David Shippey
863.521.4517

Winter Haven FL Gated Community Homes For Sale

Winter Haven FL Gated Community Real Estate listings are included below. These homes for sale in Winter Haven Florida are updated every day from our local MLS. If you would like to schedule a showing or have any questions about any of these Winter Haven FL gated community homes, please call David at 863-521-4517 or just click the "Schedule a Showing" or "Request More Info" button on any property detail pages.

Click Here to Create a Free Profile to Gain Access to Detailed MLS Information that only real estate agents have access to. Your Free Profile also enables you to save your favorite search's and homes.

Modify Search Criteria

Displaying results 91-100 of 147
39 Photos 804 Magnolia Place UNIT #804 Winter Haven, FL 33884

804 Magnolia Place UNIT #804
Winter Haven, FL 33884
Winterset 03 A Condo Ph 01
Residential

MLS# B4901906 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1012 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Winterset 03 A Condo Ph 01

What a wonderful way to end your day! Sitting on your private, screened porch, relaxing and watching amazing sunsets over Lake Winterset. Plus, you... 

More Details

$259,000
Reduced -$11,000
Provided courtesy of KLINE REAL ESTATE SERVICES
38 Photos 1620 Linz Court Winter Haven, FL 33884

1620 Linz Court
Winter Haven, FL 33884
Vienna Square Ph 2c
Residential

MLS# L4952436 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1329 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 2c

Introducing your dream retirement oasis! Nestled in a serene 55+ community, this charming 2-bedroom, 2-bathroom abode offers comfort and convenienc... 

More Details

$245,000
Reduced -$3,000
Provided courtesy of LPT REALTY, LLC
49 Photos 104 Woden Way Winter Haven, FL 33884

104 Woden Way
Winter Haven, FL 33884
Valhalla
Residential

MLS# P4934554 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2218 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Valhalla

Valhalla - A GATED subdivision with pool, club house and more! 3-bedroom, 2-bath villa home with a connecting property but considered a single fami... 

More Details

$405,000
Provided courtesy of CENTURY 21 MYERS REALTY
1 Photos 100 Lakeside Ranch Drive Winter Haven, FL 33881

100 Lakeside Ranch Drive
Winter Haven, FL 33881
Lakeside Ranch For Mobile Homes
Residential

MLS# O6303367 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1176 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Lakeside Ranch For Mobile Homes

LAKEFRONT COMMUNITY...Welcome home to Lakeside Ranch, a gated 55+ community with NO LOT RENT! This 2 Bedroom/2 Bath home features a large living ro... 

More Details

$120,000
Provided courtesy of HOME WISE REALTY GROUP, INC.
50 Photos 1415 Colonial Court Winter Haven, FL 33884

1415 Colonial Court
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential

MLS# TB8380205 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II South

PRIDE OF OWNERSHIP MOVE IN READY GREAT CURB APPEALLake Ashton is a 55 plus community in Winter Haven Florida. Lake Ashton is an immaculately kept, ... 

More Details

$474,900
Reduced -$4,100
Provided courtesy of JACK KELLER INC
71 Photos 1394 Oakmont Drive Winter Haven, FL 33884

1394 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2
Residential

MLS# L4952569 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2606 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2

Back on market! Buyer(s) contingency fell through. Discover an exceptional home for sale in the beautiful Lake Ashton Golf course community, which ... 

More Details

$565,000
Provided courtesy of AGILE GROUP REALTY
42 Photos 4420 Limewood Street Winter Haven, FL 33880

4420 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# O6305229 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1000 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Welcome HOME to upgrade your lifestyle in this wildly popular Oakwood Estates 55+ Senior Gated community! Priced to SELL, Upgraded, and Move-In Rea... 

More Details

$134,990
Provided courtesy of EXP REALTY LLC
47 Photos 2980 Dayton Drive Winter Haven, FL 33884

2980 Dayton Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4934717 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2302 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Experience the best of Floridas 55+ lifestyle at 2980 Dayton Drive. A refined offering set on a large corner lot in Traditions at Lake Ruby, one of... 

More Details

$416,900
Reduced -$8,100
Provided courtesy of NEXTHOME NORRIS & COMPANY REALTY
26 Photos 426 Gleneagles Court Winter Haven, FL 33884

426 Gleneagles Court
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential

MLS# P4934744 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1731 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Patio Homes

Located on a cul-de-sac, this 2 bedroom home overlooks a greenspace and the golf course beyond and in the front yard, it sits directly across from ... 

More Details

$255,000
Provided courtesy of LOCKHART & ASSOCIATES INC
29 Photos 7102 Fairview Village Circle Winter Haven, FL 33881

7102 Fairview Village Circle
Winter Haven, FL 33881
Fairview Village
Residential

MLS# L4952803 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 712 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Fairview Village

Welcome to this active 55+ waterfront community nestled along the peaceful canal between Lake Hamilton and Lake Henry, offering stunning lake views... 

More Details

$72,500
Reduced -$2,500
Provided courtesy of KELLER WILLIAMS REALTY SMART

Broker Reciprocity The information being provided by © 2025 My Florida Regional MLS DBA Stellar MLS is for the consumer's personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumer may be interested in purchasing. Any information relating to real estate for sale referenced on this web site comes from the Internet Data Exchange (IDX) program of the My Florida Regional MLS DBA Stellar MLS. XCELLENCE REALTY, INC is not a Multiple Listing Service (MLS), nor does it offer MLS access. This website is a service of XCELLENCE REALTY, INC, a broker participant of My Florida Regional MLS DBA Stellar MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. MLS IDX data last updated on 07-21-2025 1:57 PM EST.

Any images related to data from the MLS is the sole property of the MLS and not the responsibility of the owner of this website. This real estate website and IDX data is hosted by IDX data is Powered & Hosted by Dynamic IDX, LLC Real Estate Web Solutions

The gated community homes above are brought to you by David Shippey REALTOR®.

Not finding what you are looking for? View all Winter Haven Homes for Sale here.