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

3,584 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 - $600Ks
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
$300Ks - $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 - $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
Sun City Center 403 FULHAM CT B, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$180,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

403 FULHAM CT B, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Four Seasons at Orlando 2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$525,000

3 beds

|

2 baths

|

2,042 sq ft

|

House

2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Sun City Center 2044 SIFIELD GREENS WAY, SUN CITY CENTER..., Sun City Center, FL 33573
$289,000

2 beds

|

2 baths

|

1,410 sq ft

|

Condo

2044 SIFIELD GREENS WAY, SUN CITY CENTER...
Community: Sun City Center
Twin Lakes 2705 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$439,900

3 beds

|

2 baths

|

1,863 sq ft

|

House

2705 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Royal Highlands 5610 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

3 beds

|

2 baths

|

1,606 sq ft

|

House

5610 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Vienna Square 1703 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$259,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1703 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Stone Creek 17854 SW 72ND STREET RD, DUNNELLON, FL, ..., Dunnellon, FL 34432
$697,900

4 beds

|

3 baths

|

2,392 sq ft

|

House

17854 SW 72ND STREET RD, DUNNELLON, FL, ...
Community: Stone Creek
Cresswind at Victoria Gardens 1018 HERON POINT CIR, DELAND, FL, 32724, Deland, FL 32724
$439,999

4 beds

|

3 baths

|

2,091 sq ft

|

House

1018 HERON POINT CIR, DELAND, FL, 32724
Esplanade at Highland Ranch 1027 TIMBERVALE TRL, CLERMONT, FL, 34715, Clermont, FL 34715
$439,000

2 beds

|

2 baths

|

1,911 sq ft

|

House

1027 TIMBERVALE TRL, CLERMONT, FL, 34715
Solivita 200 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$222,000

2 beds

|

2 baths

|

1,388 sq ft

|

House

200 GRAND CANAL DR, KISSIMMEE, 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.
Stone Creek 8820 SW 58TH STREET RD, OCALA, FL, 34481, Ocala, FL 34481
$337,500

2 beds

|

2 baths

|

1,469 sq ft

|

House

8820 SW 58TH STREET RD, OCALA, FL, 34481
Community: Stone Creek
Plantation at Leesburg 4300 LEAFWAY CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$319,900

3 beds

|

2 baths

|

1,861 sq ft

|

House

4300 LEAFWAY CIR, LEESBURG, FL, 34748
Sun City Center 106 SILVERBELL CT, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$255,000

2 beds

|

2 baths

|

1,796 sq ft

|

House

106 SILVERBELL CT, SUN CITY CENTER, FL, ...
Community: Sun City Center
Thunderbird Hill 3700 SUNBIRD CIR, SEBRING, FL, 33872, Sebring, FL 33872
$200,000

2 beds

|

2 baths

|

1,038 sq ft

|

Villa

3700 SUNBIRD CIR, SEBRING, FL, 33872
Community: Thunderbird Hill
Palm Cay 8547 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481
$175,000

2 beds

|

2 baths

|

864 sq ft

|

House

8547 SW 106TH PL, OCALA, FL, 34481
Community: Palm Cay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 2916 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168
$625,000

4 beds

|

2 baths

|

2,175 sq ft

|

House

2916 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
The Country Club of Mount Dora 8012 SAINT JAMES WAY, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$400,000

3 beds

|

2 baths

|

2,062 sq ft

|

House

8012 SAINT JAMES WAY, MOUNT DORA, FL, 32...
Pine Run Estates 10035 SW 91ST TER, OCALA, FL, 34481, Ocala, FL 34481
$210,000

3 beds

|

2 baths

|

1,456 sq ft

|

House

10035 SW 91ST TER, OCALA, FL, 34481
Community: Pine Run Estates
Lakeside Landings 5466 COMPASS PT # 101, OXFORD, FL, 34484, Oxford, FL 34484
$239,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5466 COMPASS PT # 101, OXFORD, FL, 34484
Community: Lakeside Landings
Palms at Serenoa 3468 TWIN FLOWER CT, CLERMONT, FL, 34714, Clermont, FL 34714
$360,000

2 beds

|

2 baths

|

1,627 sq ft

|

Townhouse

3468 TWIN FLOWER CT, CLERMONT, FL, 34714
Community: Palms at Serenoa
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.
Ocala Palms 5347 NW 20TH PL, OCALA, FL, 34482, Ocala, FL 34482
$219,900

2 beds

|

2 baths

|

1,220 sq ft

|

House

5347 NW 20TH PL, OCALA, FL, 34482
Community: Ocala Palms
Plantation at Leesburg 3726 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$270,000

3 beds

|

2 baths

|

1,592 sq ft

|

House

3726 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Southshore Bay 17253 STAR BANKS ST, WIMAUMA, FL, 33598, Wimauma, FL 33598
$399,000

2 beds

|

2 baths

|

1,956 sq ft

|

House

17253 STAR BANKS ST, WIMAUMA, FL, 33598
Community: Southshore Bay
Cypress Lakes 2101 CYPRESS CROSS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$250,000

2 beds

|

2 baths

|

1,320 sq ft

|

Manufactured Home

2101 CYPRESS CROSS DR, LAKELAND, FL, 338...
Community: Cypress Lakes
The Villages® 13877 COUNTY ROAD 109F, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$244,999

4 beds

|

2 baths

|

1,960 sq ft

|

Manufactured Home

13877 COUNTY ROAD 109F, LADY LAKE, FL, 3...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sullivan Ranch 30300 HACKNEY LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$547,500

5 beds

|

4 baths

|

3,544 sq ft

|

House

30300 HACKNEY LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
The Country Club of Mount Dora 9048 SAINT ANDREWS WAY, MOUNT DORA, FL, ..., Mount Dora, FL 32757
$329,500

2 beds

|

2 baths

|

1,442 sq ft

|

House

9048 SAINT ANDREWS WAY, MOUNT DORA, FL, ...
The Villages® 1675 WESTMINSTER CT, THE VILLAGES, FL, 3..., The Villages, FL 32162
$389,247

3 beds

|

2 baths

|

1,587 sq ft

|

House

1675 WESTMINSTER CT, THE VILLAGES, FL, 3...
Community: The Villages®
On Top of the World 9663 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$278,000

2 beds

|

2 baths

|

1,689 sq ft

|

House

9663 SW 92ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 7729 SW 85TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$369,900

3 beds

|

2 baths

|

2,159 sq ft

|

House

7729 SW 85TH CIR, 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.
Sun City Center 1013 RICKENBACKER DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$235,000

2 beds

|

2 baths

|

1,318 sq ft

|

Villa

1013 RICKENBACKER DR, SUN CITY CENTER, F...
Community: Sun City Center
Highlands Ridge 3215 E PEBBLE CREEK DR, AVON PARK, FL, 3..., Avon Park, FL 33825
$269,900

2 beds

|

2 baths

|

1,574 sq ft

|

House

3215 E PEBBLE CREEK DR, AVON PARK, FL, 3...
Community: Highlands Ridge
Royal Harbor 5441 SEA LEOPARD ST, TAVARES, FL, 32778, Tavares, FL 32778
$299,900

3 beds

|

2 baths

|

1,597 sq ft

|

House

5441 SEA LEOPARD ST, TAVARES, FL, 32778
Community: Royal Harbor
Lake Ashton 3802 LITCHFIELD LOOP, LAKE WALES, FL, 33..., Lake Wales, FL 33859
$599,900

2 beds

|

2 baths

|

2,398 sq ft

|

House

3802 LITCHFIELD LOOP, LAKE WALES, FL, 33...
Community: Lake Ashton
Windermere 821 INVERIE DR, INVERNESS, FL, 34453, Inverness, FL 34453
$209,900

3 beds

|

3 baths

|

1,921 sq ft

|

Townhouse

821 INVERIE DR, INVERNESS, FL, 34453
Community: Windermere
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Palm Cay 11118 SW 76TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$175,500

2 beds

|

2 baths

|

932 sq ft

|

House

11118 SW 76TH AVE, OCALA, FL, 34476
Community: Palm Cay
Stone Creek 6576 SW 94TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$450,000

2 beds

|

2 baths

|

1,911 sq ft

|

House

6576 SW 94TH CIR, OCALA, FL, 34481
Community: Stone Creek
Summer Trees 62 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$239,900

2 beds

|

2 baths

|

1,309 sq ft

|

House

62 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Del Webb Sunbridge 6376 SHIMMERING SHORES LN, SAINT CLOUD, ..., Saint Cloud, FL 34771
$499,900

2 beds

|

2 baths

|

1,781 sq ft

|

House

6376 SHIMMERING SHORES LN, SAINT CLOUD, ...
Community: Del Webb Sunbridge
The Villages® 750 EDEN PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$449,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

750 EDEN PL, THE VILLAGES, FL, 32162
Community: The Villages®

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3,584 homes near Winter Garden
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