Winter Haven Homes with Association Recreation - Owned Community Features

Winter Haven Homes with Association Recreation - Owned Community Features

Welcome to Winter Haven, Florida, a charming city nestled in the heart of Polk County that perfectly blends small-town warmth with vibrant community spirit. Known for its picturesque lakes and lush landscapes, Winter Haven boasts a unique allure that attracts residents and visitors alike. With over 50 lakes, including the famous Chain of Lakes, this city is a haven for water sports enthusiasts, nature lovers, and those seeking a tranquil lifestyle.

When it comes to real estate, Winter Haven offers an array of beautiful homes, particularly in communities with association recreation features. These neighborhoods not only provide stunning residences but also foster a sense of belonging through shared amenities and activities. Imagine waking up to the serene views of shimmering lakes, enjoying leisurely strolls in landscaped parks, and engaging in community events that bring neighbors together.

Homes in these association-managed communities often come equipped with fantastic recreational facilities. Residents can enjoy access to swimming pools, tennis courts, fitness centers, and clubhouses, ensuring there's always something fun to do right at your doorstep. Whether you’re looking to host a barbecue with friends or unwind with a good book by the pool, these communities offer the perfect backdrop for a fulfilling lifestyle.

In Winter Haven, you’re not just buying a home; you’re investing in a vibrant community where friendships flourish and memories are made. Discover the charm of Winter Haven and see why so many are choosing to call this delightful city their home!

Newest Winter Haven Homes with Association Recreation - Owned Community Features

$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
$179,000
2 Beds ⋅ 2 Baths ⋅ Brookhaven Village SubDv. ⋅ 33881 Zip Code
Beautifully maintained 2-bedroom, 2-bathroom furnished home located in a well-established 55+ community that combines comfort with convenience. Roof 2025, A/C 2025, Water Softener 2026, New Carport/Shed (Right) & fresh paint. Low HOA fee of just $34 per month, giving residents access to a clubhouse, swimming pool, and planned activities. Conveniently located near shopping, dining, medical facilities, and everything. Winter Haven has to offer, this home provides excellent value and peace of mind. Schedule your private showing today.

6458 Hollyberry Lane Ne, Winter Haven
$165,900
2 Beds ⋅ 2 Baths ⋅ Eagle Pond Condo SubDv. ⋅ 33884 Zip Code
Looking for a COUNTRY CLUB LIFESTYLE? Conveniently located in Cypresswood Golf & Country Club, on Dundee Rd near HWY 27. RECENT UPDATES INCLUDE a 2 year old AC unit, and in 2026 brand New hot water heater, countertops throughout, dishwasher, microwave, disposal and kitchen faucet. This SUPER CLEAN 2 bed/2 bath condominium offers an open concept with 10' Ceilings, Crown Molding, 2" Blinds and Ceiling Fans throughout. You will love the spacious kitchen with pantry & lots of counter space. Both bedrooms feature walk in closets. Ample amount of closet space plus an outside storage room & assigned parking. Cypresswood residents enjoy a resort and country club lifestyle! The 18 hole golf course and Clubhouse with chef prepared meals & live music are open to the public. Additional amenities include Brand New tennis & pickleball courts, plus a half Olympic size pool. Located just minutes from trendy downtown Winter Haven, convenient to Hwy 27 & I-4. Close to Legoland, Bok Tower, shopping, dining, hospital and medical facilities. Just 5 minutes to BRAND NEW Publix and ALDI grocery's, 7-11 gas station & McDonalds.

508 Eagle Pond Drive Unit 508, Winter Haven
$147,500
2 Beds ⋅ 2 Baths ⋅ Lakeridge Condo SubDv. ⋅ 33881 Zip Code
Welcome to Lakeridge — Easy Florida Living with Beautiful Spring Lake Views! Take a look at this fantastic move-in-ready 2-bedroom, 2-bathroom condo in Lakeridge, a gated 55+ community in Winter Haven with great lake views. With 1,347 square feet of living space, this home offers plenty of room to relax, along with thoughtful updates and beautiful views of Spring Lake. As you step inside, you'll find an updated kitchen with plenty of updates including, soft close cabinets and drawers, granite counter tops, a pantry closet, and stainless-steel appliances. The kitchen opens into the spacious great room, making it easy to cook, visit, and entertain at the same time. The 26' x 14' great room flows into the Florida/bonus room, a comfortable spot to unwind while enjoying the lake view. Furnishings are negotiable! There's also a large storage closet for added convenience in the Florida room. The primary bedroom is approximately 16' x 14', with plenty of space for a king-size bed. It includes a walk-in closet and a private bathroom with a walk-in shower and double vanity. Spring Lake views can be enjoyed from both the primary bedroom and the main living areas. Recent updates include new energy-efficient, double pained windows, carpet and tile. The washer and dryer are included, along with all of the stainless-steel kitchen appliances, so you can move in and settle right away. The entertainment system-65" Smart TV, 5-speaker Surround System w/Subwoofer, Blue Ray, Stereo with AM/FM Radio, Speakers, and Antenna is also included and complements the built-in electric fireplace, creating a cozy space for relaxing or spending time in your space. Lakeridge makes everyday living easy and low maintenance. The monthly condominium fee includes water, sewer, cable, fiber-optic internet, trash removal, reserves, and use of the recreational facilities. Residents can enjoy a heated pool, tennis courts, shuffleboard, a community room, gated entrances, and a covered assigned parking space. An additional assigned storage bin is conveniently located on the same floor. The community also offers social activities for residents who enjoy meeting neighbors and staying involved. When you need to run errands, Lakeridge is close to shopping, grocery stores, restaurants, medical offices, and the hospital. Lakeridge is an age-restricted 55+ community. One small pet may be approved. The property is non-smoking, and an electric vehicle charger is available on-site for owners. If you're looking for a spacious condo with lake views, comfortable living areas, included amenities, and a maintenance-free lifestyle, this home is worth seeing. It could be the comfortable Florida retreat you've been waiting for. Information is believed to be accurate but is not guaranteed. Measurements are approximate.

1776 6th Street Nw Unit 504, 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
$99,900
2 Beds ⋅ 2 Baths ⋅ Winter Ridge Condo SubDv. ⋅ 33881 Zip Code
MUST SEE! Discover the perfect blend of comfort, convenience, and Florida lifestyle in this beautifully maintained 2-bedroom, 2-bathroom unit in the desirable Winter Ridge Condominium Community. Featuring new laminate flooring throughout the living areas and bedrooms, fresh paint, updated baseboards, and A/C, this move-in-ready home offers a clean, modern feel with no carpet. The open-concept layout is thoughtfully designed to maximize every square foot, creating a spacious and inviting atmosphere for everyday living or entertaining. The property also includes two dedicated parking spaces, providing added convenience for residents and guests. Enjoy resort-style community amenities including a heated pool, clubhouse, chain-of-lakes access, boat dock, and boat slips, making it easy to embrace the best of Central Florida living. The HOA includes exterior and grounds maintenance as well as trash service, helping simplify ownership and enhance the property's appeal for both homeowners and investors. Conveniently located just minutes from downtown amenities, Legoland, shopping, dining, and entertainment, this property offers an excellent opportunity for a primary residence, second home, or income-producing investment. Seller or private financing available with an easy and fast approval process and just 20% down! Don't miss this exceptional opportunity schedule your showing today before it's gone!

244 Winter Ridge Boulevard Unit 244, Winter Haven
$164,800
2 Beds ⋅ 2 Baths ⋅ Lakeside Ranch For Mobile Homes SubDv. ⋅ 33881 Zip Code
Meticulously Maintained, beautiful 2/2, move-in ready home in a quiet lake-front community. Pride of Ownership shows throughout! List of Updates attached and include finished walls, Plumbing, downspouts, Heat Pump with UV Light, Newer Appliance, Washer and Dryer (inside laundry), flooring, kitchen cabinets with soft-close, built-in pantry/storage in the Dining Room to name a few. Thoughtfully maintained, offering peace of mind and comfort from day one! BONUS=2024 Evolution C4PRO golf cart is included! The sales price includes the $11,000 share of ownership in this Co-op Community. The low $145/mo HOA fee includes water, sewer, and lawn mowing. Individual mailbox, community laundry and clothesline available. No pets. No motorcycles. Trucks ok. Located near shopping, entertainment, and health care!

628 Lakeside Ranch Lane, Winter Haven
$325,000
3 Beds ⋅ 2 Baths ⋅ Villamar Ph 6 SubDv. ⋅ 33884 Zip Code
Stunning VillaMar residence in Winter Haven, built in 2024, showcasing modern construction with a clean, contemporary design throughout. The interior features an inviting layout highlighted by a chef-style kitchen that opens seamlessly to a spacious great room, creating an ideal space for both everyday living and entertaining. This home includes a whole-house water filtration system, a screened front porch for comfortable outdoor relaxation, a fully fenced backyard for privacy, and enhanced landscaping with decorative stone accents and fresh plantings that elevate the exterior appeal. Conveniently located approximately 10 minutes from Legoland Florida and about one hour from Disney World, this property offers both comfort and an exceptional lifestyle location. Thoughtfully designed and move-in ready, it delivers style, quality, and lasting value. Schedule your private tour today! Errors, omissions, changes, withdrawal may occur. *Buyers are advised to independently verify square footage, permits, and property details.

4913 Kaia Avenue, Winter Haven
$355,000
3 Beds ⋅ 2 Baths ⋅ Lake Ashton West Ph Ii South SubDv. ⋅ 33884 Zip Code
1124 Sawgrass Drive Winter Haven, Fl. 33884 is located in Lake Ashton, an Exclusive Florida Retirement Community offering tailored activities and amenities to those seeking an Active 55 Plus lifestyle. Built in 2022 with 1,917 sq. ft. living area, this ST. MARKS floor plan home is MOVE IN READY and is located on the 10th Fairway of the West Golf Course in Lake Ashton. When you enter this home you have a direct view of the golf course thru the Triple Sliders that separate the LR from the Lanai. This Split Floor Plan offers: Formal and Casual Dining areas, a Living Room, Laundry Room, Primary Suite, 2 Bedrooms and a Flex Room with Built In Shelves. The living room is at the center of the this home with the Kitchen, Formal Dining, Primary Suite and Dinette areas flowing into the LR area. The Kitchen is spacious and offers a Breakfast Bar, SS Appliances, Recessed Lighting, Pull Out Drawers, Ample 42" Cabinetry and Granite Countertops. The Dinette area is easily accessible to the kitchen and Flex Room and Double Sliders provide direct access to the Covered and Screened Lanai. The Open and Spacious Floor Plan makes entertaining a BREEZE! The comfortable and spacious Primary Suite offers His/Her Walk in Closets, an attractive Primary Bath area with His/Her separate vanities, large soaking tub, walk in shower, separate water closet and linen closet. Glass Block accents the Primary Bath and provides an abundance of natural light into the room. Bedroom 2 and Bedroom 3 are separated by the Guest Bathroom with shower/tub combo and comfort height vanity. Each Bedroom has a built in Closet. The laundry room (washer/dryer included in the sale of the home) is sizable and is the passage from the garage to the kitchen. The garage has a separate golf cart entry and the golf cart is included with the sale of the home. Grab a great book and a cup of coffee and relax on the screened and covered lanai. Lake Ashton is a gated and guarded Florida Active Community with resort style amenities (2 Clubhouses with Movie Theater, Restaurant, Outdoor/Indoor Pools, Fitness Centers and More! Residents enjoy activities like Karaoke, Trivia, Dances, Entertainment Series, Holiday Events and so much more. You can stay busy living the Florida Retirement Dream every single day. For those that love the game of golf, there are (2) 18-Hole Golf Courses, a Pro Shop, Driving Range, Putting Green and the Eagles Nest (Hole 19). Don't wait to tour this home; tour it today!

1124 Sawgrass Drive, Winter Haven
$115,000
2 Beds ⋅ 2 Baths ⋅ Orange Manor West Coop Inc SubDv. ⋅ 33884 Zip Code
Become a share holder in this highly sought after 55+ gated community. If you are looking for the perfect retirement home, this one is for you! Located in Orange Manor West, it is one of the most popular 55+ communities in Winter Haven and surrounding area with many amenities. Pool, shuffle board, putt putt, horse shoes, crochet, bingo, lake access and much more. Legoland is around one mile away which is great for visiting family. This is a 1368 Square ft. 2 bedroom 2 bath 1984 with an attached enclosed Florida room and an enclosed carport with ac. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. It has an inside utility room with washer & dryer. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is fully furnished and ready to move in. This is also a pet free community. While it is a great winter home get away, it can also be a year round retirement home. Come see it today. This one won't last long. All measurements are approximate and should be verified by the buyer.

113 Lake Hazel Drive, Winter Haven
$399,900
4 Beds ⋅ 3 Baths ⋅ Traditions Ph 02 SubDv. ⋅ 33884 Zip Code
Welcome to this beautifully maintained, energy-efficient 4-bedroom, 3-bath home in the highly desirable Traditions at Ruby Lake, a premier 55+ gated community offering the very best of Florida resort-style living. Situated on an oversized lot, this exceptional home features a desirable split floor plan Jack and Jill bathroom w/ walk-in tub and soaring high ceilings that create a bright, open, and spacious feel throughout. Thoughtfully upgraded for both comfort and efficiency, the home offers a spacious, expanded screened lanai with brick pavers—the perfect outdoor retreat for entertaining or enjoying a quiet evening—enhanced by customizable LED lighting to create the ideal ambiance. Energy-saving features include foam-core insulation in the concrete block walls, new Andersen windows, and a freshly painted exterior. Inside, you'll find hardwood flooring in the primary bedroom and front bedroom, which also makes an ideal home office. The kitchen is beautifully appointed with custom cabinetry, granite countertops, slate stainless steel appliances, and abundant storage. Custom maple shelving in the pantry, laundry room, and both linen closets adds both elegance and functionality. The primary bath also features granite countertops, completing the home's high-quality finishes. Designed for comfortable everyday living and effortless entertaining, this home offers generous living spaces that provide both privacy and flexibility for family and guests. HOA dues provide exceptional value and include weekly lawn and landscape maintenance, Spectrum TV service, and exterior house painting every seven years. Residents also enjoy full access to the community's impressive lakefront clubhouse, featuring a resort-style pool and spa, sauna, showers, a fully equipped fitness center, staffed front desk, library, business center, billiards room, craft room, and a spacious ballroom that hosts meetings, dances, entertainment, guest speakers, clubs, and social events. Outdoor amenities are equally impressive and include tennis, basketball, bocce ball, shuffleboard, pickleball, three community boat docks, a picturesque lakeside gazebo, and a paved walking path along the lake—perfect for morning strolls or evening exercise. If you're looking for a move-in-ready home with exceptional upgrades, low-maintenance living, and an active, resort-style lifestyle, this is the one you won't want to miss!

4132 Martindale Loop, Winter Haven
$189,900
2 Beds ⋅ 2 Baths ⋅ Winterset Garden Villas SubDv. ⋅ 33884 Zip Code
Welcome to 7902 Waterview Way, a beautifully maintained low-maintenance condo nestled within a desirable gated community. Offering a perfect blend of comfort and convenience, this home features tasteful upgrades, modern finishes, and a functional layout designed for easy everyday living. Enjoy a carefree lifestyle with exterior maintenance taken care of while taking advantage of the community's exceptional amenities, creating the perfect setting to relax or stay active. Ideally located near shopping, dining, entertainment, and major roadways, this move-in-ready condo offers the perfect opportunity to enjoy low-maintenance living in a secure and welcoming neighborhood.

7902 Waterview Way, Winter Haven
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