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 41-50 of 145
55 Photos 19 Meadowlake Court Winter Haven, FL 33884

19 Meadowlake Court
Winter Haven, FL 33884
Cypresswood
Residential

MLS# O6279343 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 3257 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

New Price Reduction - Priced to Sell! Step into luxury with this stunning ranch-style home in the gated Cypresswood golf community! Nestled on a pe... 

More Details

$549,900
Reduced -$40,100
Provided courtesy of REAL BROKER, 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
20 Photos 7072 Fairview Village Circle Winter Haven, FL 33881

7072 Fairview Village Circle
Winter Haven, FL 33881
Fairview Village
Residential

MLS# L4950375 / Active
1 Beds, 1.00 Total Baths, 1 Full Bath, 680 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Fairview Village

Take a look at this 1 bedroom, 1 bathroom home with a metal roof, located in the active 55+ community of Fairview Village! This great community fea... 

More Details

$49,900
Reduced -$9,600
Provided courtesy of KELLER WILLIAMS REALTY SMART
34 Photos 148 Lake Otis Road Winter Haven, FL 33884

148 Lake Otis Road
Winter Haven, FL 33884
Lakewood
Residential

MLS# P4933622 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 2663 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Lakewood

Spacious 4-Bedroom, 3-Bath Pool Home in the admired Lakewood Community. Nestled on an oversized lot with mature trees, this remodeled tri-level hom... 

More Details

$482,000
Provided courtesy of LOCKHART & ASSOCIATES INC
26 Photos 191 Sweet Circle Winter Haven, FL 33884

191 Sweet Circle
Winter Haven, FL 33884
Orange Manor West Coop Inc
Residential

MLS# P4931913 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1176 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Orange Manor West Coop Inc

LOOK NO FURTHER!!! 2Bed/2Bath located in a fabulous 55+ gated CO-OP community in Winter Haven. The community provides a lifestyle tailored to activ... 

More Details

$67,000
Reduced -$8,000
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
21 Photos 14 Casarena Court Winter Haven, FL 33881

14 Casarena Court
Winter Haven, FL 33881
Casarena On the Lakes
Residential

MLS# L4951457 / Active
2 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 2085 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Casarena On the Lakes

Beautiful Condo featuring 2-Bedroom, 2.5-Bath in Gated Casarena on the Lakes! Located in a small community, this contemporary Mediterranean-style t... 

More Details

$270,000
Reduced -$5,000
Provided courtesy of EXP REALTY LLC
69 Photos 3565 Raleigh Drive Winter Haven, FL 33884

3565 Raleigh Drive
Winter Haven, FL 33884
Traditions Ph 02
Residential

MLS# P4934495 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1866 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Traditions Ph 02

Step into styleyour way! With an acceptable offer, the seller is offering a $5,000 flooring allowance so you can choose the perfect floors to match... 

More Details

$315,000
Provided courtesy of CENTURY 21 WATSON & MYERS REALTY
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
46 Photos 1703 Linz Court Winter Haven, FL 33884

1703 Linz Court
Winter Haven, FL 33884
Vienna Square Phase 3a
Residential

MLS# P4933885 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1164 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Vienna Square Phase 3a

NEW CONSTRUCTION! This brand-new single-story, two bedroom, two bath Villa is located in Vienna Square, a 55+ gated community in Winter Haven. Live... 

More Details

$267,000
Provided courtesy of DGCF REALTY ADVISORS LLC
19 Photos 620 Wexford Court Winter Haven, FL 33884

620 Wexford Court
Winter Haven, FL 33884
Cypresswood Patio Homes
Residential

MLS# O6281987 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1426 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Patio Homes

Welcome to your dream home-Step inside to discover this spacious and stunning MOVE-IN READY 2 bed/ 2 bath with an oversize 2 car garage located in ... 

More Details

$275,000
Provided courtesy of LPT 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 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.