maximizing the interior living space. Two secondary bedrooms and a lavish owner’s suite featuring a full bathroom comprise the second floor. Serenity at Peace Creek Reserve is a masterplan community of new townhomes with a beautiful natural creek. Winter Haven is the chain of lakes city, with over 26 linked together by a canal. There are lots of shops, restaurants, and bike paths. Peace Creek Reserve is what you have been looking for. A safe small town feel with convenience, the perfect place to raise a family.

3099 Captain Jax Way, Winter Haven
2097 Whispering Trails Boulevard, Winter Haven
$410,000
4 Beds ⋅ 3 Baths ⋅ Whispering Trails Ph 01 SubDv. ⋅ 33884 Zip Code
Discover your ideal Florida retreat in this beautifully maintained, gated Winter Haven neighborhood! Perfectly situated close to shopping centers for effortless errands, just 10 minutes from the exciting attractions of Legoland, and less than an hour from the Walt Disney World. Tampa is also within a convenient 1-hour drive, offering additional entertainment and amenities. This charming home comes move-in ready, including all essential appliances such as a range, refrigerator, microwave, garbage disposal. The secure, gated community offers peace of mind and added privacy, making it an ideal place to call home. Whether you're looking for a primary residence, vacation home, or investment property, this residence offers comfort, convenience, and easy access to some of Florida’s top attractions. Don’t miss your chance to own this fantastic 4 bed 3 full bath pool home in the fast-growing City of Winter Haven!

2097 Whispering Trails Boulevard, Winter Haven
4157 Rolling Oaks Drive, Winter Haven
$118,000
2 Beds ⋅ 2 Baths ⋅ Oakwood Estates SubDv. ⋅ 33880 Zip Code
Welcome to this well-maintained 2-bedroom, 2-bath home located in the desirable community of Oakwood Estates in Winter Haven. This home offers a peaceful, well-kept neighborhood. The roof is approximately 5 years old, offering added value and peace of mind. No lot rent—ownership includes the land, with only a low monthly HOA fee. Oakwood Estates is a gated 55+ community offering resort-style amenities including clubhouses, heated pools, fitness center, shuffleboard, tennis courts, and a full calendar of activities. Conveniently located near shopping, dining, medical facilities, and major roadways. Schedule your private showing today and experience easy living in this vibrant community.

4157 Rolling Oaks Drive, Winter Haven
3403 Julius Estates Boulevard, Winter Haven
$349,000
4 Beds ⋅ 3 Baths ⋅ Lake Smart Estates SubDv. ⋅ 33881 Zip Code
Enjoy comfortable living in this spacious home offering just under 2,400 square feet of living space in a convenient North Winter Haven location. Situated directly across from the community swimming pool, newly replaced AC this home offers easy access to neighborhood amenities, including a fishing pier. The backyard features a peaceful view overlooking a small pond, creating a relaxing setting to enjoy your outdoor space. The thoughtfully designed floor plan features an open and inviting downstairs living area with the living room, kitchen, and family room, while all bedrooms are conveniently located upstairs, providing added privacy. The kitchen is appointed with granite countertops, and the home also features a two-car garage and the added convenience of an upstairs laundry area with washer and dryer included. With quick access to Highway 27, getting around Winter Haven and the surrounding areas is a breeze. Enjoy the combination of spacious living, community amenities, peaceful water views, and a convenient location in this inviting home!

3403 Julius Estates Boulevard, Winter Haven
2332 Salzburg Loop, Winter Haven
$244,900
2 Beds ⋅ 2 Baths ⋅ Vienna Square SubDv. ⋅ 33884 Zip Code
PICTURE PERFECT! Imagine settling into this ideal low-maintenance home tailored for comfort and easy living. This 2 bedroom, 2 bathproperty is clean, move-in ready, and designed to let you spend less time on chores and more time enjoying your time.Highlights include: - Spacious Eat-In Kitchen: Features lovely granite countertops, a travertine backsplash, and an attractive black appliance package. - Bright & Open Layout: An easy floor plan with modern, low-maintenance luxury vinyl plank floors throughout the main living areasand bedrooms, plus an extra-large laundry room. - Private Outdoor Space: Enjoy a screened patio complete with slate tile floors, a ceiling fan, and roller shades for quiet privacy. - Peace of Mind: Relax knowing key big-ticket items—the roof, AC, and hot water tank—were all updated in 2025 and 2026.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. ViennaSquare is a beautifully maintained, amenity-rich community designed for easy living. Monthly fees includes lawn mowing, and a Spectrum Internet/TV package. Residents enjoy access to a communitypool, fitness center, billiards, movie theater, tennis and pickleball courts, and an active social calendar. Step inside, fall in love. Make it yours!

2332 Salzburg Loop, Winter Haven
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