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

3,865 homes near Winter Garden

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No reviews yet Del Webb Oasis
$400Ks - $1Ms
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 - $600Ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$200Ks - $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!
Questions? Call us: (689) 407-5757
3.6 rating (46 reviews) Latitude Margaritaville
$300Ks - $700Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $800Ks
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 - $400Ks
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
$200Ks - $600Ks
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 - $1Ms
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
$200Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $500Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $1Ms
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.
5 rating (8 reviews) Royal Highlands
$200Ks - $400Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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) Del Webb Sunbridge
$300Ks - $1Ms
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes
5 rating (1 reviews) VillageWalk at Lake Nona
$400Ks - $800Ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 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
$100Ks - $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 - $400Ks
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 | 1,029 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
$400Ks - $900Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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
4.3 rating (15 reviews) Del Webb Orlando
<$100k - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $800Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
The Villages® 3243 MANSFIELD ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$299,900

2 beds

|

2 baths

|

1,156 sq ft

|

House

3243 MANSFIELD ST, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 603 SAN PEDRO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$369,900

3 beds

|

2 baths

|

1,636 sq ft

|

House

603 SAN PEDRO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
JB Ranch 6365 SW 88TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$319,000

2 beds

|

2 baths

|

1,811 sq ft

|

House

6365 SW 88TH LOOP, OCALA, FL, 34476
Community: JB Ranch
The Villages® 4318 ST STEPHEN ST, THE VILLAGES, FL, 32..., The Villages, FL 32163
$479,900

3 beds

|

2 baths

|

1,923 sq ft

|

House

4318 ST STEPHEN ST, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 306 BISHOPVILLE LOOP # 117, THE VILLAGES..., The Villages, FL 32162
$375,000

3 beds

|

2 baths

|

1,991 sq ft

|

House

306 BISHOPVILLE LOOP # 117, THE VILLAGES...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 4907 W FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$519,990

3 beds

|

2 baths

|

1,863 sq ft

|

House

4907 W FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
Legacy of Leesburg 27303 GINGERBREAD PL, LEESBURG, FL, 3474..., Leesburg, FL 34748
$375,000

3 beds

|

3 baths

|

2,287 sq ft

|

House

27303 GINGERBREAD PL, LEESBURG, FL, 3474...
Community: Legacy of Leesburg
The Villages® 1751 ASHWOOD RUN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$525,000

3 beds

|

2 baths

|

2,030 sq ft

|

House

1751 ASHWOOD RUN, THE VILLAGES, FL, 3216...
Community: The Villages®
Solivita 112 SEVILLA CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$485,900

3 beds

|

3 baths

|

2,450 sq ft

|

House

112 SEVILLA CT, POINCIANA, FL, 34759
Community: Solivita
Solivita 251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$350,000

2 beds

|

2 baths

|

2,050 sq ft

|

House

251 ROCK SPRINGS DR, KISSIMMEE, FL, 3475...
Community: Solivita
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.
Pennbrooke Fairways 409 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$234,247

2 beds

|

2 baths

|

1,232 sq ft

|

House

409 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Royal Harbor 5502 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$359,565

3 beds

|

2 baths

|

1,901 sq ft

|

House

5502 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Sun City Center 1257 CORINTH GREENS DR # 1257, SUN CITY ..., Sun City Center, FL 33573
$234,000

2 beds

|

2 baths

|

1,435 sq ft

|

Condo

1257 CORINTH GREENS DR # 1257, SUN CITY ...
Community: Sun City Center
The Villages® 1065 BERG CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$410,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

1065 BERG CT, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 5746 BOTNER DR, THE VILLAGES, FL, 32163, The Villages, FL 32163
$649,900

3 beds

|

2 baths

|

1,955 sq ft

|

House

5746 BOTNER DR, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 2736 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$574,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

2736 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Trilogy® Orlando 243 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$385,000

2 beds

|

2 baths

|

1,838 sq ft

|

House

243 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
The Villages® 8195 SE 174TH ROWLAND ST, THE VILLAGES, ..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,208 sq ft

|

Villa

8195 SE 174TH ROWLAND ST, THE VILLAGES, ...
Community: The Villages®
Oak Run 11051 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476
$249,000

2 beds

|

2 baths

|

1,478 sq ft

|

House

11051 SW 73RD CT, OCALA, FL, 34476
Community: Oak Run
Sun City Center 1205 DESERT HILLS DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$289,900

2 beds

|

2 baths

|

1,533 sq ft

|

House

1205 DESERT HILLS DR, SUN CITY CENTER, F...
Community: Sun City Center
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.
Royal Harbor 5964 BRITTANIA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$338,000

2 beds

|

3 baths

|

2,080 sq ft

|

House

5964 BRITTANIA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
Royal Highlands 20936 ROYAL ST GEORGES LN, LEESBURG, FL,..., Leesburg, FL 34748
$449,000

3 beds

|

2 baths

|

2,380 sq ft

|

House

20936 ROYAL ST GEORGES LN, LEESBURG, FL,...
Community: Royal Highlands
Royal Harbor 5562 CHARLESTON AVE, TAVARES, FL, 32778, Tavares, FL 32778
$330,000

3 beds

|

2 baths

|

1,592 sq ft

|

House

5562 CHARLESTON AVE, TAVARES, FL, 32778
Community: Royal Harbor
Heritage Hills 3606 SOLANA CIR, CLERMONT, FL, 34711, Clermont, FL 34711
$448,500

3 beds

|

3 baths

|

2,006 sq ft

|

House

3606 SOLANA CIR, CLERMONT, FL, 34711
Community: Heritage Hills
Royal Harbor 2821 MEDITERRANEAN LOOP, TAVARES, FL, 32..., Tavares, FL 32778
$269,000

2 beds

|

2 baths

|

1,167 sq ft

|

House

2821 MEDITERRANEAN LOOP, TAVARES, FL, 32...
Community: Royal Harbor
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Ashton 4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$225,000

2 beds

|

2 baths

|

1,083 sq ft

|

House

4488 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$579,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Royal Highlands 4547 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$375,000

3 beds

|

2 baths

|

1,886 sq ft

|

House

4547 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 1914 ARMONDO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$434,900

3 beds

|

2 baths

|

1,634 sq ft

|

House

1914 ARMONDO DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1318 GUERRA AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$369,000

3 beds

|

2 baths

|

1,561 sq ft

|

House

1318 GUERRA AVE, THE VILLAGES, FL, 32159
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.
Royal Harbor 5075 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778
$369,900

3 beds

|

2 baths

|

2,044 sq ft

|

House

5075 CHINA SEA DR, TAVARES, FL, 32778
Community: Royal Harbor
Stonecrest 12147 SE 173RD PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$305,000

3 beds

|

2 baths

|

1,330 sq ft

|

House

12147 SE 173RD PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Sun City Center 1112 JASMINE CREEK CT, SUN CITY CENTER, ..., Sun City Center, FL 33573
$339,000

3 beds

|

2 baths

|

1,497 sq ft

|

House

1112 JASMINE CREEK CT, SUN CITY CENTER, ...
Community: Sun City Center
Venetian Bay 3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$509,000

3 beds

|

2 baths

|

2,174 sq ft

|

House

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
The Villages® 919 MEDIRA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$295,500

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

919 MEDIRA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 13196 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,900

2 beds

|

2 baths

|

1,488 sq ft

|

House

13196 SE 86TH CIR, SUMMERFIELD, FL, 3449...
Plantation at Leesburg 25524 MAUREPAS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$399,900

2 beds

|

2 baths

|

2,462 sq ft

|

House

25524 MAUREPAS LN, LEESBURG, FL, 34748
The Villages® 2071 WESTCHESTER WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$499,950

3 beds

|

2 baths

|

2,060 sq ft

|

House

2071 WESTCHESTER WAY, THE VILLAGES, FL, ...
Community: The Villages®
Royal Harbor 5305 INDIAN OCEAN LOOP, TAVARES, FL, 327..., Tavares, FL 32778
$353,500

3 beds

|

2 baths

|

1,824 sq ft

|

House

5305 INDIAN OCEAN LOOP, TAVARES, FL, 327...
Community: Royal Harbor
Spruce Creek South 9948 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,878 sq ft

|

House

9948 SE 175TH PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South

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3,865 homes near Winter Garden
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