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Winter Garden, FL 55+ active adult communities & homes for sale - Page 3

109 communities near Winter Garden

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Lake James
$300Ks - $500Ks
Lake James, Lakeland, FL
New and Resale | 55+ age-restricted | Built 2004 - present | 216 homes
Gatherings of Lake Nona
$300Ks - $400Ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
Vienna Square
$200Ks - $300Ks
Vienna Square, Winter Haven, FL
New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes
Windermere
$100Ks - $300Ks
Windermere, Inverness, FL
Resale Only | Age-targeted | Built 1989 - present | 180 homes
Heritage - The Cottages o...
$200Ks - $300Ks
Heritage - The Cottages o..., Okahumpka, FL
New Construction | 55+ age-restricted | Built 2022 - present | 179 homes
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Carlsberg Estates on Lake...
$100Ks - $300Ks
Carlsberg Estates on Lake..., Lake Wales, FL
Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes
Tarawood
$200Ks
Tarawood, Floral City, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 150 homes
5 rating (1 reviews) Silver Lakes
$200Ks - $400Ks
Silver Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes
Enclave at VillageWalk
$1Ms
Enclave at VillageWalk, Orlando, FL
Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes
Villas On The Green
$200Ks
Villas On The Green, Riverview, FL
Resale Only | 55+ age-restricted | Built 1989 - 1992 | 105 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Thunderbird Hill
$100Ks - $200Ks
Thunderbird Hill, Sebring, FL
Resale Only | 55+ age-restricted | Built 1984 - 2000 | 103 homes
Liberty Village
$200Ks - $300Ks
Liberty Village, Ocala, FL
New and Resale | 55+ age-restricted | Built 2023 - present | 100 homes
Fountain View
$300Ks - $400Ks
Fountain View, Ormond Beach, FL
New Construction | 55+ age-restricted | Built 2023 - present | 100 homes
Archers Mill
$300Ks - $400Ks
Archers Mill, Ormond Beach, FL
New Construction | Age-targeted | 94 homes
Serenity Reserve
$500Ks - $600Ks
Serenity Reserve, St. Cloud, FL
Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Spring Lake Towers
$100Ks
Spring Lake Towers, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes
The Wellington
$100Ks - $200Ks
The Wellington, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes
Lakes at Laurel Highlands
$300Ks
Lakes at Laurel Highlands, Lakeland, FL
New Construction | Age-targeted | Built 2017 - present | 65 homes
2 rating (1 reviews) Heritage Landings
$300Ks
Heritage Landings, Lakeland, FL
New Construction | 55+ age-restricted | Built 2017 - 2020 | 65 homes
Bridgewater Landing
$300Ks
Bridgewater Landing, Riverview, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 64 homes
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Summit Chase Villas
$100Ks
Summit Chase Villas, Tavares, FL
Resale Only | 55+ age-restricted | Built 1982 - 1989 | 60 homes
Alhambra Villas Condomini...
$100Ks - $200Ks
Alhambra Villas Condomini..., DeLand, FL
Resale Only | 55+ age-restricted | Built 1970 - 1972 | 60 homes
El Dorado
$500Ks - $800Ks
El Dorado, Ocala, FL
Resale Only | Age-targeted | Built 1978 - 2003 | 56 homes
Hidden Creek
$100Ks - $200Ks
Hidden Creek, Sebring, FL
Resale Only | 55+ age-restricted | Built 1986 - 2007 | 55 homes
Poinsettia Heights
$100Ks - $200Ks
Poinsettia Heights, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Oakview
$100Ks - $200Ks
Oakview, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes
Preserve at Lakeside Land...
$300Ks
Preserve at Lakeside Land..., Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes
Del Webb Minneola
$400Ks - $800Ks
Del Webb Minneola, Minneola, FL
New Construction | 55+ age-restricted | Built 2020 - present
Ridgehaven
$200Ks - $500Ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
Spruce Creek South 9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$319,000

3 beds

|

2 baths

|

1,450 sq ft

|

House

9645 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
On Top of the World 9686 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$272,000

2 beds

|

2 baths

|

1,515 sq ft

|

House

9686 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
Pine Run Estates 10040 SW 98TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$168,000

2 beds

|

2 baths

|

1,144 sq ft

|

House

10040 SW 98TH AVE, OCALA, FL, 34481
Community: Pine Run Estates
Valencia Ridge 32608 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$669,900

3 beds

|

3 baths

|

2,209 sq ft

|

House

32608 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
Del Webb Sunbridge 6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$450,000

3 beds

|

3 baths

|

1,738 sq ft

|

Townhouse

6501 CYRILS DR, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 5333 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$275,000

2 beds

|

2 baths

|

1,368 sq ft

|

Halfplex

5333 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
Pelican Bay Daytona Beach 149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$190,000

2 beds

|

2 baths

|

1,192 sq ft

|

Condo

149 BLUE HERON DR C, DAYTONA BEACH, FL, ...
On Top of the World 9662 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481
$174,500

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9662 SW 95TH CT A, OCALA, FL, 34481
Community: On Top of the World
Stone Creek 9009 SW 52ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$392,810

2 beds

|

3 baths

|

2,080 sq ft

|

House

9009 SW 52ND PLACE RD, OCALA, FL, 34481
Community: Stone Creek
New Sandpiper Golf & Country Club 6119 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$245,000

2 beds

|

2 baths

|

1,148 sq ft

|

House

6119 SANDPIPERS DR, LAKELAND, FL, 33809
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
Stonecrest 12135 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$450,000

3 beds

|

2 baths

|

2,031 sq ft

|

House

12135 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Sun City Center 802 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$295,000

3 beds

|

2 baths

|

1,568 sq ft

|

Villa

802 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Palms at Serenoa 17581 SUMMERSWEET WAY, CLERMONT, FL, 347..., Clermont, FL 34714
$325,000

2 beds

|

2 baths

|

1,627 sq ft

|

Villa

17581 SUMMERSWEET WAY, CLERMONT, FL, 347...
Community: Palms at Serenoa
The Villages® 5617 STRICKLIN ST, THE VILLAGES, FL, 321..., The Villages, FL 32163
$499,000

3 beds

|

2 baths

|

1,696 sq ft

|

House

5617 STRICKLIN ST, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation at Leesburg 25129 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,900

2 beds

|

2 baths

|

2,063 sq ft

|

House

25129 RIVERWALK DR, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Cresswind at Victoria Gardens 1128 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$577,500

2 beds

|

3 baths

|

2,670 sq ft

|

House

1128 HERON POINT WAY, DELAND, FL, 32724
Cherrywood 10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$190,000

3 beds

|

2 baths

|

1,667 sq ft

|

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Solivita 274 MARABELLA LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$325,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

274 MARABELLA LOOP, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1428 ALMANZA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$320,000

2 beds

|

2 baths

|

1,174 sq ft

|

Villa

1428 ALMANZA DR, THE VILLAGES, FL, 32159
Community: The Villages®
New Plantation at Leesburg 25205 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$255,000

2 beds

|

2 baths

|

1,328 sq ft

|

House

25205 CRANES ROOST CIR, LEESBURG, FL, 34...
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
New Ocala Preserve 3399 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$650,000

3 beds

|

3 baths

|

2,763 sq ft

|

House

3399 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 17602 SE 82ND WOODLAWN AVE, THE VILLAGES..., The Villages, FL 32162
$459,000

3 beds

|

2 baths

|

1,924 sq ft

|

House

17602 SE 82ND WOODLAWN AVE, THE VILLAGES...
Community: The Villages®
The Villages® 2737 AVA ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$725,000

3 beds

|

2 baths

|

1,630 sq ft

|

House

2737 AVA ST, THE VILLAGES, FL, 32163
Community: The Villages®
New The Villages® 13651 COUNTY ROAD 109H, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$199,000

3 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

13651 COUNTY ROAD 109H, LADY LAKE, FL, 3...
Community: The Villages®
The Villages® 802 MIRANDA WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$349,000

2 beds

|

2 baths

|

1,471 sq ft

|

House

802 MIRANDA WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
The Lakes at Harmony 3443 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$309,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

3443 SAGEBRUSH ST, HARMONY, FL, 34773
New The Villages® 565 SOCIETY HILL CIR, THE VILLAGES, FL, ..., The Villages, FL 32162
$759,000

3 beds

|

2 baths

|

1,899 sq ft

|

House

565 SOCIETY HILL CIR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 859 KLINE ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$424,900

3 beds

|

2 baths

|

1,861 sq ft

|

House

859 KLINE ST, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 1403 ESPINOZA LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$281,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1403 ESPINOZA LN, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 2935 CEDAR GROVE LOOP, THE VILLAGES, FL,..., The Villages, FL 32163
$895,000

3 beds

|

2 baths

|

3,466 sq ft

|

House

2935 CEDAR GROVE LOOP, THE VILLAGES, FL,...
Community: The Villages®
Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.
The Villages® 3377 QUAIL HOLLOW CT, THE VILLAGES, FL, ..., The Villages, FL 32163
$334,900

3 beds

|

2 baths

|

1,488 sq ft

|

House

3377 QUAIL HOLLOW CT, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 1096 STRADINGER ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$499,900

3 beds

|

2 baths

|

1,998 sq ft

|

House

1096 STRADINGER ST, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 3753 COYNE LOOP, THE VILLAGES, FL, 32163, The Villages, FL 32163
$728,900

3 beds

|

2 baths

|

1,956 sq ft

|

House

3753 COYNE LOOP, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek Preserve 11655 SW 140TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$249,900

2 beds

|

2 baths

|

1,866 sq ft

|

House

11655 SW 140TH LN, DUNNELLON, FL, 34432
Stone Creek 5457 SW 82ND TER, OCALA, FL, 34481, Ocala, FL 34481
$327,580

2 beds

|

2 baths

|

1,433 sq ft

|

House

5457 SW 82ND TER, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden, FL? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 5953 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$524,390

3 beds

|

3 baths

|

2,483 sq ft

|

House

5953 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
On Top of the World 10248 SW 93RD PL, OCALA, FL, 34481, Ocala, FL 34481
$625,000

3 beds

|

3 baths

|

2,828 sq ft

|

House

10248 SW 93RD PL, OCALA, FL, 34481
Community: On Top of the World
Cherrywood 9627 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$249,990

3 beds

|

2 baths

|

1,615 sq ft

|

House

9627 SW 62ND CT, OCALA, FL, 34476
Community: Cherrywood
Cherrywood 9595 SW 62ND CT, OCALA, FL, 34476, Ocala, FL 34476
$254,990

3 beds

|

2 baths

|

1,615 sq ft

|

House

9595 SW 62ND CT, OCALA, FL, 34476
Community: Cherrywood
Stone Creek 5230 SW 88TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$397,140

2 beds

|

2 baths

|

1,948 sq ft

|

House

5230 SW 88TH CIR, OCALA, FL, 34481
Community: Stone Creek

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109 communities near Winter Garden
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