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

3,648 homes near Winter Garden

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5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
Del Webb Oasis, Winter Garden, FL
New Construction | 55+ age-restricted | Built 2020 - present | 422 homes
4 rating (17 reviews) The Villages®
<$100k - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
4.1 rating (55 reviews) On Top of the World
$100Ks - $600Ks
On Top of the World, Ocala, FL
New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes
3.8 rating (14 reviews) Sun City Center
<$100k - $500Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$100Ks - $700Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
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3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.1 rating (29 reviews) Oak Run
$100Ks - $300Ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
4.5 rating (11 reviews) Spruce Creek Country Club
$200Ks - $500Ks
Spruce Creek Country Club, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes
5 rating (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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.
5 rating (3 reviews) Stonecrest
<$100k - $500Ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (7 reviews) Kings Ridge
$200Ks - $400Ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (3 reviews) Twin Lakes
$200Ks - $900Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
$100Ks - $600Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.6 rating (5 reviews) Ocala Preserve
$200Ks - $600Ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
4.7 rating (11 reviews) Valencia Lakes
$200Ks - $900Ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$300Ks - $2Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $500Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
5 rating (8 reviews) Royal Highlands
$200Ks - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Tampa Bay Golf and Countr...
$200Ks - $400Ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
5 rating (1 reviews) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300Ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Sandpiper Golf & Coun...
$200Ks - $300Ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
3.6 rating (5 reviews) Heritage Hills
$200Ks - $500Ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Ocala Palms
$100Ks - $500Ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300Ks - $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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.
5 rating (5 reviews) SummerGlen
$200Ks - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Legacy of Leesburg
$200Ks - $400Ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
No reviews yet Breakaway Trails
$300Ks - $1Ms
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$400Ks - $900Ks
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4 rating (2 reviews) Harbor Hills Country Club
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.8 rating (6 reviews) Highland Lakes
$200Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$300Ks - $1Ms
Lake Jovita Golf and Coun..., Dade City, FL
New and Resale | Age-targeted | Built 1999 - present | 875 homes
No reviews yet Esplanade at Wiregrass Ra...
$400Ks - $1Ms
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Royal Highlands 21815 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

3 baths

|

2,369 sq ft

|

House

21815 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
Plantation at Leesburg 25043 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748
$199,900

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

25043 BELLEVUE, LEESBURG, FL, 34748
On Top of the World 9088 SW 95TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$249,000

3 beds

|

2 baths

|

1,745 sq ft

|

House

9088 SW 95TH AVE, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1643 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$375,000

2 beds

|

2 baths

|

1,947 sq ft

|

House

1643 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Spruce Creek North 10986 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$213,000

3 beds

|

2 baths

|

1,482 sq ft

|

House

10986 SW 65TH AVE, OCALA, FL, 34476
Community: Spruce Creek North
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Windermere 820 LANARK DR, INVERNESS, FL, 34453, Inverness, FL 34453
$209,900

2 beds

|

2 baths

|

1,169 sq ft

|

House

820 LANARK DR, INVERNESS, FL, 34453
Community: Windermere
Del Webb Orlando 418 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$356,400

3 beds

|

2 baths

|

1,713 sq ft

|

House

418 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Esplanade at Wiregrass Ranch 4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543
$875,000

3 beds

|

3 baths

|

3,087 sq ft

|

House

4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33...
On Top of the World 8584 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$379,000

3 beds

|

2 baths

|

1,846 sq ft

|

House

8584 SW 86TH CIR, OCALA, FL, 34481
Community: On Top of the World
Scottish Highlands 10 BRIGADOON CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$188,500

2 beds

|

2 baths

|

1,336 sq ft

|

House

10 BRIGADOON CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
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.
On Top of the World 8723 SW 93RD LN A, OCALA, FL, 34481, Ocala, FL 34481
$140,000

2 beds

|

2 baths

|

1,369 sq ft

|

Villa

8723 SW 93RD LN A, OCALA, FL, 34481
Community: On Top of the World
The Villages® 17773 SE 91ST FREEDOM CT, THE VILLAGES, ..., The Villages, FL 32162
$317,900

2 beds

|

2 baths

|

1,165 sq ft

|

Villa

17773 SE 91ST FREEDOM CT, THE VILLAGES, ...
Community: The Villages®
On Top of the World 10418 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$375,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

10418 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
The Villages® 2412 MERIDA CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$310,000

3 beds

|

2 baths

|

1,527 sq ft

|

House

2412 MERIDA CIR, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 7326 SE 173RD ARLINGTON LOOP, THE VILLAG..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

7326 SE 173RD ARLINGTON LOOP, THE VILLAG...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 17608 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162
$369,000

3 beds

|

2 baths

|

1,500 sq ft

|

House

17608 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
Sun City Center 1238 FORDHAM DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$280,000

2 beds

|

2 baths

|

1,024 sq ft

|

House

1238 FORDHAM DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
The Villages® 1380 TALLOWTREE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$260,000

3 beds

|

2 baths

|

1,240 sq ft

|

House

1380 TALLOWTREE DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 318 DEL MAR DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$299,900

2 beds

|

2 baths

|

1,818 sq ft

|

House

318 DEL MAR DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 3312 BARRINGTON CT, THE VILLAGES, FL, 32..., The Villages, FL 32162
$795,000

3 beds

|

2 baths

|

1,898 sq ft

|

House

3312 BARRINGTON CT, THE VILLAGES, FL, 32...
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.
On Top of the World 9790 SW 99TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$229,999

2 beds

|

2 baths

|

1,569 sq ft

|

House

9790 SW 99TH AVE, OCALA, FL, 34481
Community: On Top of the World
The Villages® 1708 MORENO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$211,900

1 beds

|

1 baths

|

961 sq ft

|

Villa

1708 MORENO PL, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 987 FREDERICK TER, THE VILLAGES, FL, 321..., The Villages, FL 32163
$815,000

3 beds

|

2 baths

|

2,060 sq ft

|

House

987 FREDERICK TER, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 16822 SE 80TH BELLAVISTA CIR, THE VILLAG..., The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

1,995 sq ft

|

House

16822 SE 80TH BELLAVISTA CIR, THE VILLAG...
Community: The Villages®
The Villages® 1001 GREYFORD LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$314,900

2 beds

|

2 baths

|

1,351 sq ft

|

Villa

1001 GREYFORD LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8380 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$309,900

3 beds

|

2 baths

|

1,701 sq ft

|

House

8380 SW 82ND CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 616 HARTFORD LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$449,000

3 beds

|

2 baths

|

2,075 sq ft

|

House

616 HARTFORD LN, THE VILLAGES, FL, 32162
Community: The Villages®
Plantation at Leesburg 4644 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$250,000

2 beds

|

2 baths

|

1,469 sq ft

|

House

4644 RIVER RIDGE DR, LEESBURG, FL, 34748
On Top of the World 9120 SW 91ST TER, OCALA, FL, 34481, Ocala, FL 34481
$389,900

2 beds

|

2 baths

|

2,740 sq ft

|

House

9120 SW 91ST TER, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9770 SW 97TH PL, OCALA, FL, 34481, Ocala, FL 34481
$259,900

3 beds

|

3 baths

|

1,736 sq ft

|

House

9770 SW 97TH PL, OCALA, FL, 34481
Community: On Top of the World
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 Lakes at Harmony 3415 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$285,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

3415 SAGEBRUSH ST, HARMONY, FL, 34773
Pennbrooke Fairways 734 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,000

3 beds

|

2 baths

|

1,595 sq ft

|

House

734 GRAND VISTA TRL, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Cresswind at Victoria Gardens 516 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$369,900

3 beds

|

2 baths

|

1,820 sq ft

|

House

516 HERON POINT WAY, DELAND, FL, 32724
On Top of the World 9275 SW 97TH LN B, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,470 sq ft

|

Villa

9275 SW 97TH LN B, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9729 SW 97TH ST, OCALA, FL, 34481, Ocala, FL 34481
$219,900

2 beds

|

2 baths

|

1,230 sq ft

|

House

9729 SW 97TH ST, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spring Lake Towers 700 MIRROR TER 603, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$100,000

2 beds

|

2 baths

|

1,190 sq ft

|

Condo

700 MIRROR TER 603, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Lake Ashton 4111 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$324,900

2 beds

|

2 baths

|

1,688 sq ft

|

House

4111 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
The Villages® 9231 SE 171ST COOPER LOOP, THE VILLAGES,..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,850 sq ft

|

House

9231 SE 171ST COOPER LOOP, THE VILLAGES,...
Community: The Villages®
Oak Run 8137 SW 117TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$198,999

2 beds

|

2 baths

|

1,148 sq ft

|

House

8137 SW 117TH LOOP, OCALA, FL, 34481
Community: Oak Run
Pennbrooke Fairways 143 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$144,900

2 beds

|

2 baths

|

1,148 sq ft

|

Manufactured Home

143 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways

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3,648 homes near Winter Garden
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