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 149
41 Photos 506 Sweet Bay Circle UNIT #506 Winter Haven, FL 33884

506 Sweet Bay Circle UNIT #506
Winter Haven, FL 33884
Winterset 01 A Condo 02 Amd
Residential

MLS# L4954685 / 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

Welcome to 506 Sweet Bay Circle, a stunning FULLY RENOVATED lakefront condo located in the highly desirable gated community of Winterset in Winter ... 

More Details

$234,900
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
36 Photos
Open House: Sat Jul 26th, 11:00am - 2:00pm
718 Canberra Road Winter Haven, FL 33884

718 Canberra Road
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential

MLS# L4954473 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2159 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Patio Homes

Elevated Living on the Fairway - Fully Renovated & ReadyWelcome to 718 Canberra Roadwhere luxury living meets peace of mind. This completely renova... 

More Details

$379,999
Provided courtesy of LA ROSA REALTY PRESTIGE
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
40 Photos
Open House: Today 1:00pm - 3:00pm
1129 Bowline Street Winter Haven, FL 33880

1129 Bowline Street
Winter Haven, FL 33880
Shores At Lake Sears
Residential

MLS# L4953684 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1499 Sqft
Area: 33880 - Winter Haven/eloise/jpv/wahnetta, Subdivision: Shores At Lake Sears

***$10k PRICE REDUCTION***Welcome to 1129 Bowline Street - a beautifully maintained home nestled in a quiet and desirable GATED neighborhood in Win... 

More Details

$299,900
Reduced -$10,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
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
29 Photos 7102 Fairview Village Circle Winter Haven, FL 33881

7102 Fairview Village Circle
Winter Haven, FL 33881
Fairview Village
Residential

MLS# L4952803 / Active
2 Beds, 1.00 Total Baths, 1 Full Bath, 712 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Fairview Village

Welcome to this active 55+ waterfront community nestled along the peaceful canal between Lake Hamilton and Lake Henry, offering stunning lake views... 

More Details

$72,500
Reduced -$2,500
Provided courtesy of KELLER WILLIAMS REALTY SMART
71 Photos 1394 Oakmont Drive Winter Haven, FL 33884

1394 Oakmont Drive
Winter Haven, FL 33884
Lake Ashton West Ph 2
Residential

MLS# L4952569 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2606 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lake Ashton West Ph 2

Back on market! Buyer(s) contingency fell through. Discover an exceptional home for sale in the beautiful Lake Ashton Golf course community, which ... 

More Details

$565,000
Provided courtesy of AGILE GROUP REALTY
38 Photos 1620 Linz Court Winter Haven, FL 33884

1620 Linz Court
Winter Haven, FL 33884
Vienna Square Ph 2c
Residential

MLS# L4952436 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1329 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Ph 2c

Introducing your dream retirement oasis! Nestled in a serene 55+ community, this charming 2-bedroom, 2-bathroom abode offers comfort and convenienc... 

More Details

$245,000
Reduced -$3,000
Provided courtesy of LPT REALTY, LLC
46 Photos 375 Troon Court Winter Haven, FL 33884

375 Troon Court
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential

MLS# L4952323 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1725 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Patio Homes

Attention Investors & Home Buyers! Located in the desirable Cypresswood Golf & Country Club in Winter Haven, with a LOW HOA FEE of $128.00 MONTHLY,... 

More Details

$269,999
Increase +$14,999
Provided courtesy of REMAX EXPERTS
40 Photos 7046 Fairview Village Circle Winter Haven, FL 33881

7046 Fairview Village Circle
Winter Haven, FL 33881
Fairview Village
Residential

MLS# L4951816 / Active
3 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 700 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Fairview Village

Do you have dreams of easy mornings on your front porch sipping your perfect cup of coffee with a spectacular view of Lake Henry. This great commun... 

More Details

$85,000
Reduced -$15,000
Provided courtesy of KELLER WILLIAMS REALTY SMART

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 07-27-2025 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.