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 61-70 of 147
31 Photos 2254 Firestone Place UNIT #2254 Winter Haven, FL 33884

2254 Firestone Place UNIT #2254
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential

MLS# P4933928 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1430 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas

One or more photo(s) has been virtually staged. Welcome home to this spacious 2-bedroom/2-bathroom Golf Villa located in the highly-sought-after Cy... 

More Details

$219,900
Provided courtesy of JOHN WOOD REALTY, INC.
81 Photos 3686 Plymouth Drive Winter Haven, FL 33884

3686 Plymouth Drive
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# P4933851 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2404 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

This beautifully updated 4-bedroom, 3-bath residence offers a spacious and thoughtfully designed layout with 2,404 sq ft of comfortable living spac... 

More Details

$399,900
Provided courtesy of GLOBAL LIFESTYLE LLC
15 Photos 2284 Firestone Place Winter Haven, FL 33884

2284 Firestone Place
Winter Haven, FL 33884
Cypresswood Golf Villas Un 3 B
Residential

MLS# O6282413 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1164 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas Un 3 B

**""Embrace comfort and elegance in this beautiful 2-bedroom, 2-bathroom villa, offering nearly 1,400 sq. ft. of well-designed living space. Enjoy ... 

More Details

$230,000
Provided courtesy of MERVIN MORGAN REALTY & PROPERTY MANAGEMENT LLC
39 Photos 447 Lanham Drive Winter Haven, FL 33881

447 Lanham Drive
Winter Haven, FL 33881
Sanctuary By the Lake Ph 2
Residential

MLS# P4933969 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 1845 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Sanctuary By the Lake Ph 2

One or more photo(s) has been virtually staged. Welcome to this stunning 4-bedroom, 2-bathroom home nestled in a prestigious gated, waterfront comm... 

More Details

$324,800
Reduced -$14,700
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
69 Photos 5268 Pebble Beach Boulevard Winter Haven, FL 33884

5268 Pebble Beach Boulevard
Winter Haven, FL 33884
Lake Ashton West Ph 01
Residential

MLS# P4933937 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2354 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 01

CDD DEBT PAID IN FULL! Golf Course Frontage and Amazing Water Views! Welcome to luxury living at its finest in the sought-after Lake Ashton 55+ com... 

More Details

$599,000
Provided courtesy of LAKE ASHTON REALTY INC.
45 Photos 404 Laurel Cove Way UNIT #404 Winter Haven, FL 33884

404 Laurel Cove Way UNIT #404
Winter Haven, FL 33884
Winterset 01 A Condo 02 Amd
Residential

MLS# P4934001 / 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

PRICE IMPROVEMENT...WATERFRONT CONDO IN GATED WINTERSET COMMUNITY!! This inviting ground level, 2 Bedroom/2 Bathroom Condo offers an exceptional co... 

More Details

$165,000
Reduced -$4,900
Provided courtesy of COLDWELL BANKER REALTY
48 Photos 507 Eagle Pond Drive UNIT #507 Winter Haven, FL 33884

507 Eagle Pond Drive UNIT #507
Winter Haven, FL 33884
Eagle Pond Condo
Residential

MLS# L4951021 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1017 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Eagle Pond Condo

FOR SALE - 2 Bedroom/2 Bath Condo in lovely Cypresswood Gulf and Country Club. This condo overlooks a pond and beautiful cypress trees. It is very ... 

More Details

$186,000
Reduced -$12,500
Provided courtesy of COLDWELL BANKER REALTY
51 Photos 2885 Attwater Loop Winter Haven, FL 33884

2885 Attwater Loop
Winter Haven, FL 33884
Traditions Villas
Residential

MLS# S5122423 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1400 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Villas

Prime LOCATION in Traditions - A Premier 55+ CommunityDiscover the perfect blend of comfort and convenience in this charming 2-bedroom, 2-bathroom ... 

More Details

$215,000
Reduced -$14,998
Provided courtesy of EXP REALTY LLC
60 Photos 4424 Limewood Street Winter Haven, FL 33880

4424 Limewood Street
Winter Haven, FL 33880
Oakwood Estates
Residential

MLS# P4934135 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1440 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Oakwood Estates

Spacious is the best word to describe this home. The home has 1440 sf plus a side porch for additional entertaining space. The home has two living ... 

More Details

$129,000
Provided courtesy of COLDWELL BANKER REALTY
91 Photos 121 Greenfield Road Winter Haven, FL 33884

121 Greenfield Road
Winter Haven, FL 33884
Cypresswood
Residential

MLS# L4951357 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2900 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

Truly one of a kind home in the sought after neighborhood of Cypresswood Golf and Country Club. This is the only home with a fenced in yard that is... 

More Details

$499,900
Provided courtesy of REMAX EXPERTS

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 7:25 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.