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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
Stonecrest 17471 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$374,000

3 beds

|

2 baths

|

1,768 sq ft

|

House

17471 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
Stonecrest 11092 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$379,000

3 beds

|

3 baths

|

2,071 sq ft

|

House

11092 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Spruce Creek South 9885 SE 177TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$220,000

2 beds

|

2 baths

|

1,008 sq ft

|

House

9885 SE 177TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Stonecrest 12101 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$425,000

3 beds

|

2 baths

|

1,952 sq ft

|

House

12101 SE 172ND LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Spruce Creek Country Club 11759 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$399,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

11759 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 4552 PEACH TREE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$279,900

3 beds

|

2 baths

|

1,709 sq ft

|

House

4552 PEACH TREE ST, LEESBURG, FL, 34748
New Sun City Center 1226 HUNTINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573
$260,000

2 beds

|

2 baths

|

1,195 sq ft

|

Condo

1226 HUNTINGTON GREENS DR, SUN CITY CENT...
Community: Sun City Center
High Vista at Ridgewood Lakes 457 GOLF VISTA CIR, DAVENPORT, FL, 33837, Davenport, FL 33837
$405,000

4 beds

|

3 baths

|

2,211 sq ft

|

House

457 GOLF VISTA CIR, DAVENPORT, FL, 33837
Lakeside Landings 10357 SILVER MAPLE AVE, OXFORD, FL, 3448..., Oxford, FL 34484
$389,000

4 beds

|

3 baths

|

2,003 sq ft

|

House

10357 SILVER MAPLE AVE, OXFORD, FL, 3448...
Community: Lakeside Landings
Cherrywood 10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$205,000

2 beds

|

2 baths

|

1,667 sq ft

|

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
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 Oak Run 8045 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$189,900

2 beds

|

2 baths

|

1,148 sq ft

|

House

8045 SW 108TH LOOP, OCALA, FL, 34481
Community: Oak Run
Valencia Lakes 16244 DIAMOND BAY DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$569,000

3 beds

|

3 baths

|

2,436 sq ft

|

House

16244 DIAMOND BAY DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
New Sun City Center 2208 HIGHCLERE CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$135,000

2 beds

|

2 baths

|

1,149 sq ft

|

Condo

2208 HIGHCLERE CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Tampa Bay Golf and Country Club 29405 COCHITI LAKE DR, SAN ANTONIO, FL, ..., San Antonio, FL 33576
$349,900

3 beds

|

2 baths

|

1,731 sq ft

|

House

29405 COCHITI LAKE DR, SAN ANTONIO, FL, ...
Del Webb Orlando 672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$389,900

2 beds

|

2 baths

|

1,956 sq ft

|

House

672 CORDOBA DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Breakaway Trails 61 COQUINA RIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$599,900

4 beds

|

3 baths

|

2,566 sq ft

|

House

61 COQUINA RIDGE WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
The Villages® 1303 E SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$208,500

2 beds

|

2 baths

|

1,485 sq ft

|

Manufactured Home

1303 E SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 219 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$695,000

3 beds

|

2 baths

|

1,831 sq ft

|

House

219 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 517 SAN PEDRO DR, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$275,000

2 beds

|

2 baths

|

1,066 sq ft

|

House

517 SAN PEDRO DR, THE VILLAGES, FL, 3215...
Community: The Villages®
The Villages® 428 TARRSON BLVD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$364,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

428 TARRSON BLVD, LADY LAKE, FL, 32159
Community: The Villages®
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 The Villages® 3440 GALESBURG CT, THE VILLAGES, FL, 321..., The Villages, FL 32162
$349,918

3 beds

|

2 baths

|

1,920 sq ft

|

House

3440 GALESBURG CT, THE VILLAGES, FL, 321...
Community: The Villages®
Del Webb Oasis 13069 SUNRISE HARVEST DR, WINTER GARDEN,..., Winter Garden, FL 34787
$725,000

4 beds

|

3 baths

|

2,120 sq ft

|

House

13069 SUNRISE HARVEST DR, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Oasis 16235 HONEY HARVEST ST, WINTER GARDEN, F..., Winter Garden, FL 34787
$800,000

5 beds

|

4 baths

|

2,670 sq ft

|

House

16235 HONEY HARVEST ST, WINTER GARDEN, F...
Community: Del Webb Oasis
Del Webb Oasis 13536 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787
$470,000

3 beds

|

3 baths

|

1,785 sq ft

|

Townhouse

13536 AUTUMN HARVEST AVE, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Oasis 13809 LUNA HARVEST AVE, WINTER GARDEN, F..., Winter Garden, FL 34787
$440,000

3 beds

|

3 baths

|

1,785 sq ft

|

Townhouse

13809 LUNA HARVEST AVE, WINTER GARDEN, F...
Community: Del Webb Oasis
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Del Webb Oasis 13528 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787
$490,000

3 beds

|

3 baths

|

1,955 sq ft

|

Townhouse

13528 AUTUMN HARVEST AVE, WINTER GARDEN,...
Community: Del Webb Oasis
Del Webb Oasis 13532 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787
$470,000

3 beds

|

3 baths

|

1,785 sq ft

|

Townhouse

13532 AUTUMN HARVEST AVE, WINTER GARDEN,...
Community: Del Webb Oasis
Oak Run 6707 SW 113TH PL, OCALA, FL, 34476, Ocala, FL 34476
$399,000

3 beds

|

2 baths

|

2,527 sq ft

|

House

6707 SW 113TH PL, OCALA, FL, 34476
Community: Oak Run
The Villages® 1201 DE LA FUENTE CT, THE VILLAGES, FL, ..., The Villages, FL 32162
$295,000

2 beds

|

2 baths

|

1,383 sq ft

|

House

1201 DE LA FUENTE CT, THE VILLAGES, FL, ...
Community: The Villages®
Lake Ashton 4315 ASHTON CLUB DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$519,900

3 beds

|

2 baths

|

2,229 sq ft

|

House

4315 ASHTON CLUB DR, LAKE WALES, FL, 338...
Community: Lake Ashton
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 The Villages® 4234 MCCLOY AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$640,000

3 beds

|

3 baths

|

2,033 sq ft

|

House

4234 MCCLOY AVE, THE VILLAGES, FL, 32163
Community: The Villages®
New Cresswind at Victoria Gardens 1627 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724
$407,000

3 beds

|

2 baths

|

1,947 sq ft

|

House

1627 VICTORIA GARDENS DR, DELAND, FL, 32...
New Pine Run Estates 10405 SW 98TH TER, OCALA, FL, 34481, Ocala, FL 34481
$174,750

2 beds

|

2 baths

|

1,040 sq ft

|

House

10405 SW 98TH TER, OCALA, FL, 34481
Community: Pine Run Estates
New The Villages® 3427 NEAPTIDE PATH, THE VILLAGES, FL, 32..., The Villages, FL 32163
$388,000

3 beds

|

2 baths

|

1,584 sq ft

|

House

3427 NEAPTIDE PATH, THE VILLAGES, FL, 32...
Community: The Villages®
Solivita 1825 PELICAN HILL WAY, KISSIMMEE, FL, 34..., Kissimmee, FL 34759
$250,000

2 beds

|

2 baths

|

1,515 sq ft

|

House

1825 PELICAN HILL WAY, KISSIMMEE, FL, 34...
Community: Solivita
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1639 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$279,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1639 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
Sun City Center 1348 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$379,900

3 beds

|

2 baths

|

1,860 sq ft

|

Condo

1348 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Lake Jovita Golf and Country Club 14174 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$600,000

3 beds

|

3 baths

|

2,133 sq ft

|

House

14174 THOROUGHBRED DR, DADE CITY, FL, 33...
The Villages® 3942 ZENITH LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$524,000

3 beds

|

2 baths

|

1,922 sq ft

|

House

3942 ZENITH LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
New Latitude Margaritaville 279 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$435,000

2 beds

|

2 baths

|

1,205 sq ft

|

House

279 LATITUDE DR, DAYTONA BEACH, FL, 3212...

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3,573 homes near Winter Garden
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