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 1-10 of 144
76 Photos 4220 Cedarwood Street Winter Haven, FL 33880

4220 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4935575 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1368 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

You won't want to miss this opportunity. This home comes furnished with what you see. As you walk into the front door you see the inviting Florida ... 

More Details

$139,000
Provided courtesy of COLDWELL BANKER REALTY
70 Photos 1182 Sawgrass Drive Winter Haven, FL 33884

1182 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2 South
Residential

MLS# P4935514 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2045 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2 South

Look No Further! This home is SIMPLY BEAUTIFUL! This open-concept Sebastian home design features ample square footage, several upgrade options both... 

More Details

$449,000
Provided courtesy of LAKE ASHTON REALTY INC.
77 Photos 6112 Pebble Beach Boulevard Winter Haven, FL 33884

6112 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph II North
Residential

MLS# P4935515 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2535 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph II North

**GOLF COURSE and WATER VIEWS*** Located behind the security gates of the coveted community of Lake Ashton, the attention to detail is evident thro... 

More Details

$539,000
Provided courtesy of LAKE ASHTON REALTY INC.
32 Photos 5384 Hogan Lane Winter Haven, FL 33884

5384 Hogan Lane
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4935506 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1682 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

***Motivated Seller*** Your Florida Oasis Awaits!! Step into comfort and convenience with this beautifully maintained 2-bedroom, 2-bathroom home fe... 

More Details

$380,000
Provided courtesy of LAKE ASHTON REALTY INC.
38 Photos 1218 Vienna Square Dr Winter Haven, FL 33884

1218 Vienna Square Dr
Winter Haven, FL 33884
Vienna Square Ph 01
Residential

MLS# O6326308 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1369 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 01

**This property qualifies for a closing cost credit up to $3,600 through the Sellers preferred lender plus an additional $1,000 credit for carpet f... 

More Details

$245,000
Provided courtesy of KELLER WILLIAMS REALTY AT THE PARKS
64 Photos 4090 Rolling Oaks Drive Winter Haven, FL 33880

4090 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4935321 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1344 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Move right into this spacious home located on a corner lot in Oakwood Estates, a 55+ community. The furnishings currently in the home will remain. ... 

More Details

$129,000
Provided courtesy of COLDWELL BANKER REALTY
27 Photos 4246 Cedarwood Street Winter Haven, FL 33880

4246 Cedarwood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# O6325757 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1008 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Welcome to your move in ready home in Oakwood Estates, a gated community designed for those aged 55 and older. This beautifully maintained 2-bedroo... 

More Details

$114,000
Provided courtesy of LPT REALTY, LLC
68 Photos 4153 Rolling Oaks Drive Winter Haven, FL 33880

4153 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4935384 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1368 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Check out this amazing home located in Oakwood Estates, a 55+ community. The very functional kitchen has updated cabinetry and countertops. The pri... 

More Details

$145,000
Provided courtesy of COLDWELL BANKER REALTY
1 Photos 963 Lunar Lane Winter Haven, FL 33884

963 Lunar Lane
Winter Haven, FL 33884
Crescent Pointe
Residential

MLS# R4909576 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1447 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Crescent Pointe

Under Construction. Crescent Pointe is a brand new community located in Winter Haven, FL, conveniently situated off State Rd 653 and boasting easy ... 

More Details

$305,226
Provided courtesy of VANTAGE PROPERTY MANAGEMENT LLC
41 Photos 205 Loma Drive Winter Haven, FL 33881

205 Loma Drive
Winter Haven, FL 33881
Hartridge Hills
Residential

MLS# P4935287 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2069 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Hartridge Hills

3 BEDROOM, 2 BATH HOME IN QUAINT LAKEFRONT GATED NEIGHBORHOOD WITH ACCESS TO THE CHAIN OF LAKES VIA COMMUNITY BOAT RAMP. This home boasts an open f... 

More Details

$355,000
Provided courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY

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 07-20-2025 3:32 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.