Winter Haven Homes with Association Recreation - Owned Community Features

Winter Haven Homes with Association Recreation - Owned Community Features

Nestled in the heart of Polk County, Florida, Winter Haven is a vibrant city known for its charming neighborhoods and picturesque landscapes. Located in the Sunshine State, Winter Haven offers residents a perfect combination of warm weather, natural beauty, and a close-knit community.

As part of Polk County, Winter Haven benefits from its central location, providing easy access to major cities like Orlando and Tampa. Residents can enjoy the best of both worlds, with the tranquility of a small town and the amenities of larger urban areas just a short drive away.

One of the standout features of Winter Haven is its abundance of homes with Association Recreation - Owned Community amenities. These communities offer residents access to a variety of recreational facilities, such as swimming pools, fitness centers, tennis courts, and clubhouses. Whether you're looking for an active lifestyle or a place to relax and unwind, these communities provide the perfect setting for residents to enjoy their leisure time.

In addition to the community amenities, Winter Haven boasts a range of outdoor activities. The city is known for its chain of lakes, offering opportunities for boating, fishing, and water sports. The famous LEGOLAND Florida Resort is also located in Winter Haven, attracting visitors from all over the world.

With its welcoming atmosphere, convenient location, and abundance of recreational opportunities, Winter Haven is an ideal place to call home. Whether you're seeking a peaceful retirement or a family-friendly community, Winter Haven has something for everyone.

Newest Winter Haven Homes with Association Recreation - Owned Community Features

$235,000
2 Beds ⋅ 2 Baths ⋅ Winterset 03 A Condo Ph 01 SubDv. ⋅ 33884 Zip Code
Waterfront Living • Renovated Interior • Private Garage. Imagine ending your day with a beautiful Florida sunset over Lake Winterset. This beautifully renovated 2-bedroom, 2-bath condominium offers something that is hard to find in condo living—a private 1-car garage, expansive waterfront views, and the added character of a second-floor residence with vaulted ceilings and skylights. Located in the gated Winterset community, this home combines a relaxed lakefront lifestyle with a thoughtfully updated interior that is comfortable, stylish, and move-in ready. The kitchen is truly the centerpiece, featuring abundant cabinetry, granite countertops, stainless-steel appliances, a stylish tile backsplash, and an oversized counter with generous breakfast-bar seating. The open design creates a spacious connection between the kitchen and living area. The main living area features rich wood flooring and a striking built-in entertainment center with display shelving and architectural detail. Step through the sliding glass doors and enjoy the true highlight of this home—the enclosed waterfront lanai overlooking Lake Winterset. With room for both dining and comfortable seating, this becomes an extension of the living space and an ideal place to enjoy the beauty of Florida's nature. Imagine starting your morning with coffee overlooking the lake or relaxing at the end of the day as the sun sets across the water. The views aren't simply outside your door—they become part of everyday life. Renovated throughout, this home offers a cohesive blend of comfort and style. Plantation shutters, updated bathrooms, wood flooring, and carefully selected finishes create a polished feel throughout. The primary bedroom offers beautiful lake views, while the second bedroom provides flexibility for guests, an office, or additional living space. A unique feature of this residence is the installed stair chair, providing added convenience between the garage level and the second-floor home. A 1-car garage is an especially desirable feature for condo living, providing secure parking and valuable additional storage. Having your own garage adds a level of convenience that is not commonly found with condominium living. Set within the gated Winterset community, this home offers a welcoming waterfront lifestyle surrounded by beautiful lakes, mature landscaping, and green spaces. Residents can enjoy the waterfront clubhouse, pool and spa, along with an active and social community atmosphere. Winterset provides opportunities for boating, fishing, and enjoying the peaceful waterfront setting, while remaining conveniently close to shopping, dining, entertainment, theme parks, airports, and Florida's east and west coast beaches. Whether you're looking for a full-time residence, seasonal retreat, or an easy-to-maintain Florida getaway, 809 Magnolia Place offers the rare combination of lakefront views, thoughtful renovations, vaulted ceilings, a private garage, and a lifestyle centered around the water.

809 Magnolia Place Unit 809, Winter Haven
$99,500
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 1144 Square ft. 2 bedroom 2 bath 1983 Fleetwood mobile home with a front facing enclosed Florida room with a view of the clubhouse and recreation grounds. The king size master bedroom has a walk-in closet and a private bathroom with step in shower. The guest bedroom also has a walk-in closet. The monthly maintenance fee is $279.00 a month which includes cable, internet, trash pickup, and amenities. This house is partially furnished and ready to move in. The guest bedroom is not furnished. 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.

66 Joppa Drive, Winter Haven
$79,500
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 989 Square ft. 2 bedroom 2 bath 1984 Homes of Merit with an enclosed front facing Florida. The king size master bedroom has a walk-in closet and a private bathroom with a tub shower. The guest bedroom also has a walk-in closet. 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.

97 Parson Drive, 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 water 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 water views from this coveted lot location are spectacular! 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
$164,900
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 Carpet, 2 year old AC unit, 2026 UPDATES - BRAND NEW hot water heater, countertops throughout, dishwasher, microwave, disposal, kitchen faucet. This PRISTINE 2 Bed /2 Bath condominium offers 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! There's an 18 hole championship golf course with a Clubhouse that offers chef prepared meals & live music. Also open to the public. Additional owner amenities include Brand New tennis & pickleball courts, and 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
$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
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