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

3,958 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
<$100k - $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
<$100k - $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
$200Ks - $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 - $900Ks
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 - $1Ms
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...
$100Ks - $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
$300Ks - $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 - $700Ks
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
$100Ks - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Stonecrest 11010 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$355,000

3 beds

|

2 baths

|

1,793 sq ft

|

House

11010 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Sun City Center 401 DORCHESTER PL APT 69, SUN CITY CENTE..., Sun City Center, FL 33573
$155,000

1 beds

|

2 baths

|

820 sq ft

|

Condo

401 DORCHESTER PL APT 69, SUN CITY CENTE...
Community: Sun City Center
Ocala Preserve 4747 NW 35TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$355,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

4747 NW 35TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Del Webb Orlando 333 ALMANSA ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$359,900

2 beds

|

2 baths

|

1,655 sq ft

|

House

333 ALMANSA ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Stone Creek 6046 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$328,180

2 beds

|

2 baths

|

1,404 sq ft

|

House

6046 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 300 OAK BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785
$124,900

2 beds

|

2 baths

|

864 sq ft

|

Manufactured Home

300 OAK BLVD, WILDWOOD, FL, 34785
Community: The Villages®
The Villages® 23104 SANDALWOOD DR # 104, WILDWOOD, FL,..., Wildwood, FL 34785
$134,900

2 beds

|

2 baths

|

1,110 sq ft

|

Condo

23104 SANDALWOOD DR # 104, WILDWOOD, FL,...
Community: The Villages®
Pine Run Estates 8917 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,040 sq ft

|

House

8917 SW 101ST LN, OCALA, FL, 34481
Community: Pine Run Estates
On Top of the World 9267 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$279,900

3 beds

|

2 baths

|

1,825 sq ft

|

House

9267 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Cresswind at Victoria Gardens 1112 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$699,900

3 beds

|

3 baths

|

3,207 sq ft

|

House

1112 HERON POINT WAY, DELAND, FL, 32724
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.
Sun City Center 334 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$219,900

2 beds

|

2 baths

|

1,516 sq ft

|

Condo

334 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Kings Ridge 3713 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711
$355,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

3713 DOUNE WAY, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 3337 ASHBROOK PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$324,900

3 beds

|

2 baths

|

1,240 sq ft

|

House

3337 ASHBROOK PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Sun City Center 2122 HEREFORD DR # 511, SUN CITY CENTER,..., Sun City Center, FL 33573
$199,500

2 beds

|

2 baths

|

1,150 sq ft

|

Condo

2122 HEREFORD DR # 511, SUN CITY CENTER,...
Community: Sun City Center
Marion Landing 6490 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476
$254,000

2 beds

|

2 baths

|

1,758 sq ft

|

House

6490 SW 84TH ST, OCALA, FL, 34476
Community: Marion Landing
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 918 REGAL MANOR WAY, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$324,900

2 beds

|

2 baths

|

1,380 sq ft

|

House

918 REGAL MANOR WAY, SUN CITY CENTER, FL...
Community: Sun City Center
Trilogy® Orlando 409 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$375,000

2 beds

|

2 baths

|

1,617 sq ft

|

House

409 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Trilogy® Orlando 96 SILVER MAPLE RD, GROVELAND, FL, 34736, Groveland, FL 34736
$469,900

2 beds

|

3 baths

|

2,068 sq ft

|

House

96 SILVER MAPLE RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Liberty Village 7412 SW 76TH TER, OCALA, FL, 34481, Ocala, FL 34481
$375,000

3 beds

|

2 baths

|

1,712 sq ft

|

House

7412 SW 76TH TER, OCALA, FL, 34481
Community: Liberty Village
Lake Ashton 4120 LIMERICK DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$999,000

3 beds

|

4 baths

|

2,968 sq ft

|

House

4120 LIMERICK DR, LAKE WALES, FL, 33859
Community: Lake Ashton
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.
Southshore Bay 17418 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$400,000

2 beds

|

2 baths

|

1,959 sq ft

|

House

17418 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
Foxwood Lake Estates 4910 LOCH NESS DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$200,000

2 beds

|

2 baths

|

1,404 sq ft

|

Manufactured Home

4910 LOCH NESS DR, LAKELAND, FL, 33810
Pelican Bay Daytona Beach 129 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$219,900

3 beds

|

2 baths

|

1,347 sq ft

|

Condo

129 BLUE HERON DR A, DAYTONA BEACH, FL, ...
The Villages® 12312 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484
$289,900

4 beds

|

4 baths

|

1,912 sq ft

|

House

12312 NE 48TH LOOP, OXFORD, FL, 34484
Community: The Villages®
Solivita 188 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$299,999

2 beds

|

2 baths

|

1,250 sq ft

|

House

188 OLYMPUS WAY, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 672 ALLEGHENY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$545,000

4 beds

|

3 baths

|

1,684 sq ft

|

House

672 ALLEGHENY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
The Villages® 2142 MARGARITA DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$399,900

3 beds

|

2 baths

|

1,904 sq ft

|

House

2142 MARGARITA DR, THE VILLAGES, FL, 321...
Community: The Villages®
Sun City Center 322 CLUB MANOR DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$197,000

2 beds

|

2 baths

|

1,686 sq ft

|

Villa

322 CLUB MANOR DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Kings Ridge 3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$370,000

2 beds

|

2 baths

|

1,552 sq ft

|

House

3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
Twin Lakes 5006 SUNFALLS AVE, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$399,900

2 beds

|

2 baths

|

1,624 sq ft

|

House

5006 SUNFALLS AVE, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
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.
Del Webb Sunbridge 6145 CITRUS GROVE CT, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34771
$529,000

2 beds

|

2 baths

|

2,077 sq ft

|

House

6145 CITRUS GROVE CT, SAINT CLOUD, FL, 3...
Community: Del Webb Sunbridge
Sun City Center 633 TREMONT GREENS LN # 16, SUN CITY CEN..., Sun City Center, FL 33573
$209,000

2 beds

|

2 baths

|

974 sq ft

|

Condo

633 TREMONT GREENS LN # 16, SUN CITY CEN...
Community: Sun City Center
The Villages® 4774 COSENTINO CT, THE VILLAGES, FL, 321..., The Villages, FL 32163
$765,000

3 beds

|

2 baths

|

2,024 sq ft

|

House

4774 COSENTINO CT, THE VILLAGES, FL, 321...
Community: The Villages®
On Top of the World 9077 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$239,900

2 beds

|

2 baths

|

1,569 sq ft

|

House

9077 SW 91ST CIR, OCALA, FL, 34481
Community: On Top of the World
Lake Jovita Golf and Country Club 12632 OAK HOLLOW CT, DADE CITY, FL, 3352..., Dade City, FL 33525
$899,900

4 beds

|

4 baths

|

2,711 sq ft

|

House

12632 OAK HOLLOW CT, DADE CITY, FL, 3352...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Jovita Golf and Country Club 13315 CARNOUSTIE CIR, DADE CITY, FL, 335..., Dade City, FL 33525
$1,012,000

4 beds

|

3 baths

|

3,322 sq ft

|

House

13315 CARNOUSTIE CIR, DADE CITY, FL, 335...
Lake Jovita Golf and Country Club 13744 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,295,000

3 beds

|

4 baths

|

3,202 sq ft

|

House

13744 CARRYBACK DR, DADE CITY, FL, 33525
High Vista at Ridgewood Lakes 117 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$299,500

2 beds

|

2 baths

|

2,013 sq ft

|

House

117 RIDGE VIEW DR, DAVENPORT, FL, 33837
Twin Lakes 5151 TWIN LAKES BLVD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$385,000

2 beds

|

2 baths

|

1,624 sq ft

|

House

5151 TWIN LAKES BLVD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Esplanade at Wiregrass Ranch 4228 ISONZO WAY, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$725,000

2 beds

|

3 baths

|

2,118 sq ft

|

House

4228 ISONZO WAY, WESLEY CHAPEL, FL, 3354...

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3,958 homes near Winter Garden
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