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 121-130 of 144
39 Photos 104 Morning Glory Circle Winter Haven, FL 33884

104 Morning Glory Circle
Winter Haven, FL 33884
Morningside
Residential

MLS# L4953781 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1806 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Morningside

NEW ROOF ~ PERFECT FOR BUYERS INSURANCE PREMIUM! Just listed in the desirable Morningside at Lake Winterset Community! Welcome to luxury living in ... 

More Details

$328,000
Provided courtesy of COLDWELL BANKER REALTY
22 Photos 4747 Mandolin Loop Winter Haven, FL 33884

4747 Mandolin Loop
Winter Haven, FL 33884
Mandolin 02
Residential

MLS# P4935261 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1506 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Mandolin 02

Auction Property. Welcome! Located in a desirable gated community in Southeast Winter Haven. This inviting property offers 3 spacious bedrooms and ... 

More Details

$210,600
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
46 Photos 13 Enclave Drive Winter Haven, FL 33884

13 Enclave Drive
Winter Haven, FL 33884
Cypresswood Enclave Ph 01
Residential

MLS# P4935271 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1526 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Enclave Ph 01

Welcome to this maintained 3 bedroom, 2 bath one-story villa/townhouse located in Enclave, a quiet and desirable neighborhood within the gated golf... 

More Details

$264,900
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
60 Photos 1104 Sawgrass Drive Winter Haven, FL 33884

1104 Sawgrass Drive
Winter Haven, FL 33884
Lake Ashton West Ph II South
Residential

MLS# O6319428 / 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

This is a must see. Located in the prestigious 55+ community of Lake Ashton, welcome to this impeccably designed 2021-built Sebastian model home, w... 

More Details

$439,500
Provided courtesy of ATRIUM REALTY, LLC
52 Photos 301 Terranova Boulevard Winter Haven, FL 33884

301 Terranova Boulevard
Winter Haven, FL 33884
Terranova Phase IV
Residential

MLS# S5129533 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1960 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Terranova Phase IV

Welcome to your dream home at 301 Terranova Blvd, Winter Haven, FL! Located within an exclusive gated community that offers privacy, security, and ... 

More Details

$420,000
Provided courtesy of LPT REALTY, LLC
46 Photos 1077 Medinah Way Winter Haven, FL 33884

1077 Medinah Way
Winter Haven, FL 33884
Cypresswood Tennis Villas
Residential

MLS# K4902980 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1278 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Tennis Villas

HARD TO FIND ...YET EASY TO OWN.!!! ENJOY COMING HOME TO THIS WONDERFUL COMMUNITY IN A TENNIS VILLA, END UNIT IN BEAUTIFUL CYPRESSWOOD WITH LOTS OF... 

More Details

$234,900
Provided courtesy of WESTLAKE REAL ESTATE CO., INC.
75 Photos 4113 Rolling Oaks Drive Winter Haven, FL 33880

4113 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4935311 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1392 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

You won't believe this amazing home that goes on and on. Walk into the front porch area which is finished for additional living space. Then pass in... 

More Details

$129,900
Provided courtesy of COLDWELL BANKER REALTY
79 Photos 1836 Woodpointe Drive Winter Haven, FL 33884

1836 Woodpointe Drive
Winter Haven, FL 33884
Woodpointe Ph 02
Residential

MLS# P4935305 / Active
5 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 4021 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Woodpointe Ph 02

Tucked inside one of Winter Havens most sought-after gated communities, this custom-built lakefront estate on the sparkling, spring-fed Lake Daisy ... 

More Details

$1,050,000
Provided courtesy of JOHN WOOD REALTY, INC.
68 Photos 4115 Rolling Oaks Drive Winter Haven, FL 33880

4115 Rolling Oaks Drive
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4935353 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1416 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

This is a must see home!! This home has two porch areas plus a bonus room. The side porch is perfect for enjoying your morning coffee and watching ... 

More Details

$128,900
Provided courtesy of COLDWELL BANKER REALTY
72 Photos 5200 Pebble Beach Boulevard Winter Haven, FL 33884

5200 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4935325 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2443 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

With fabulous WATER VIEWS and GOLF COURSE views, this elegant residence offers a perfect tropical retreat. A large pool with a attached spa invites... 

More Details

$555,000
Provided courtesy of LAKE ASHTON REALTY INC.

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 2:01 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.