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Winter Haven, FL 55+ Retirement Communities and Homes

Winter Haven, Florida, is a charming city perfect for active adults 55+, known for its beautiful chain of lakes and relaxed lifestyle. With a warm climate and picturesque surroundings, Winter Haven offers plenty of outdoor activities, including boating, fishing, and watersports. Residents can explore the scenic beauty of Bok Tower Gardens, stroll along the historic downtown area, and enjoy local shops and restaurants. The city also boasts a vibrant arts and cultural scene, with theaters and music venues. Winter Haven provides a welcoming and engaging environment for a fulfilling retirement.

55+ communities, or active adult communities, are residential areas designed for individuals aged 55 and older. These communities offer a lifestyle tailored to older adults, featuring low-maintenance housing and various amenities such as fitness centers, swimming pools, and walking trails. Social interaction is encouraged through organized events, hobby groups, and recreational activities. Many communities provide additional services like healthcare facilities, transportation, and dining options. Located in desirable climates and scenic areas, they offer a serene and enjoyable living environment. The primary goal is to foster a vibrant, supportive atmosphere where residents can enjoy their retirement years with a focus on health, wellness, and social connections.

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Four Lakes Golf Club

Exact Location MatchExact Location Match

3 Beds | 2 Baths | 1534 Sq. Ft.

1110 La Costa
Winter Haven, FL 33881

Lot 658

LAKE FRONT AT FOUR LAKES! 2001 Jacobsen Lot 658 | $130,000 | 3 Bed |2 Bath | Golf Course & Water Views A sweet Florida retreat in Four Lakes Golf Club Retirement Community! This spacious home features an open layout, an eat-in kitchen with golf course ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near), Rental Homes

Four Lakes Golf Club

Exact Location MatchExact Location Match

3 Beds | 2 Baths | 1568 Sq. Ft.

1412 Wild Dunes Ct,
Winter Haven, FL 33881

54

BRAND NEW - 2025 CHAMPION - 3 BED,2 BATH - 1568 SQ. FT. -Reduced to $189,900 ZERO LOT RENT IN 2025! Pay no lot rent until January 2026! Step into luxury and practicality with this stunning 2025 Champion Live Oak home. This 1568 Sq. Ft. meticulously ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near), Rental Homes

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1568 Sq. Ft.

21 CYPRESS LOOP
Lake Alfred, FL 33850

Site # 0021 Addr: 21 CYPRESS LOOP

Discover this beautifully maintained 2-bed, 2-bath home offering 1,868 total sq. ft. of comfortable living space Cypress Greens golf and tennis community! The split floor plan includes a large living room, tile kitchen with stainless steel appliances, ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Kings Pointe - Sun Communities

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1 Beds | 2 Baths | 864 Sq. Ft.

135 Winterdale Dr. S
Lake Alfred, FL 33850

Site # 0212 Addr: 135 Winterdale Dr. S

This beautifully renovated 1-bedroom, 2-bath home is a true standout, blending timeless elegance with everyday comfort. Inside, you ll find stunning real wood cabinetry complemented by sleek, modern finishes throughout. Step outside to your private backyard ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Kings Pointe - Sun Communities

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2 Beds | 2 Baths | 1200 Sq. Ft.

142 Winterdale Dr. N
Lake Alfred, FL 33850

Site # 0185 Addr: 142 Winterdale Dr. N

WOW! Don t miss the opportunity to own this beautiful 2-bedroom, 2-bath home featuring a spacious garage and ample storage. The open-concept living room, dining area, and kitchen create an inviting space that s perfect for entertaining. The large primary ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

3 Beds | 2 Baths | 1536 Sq. Ft.

136 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0136 Addr: 136 CYPRESS WAY

Welcome to this charming 3-bedroom, 2-bath manufactured home in a desirable 55+ golf community! This well-maintained home offers a split floor plan for privacy and convenience. The open-concept layout connects the kitchen, dining, and living areas, creating ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1056 Sq. Ft.

458 Gulf Stream Dr. N
Lake Alfred, FL 33850

Site # 0054 Addr: 458 Gulf Stream Dr. N

Charming 2-bedroom, 2-bath home in a beautiful gated 55+ community! This home features a bright open floorplan, brand-new carpet in the bedrooms, and a cozy kitchen nook perfect for casual dining. Enjoy the Florida lifestyle on the perfectly sized lanai, ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1248 Sq. Ft.

109 Winterdale Dr. S
Lake Alfred, FL 33850

Site # 0225 Addr: 109 Winterdale Dr. S

Step into comfort and style with this beautifully updated home located in a desirable 55+ gated community. From the moment you enter, you ll appreciate the bright open floorplan designed for easy living and entertaining. The home features brand-new flooring ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Kings Pointe - Sun Communities

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2 Beds | 2 Baths | 1152 Sq. Ft.

307 Winter Garden Ct.
Lake Alfred, FL 33850

Site # 0122 Addr: 307 Winter Garden Ct.

This newly listed 2 bedroom 2 bath home has new windows and new siding and so much more. Walk into the kitchen past the formal dining area with a breakfast nook looking out the front bay windows. Large living room with a lanai at the front of the ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

3 Beds | 2 Baths | 1200 Sq. Ft.

114 Winterdale Dr. S
Lake Alfred, FL 33850

Site # 0199 Addr: 114 Winterdale Dr. S

Welcome to your slice of sweet Southern charm in one of Florida s premier 55+ communities! This beautiful 3-bedroom, 2-bath home combines comfort, convenience, and timeless style. You'll love the spacious kitchen, which features abundant cabinetry and ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1248 Sq. Ft.

228 GUM LANE
Lake Alfred, FL 33850

Site # 0228 Addr: 228 GUM LANE

Enjoy resort-style living in this beautifully maintained 2018-built home featuring 2 bedrooms, 2 baths, and a versatile den. The spacious layout includes a cozy carpeted living room and wood-look vinyl flooring throughout the rest of the home. The bright ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1232 Sq. Ft.

194 MAGNOLIA RUN
Lake Alfred, FL 33850

Site # 0194 Addr: 194 MAGNOLIA RUN

Pack your bags and get ready to enjoy your new home in an active 55+ community! 2 bed/2 bath home offers a perfect blend of comfort, space, and modern updates. Open floor plan seamlessly connects living, dining, and kitchen areas, perfect for entertaining ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1248 Sq. Ft.

94 PALM LANE
Lake Alfred, FL 33850

Site # 0094 Addr: 94 PALM LANE

Charming 2-bedroom, 2-bath home comes partially furnished and includes a golf cart! Enjoy peace of mind with 2023 updates new roof, HVAC system, and stainless-steel kitchen appliances. The spacious primary suite features an ensuite bath with walk-in ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1352 Sq. Ft.

49 CREEK CIRCLE
Lake Alfred, FL 33850

Site # 0049 Addr: 49 CREEK CIRCLE

Discover comfort and convenience in this partially furnished 2 bedroom, 2 bath home located in a vibrant 55+ golf community. Wake up to beautiful golf course views and enjoy the ease of having a golf cart included. The spacious primary suite features ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1800 Sq. Ft.

149 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0149 Addr: 149 CYPRESS WAY

Welcome to this spacious unfurnished 2 bed, 2 bath + den home with a 1-car attached garage, offering approximately 1,400 square feet of living space, located in the Cypress Greens active 55+ golf and tennis community. This newer home features an open ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1198 Sq. Ft.

173 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0173 Addr: 173 CYPRESS WAY

Beautifully updated 2-bedroom, 2-bath waterfront home in a desirable 55+ golf course community! Fully furnished and move-in ready, home features an open-concept floor plan connecting the kitchen, dining, and living areas, creating a bright, open, and ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1080 Sq. Ft.

157 Winterdale Dr. N
Lake Alfred, FL 33850

Site # 0174 Addr: 157 Winterdale Dr. N

his beautifully maintained 2-bedroom, 2-bath home offers a bright open floor plan designed for comfort and convenience. Located in a desirable 55+ gated community, this home is perfect for relaxed, low-maintenance living. Enjoy a spacious living and ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Cypress Greens - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1920 Sq. Ft.

168 CYPRESS WAY
Lake Alfred, FL 33850

Site # 0168 Addr: 168 CYPRESS WAY

Spacious 2-bedroom, 2-bath home with desirable split floor plan, includes a private in-law suite with its own bedroom, den, and kitchenette. Primary bedroom offers an ensuite bath with a walk-in shower. Large open living / dining area creates an inviting ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes, Golf Course Living, Waterfront Living (or near)

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

3 Beds | 2 Baths | 1248 Sq. Ft.

536 Club Hill Road
Lake Alfred, FL 33850

Site # 0018 Addr: 536 Club Hill Road

This stunning 2-bedroom, 2-bath residence showcases a beautifully designed open-concept floor plan, offering an effortless blend of sophistication and comfort. Rich hardwood flooring flows seamlessly throughout the home, creating a warm and refined ambiance. The ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Kings Pointe - Sun Communities

Nearby Location MatchNearby Location Match

2 Beds | 2 Baths | 1040 Sq. Ft.

508 Club Hill Road
Lake Alfred, FL 33850

Site # 0004 Addr: 508 Club Hill Road

Don t miss out on this beautiful 2-bedroom, 2-bath home featuring a bright and spacious open floor plan. Enjoy brand-new stainless steel appliances, a generous walk-in closet, and a screened-in lanai perfect for relaxing with your morning coffee or unwinding ...

Community Lifestyles: 55+ Communities, Active Retirement, Manufactured Homes

Winter Haven, Florida, is a charming city perfect for active adults 55+, known for its beautiful chain of lakes and relaxed lifestyle. With a warm climate and picturesque surroundings, Winter Haven offers plenty of outdoor activities, including boating, fishing, and watersports. Residents can explore the scenic beauty of Bok Tower Gardens, stroll along the historic downtown area, and enjoy local shops and restaurants. The city also boasts a vibrant arts and cultural scene, with theaters and music venues. Winter Haven provides a welcoming and engaging environment for a fulfilling retirement.

55+ communities, or active adult communities, are residential areas designed for individuals aged 55 and older. These communities offer a lifestyle tailored to older adults, featuring low-maintenance housing and various amenities such as fitness centers, swimming pools, and walking trails. Social interaction is encouraged through organized events, hobby groups, and recreational activities. Many communities provide additional services like healthcare facilities, transportation, and dining options. Located in desirable climates and scenic areas, they offer a serene and enjoyable living environment. The primary goal is to foster a vibrant, supportive atmosphere where residents can enjoy their retirement years with a focus on health, wellness, and social connections.

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