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 101-110 of 147
58 Photos 3844 Bedford Avenue Winter Haven, FL 33884

3844 Bedford Avenue
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# P4934764 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 1919 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

Welcome to Traditions, the premier 55+ maintenance-free gated community, where comfort, style, and convenience come together in this beautifully ma... 

More Details

$359,999
Provided courtesy of CENTURY 21 MYERS REALTY LAKE WALES
1 Photos 985 Lunar Lane Winter Haven, FL 33884

985 Lunar Lane
Winter Haven, FL 33884
Crescent Pointe
Residential

MLS# R4909228 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1266 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

$286,232
Reduced -$668
Provided courtesy of VANTAGE PROPERTY MANAGEMENT LLC
89 Photos 255 Lake Link Road Winter Haven, FL 33884

255 Lake Link Road
Winter Haven, FL 33884
Lakewood Add
Residential

MLS# P4934836 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2627 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lakewood Add

Welcome to your dream retreat on the shimmering shores of Lake Link in beautiful Winter Haven, Florida offering a 2-year paid Home Warranty! This s... 

More Details

$625,000
Reduced -$25,000
Provided courtesy of DALTON WADE INC
31 Photos 560 Saint Andrews Road Winter Haven, FL 33884

560 Saint Andrews Road
Winter Haven, FL 33884
Cypresswood
Residential

MLS# P4934871 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1922 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

Immaculate POOL HOME in CYPRESSWOOD - Fully Renovated & Located in a gated golf community!!!Welcome to your dream home in the highly desirable Cypr... 

More Details

$327,000
Reduced -$12,500
Provided courtesy of BETTER HOMES AND GARDENS REAL ESTATE LIFESTYLES REALTY
36 Photos 188 Morning Dew Court Winter Haven, FL 33884

188 Morning Dew Court
Winter Haven, FL 33884
Morningside Ph 02
Residential

MLS# L4953123 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1730 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Morningside Ph 02

Price Reduction! Seller is Motivated! Welcome to this beautifully maintained Mediterranean-style home, nestled in the sought-after, gated Winterset... 

More Details

$282,000
Provided courtesy of REMAX EXPERTS
42 Photos 103 Odin Drive Winter Haven, FL 33884

103 Odin Drive
Winter Haven, FL 33884
Valhalla
Residential

MLS# O6311939 / Active
3 Beds, 4.00 Total Baths, 3 Full Bath, 1 Half Bath, 3062 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Valhalla

Gorgeous oversized town home with two car garage. All inquiries please go through listing agent. House is not vacant. 

More Details

$499,000
Provided courtesy of LIFESTYLE INTERNATIONAL REALTY
48 Photos 380 Niblick Cir Winter Haven, FL 33881

380 Niblick Cir
Winter Haven, FL 33881
Gates Lake Region
Residential

MLS# P4934969 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1603 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Gates Lake Region

New Price Alert! We've just adjusted the price on this beautiful homemaking it an even better value. Plus, take advantage of an Assumable VA Loan f... 

More Details

$325,000
Reduced -$6,000
Provided courtesy of CROSBY & ASSOCIATES, INC.
20 Photos 2202 Garden Lake Drive Winter Haven, FL 33884

2202 Garden Lake Drive
Winter Haven, FL 33884
Richmond Square Sub
Residential

MLS# TB8390860 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1442 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Richmond Square Sub

Welcome to beautiful southeast Winter Haven, home to the Chain of Lakes and Legoland! This spacious 3-bedroom, 2-bath home is in move-in ready cond... 

More Details

$279,000
Reduced -$10,000
Provided courtesy of FLAT FEE MLS REALTY
12 Photos 2919 Woodward Lane Winter Haven, FL 33884

2919 Woodward Lane
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# S5128004 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1649 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

This beautifully maintained home in a 55+ community offers comfort, with access to luxury amenities including a clubhouse, heated pool, fitness cen... 

More Details

$350,000
Provided courtesy of ZARZUELA REALTY, LLC
49 Photos 413 Ruby Lake Place Winter Haven, FL 33884

413 Ruby Lake Place
Winter Haven, FL 33884
Ruby Lake Ph 4
Residential

MLS# P4934997 / Active
4 Beds, 2.00 Total Baths, 2 Full Bath, 2172 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Ruby Lake Ph 4

Welcome to this beautifully maintained pool home offering comfort, space, and style in a prime location! As you enter the walkway, youll be greeted... 

More Details

$514,000
Reduced -$1,000
Provided courtesy of STACEY TOWNS REALTY LLC

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 6:04 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.