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

3,952 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 - $1Ms
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
$200Ks - $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 - $300Ks
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 - $600Ks
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 - $1Ms
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
No reviews yet Pelican Bay Daytona Beach
<$100k - $600Ks
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
$200Ks - $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 - $900Ks
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
$200Ks - $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) 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 - $1Ms
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
$300Ks - $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 - $500Ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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
$400Ks - $700Ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
4 rating (4 reviews) Lakes of Mount Dora
$200Ks - $800Ks
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 - $800Ks
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 - $500Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
$100Ks - $400Ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
No reviews yet Lake Jovita Golf and Coun...
$400Ks - $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 - $900Ks
Esplanade at Wiregrass Ra..., Wesley Chapel, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes
Kings Ridge 4088 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$374,900

2 beds

|

2 baths

|

1,975 sq ft

|

House

4088 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Sun City Center 1110 MCDANIEL ST # 1110, SUN CITY CENTER..., Sun City Center, FL 33573
$210,000

2 beds

|

2 baths

|

1,559 sq ft

|

Condo

1110 MCDANIEL ST # 1110, SUN CITY CENTER...
Community: Sun City Center
Highlands Ridge 2835 S MAINSAIL DR, AVON PARK, FL, 33825, Avon Park, FL 33825
$119,000

2 beds

|

2 baths

|

1,200 sq ft

|

Mobile Home

2835 S MAINSAIL DR, AVON PARK, FL, 33825
Community: Highlands Ridge
Spruce Creek Country Club 12133 SE 91ST TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$379,900

3 beds

|

2 baths

|

1,958 sq ft

|

House

12133 SE 91ST TER, SUMMERFIELD, FL, 3449...
Harbor Hills Country Club 5195 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$650,000

3 beds

|

3 baths

|

2,696 sq ft

|

House

5195 GREENS DR, LADY LAKE, FL, 32159
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$850,000

3 beds

|

3 baths

|

2,959 sq ft

|

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 705 CORTEZ AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$260,000

2 beds

|

2 baths

|

1,398 sq ft

|

House

705 CORTEZ AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Lakes at Harmony 3402 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$295,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

3402 SAGEBRUSH ST, HARMONY, FL, 34773
Ocala Preserve 3558 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482
$475,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

3558 NW 56TH AVE, OCALA, FL, 34482
Community: Ocala Preserve
Venetian Bay 354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$345,000

2 beds

|

3 baths

|

1,837 sq ft

|

Townhouse

354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...
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.
Venetian Bay 3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$835,000

3 beds

|

3 baths

|

2,811 sq ft

|

House

3470 TESORO CIR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Sun City Center 2258 PRESERVATION GREEN CT, SUN CITY CEN..., Sun City Center, FL 33573
$325,000

3 beds

|

2 baths

|

1,490 sq ft

|

House

2258 PRESERVATION GREEN CT, SUN CITY CEN...
Community: Sun City Center
Summer Trees 98 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$225,000

2 beds

|

2 baths

|

1,004 sq ft

|

House

98 CYPRESS POND RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Venetian Bay 3587 CASALTA CIR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$349,999

3 beds

|

3 baths

|

2,124 sq ft

|

Townhouse

3587 CASALTA CIR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Lakeside Landings 5340 EDGEWATER WAY # 1, OXFORD, FL, 3448..., Oxford, FL 34484
$223,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5340 EDGEWATER WAY # 1, OXFORD, FL, 3448...
Community: Lakeside Landings
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Plantation at Leesburg 25331 HIBISCUS ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$233,900

2 beds

|

2 baths

|

1,413 sq ft

|

House

25331 HIBISCUS ST, LEESBURG, FL, 34748
Stonecrest 12342 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$358,900

2 beds

|

2 baths

|

1,764 sq ft

|

House

12342 SE 176TH LOOP, SUMMERFIELD, FL, 34...
Community: Stonecrest
Solivita 900 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$349,000

2 beds

|

2 baths

|

2,055 sq ft

|

House

900 SHOREHAVEN DR, POINCIANA, FL, 34759
Community: Solivita
Spruce Creek South 17807 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$229,999

3 beds

|

2 baths

|

1,450 sq ft

|

House

17807 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Spruce Creek South 10689 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$229,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

10689 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
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 Preserve 15024 SW 112TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$295,000

3 beds

|

2 baths

|

1,835 sq ft

|

House

15024 SW 112TH CIR, DUNNELLON, FL, 34432
SummerGlen 16417 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$330,000

3 beds

|

2 baths

|

2,279 sq ft

|

House

16417 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Sun City Center 705 CHURCHILL PL, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$199,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

705 CHURCHILL PL, SUN CITY CENTER, FL, 3...
Community: Sun City Center
SummerGlen 15692 SW 11TH COURT RD, OCALA, FL, 34473, Ocala, FL 34473
$405,000

3 beds

|

2 baths

|

1,768 sq ft

|

House

15692 SW 11TH COURT RD, OCALA, FL, 34473
Community: SummerGlen
Venetian Bay 287 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$429,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

287 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 9866 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481
$266,500

2 beds

|

2 baths

|

1,904 sq ft

|

House

9866 SW 97TH LN, OCALA, FL, 34481
Community: On Top of the World
Vienna Square 1561 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$229,000

2 beds

|

2 baths

|

1,231 sq ft

|

Villa

1561 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Oak Run 11091 SW 73RD CT, OCALA, FL, 34476, Ocala, FL 34476
$278,000

2 beds

|

2 baths

|

1,778 sq ft

|

House

11091 SW 73RD CT, OCALA, FL, 34476
Community: Oak Run
Legacy of Leesburg 27601 COUNTRY STONE CT, LEESBURG, FL, 34..., Leesburg, FL 34748
$440,000

3 beds

|

2 baths

|

2,066 sq ft

|

House

27601 COUNTRY STONE CT, LEESBURG, FL, 34...
Community: Legacy of Leesburg
Latitude Margaritaville 148 SIX STRING DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$719,900

2 beds

|

3 baths

|

2,347 sq ft

|

House

148 SIX STRING DR, DAYTONA BEACH, FL, 32...
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.
The Villages® 1938 SASSPARILLA WAY, THE VILLAGES, FL, ..., The Villages, FL 32162
$519,900

3 beds

|

2 baths

|

1,907 sq ft

|

House

1938 SASSPARILLA WAY, THE VILLAGES, FL, ...
Community: The Villages®
Del Webb Sunbridge 6525 ROVER WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$500,000

3 beds

|

3 baths

|

2,405 sq ft

|

House

6525 ROVER WAY, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Latitude Margaritaville 713 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$639,900

2 beds

|

2 baths

|

1,939 sq ft

|

House

713 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Spruce Creek North 6263 SW 107TH ST, OCALA, FL, 34476, Ocala, FL 34476
$177,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

6263 SW 107TH ST, OCALA, FL, 34476
Community: Spruce Creek North
Stone Creek 7387 SW 99TH CT, OCALA, FL, 34481, Ocala, FL 34481
$298,800

2 beds

|

2 baths

|

1,596 sq ft

|

House

7387 SW 99TH CT, OCALA, FL, 34481
Community: Stone Creek
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 123 GULF DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$237,900

2 beds

|

2 baths

|

1,317 sq ft

|

Halfplex

123 GULF DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 2544 ASHVILLE AVE, THE VILLAGES, FL, 321..., The Villages, FL 32162
$695,000

3 beds

|

2 baths

|

2,725 sq ft

|

House

2544 ASHVILLE AVE, THE VILLAGES, FL, 321...
Community: The Villages®
Latitude Margaritaville 227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$507,900

2 beds

|

2 baths

|

1,786 sq ft

|

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Sun City Center 404 GRAND CHATEAUX WAY, SUN CITY CENTER,..., Sun City Center, FL 33573
$357,000

2 beds

|

2 baths

|

1,963 sq ft

|

House

404 GRAND CHATEAUX WAY, SUN CITY CENTER,...
Community: Sun City Center
Twin Lakes 5043 VANTAGE CT, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$599,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

5043 VANTAGE CT, SAINT CLOUD, FL, 34772
Community: Twin Lakes

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3,952 homes near Winter Garden
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