Winter Haven Retirement Communities

Winter Haven offers numerous options when searching for retirement or senior communities. There are several 55+ communities in Winter Haven including gated lakefront communities, golf course communities, condos, villas, mobile homes and more. If you are looking for an age restricted community, contact us and we will be happy to help.

To view homes for sale in this area, contact the The Stones Real Estate Firm!  To see all homes for sale in the city, click Winter Haven Real Estate.

Take a look at our FREE Buyer’s Guide.  You can also find other homes with our MLS Map Search. Read our blog to find Current Events, or browse information about Schools and Community Information.

If you would like more information about buying or selling in an adult lifestyle community, contact us. Michael Stone: 863.412.9733 – Deanna Stone: 863.412.2080

Price
Beds
Baths
For Sale / All Types
Advanced Search
New Listing - yesterday
$104,000
2
BED
2
TOTAL BATHS
1,275
SQFT
6728 Canterbury Drive NE Winter Haven, FL 33881
Mobile Home For Sale
- Active

Corner lot and lake view! Check out this really updated home! This home shows pride of ownership! Nicely furnished! No lot rent you own your home with lot! HEATED POOL AND HOT TUB! line dancing ,shuffle board, BINGO, JOKER, POT LUCK DINNERS, LOCATE

New Listing - yesterday
$89,900
2
BED
2
TOTAL BATHS
1,152
SQFT
6401 Lollybay Loop NE Winter Haven, FL 33881
Mobile Home For Sale
- Active

55 plus community in central Florida! GOLF CARTS ARE OK SUFFLEBOARD Heated pool, nice and redecorated club house! Bingo, coffee,cards Lot's of activities. Diving only 45 min, to Orlando Airport,Theme parks,shopping and lot's of churches! Real nice

New Listing - yesterday
$84,999
2
BED
2
TOTAL BATHS
1,347
SQFT
1776 6th Street NW #402 Winter Haven, FL 33881
Condo For Sale
- Active

CENTRAL FLORIDA MOVE IN READY Located in the beautiful gated 55+ community, this spacious, 2 BR/2 BA condo is located on the 4th floor in the community of Lakeridge. The charming kitchen even includes a breakfast bar. The open floor plan is evident

New Listing - 2 days online
$159,900
2
BED
2
TOTAL BATHS
1,275
SQFT
3497 Raleigh Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Beautiful 2 bed/ 2 bath home located in Traditions, a 55+ community in SE Winter Haven that offers a large recreation building, community pool, lake access and much more. The home has a 2 car garage and screened in lanai. The home also has a large k

New Listing - 4 days online
$56,900
2
BED
2
TOTAL BATHS
1,008
SQFT
194 Sweet Circle Winter Haven, FL 33884
Mobile Home For Sale
- Active

Lovely updated mobile home in the exclusive gated Orange Manor West community. Park in the carport just in front of the outdoor sitting area on the side of the home. Just inside the shed you will find plenty of storage and a washer and dryer that c

New Listing - 5 days online
$86,000
2
BED
2
TOTAL BATHS
1,104
SQFT
6424 Jacaranda Avenue NE Winter Haven, FL 33881
Mobile Home For Sale
- Pending

ENJOY THIS LOVELY RECENTLY UPDATED 2BR/2BA HOME IN 55 AND OVER COMMUNITY. . OWN YOUR OWN LOT. ALL FLOORS ARE NEW. KITCHEN UPDATED AND NEW CABINETS. AIR CONDITIONER NEW 2015. ALL APPLIANCES STAY. GUEST BEDROOM FURNITURE STAYS. ALL NEW INSIDE AND OUTSI

New Listing - 5 days online
$229,500
2
BED
2
TOTAL BATHS
1,935
SQFT
2920 Dayton Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

This Fabulous 2 Bedroom with a Den Home is located on a Corner Lot in the Desirable Maintenance Free Gated Community of Traditions at Lake Ruby. The Home features a Spacious Open Floor Plan that was designed for entertaining. The Generously Sized Eat

New Listing - 6 days online
$227,500
3
BED
2
TOTAL BATHS
1,677
SQFT
2705 Attwater Loop Winter Haven, FL 33884
Single Family Home For Sale
- Active

Immaculate 3 bedroom/2 bathroom home in beautiful Traditions South in desirable SE Winter Haven. Live in paradise with tons of amenities. Built by Lennar Homes in November 2018, this home shows like a new build! Beautiful 42" cabinets with crown i

New Listing - 6 days online
$94,900
2
BED
2
TOTAL BATHS
1,144
SQFT
6714 NE Canterbury Drive NE Winter Haven, FL 33881
Mobile Home For Sale
- Active

You own your lot! No monthly fees! Central Florida Enjoy fishing in a good fishing lake, Heated pool and hot tub. This home shows pride of ownership! Enjoy the shuffleboard court or the line dancing or BINGO! Affordable living HOA $400 a year! Thi

New Listing - a week online
$225,000
2
BED
2
TOTAL BATHS
1,821
SQFT
5304 Green Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Your search is over… You must see this exceptional single-story extended Bali home in Lake Ashton… As you step through the beveled glass entry doors you will see the spacious open floor plan and all the upgrades… No expense has been sparred inside an

New Listing - a week online
$188,000
2
BED
2
TOTAL BATHS
1,530
SQFT
5313 Nicklaus Drive Winter Haven, FL 33884
Single Family Home For Sale
- Active

Make this home your very own! New Laminate Flooring Added 2019. Located behind the gates of Lake Ashton, a 55+ community in the Winter Haven/Lake Wales area, this open floor plan home is bright and cheerful. A paver driveway and paver sidewalk to the

New Listing - a week online
$399,000
3
BED
2
TOTAL BATHS
2,479
SQFT
5244 Pebble Beach Boulevard Winter Haven, FL 33884
Single Family Home For Sale
- Active

Exceptional home in the highly sought after gated community of Lake Ashton… The elegance of this home is immediately apparent as you enter through the front doors… The open floor plan, volume ceilings and oversized windows create an energizing flow o

New Listing - 2 weeks online
$78,900
2
BED
2
TOTAL BATHS
1,392
SQFT
4327 Cherrywood Street Winter Haven, FL 33880
Mobile Home For Sale
- Active

Check out this immaculate home!! The home has recently been painted with new gutters. The landscaping has been recently done with water diversion away from the home. There is lots and lots of space in this home. In addition to a living room, the

New Listing - 2 weeks online
$429,900
3
BED
2
TOTAL BATHS
2,045
SQFT
1527 Riviera Court Winter Haven, FL 33884
Single Family Home For Sale
- Active

This incredible 2-year old, 3-bedroom home is priced over $100,000 below construction plus post-purchase upgrades cost. CDD debt is fully paid. The home’s flooring is 18” ceramic tile with epoxy grout. The air conditioning system has 4 individuall

New Listing - 2 weeks online
$145,000
3
BED
2
TOTAL BATHS
1,493
SQFT
1599 Oakview Circle SE Winter Haven, FL 33880
Villa For Sale
- Pending

The villa you are inquiring about is located in a quiet SE Winter Haven 55+ retirement community called Oakview. This community is well maintained by the HOA and has a low affordable HOA fee. This is a clean, 3 BR/2 BA, unit that has been well maint

New Listing - 2 weeks online
$239,900
3
BED
3
TOTAL BATHS
2,006
SQFT
2907 Woodward Lane Winter Haven, FL 33884
Single Family Home For Sale
- Active

This beautiful home is centrally located between Orlando and Tampa! Includes three bedrooms, 3 baths, den, two car garage, Open-floor plan kitchen with breakfast nook looks onto the dining and family room. The master bedroom has a private bathroom wi

New Listing - 2 weeks online
$95,000
2
BED
2
TOTAL BATHS
1,152
SQFT
6211 Knotty Pine Drive SE Winter Haven, FL 33884
Mobile Home For Sale
- Pending

HOME IN DESIRABLE GARDEN GROVE OAKS! This lovely manufactured home is move-in ready and has everything you've been looking for in affordable Florida Living. It has been well maintained and boasts a fantastic floor plan with room for everyone. The hom

New Listing - 3 weeks online
$54,000
2
BED
2
TOTAL BATHS
1,056
SQFT
23 Kinsmen Drive Winter Haven, FL 33884
Mobile Home For Sale
- Pending

This lovely well kept home in 55+Community was lived in year round and the care and attention to the detail shows. Fully furnished with upgraded newer wall to wall carpeting with 2 bedrooms and 2 baths and approximately 1100 square feet of living sp

New Listing - 3 weeks online
$174,440
2
BED
2
TOTAL BATHS
1,517
SQFT
2915 Traditions Boulevard Winter Haven, FL 33884
Villa For Sale
- Active

Traditions is an age restricted over 55 community. Isn’t it time to upgrade your life? This luxurious single-story villa features 2 bedrooms, 2 bathrooms, a separate dining area, and a Flex room. The Flex Room location will enable you to convenientl

New Listing - 3 weeks online
$172,155
2
BED
2
TOTAL BATHS
1,400
SQFT
2841 Attwater Loop Winter Haven, FL 33884
Villa For Sale
- Active

Traditions is an age restricted over 55 community. Step into luxury with St Lucia plan! This lovely villa home features 2 bedrooms, 2 bathrooms, and a Flex room. The Flex Room location will enable you to conveniently turn it into a quiet retreat, or

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