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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!
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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 - $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
Plantation at Leesburg 24502 PARLANGE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$329,000

2 beds

|

2 baths

|

1,880 sq ft

|

House

24502 PARLANGE CT, LEESBURG, FL, 34748
Highlands Ridge 4287 NORTH COURSE LN, AVON PARK, FL, 338..., Avon Park, FL 33825
$425,000

3 beds

|

2 baths

|

2,127 sq ft

|

House

4287 NORTH COURSE LN, AVON PARK, FL, 338...
Community: Highlands Ridge
Spruce Creek South 10185 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,500

2 beds

|

3 baths

|

1,982 sq ft

|

House

10185 SE 175TH LN, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Stone Creek 6816 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$474,999

2 beds

|

2 baths

|

1,969 sq ft

|

House

6816 SW 95TH CIR, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 7335 SW 97TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481
$438,834

2 beds

|

2 baths

|

2,194 sq ft

|

House

7335 SW 97TH TERRACE RD, OCALA, FL, 3448...
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 5564 SW 90TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$610,000

3 beds

|

4 baths

|

2,990 sq ft

|

House

5564 SW 90TH AVE, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 1508 INGRAM DR # 20, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$210,000

2 beds

|

2 baths

|

1,857 sq ft

|

Condo

1508 INGRAM DR # 20, SUN CITY CENTER, FL...
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
Sun City Center 2618 NEWCOMB CT # 12, SUN CITY CENTER, F..., Sun City Center, FL 33573
$160,000

2 beds

|

2 baths

|

963 sq ft

|

Condo

2618 NEWCOMB CT # 12, SUN CITY CENTER, F...
Community: Sun City Center
Twin Lakes 5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$435,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

5017 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
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.
Royal Highlands 6307 BERKSHIRE PASS, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

2 baths

|

1,748 sq ft

|

House

6307 BERKSHIRE PASS, LEESBURG, FL, 34748
Community: Royal Highlands
Oak Run 11159 SW 68TH CT, OCALA, FL, 34476, Ocala, FL 34476
$235,000

2 beds

|

2 baths

|

1,380 sq ft

|

House

11159 SW 68TH CT, OCALA, FL, 34476
Community: Oak Run
Lakeside Landings 10274 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$355,000

3 beds

|

2 baths

|

1,616 sq ft

|

House

10274 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
Tohoqua Reserve 1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$355,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

1875 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
The Villages® 2530 HANLON TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$374,900

2 beds

|

2 baths

|

1,724 sq ft

|

House

2530 HANLON TER, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Royal Highlands 21815 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$399,000

3 beds

|

3 baths

|

2,369 sq ft

|

House

21815 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
Four Seasons at Orlando 7977 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$554,900

3 beds

|

2 baths

|

2,130 sq ft

|

House

7977 HANSON BAY PL, KISSIMMEE, FL, 34747
Royal Highlands 4609 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$400,000

3 beds

|

3 baths

|

2,294 sq ft

|

House

4609 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
Royal Highlands 21509 CASTLE VIEW CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$325,000

3 beds

|

3 baths

|

1,913 sq ft

|

House

21509 CASTLE VIEW CT, LEESBURG, FL, 3474...
Community: Royal Highlands
Sun City Center 1120 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$455,000

2 beds

|

2 baths

|

1,885 sq ft

|

House

1120 EMERALD DUNES DR, SUN CITY CENTER, ...
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.
Sun City Center 832 KING LEON WAY, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$345,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

832 KING LEON WAY, SUN CITY CENTER, FL, ...
Community: Sun City Center
Lake Ashton 5384 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$380,000

2 beds

|

2 baths

|

1,682 sq ft

|

House

5384 HOGAN LN, WINTER HAVEN, FL, 33884
Community: Lake Ashton
The Villages® 518 SAINT ANDREWS BLVD, THE VILLAGES, FL..., The Villages, FL 32159
$240,000

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

518 SAINT ANDREWS BLVD, THE VILLAGES, FL...
Community: The Villages®
Spruce Creek South 10476 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$239,000

2 beds

|

2 baths

|

1,473 sq ft

|

House

10476 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Plantation at Leesburg 3644 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748
$320,000

2 beds

|

2 baths

|

1,862 sq ft

|

House

3644 PLANTATION BLVD, LEESBURG, FL, 3474...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 17446 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$329,900

3 beds

|

2 baths

|

1,681 sq ft

|

House

17446 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Spruce Creek South 10492 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$260,000

2 beds

|

2 baths

|

1,066 sq ft

|

House

10492 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Spruce Creek Country Club 9120 SE 125TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$399,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

9120 SE 125TH LOOP, SUMMERFIELD, FL, 344...
Venetian Bay 3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$600,000

3 beds

|

2 baths

|

2,214 sq ft

|

House

3048 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Del Webb Oasis 12259 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$555,000

4 beds

|

3 baths

|

2,082 sq ft

|

House

12259 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
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.
Spruce Creek Country Club 9891 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

9891 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Plantation at Leesburg 25057 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$377,500

3 beds

|

3 baths

|

2,676 sq ft

|

House

25057 RIVERWALK DR, LEESBURG, FL, 34748
Del Webb Oasis 12253 BRACCO ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787
$544,950

3 beds

|

3 baths

|

1,788 sq ft

|

House

12253 BRACCO ST, WINTER GARDEN, FL, 3478...
Community: Del Webb Oasis
Sun City Center 1710 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$474,900

2 beds

|

2 baths

|

2,078 sq ft

|

House

1710 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Plantation at Leesburg 25517 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748
$399,900

3 beds

|

2 baths

|

2,381 sq ft

|

House

25517 LAUREL VALLEY RD, LEESBURG, FL, 34...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Quail Meadow 1795 NW 44TH COURT RD, OCALA, FL, 34482, Ocala, FL 34482
$374,900

5 beds

|

3 baths

|

2,445 sq ft

|

House

1795 NW 44TH COURT RD, OCALA, FL, 34482
Community: Quail Meadow
Plantation at Leesburg 4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$434,900

3 beds

|

3 baths

|

2,780 sq ft

|

House

4822 SAWGRASS LAKE CIR, LEESBURG, FL, 34...
Royal Highlands 5430 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$292,000

3 beds

|

2 baths

|

1,986 sq ft

|

House

5430 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Del Webb Orlando 500 PLAYA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$335,000

2 beds

|

2 baths

|

1,728 sq ft

|

House

500 PLAYA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Plantation at Leesburg 4525 EAGLEWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,214 sq ft

|

House

4525 EAGLEWOOD DR, LEESBURG, FL, 34748

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3,584 homes near Winter Garden
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