Winter Haven Homes with Pool Amenities

Winter Haven Homes with Pool Amenities

Welcome to Winter Haven, Florida—a charming city nestled in the heart of Polk County, known for its stunning lakes, vibrant community, and a plethora of recreational activities. With its picturesque landscapes and warm, sunny climate, Winter Haven is the perfect place to call home. The city is renowned for its beautiful chain of lakes, which offers residents endless opportunities for boating, fishing, and enjoying the great outdoors.

When it comes to real estate, Winter Haven boasts an impressive selection of homes, many of which come with delightful pool amenities. Imagine coming home after a long day to your own private oasis, where you can relax by the poolside, host summer barbecues, or enjoy a refreshing swim under the Florida sun. Homes with pool amenities in Winter Haven are designed for both comfort and entertainment, providing the perfect backdrop for creating lasting memories with family and friends.

In addition to its beautiful homes, Winter Haven is home to a thriving community with a rich cultural heritage. Residents enjoy access to excellent schools, parks, and a variety of shopping and dining options. With its friendly atmosphere and strong sense of community, Winter Haven is an ideal place for families, retirees, and everyone in between.

Whether you’re looking for a cozy single-family home or a spacious property with a stunning pool, Winter Haven has something to offer everyone. Discover the charm of this lovely city and make it your home today!

Newest Winter Haven Homes with Pool Amenities

$220,240
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.

3067 Captain Jax Way, Winter Haven
$345,690
4 Beds ⋅ 2 Baths ⋅ Willowbrook North SubDv. ⋅ 33881 Zip Code
Beautiful Single Level, 2 Car Garage Home with Open Concept Living and 4 Bedrooms! The Baker plan is in Farmhouse exterior design. Adjacent the foyer you'll find 3 secondary bedrooms and a full bathroom. The well-appointed island kitchen overlooks the spacious family room and adjoining cafe with access to the covered lanai. The primary suite boasts an en suite bathroom with dual sink vanity, shower, private water closet, and large walk-in closet.

815 Andrew Street, Winter Haven
$549,999
3 Beds ⋅ 3 Baths ⋅ Lake Ashton West Ph Ii North SubDv. ⋅ 33884 Zip Code
*GOLF COURSE and WATER VIEWS*** Located behind the secure gates of the coveted 55 + community of Lake Ashton, the views from the covered and screened lanai are superb! Built in 2019, this home offers TWO SUITES, ONE GUEST BEDROOM and THREE BATHS. This split floor plan home offers great curb appeal with a FRESH NEW EXTERIOR COAT OF PAINT, Paver Driveway and Well Maintained Landscape. The lawn is "watered" by an irrigation system. As you enter thru the double glass doors of this home you are greeted by a large open floor plan offering expansive views of the golf course and lake beyond. The views from this coveted lot location are spectacular so make sure you bring your binoculars! The living room, formal dining area and kitchen flow seamlessly together in this modified ASHTON Floor plan home, making entertaining easy and fun! The spacious Living Room has a tray ceiling, floor outlets, ceiling fan and triple sliders that stack and open to the covered and screened lanai. A formal dining area is located to the left of the front entry and the arched double windows add a touch of class! The Kitchen features 42" wood cabinetry, breakfast bar, pendant lighting, granite countertops, SS appliances (microwave replaced Sept. 2026) and ample counter top space for food prep and food display. The Dinette area is conveniently located off of the kitchen and the double windows provide an abundance of natural light into the home. Double sliders provide access to the lanai from the dinette area. The spacious and oversized Primary Suite with double door entry makes up the right wing of the home. It showcases two large walk-in closets, a separate water closet with window, a linen closet, a large, tiled walk in shower with grab bars and a tiled bench to sit on. The vanity with double sinks compliments the bathroom area. The Primary Suite with trey ceiling and ceiling fans can accommodate a separate sitting area for relaxation or larger bedroom furniture. The 2nd Suite with double door entry is on the left side of the home. It's accessible from the dinette area and from the hallway that leads to the 3rd Bedroom/3 Bath. The 2nd Suite has a private bath and built in closet. The 2nd Suite Bath features a comfort height vanity, walk in shower with glass enclosure, grab bars, foot rest and comfort height toilet. Overnight Guests will enjoy their own bedroom and bath with shower/tub combo and comfort height vanity. The Laundry Room (FLEX ROOM) is spacious and well designed with a wash tub and portable storage units for your personal items. The washer/dryer are included in the sale of this home. The outdoor living space offers a delightful place for entertaining. There are two OPTIONS: You can enjoy the covered portion of the lanai or the extended/uncovered screened lanai with direct views of the golf course and lake. The double car garage is sizeable and there is a separate golf cart entrance. The home also has a WHOLE HOUSE GENERAC- this is a huge bonus! ADDITIONAL IMPROVEMENTS to this home include: NEW INTERIOR PAINT and NEW LUXURY VINYL FLOORING. The community of Lake Ashton is a hidden treasure with an aura of peace and tranquility, and offers 2 golf courses, tennis courts, 2 pools (one indoor and one outdoor) movie theater, bowling lanes, card, craft and billiard rooms, fitness centers, pickleball courts, indoor basketball, indoor racquetball, numerous recreational activities, and restaurants. Make an appointment today to TOUR THIS HOME!

6136 Pebble Beach Boulevard, Winter Haven
$106,000
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
**THIS CONDO IS PRICE TO SELL !!**CENTRAL FLORIDA 55+ Age GATED CONDOMINIUM COMPLEX WITH LAKE AND CITY VIEW. All new insulated windows throughout. This condominium provides 1,347 sq. ft. of living area & is located in the beautiful "Chain Of Lakes" City of Winter Haven, Fl. Very friendly complex w/ social activities offered if you wish to participate. Monthly association fee includes water, sewer, trash, fiber optic cable & internet, condo reserves, manager and use of recreational facilities. Lakeridge Condominiums offers a maintenance-free lifestyle w/ heated pool, tennis, shuffleboard, community room, gated entrances & covered assigned parking space. The large bright kitchen has plenty of cabinets & great counter space, appliances (dishwasher does not work) & pantry closet. The kitchen overlooks the 26'x14' great room that also adjoins the additional bonus space & storage closet. The 16X14 foot Primary bedroom suite has a walk in closet & bathroom w/ walk-in shower. Beautiful views of Spring Lake can be enjoyed from Primary bedroom & living areas. The 2nd bedroom & bath can be a private guest area or for your personal use for office, hobbies etc. The washer & dryer are included in the sale. Central heat and air conditioning. Convenient proximity to shopping, places of worship, groceries & restaurants. Extra assigned storage bin on same floor. Make this your full time home, winter home or investment property to update. Lakeridge Condominiums is an age-restricted, well-maintained & well-managed community. Sharepoint car charger provided for those with electric cars. Non-smoking property. 1 pet, 20 pounds or under may be approved.

1776 6th Street Nw Unit 304, Winter Haven
$199,900
Village Spirit Lake Ph 01 SubDv. ⋅ 33880 Zip Code
LAST BUILDING LOT ON SPIRIT LAKE IN THE VILLAGES OF SPIRIT LAKE, SO BRING YOUR PLANS AND START ENJOYING THIS GATED COMMUNITY. OFFERING A PRIVATE BOAT LAUNCH, FISHING DOCK PLUS COMMUNITY POOL, CLUBHOUSE, PLAY GROUND, TENNIS, BASKETBALL AND PICKLEBOARD COURTS. EAST ACCESS TO THE POLK PARKWAY SO COMMUTES TO TAMPA OR ORLANDO MAKE IT EASY. OWNER TERMS AVAILABLE IF NEEDED WHILTE GETTING YOUR CONSTRUCTION PLANS TOGETHER.

Archaic Drive, Winter Haven
$145,000
3 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
**Welcome to Imperial Harbours, a beautifully maintained 55+ active community surrounded by gorgeous landscaping and offering access to Winter Haven’s Chain of Lakes!** This spacious **3-bedroom, 2-bath second-floor corner condo** offers over 1,226 sq. ft. of comfortable living with an open-concept living/dining area, lovely kitchen with beautiful countertops and abundant cabinetry, plus an enclosed bonus room perfect for an office, sitting area, or hobby space. The generous primary suite features a private bath and large walk-in closet. Enjoy the peace of mind of a **BRAND-NEW A/C**, newer double-pane windows, updated bathroom vanities, fresh interior paint, and an in-unit washer and dryer. Additional features include an exterior storage unit, elevator access, covered assigned parking, guest parking, and community car wash. Enjoy resort-style amenities including a **heated pool, fitness room, billiards, recreation room, shuffleboard, BBQ grills, gazebo, fishing, dock access, and nearby boat ramp.** HOA includes **water, internet, cable, and trash!** Conveniently located near hospitals, restaurants, shopping, and everyday essentials. **Come experience the Florida lifestyle at Imperial Harbours—schedule your private showing today!**

333 Lake Howard Drive Nw Unit 204D, Winter Haven
$184,900
2 Beds ⋅ 2 Baths ⋅ Hartridge Landing SubDv. ⋅ 33881 Zip Code
Great condo in Hartridge Landings. A premier 55+ small 42 unit custom condominium complex Walking out the front door one can find themselves only a few steps from the clubhouse, pool and the famous Chain of Lakes...Lake Hartridge. 17-lake chain of inter-connected lakes. Boating and fishing enthusiasts paradise! Well maintained. This home comes with several skylights to brighten your day. It also has several custom shelves and engineered closet built-ins. Large totally private rear patio area that's great for entertaining outside and room to add a portable spa. Large double car garage with some storage closets. New TPO roof, re-piped plumbing and a/c system in 2022. Vacant and easy to show.

2215 Starboard Drive Unit 29, Winter Haven
$152,000
2 Beds ⋅ 2 Baths ⋅ Brookhaven Village SubDv. ⋅ 33881 Zip Code
Located in the 55+ community of Brookhaven Village, this home features 2 bedrooms and 2 bathrooms, with vinyl and carpet flooring. You own your lot! Low HOA fee of just $34 month, giving residents access to a clubhouse, swimming pool, and planned activities. Conveniently located near shopping, dining, medical services, and everything Winter Haven has to offer, this home provides comfort and peace of mind. Solar panels are leased and installed on a cement beam. Buyers interested will just need to transfer the solar lease to their name. Lease payment is $87 monthly, and the electricity bill is around $18 monthly. Schedule a showing today.

6455 Hollyberry Lane Ne, Winter Haven
$175,000
2 Beds ⋅ 2 Baths ⋅ Garden Grove Oaks SubDv. ⋅ 33884 Zip Code
Welcome home to 6107 Grand Oaks Dr SE, nestled in the friendly Garden Grove Oaks 55+ community, where YOU OWN YOUR LAND—NO LOT RENT! Situated on a beautifully landscaped DOUBLE LOT, this charming 2-bedroom, 2-bath home offers plenty of space inside and out. The second lot is a true highlight, featuring beautiful landscaping and a large pergola that creates the perfect spot to relax, entertain, or simply enjoy the Florida sunshine.Inside, you'll love the beautiful kitchen with gas range, spacious primary bedroom with walk-in closet, and air-conditioned side porch providing additional year-round living space. Double-pane windows installed in 2017 come with a transferable lifetime warranty, while the vinyl roof-over installed in 2013 also carries a lifetime warranty. Natural gas heating, clothes dryer, and hot water heater add to the home's comfort and convenience. Garden Grove Oaks offers a welcoming 55+ lifestyle with a clubhouse, heated community pool and spa, shuffleboard and a variety of activities to enjoy. Conveniently located in SE Winter Haven near shopping, restaurants, medical facilities and Hwy 27, everything you need is just minutes away. Come discover the extra space, comfortable Florida lifestyle, and wonderful community!

6107 Grand Oaks Drive Se, Winter Haven
$107,000
2 Beds ⋅ 2 Baths ⋅ Imperial Harboursphases 01 & 02 SubDv. ⋅ 33880 Zip Code
This fully furnished 2-bedroom, 2-bathroom condominium is located on the third floor of the Imperial Harbours 55+ active community in Winter Haven, Florida. Situated directly along Lake Howard with direct entry to the Chain of Lakes, the 1,134-square-foot unit offers water views, updated laminate flooring, a walk-in primary closet, and a dedicated Florida room. Residents enjoy a low-maintenance lifestyle with a monthly $440 condo fee covering community pool access, dock and fishing pier amenities, cable TV, and exterior insurance, along with an assigned carport space and elevator access. A perfect winter home...no snow shovel needed!

333 Lake Howard Drive Nw Unit 302B, Winter Haven
$198,000
2 Beds ⋅ 2 Baths ⋅ Lake N Golf Estates Add SubDv. ⋅ 33881 Zip Code
Welcome to this UPDATED & WELL-MAINTAINED home located in Lake N Golf Estates, a desirable LAKEFRONT, LAND-OWNED, no pet 55+ community in Winter Haven. This SPACIOUS home features an OPEN FLOOR PLAN with vaulted ceilings and offers 2 bedrooms and 2 bathrooms, plus a living room, family room, dining room, dinette, bonus room, office, walk in storage closet, enclosed Florida room, and a workshop, providing over 2600 total SF. This home also comes partially furnished. The spacious island kitchen features GRANITE countertops, a breakfast bar, coffee bar, glass cooktop, Stainless appliances and a walk-in pantry. The family room has a built-in entertainment center with cabinets, TV included. Dinette has wainscoting. The dining room has a bay window. Both bedrooms have walk in closets. The home office has a mini-split air conditioner and comes equipped with a large desk/workstation and bookshelves. Numerous major updates were completed in 2024, including a NEW ROOF, A/C, CARPORT, SIDING, ELECTRICAL BREAKER BOX and REFRIGERATOR, upgraded insulation in roof over carport and enclosed Florida room. Additional improvements include updated Window World windows, updated flooring and a water purifier, making this home truly move-in ready. A GOLF CART IS ALSO INCLUDED! Oversized lot (126x51). Lake N Golf Estates offers an affordable Florida lifestyle with LOW HOA FEES of just $550 per year. Residents enjoy access to community amenities including a swimming pool, spa, clubhouse, shuffleboard, community boat ramp and dock, with boat slips available subject to availability. Conveniently located near Hwy 27 with easy access to shopping, dining, medical facilities and everything Winter Haven has to offer. Don't miss the opportunity to enjoy comfortable Florida living in this established lakefront community!

6627 Westchester Drive Ne, Winter Haven
$134,990
1 Beds ⋅ 1 Baths ⋅ Fairview Village SubDv. ⋅ 33881 Zip Code
Welcome Home to Easy Florida Living! Come discover this beautifully maintained 2023 Skyline Park Model, installed in August 2022 and thoughtfully designed with comfort, convenience, and relaxation in mind. From the moment you arrive, you’ll appreciate the new concrete driveway, newer roof, central air, spacious storage, and inviting outdoor living opportunities. Inside, the home offers an open and comfortable layout with a large pantry, dining island, electric fireplace, walk-in shower, and a bedroom spacious enough for a king-size bed. The home is being offered with many furnishings and features, including a French-door refrigerator, electric range, microwave, washer/dryer combo, water softener, blinds, generator ready and more. The lifestyle is just as appealing! The 99-year perpetual lease is renewable for only $1, while the current $90 monthly association fee includes water, sewer, trash, seasonal lawn maintenance, heated pool access, clubhouse, and a variety of community activities. Enjoy shuffleboard, horseshoes, billiards, ping pong, and a community dock with direct canal access to Lake Henry, complete with a pier bench and fire pit. Whether you’re looking for a seasonal retreat, a comfortable Florida getaway, or a place to enjoy the relaxed community lifestyle, this one is ready for you to come see and fall in love with it! Financing Available!

7060 Fairview Village Circle, Winter Haven
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