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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
<$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
$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.
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) 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
Highland Lakes 26608 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$264,900

2 beds

|

2 baths

|

1,499 sq ft

|

House

26608 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
On Top of the World 6571 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$229,990

3 beds

|

3 baths

|

1,458 sq ft

|

Townhouse

6571 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
Royal Harbor 5971 BRITTANIA BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$329,900

2 beds

|

3 baths

|

1,834 sq ft

|

House

5971 BRITTANIA BLVD, TAVARES, FL, 32778
Community: Royal Harbor
The Lakes at Harmony 3447 FEATHERGRASS CT, HARMONY, FL, 34773, Harmony, FL 34773
$482,500

5 beds

|

4 baths

|

3,300 sq ft

|

House

3447 FEATHERGRASS CT, HARMONY, FL, 34773
Tampa Bay Golf and Country Club 10520 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$385,900

3 beds

|

2 baths

|

2,046 sq ft

|

House

10520 COLLAR DR, SAN ANTONIO, FL, 33576
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 17738 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$199,000

3 beds

|

2 baths

|

1,466 sq ft

|

House

17738 SE 95TH CIR, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Stone Creek 5599 SW 92ND AVENUE RD, OCALA, FL, 34481, Ocala, FL 34481
$724,900

3 beds

|

3 baths

|

2,515 sq ft

|

House

5599 SW 92ND AVENUE RD, OCALA, FL, 34481
Community: Stone Creek
Esplanade at Highland Ranch 967 BRAEWOOD DR, CLERMONT, FL, 34715, Clermont, FL 34715
$471,000

2 beds

|

2 baths

|

1,778 sq ft

|

House

967 BRAEWOOD DR, CLERMONT, FL, 34715
Plantation at Leesburg 25333 CASA DEL LAGO LN, LEESBURG, FL, 34..., Leesburg, FL 34748
$214,999

2 beds

|

2 baths

|

936 sq ft

|

Manufactured Home

25333 CASA DEL LAGO LN, LEESBURG, FL, 34...
On Top of the World 8625 SW 94TH LN A, OCALA, FL, 34481, Ocala, FL 34481
$154,900

2 beds

|

2 baths

|

1,484 sq ft

|

Villa

8625 SW 94TH LN A, 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.
Trilogy® Orlando 409 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$350,000

3 beds

|

2 baths

|

1,617 sq ft

|

House

409 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Sun City Center 1038 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$410,000

2 beds

|

2 baths

|

1,821 sq ft

|

House

1038 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Sun City Center 334 NORTHWAY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$407,800

2 beds

|

2 baths

|

1,960 sq ft

|

House

334 NORTHWAY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Sun City Center 1820 EL RANCHO DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$369,900

3 beds

|

2 baths

|

1,597 sq ft

|

House

1820 EL RANCHO DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Palm Cay 8200 SW 107TH LN, OCALA, FL, 34481, Ocala, FL 34481
$165,000

2 beds

|

2 baths

|

864 sq ft

|

House

8200 SW 107TH LN, 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
Traditions at Lake Ruby 2877 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$229,500

2 beds

|

2 baths

|

1,385 sq ft

|

Villa

2877 ATTWATER LOOP, WINTER HAVEN, FL, 33...
Oak Run 6682 SW 117TH ST, OCALA, FL, 34476, Ocala, FL 34476
$295,000

2 beds

|

2 baths

|

1,730 sq ft

|

House

6682 SW 117TH ST, OCALA, FL, 34476
Community: Oak Run
The Villages® 2630 CARIBE DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,674 sq ft

|

House

2630 CARIBE DR, THE VILLAGES, FL, 32162
Community: The Villages®
SummerGlen 15541 SW 11TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473
$329,900

3 beds

|

2 baths

|

1,869 sq ft

|

House

15541 SW 11TH TERRACE RD, OCALA, FL, 344...
Community: SummerGlen
SummerGlen 16052 SW 15TH CT, OCALA, FL, 34473, Ocala, FL 34473
$295,500

3 beds

|

3 baths

|

1,759 sq ft

|

House

16052 SW 15TH CT, OCALA, FL, 34473
Community: SummerGlen
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.
Pennbrooke Fairways 721 TIMBERCREST DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

1,667 sq ft

|

House

721 TIMBERCREST DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Stone Creek 6639 SW 91ST CIR, OCALA, FL, 34481, Ocala, FL 34481
$256,652

2 beds

|

2 baths

|

1,556 sq ft

|

Villa

6639 SW 91ST CIR, OCALA, FL, 34481
Community: Stone Creek
Venetian Bay 3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$524,999

4 beds

|

3 baths

|

2,338 sq ft

|

House

3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
The Villages® 725 BELDON CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$439,900

3 beds

|

2 baths

|

1,649 sq ft

|

House

725 BELDON CT, THE VILLAGES, FL, 32162
Community: The Villages®
On Top of the World 8298 SW 79TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$329,900

3 beds

|

2 baths

|

2,026 sq ft

|

House

8298 SW 79TH CIR, OCALA, FL, 34476
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
Oak Run 6758 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$229,900

2 beds

|

2 baths

|

1,550 sq ft

|

House

6758 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Oak Run
Stonecrest 12342 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$358,900

3 beds

|

2 baths

|

1,764 sq ft

|

House

12342 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Summer Trees 102 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$289,000

2 beds

|

2 baths

|

1,370 sq ft

|

House

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...
Community: Summer Trees
The Villages® 1324 BALBOA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$249,900

2 beds

|

2 baths

|

1,094 sq ft

|

House

1324 BALBOA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Venetian Bay 367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$422,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

367 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
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.
Stonecrest 10994 SE 168TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$499,900

3 beds

|

3 baths

|

2,742 sq ft

|

House

10994 SE 168TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Highlands Ridge 3120 S PRESTWICK DR, AVON PARK, FL, 3382..., Avon Park, FL 33825
$289,900

3 beds

|

2 baths

|

1,901 sq ft

|

House

3120 S PRESTWICK DR, AVON PARK, FL, 3382...
Community: Highlands Ridge
Southshore Bay 17255 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$325,000

2 beds

|

2 baths

|

1,614 sq ft

|

Townhouse

17255 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
The Villages® 1142 W BOONE CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$289,000

2 beds

|

2 baths

|

1,120 sq ft

|

House

1142 W BOONE CT, THE VILLAGES, FL, 32159
Community: The Villages®
Heritage Hills 3604 CORSICA LN, CLERMONT, FL, 34711, Clermont, FL 34711
$448,800

3 beds

|

3 baths

|

2,006 sq ft

|

House

3604 CORSICA LN, CLERMONT, FL, 34711
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 22103 SANDALWOOD DR # 103, WILDWOOD, FL,..., Wildwood, FL 34785
$145,000

2 beds

|

2 baths

|

1,156 sq ft

|

Condo

22103 SANDALWOOD DR # 103, WILDWOOD, FL,...
Community: The Villages®
On Top of the World 8681 SW 93RD PL B, OCALA, FL, 34481, Ocala, FL 34481
$197,000

2 beds

|

2 baths

|

1,409 sq ft

|

Villa

8681 SW 93RD PL B, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 8831 SW 94TH LN H, OCALA, FL, 34481, Ocala, FL 34481
$180,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

8831 SW 94TH LN H, OCALA, FL, 34481
Community: On Top of the World
Pelican Bay Daytona Beach 148 SURF SCOOTER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$235,000

3 beds

|

3 baths

|

1,535 sq ft

|

Townhouse

148 SURF SCOOTER DR, DAYTONA BEACH, FL, ...
Huntington at Hunter's Ridge 19 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$414,000

3 beds

|

2 baths

|

1,837 sq ft

|

House

19 HUNTINGTON PL, ORMOND BEACH, FL, 3217...

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3,584 homes near Winter Garden
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