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

3,573 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 - $2Ms
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
$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 (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 - $500Ks
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 - $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 - $500Ks
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.
3.8 rating (6 reviews) Trilogy® Orlando
$300Ks - $600Ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
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) 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 - $900Ks
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 - $400Ks
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
4.3 rating (15 reviews) Del Webb Orlando
$200Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $400Ks
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 21125 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,868 sq ft

|

House

21125 BRAVEHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
Stonecrest 11961 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$375,000

3 beds

|

2 baths

|

1,723 sq ft

|

House

11961 SE 176TH PLACE RD, SUMMERFIELD, FL...
Community: Stonecrest
The Villages® 3198 ABANA PATH, THE VILLAGES, FL, 32163, The Villages, FL 32163
$400,000

3 beds

|

2 baths

|

1,665 sq ft

|

House

3198 ABANA PATH, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 1751 BRANDENBURG CT, THE VILLAGES, FL, 3..., The Villages, FL 32163
$375,000

2 beds

|

2 baths

|

1,220 sq ft

|

Villa

1751 BRANDENBURG CT, THE VILLAGES, FL, 3...
Community: The Villages®
The Villages® 2002 ENRIQUE DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$498,500

3 beds

|

2 baths

|

2,242 sq ft

|

House

2002 ENRIQUE 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
Lake Jovita Golf and Country Club 13342 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525
$689,000

3 beds

|

3 baths

|

2,312 sq ft

|

House

13342 TRAILING MOSS DR, DADE CITY, FL, 3...
The Villages® 12046 NE 51ST CIR, OXFORD, FL, 34484, Oxford, FL 34484
$310,000

3 beds

|

2 baths

|

1,572 sq ft

|

House

12046 NE 51ST CIR, OXFORD, FL, 34484
Community: The Villages®
Palms at Serenoa 17571 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$425,000

3 beds

|

2 baths

|

1,822 sq ft

|

House

17571 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
On Top of the World 7682 SW 89TH CT, OCALA, FL, 34481, Ocala, FL 34481
$354,900

3 beds

|

2 baths

|

1,959 sq ft

|

House

7682 SW 89TH CT, OCALA, FL, 34481
Community: On Top of the World
Foxwood Lake Estates 4886 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$199,000

2 beds

|

2 baths

|

1,680 sq ft

|

Manufactured Home

4886 DEERWOOD DR, LAKELAND, FL, 33810
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® 611 ALLENWOOD LOOP, THE VILLAGES, FL, 32..., The Villages, FL 32162
$449,999

3 beds

|

2 baths

|

1,927 sq ft

|

House

611 ALLENWOOD LOOP, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 1818 TRIMARCHE TER, THE VILLAGES, FL, 32..., The Villages, FL 32163
$487,500

3 beds

|

2 baths

|

1,630 sq ft

|

Villa

1818 TRIMARCHE TER, THE VILLAGES, FL, 32...
Community: The Villages®
Pelican Bay Daytona Beach 176 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$325,000

2 beds

|

2 baths

|

1,335 sq ft

|

House

176 PALM SPARROW CT, DAYTONA BEACH, FL, ...
Venetian Bay 3008 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$339,000

3 beds

|

3 baths

|

1,672 sq ft

|

Townhouse

3008 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Latitude Margaritaville 429 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$550,000

3 beds

|

2 baths

|

1,848 sq ft

|

House

429 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Summer Trees 39 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$280,000

2 beds

|

2 baths

|

1,406 sq ft

|

House

39 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Summer Trees 109 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$273,827

2 beds

|

2 baths

|

1,106 sq ft

|

House

109 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
New JB Ranch 6138 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476
$307,000

3 beds

|

2 baths

|

1,857 sq ft

|

House

6138 SW 89TH LANE RD, OCALA, FL, 34476
Community: JB Ranch
New On Top of the World 9790 SW 99TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$234,500

2 beds

|

2 baths

|

1,569 sq ft

|

House

9790 SW 99TH AVE, OCALA, FL, 34481
Community: On Top of the World
Esplanade at Highland Ranch 1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$459,000

2 beds

|

2 baths

|

1,710 sq ft

|

House

1282 ZEEK RIDGE ST, CLERMONT, FL, 34715
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.
Venetian Bay 3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$625,000

3 beds

|

2 baths

|

1,916 sq ft

|

House

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Sun City Center 2419 RICHMOND GREENS CT, SUN CITY CENTER..., Sun City Center, FL 33573
$375,000

2 beds

|

2 baths

|

1,854 sq ft

|

Condo

2419 RICHMOND GREENS CT, SUN CITY CENTER...
Community: Sun City Center
VillageWalk at Lake Nona 12185 OBELIA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$645,000

3 beds

|

3 baths

|

2,022 sq ft

|

House

12185 OBELIA LN, ORLANDO, FL, 32827
The Villages® 1405 ESPINOZA LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$230,000

1 beds

|

1 baths

|

804 sq ft

|

Villa

1405 ESPINOZA LN, THE VILLAGES, FL, 3215...
Community: The Villages®
New Latitude Margaritaville 614 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$439,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

614 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 5535 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,522 sq ft

|

House

5535 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Mirada 31734 CABANA RYE AVE, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$350,000

2 beds

|

2 baths

|

1,683 sq ft

|

House

31734 CABANA RYE AVE, SAN ANTONIO, FL, 3...
Community: Mirada
Stone Creek 6046 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$595,000

3 beds

|

4 baths

|

2,809 sq ft

|

House

6046 SW 86TH CIR, OCALA, FL, 34481
Community: Stone Creek
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$569,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Spruce Creek North 10980 SW 62ND AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34476
$201,500

3 beds

|

2 baths

|

1,526 sq ft

|

House

10980 SW 62ND AVENUE RD, OCALA, FL, 3447...
Community: Spruce Creek North
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.
Solivita 1014 UMBRIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$269,900

2 beds

|

2 baths

|

1,365 sq ft

|

House

1014 UMBRIA DR, KISSIMMEE, FL, 34759
Community: Solivita
Plantation at Leesburg 3733 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$379,900

3 beds

|

3 baths

|

2,868 sq ft

|

House

3733 PLANTATION BLVD, LEESBURG, FL, 3474...
Trilogy® Orlando 228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736
$465,000

2 beds

|

2 baths

|

2,197 sq ft

|

House

228 BAYOU BEND RD, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Del Webb Sunbridge 6507 TRAILBLAZE BND, SAINT CLOUD, FL, 34..., Saint Cloud, FL 34771
$374,990

3 beds

|

3 baths

|

1,744 sq ft

|

Townhouse

6507 TRAILBLAZE BND, SAINT CLOUD, FL, 34...
Community: Del Webb Sunbridge
Del Webb Sunbridge 2904 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$409,990

3 beds

|

3 baths

|

1,744 sq ft

|

Townhouse

2904 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 5953 SW 82ND TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$548,200

3 beds

|

3 baths

|

2,483 sq ft

|

House

5953 SW 82ND TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
Spruce Creek Country Club 13535 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$429,000

3 beds

|

3 baths

|

2,262 sq ft

|

House

13535 SE 97TH TERRACE RD, SUMMERFIELD, F...
Stone Creek 5226 SW 88TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$431,320

2 beds

|

2 baths

|

1,889 sq ft

|

House

5226 SW 88TH CIR, OCALA, FL, 34481
Community: Stone Creek
Del Webb Minneola 1336 ORANGE VALLEY RD, MINNEOLA, FL, 347..., Minneola, FL 34715
$448,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

1336 ORANGE VALLEY RD, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Del Webb Minneola 1389 ZESTY CITRUS LN, MINNEOLA, FL, 3471..., Minneola, FL 34715
$773,000

2 beds

|

3 baths

|

2,114 sq ft

|

House

1389 ZESTY CITRUS LN, MINNEOLA, FL, 3471...
Community: Del Webb Minneola

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3,573 homes near Winter Garden
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