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.

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Displaying results 1-10 of 116
45 Photos 9705 Lake Bess Road UNIT #709 Winter Haven, FL 33884

9705 Lake Bess Road UNIT #709
Winter Haven, FL 33884
Carefree
Residential

MLS# P4930199 / Active
2 Beds, 2.00 Total Baths, 1 Full Bath, 1 Half Bath, 840 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Carefree

Carefree Country Club 55+ gated golf community. This lakeview home consists of Living Room, Dining room, Primary bedroom with built in shelving and... 

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$119,900
Provided courtesy of KELLER WILLIAMS REALTY SMART 1
87 Photos 4 Casarena Court Winter Haven, FL 33881

4 Casarena Court
Winter Haven, FL 33881
Casarena On Lakes
Residential

MLS# L4941142 / Active
3 Beds, 3.00 Total Baths, 2 Full Bath, 1 Half Bath, 3000 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Casarena On Lakes

Enjoy lake and tennis living in a gated community on the Chain of Lakes conveniently located right next to the community pool, hot tub, tennis cour... 

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$549,900
Provided courtesy of EXP REALTY LLC
76 Photos 2 Casarena Court Winter Haven, FL 33881

2 Casarena Court
Winter Haven, FL 33881
Casarena On Lakes
Residential

MLS# B4901400 / Active
3 Beds, 3.00 Total Baths, 3 Full Bath, 2377 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Casarena On Lakes

PRICE ADJUSTMENT......Welcome Home! Located in the highly desirable gated community of Casarena on the Lakes this 3 bedroom 3 full bathroom townhom... 

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$379,900
Reduced -$5,100
Provided courtesy of CRAIG BURKE REAL ESTATE GROUP, LLC
17 Photos 207 Country Ln Ne #207 Winter Haven, FL 33881

207 Country Ln Ne #207
Winter Haven, FL 33881
Country Lake Condo Ph 01
Residential

MLS# O6130677 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1252 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Country Lake Condo Ph 01

Stunning 3Bedroom 2BathSituated in Country Lake a peace of mind Gated community This unit is on the second floor Which features an open floor Plan.... 

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$164,900
Provided courtesy of LA ROSA REALTY KISSIMMEE
22 Photos 1992 Crossroads Boulevard Winter Haven, FL 33881

1992 Crossroads Boulevard
Winter Haven, FL 33881
Crossroads/lk Region
Residential

MLS# O6169343 / Active
4 Beds, 3.00 Total Baths, 3 Full Bath, 1889 Sqft
Area: 33881 - Winter Haven / Florence Villa, Subdivision: Crossroads/lk Region

Charming Winter Haven Home in Gated Community. Step into the epitome of comfort with this stunning 4-bedroom, 3-bathroom residence nestled in the c... 

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$345,000
Reduced -$5,000
Provided courtesy of KELLER WILLIAMS ADVANTAGE III REALTY
69 Photos 3155 Beauchamp Court Winter Haven, FL 33884

3155 Beauchamp Court
Winter Haven, FL 33884
Cypresswood
Residential

MLS# P4928750 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 2103 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

Welcome to your meticulously maintained home at 3155 Beauchamp Ct. in the Plantation area of the Cypresswood golf community! This well maintained 3... 

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$460,000
Reduced -$5,000
Provided courtesy of RE/MAX HERITAGE PROFESSIONALS
86 Photos 341 Greenfield Road Winter Haven, FL 33884

341 Greenfield Road
Winter Haven, FL 33884
Cypresswood
Residential

MLS# O6188721 / Active
4 Beds, 4.00 Total Baths, 2 Full Bath, 2 Half Bath, 2893 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood

If youre looking for a wonderful home in a sought-after Golf and Country Club community check out this 4 bedroom, 2 full bath and 2 half bath home ... 

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$515,500
Reduced -$2,500
Provided courtesy of KELLER WILLIAMS CLASSIC
27 Photos 2210 Sawgrass Court Winter Haven, FL 33884

2210 Sawgrass Court
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential

MLS# P4929192 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1724 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas

This well maintained 2 bedroom 2 bathroom golf villa features recent updates including a new AC system (July 2023) and a new water heater (December... 

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$239,900
Provided courtesy of LOCKHART & ASSOCIATES INC
33 Photos 2809 Wingfoot Court Winter Haven, FL 33884

2809 Wingfoot Court
Winter Haven, FL 33884
Cypresswood Golf Villas
Residential

MLS# O6189503 / Active
2 Beds, 2.00 Total Baths, 2 Full Bath, 1682 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Golf Villas

New Price! Awesome Golf Villa with a Golf Course Fairway View! Check out this lovingly maintained home. View the Cypresswoods Golf Course 8th hole ... 

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$260,000
Reduced -$9,000
Provided courtesy of HAPPY DAYS REALTY LLC
30 Photos 416 Sandestin Drive Winter Haven, FL 33884

416 Sandestin Drive
Winter Haven, FL 33884
Cypresswood Meadows
Residential

MLS# P4929557 / Active
3 Beds, 2.00 Total Baths, 2 Full Bath, 1744 Sqft
Area: 33884 - Winter Haven / Cypress Gardens, Subdivision: Cypresswood Meadows

UPSCALE HOME IN CYPRESSWOOD GOLF COMMUNITY. Beautifully remodeled and ready for the discerning buyer. Large 3 BR/2BA patio home located in beautifu... 

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$369,000
Provided courtesy of CENTURY 21 WATSON & MYERS REALTY

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