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 111-120 of 145
54 Photos 4142 Sprucewood Street Winter Haven, FL 33880

4142 Sprucewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4933428 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1104 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Move right into this beautifully furnished home. This home features a nice open living area with vinyl plank flooring throughout. The kitchen is op... 

More Details

$118,000
Reduced -$6,000
Provided courtesy of COLDWELL BANKER REALTY
64 Photos 2683 Wyndsor Oaks Way Winter Haven, FL 33884

2683 Wyndsor Oaks Way
Winter Haven, FL 33884
Wyndsor At Lake Winterset
Residential

MLS# P4933374 / Active
4 Beds, 4.00 Total Baths, 4 Full Bath, 3440 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Wyndsor At Lake Winterset

Welcome to 2683 Wyndsor Oaks Way, Winter Haven, FL - an extraordinary residence in the highly sought-after gated Wyndsor at Lake Winterset communit... 

More Details

$849,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
33 Photos 111 Woden Way Winter Haven, FL 33884

111 Woden Way
Winter Haven, FL 33884
Valhalla
Residential

MLS# P4933285 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3109 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Valhalla

Discover this exquisite 4-bedroom, 3-bath home that perfectly combines elegance and comfort. The primary bedroom features an en-suite bathroom and ... 

More Details

$399,900
Provided courtesy of NEXTHOME NORRIS & COMPANY REALTY
46 Photos 2428 Wildwood Court Winter Haven, FL 33884

2428 Wildwood Court
Winter Haven, FL 33884
Eloise Pointe Estates
Residential

MLS# P4933270 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3001 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eloise Pointe Estates

****Veterans: Take Advantage of a 4.875% Assumable VA Loan!****Welcome to the lifestyle youve been dreaming of. Nestled within the gated enclave of... 

More Details

$640,000
Reduced -$10,000
Provided courtesy of EXP REALTY LLC
43 Photos 4068 Carteret Drive Winter Haven, FL 33884

4068 Carteret Drive
Winter Haven, FL 33884
Traditions Ph 01
Residential

MLS# P4933272 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1928 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 01

Welcome to your dream retirement home! This charming and spacious 3-bedroom, 2-bathroom gem is nestled within a desirable 55+ community, offering t... 

More Details

$287,000
Reduced -$2,250
Provided courtesy of THE STONES REAL ESTATE FIRM
54 Photos 4343 Cherrywood Street Winter Haven, FL 33880

4343 Cherrywood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4933061 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1152 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Walk right into your new home. This home comes fully furnished with everything you might need. The living area is perfect for relaxing and enjoying... 

More Details

$129,000
Provided courtesy of COLDWELL BANKER REALTY
35 Photos 603 Sweet Bay Circle UNIT #603 Winter Haven, FL 33884

603 Sweet Bay Circle UNIT #603
Winter Haven, FL 33884
Winterset 01 A Condo 02 Amd
Residential

MLS# P4933059 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1090 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Winterset 01 A Condo 02 Amd

Charming and move-in ready, this 2-bedroom, 2-bathroom condo in Winter Havens desirable Winterset community offers a comfortable and low-maintenanc... 

More Details

$167,900
Reduced -$27,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
71 Photos 4161 Rolling Oaks Drive Winter Haven, FL 33880

4161 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4933050 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1104 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Move right into this beautiful home, located in Oakwood Estates, a 55+ community. This home will be furnished with what you see. The living area is... 

More Details

$130,000
Reduced -$2,000
Provided courtesy of COLDWELL BANKER REALTY
52 Photos 3206 Heron Cove Winter Haven, FL 33884

3206 Heron Cove
Winter Haven, FL 33884
Heron Cay
Residential

MLS# L4949141 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3050 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Heron Cay

Welcome to 3206 Heron Cove. As you step into the foyer, you'll find an expansive main living area which boasts spacious living & dining areas, as w... 

More Details

$645,000
Reduced -$4,900
Provided courtesy of THE MARKET REALTY COMPANY
46 Photos 2825 Attwater Loop Winter Haven, FL 33884

2825 Attwater Loop
Winter Haven, FL 33884
Traditions Ph 2a
Residential

MLS# O6260348 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1385 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 2a

Motivated seller offering $2,000 in closing costs plus a 1-year HOA credit. Located in the highly desirable 55+ community of Traditions in Winter H... 

More Details

$233,000
Provided courtesy of MILLENIUM REALTY GROUP

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 9:39 AM 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.