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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!
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 - $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) VillageWalk at Lake Nona
$400Ks - $900Ks
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
$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
Marco Polo Village 5312 SW 109TH PLACE ROAD RD, OCALA, FL, ..., Ocala, FL 34476
$274,900

3 beds

|

2 baths

|

1,758 sq ft

|

House

5312 SW 109TH PLACE ROAD RD, OCALA, FL, ...
Community: Marco Polo Village
New Tampa Bay Golf and Country Club 10711 CUP DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$319,900

3 beds

|

2 baths

|

1,604 sq ft

|

House

10711 CUP DR, SAN ANTONIO, FL, 33576
On Top of the World 8530 SW 92ND ST D, OCALA, FL, 34481, Ocala, FL 34481
$219,900

2 beds

|

2 baths

|

1,856 sq ft

|

Villa

8530 SW 92ND ST D, OCALA, FL, 34481
Community: On Top of the World
New The Villages® 1079 WOODRUFF ST, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$350,000

3 beds

|

2 baths

|

1,584 sq ft

|

House

1079 WOODRUFF ST, THE VILLAGES, FL, 3216...
Community: The Villages®
New On Top of the World 8705 SW 95TH ST C, OCALA, FL, 34481, Ocala, FL 34481
$169,900

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8705 SW 95TH ST C, 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
New Valencia Lakes 5024 RUBY FLATS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$613,995

2 beds

|

3 baths

|

2,795 sq ft

|

House

5024 RUBY FLATS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Sun City Center 401 DORCHESTER PL 55, SUN CITY CENTER, F..., Sun City Center, FL 33573
$149,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

401 DORCHESTER PL 55, SUN CITY CENTER, F...
Community: Sun City Center
New The Villages® 1848 HARTFORD PATH, THE VILLAGES, FL, 32..., The Villages, FL 32162
$540,000

3 beds

|

3 baths

|

2,270 sq ft

|

House

1848 HARTFORD PATH, THE VILLAGES, FL, 32...
Community: The Villages®
New Venetian Bay 3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$312,000

3 beds

|

3 baths

|

1,614 sq ft

|

Townhouse

3057 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Stone Creek 9773 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$493,900

2 beds

|

3 baths

|

2,261 sq ft

|

House

9773 SW 63RD LOOP, OCALA, FL, 34481
Community: Stone Creek
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.
Highland Fairways 3341 HIGHLAND FAIRWAYS BLVD, LAKELAND, F..., Lakeland, FL 33810
$232,900

2 beds

|

2 baths

|

1,235 sq ft

|

House

3341 HIGHLAND FAIRWAYS BLVD, LAKELAND, F...
Community: Highland Fairways
Sun City Center 1903 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$389,000

2 beds

|

2 baths

|

1,955 sq ft

|

House

1903 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
New On Top of the World 8883 SW 94TH LN G, OCALA, FL, 34481, Ocala, FL 34481
$229,900

2 beds

|

2 baths

|

1,571 sq ft

|

Villa

8883 SW 94TH LN G, OCALA, FL, 34481
Community: On Top of the World
New Sun City Center 2204 HARTLEBURY WAY # 460, SUN CITY CENT..., Sun City Center, FL 33573
$149,900

2 beds

|

2 baths

|

1,203 sq ft

|

Condo

2204 HARTLEBURY WAY # 460, SUN CITY CENT...
Community: Sun City Center
Pine Run Estates 9430 SW 102ND PL, OCALA, FL, 34481, Ocala, FL 34481
$148,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

9430 SW 102ND PL, OCALA, FL, 34481
Community: Pine Run Estates
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 703 RUTGERS PL, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$290,000

2 beds

|

2 baths

|

1,141 sq ft

|

Condo

703 RUTGERS PL, SUN CITY CENTER, FL, 335...
Community: Sun City Center
New Stone Creek 8343 SW 58TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$374,910

4 beds

|

2 baths

|

1,850 sq ft

|

House

8343 SW 58TH LOOP, OCALA, FL, 34481
Community: Stone Creek
SummerGlen 15304 SW 15TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473
$398,500

4 beds

|

3 baths

|

2,580 sq ft

|

House

15304 SW 15TH TERRACE RD, OCALA, FL, 344...
Community: SummerGlen
Twin Lakes 2426 YELLOW BRICK RD, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772
$260,000

2 beds

|

2 baths

|

1,261 sq ft

|

Halfplex

2426 YELLOW BRICK RD, SAINT CLOUD, FL, 3...
Community: Twin Lakes
Harbor Hills Country Club 39539 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$469,900

3 beds

|

3 baths

|

2,303 sq ft

|

House

39539 HARBOR HILLS BLVD, LADY LAKE, FL, ...
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 5316 STOIC VALE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$330,000

2 beds

|

2 baths

|

1,636 sq ft

|

Villa

5316 STOIC VALE DR, WIMAUMA, FL, 33598
Community: Southshore Bay
Royal Palm 5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128
$409,900

3 beds

|

2 baths

|

3,293 sq ft

|

House

5415 SWORDFERN CT, PORT ORANGE, FL, 3212...
Community: Royal Palm
New Sandpiper Golf & Country Club 570 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$235,000

2 beds

|

2 baths

|

1,132 sq ft

|

House

570 EAGLE RUN, LAKELAND, FL, 33809
The Villages® 902 ROSE LN, THE VILLAGES, FL, 32159, The Villages, FL 32159
$175,900

2 beds

|

2 baths

|

1,036 sq ft

|

Manufactured Home

902 ROSE LN, THE VILLAGES, FL, 32159
Community: The Villages®
Tampa Bay Golf and Country Club 11116 JENKINS CT, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$299,900

3 beds

|

2 baths

|

1,564 sq ft

|

House

11116 JENKINS CT, SAN ANTONIO, FL, 33576
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates 10161 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481
$169,500

3 beds

|

2 baths

|

1,456 sq ft

|

House

10161 SW 87TH TER, OCALA, FL, 34481
Community: Pine Run Estates
Spruce Creek South 17392 SE 98TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,900

2 beds

|

2 baths

|

1,605 sq ft

|

House

17392 SE 98TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
The Villages® 1401 MADRIGAL LN, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$334,900

3 beds

|

2 baths

|

1,906 sq ft

|

House

1401 MADRIGAL LN, THE VILLAGES, FL, 3215...
Community: The Villages®
New The Villages® 4038 SWAYING PALM CT, THE VILLAGES, FL, ..., The Villages, FL 32163
$1,195,000

3 beds

|

3 baths

|

3,365 sq ft

|

House

4038 SWAYING PALM CT, THE VILLAGES, FL, ...
Community: The Villages®
Solivita 572 SIENNA DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$299,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

572 SIENNA DR, POINCIANA, FL, 34759
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.
New Sun City Center 2315 LANCASTER DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$229,900

2 beds

|

2 baths

|

1,642 sq ft

|

Condo

2315 LANCASTER DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Lakeside Landings 10069 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484
$474,900

3 beds

|

2 baths

|

2,059 sq ft

|

House

10069 LAKE MIONA WAY, OXFORD, FL, 34484
Community: Lakeside Landings
Liberty Village 7651 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$337,000

4 beds

|

3 baths

|

2,039 sq ft

|

House

7651 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
New VillageWalk at Lake Nona 11858 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827
$625,000

3 beds

|

2 baths

|

1,941 sq ft

|

House

11858 BARLETTA DR, ORLANDO, FL, 32827
Oak Run 11465 SW 75TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$279,000

3 beds

|

2 baths

|

1,842 sq ft

|

House

11465 SW 75TH TERRACE RD, OCALA, FL, 344...
Community: Oak Run
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
New The Villages® 3006 ROSEBRIAR LN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$449,675

3 beds

|

2 baths

|

1,664 sq ft

|

House

3006 ROSEBRIAR LN, THE VILLAGES, FL, 321...
Community: The Villages®
New Spruce Creek South 15865 SE 101ST CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$311,070

4 beds

|

2 baths

|

1,828 sq ft

|

House

15865 SE 101ST CIR, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
New Spruce Creek Country Club 12792 SE 90TH COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$309,900

2 beds

|

2 baths

|

1,598 sq ft

|

House

12792 SE 90TH COURT RD, SUMMERFIELD, FL,...
Marco Polo Village 5336 SW 109TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$280,000

3 beds

|

2 baths

|

1,855 sq ft

|

House

5336 SW 109TH PLACE RD, OCALA, FL, 34476
Community: Marco Polo Village
Spruce Creek South 17970 SE 102ND CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$289,000

3 beds

|

2 baths

|

1,708 sq ft

|

House

17970 SE 102ND CT, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South

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3,573 homes near Winter Garden
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