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

3,631 homes near Winter Garden

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5 rating (1 reviews) Del Webb Oasis
$400Ks - $900Ks
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
$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 (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
4.2 rating (10 reviews) Stone Creek
$200Ks - $700Ks
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 - $500Ks
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
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
No reviews yet Venetian Bay
$200Ks - $2Ms
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 - $500Ks
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
<$100k - $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 - $500Ks
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 | 1,024 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
$400Ks - $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
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
No reviews yet Pine Run Estates
<$100k - $300Ks
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
Breakaway Trails 8 WILD CREEK WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$774,000

5 beds

|

4 baths

|

3,367 sq ft

|

House

8 WILD CREEK WAY, ORMOND BEACH, FL, 3217...
Community: Breakaway Trails
Venetian Bay 112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$725,000

3 beds

|

2 baths

|

2,372 sq ft

|

House

112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
Breakaway Trails 94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$675,000

4 beds

|

3 baths

|

3,261 sq ft

|

House

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
VillageWalk at Lake Nona 12244 PESCARA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$450,000

3 beds

|

2 baths

|

1,542 sq ft

|

Villa

12244 PESCARA LN, ORLANDO, FL, 32827
Highland Lakes 6033 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,632 sq ft

|

House

6033 WADE ST, LEESBURG, FL, 34748
Community: Highland Lakes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Highland Lakes 27107 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

2 beds

|

2 baths

|

1,474 sq ft

|

House

27107 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Marco Polo Village 5268 SW 110TH PL, OCALA, FL, 34476, Ocala, FL 34476
$299,900

3 beds

|

2 baths

|

1,852 sq ft

|

House

5268 SW 110TH PL, OCALA, FL, 34476
Community: Marco Polo Village
Ocala Preserve 3645 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$370,000

2 beds

|

2 baths

|

1,666 sq ft

|

House

3645 NW 55TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Oak Run 11127 SW 73RD CIR, OCALA, FL, 34476, Ocala, FL 34476
$324,000

3 beds

|

2 baths

|

2,016 sq ft

|

House

11127 SW 73RD CIR, OCALA, FL, 34476
Community: Oak Run
Stone Creek 9761 SW 74TH PL, OCALA, FL, 34481, Ocala, FL 34481
$505,000

3 beds

|

3 baths

|

2,530 sq ft

|

House

9761 SW 74TH PL, OCALA, FL, 34481
Community: Stone Creek
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.
Southshore Bay 17026 CLEAR CORK DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$325,000

2 beds

|

2 baths

|

1,636 sq ft

|

Villa

17026 CLEAR CORK DR, WIMAUMA, FL, 33598
Community: Southshore Bay
On Top of the World 7774 SW 80TH PLACE RD, OCALA, FL, 34476, Ocala, FL 34476
$345,000

2 beds

|

2 baths

|

2,108 sq ft

|

House

7774 SW 80TH PLACE RD, OCALA, FL, 34476
Community: On Top of the World
Tampa Bay Golf and Country Club 29417 CADDYSHACK LN, SAN ANTONIO, FL, 33..., San Antonio, FL 33576
$269,000

3 beds

|

2 baths

|

1,384 sq ft

|

Villa

29417 CADDYSHACK LN, SAN ANTONIO, FL, 33...
Lake Jovita Golf and Country Club 12306 WOODLANDS CIR, DADE CITY, FL, 3352..., Dade City, FL 33525
$450,000

4 beds

|

3 baths

|

2,322 sq ft

|

House

12306 WOODLANDS CIR, DADE CITY, FL, 3352...
VillageWalk at Lake Nona 12021 JEWEL FISH LN, ORLANDO, FL, 32827, Orlando, FL 32827
$749,000

4 beds

|

4 baths

|

2,667 sq ft

|

House

12021 JEWEL FISH LN, ORLANDO, FL, 32827
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates 9035 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481
$159,500

2 beds

|

2 baths

|

1,144 sq ft

|

House

9035 SW 101ST LN, OCALA, FL, 34481
Community: Pine Run Estates
On Top of the World 8883 SW 93RD LN F, OCALA, FL, 34481, Ocala, FL 34481
$213,000

2 beds

|

2 baths

|

1,369 sq ft

|

Condo

8883 SW 93RD LN F, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 453 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168
$585,000

5 beds

|

4 baths

|

3,051 sq ft

|

House

453 VENETIAN VILLA DR, NEW SMYRNA BEACH,...
Community: Venetian Bay
Royal Highlands 4854 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$289,000

3 beds

|

2 baths

|

1,469 sq ft

|

House

4854 GLEN COE ST, LEESBURG, FL, 34748
Community: Royal Highlands
Liberty Village 7867 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$299,900

3 beds

|

2 baths

|

1,755 sq ft

|

House

7867 SW 74TH LOOP, OCALA, FL, 34481
Community: Liberty Village
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 Lakes at Harmony 7651 FIVE OAKS DR, HARMONY, FL, 34773, Harmony, FL 34773
$500,000

3 beds

|

3 baths

|

2,355 sq ft

|

House

7651 FIVE OAKS DR, HARMONY, FL, 34773
The Villages® 1130 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159
$465,000

2 beds

|

3 baths

|

1,780 sq ft

|

Condo

1130 AVENIDA DE LAS CASAS, LADY LAKE, FL...
Community: The Villages®
The Villages® 1013 ANN AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$219,500

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

1013 ANN AVE, LADY LAKE, FL, 32159
Community: The Villages®
Vienna Square 1613 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$197,000

2 beds

|

2 baths

|

1,151 sq ft

|

Villa

1613 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Vienna Square 1709 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$259,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1709 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 917 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$875,000

3 beds

|

2 baths

|

2,082 sq ft

|

House

917 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
The Lakes at Harmony 3443 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$315,000

2 beds

|

2 baths

|

1,637 sq ft

|

House

3443 SAGEBRUSH ST, HARMONY, FL, 34773
Spruce Creek Country Club 13015 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$469,999

3 beds

|

3 baths

|

2,429 sq ft

|

House

13015 SE 93RD CIR, SUMMERFIELD, FL, 3449...
The Villages® 1649 CAMPOS DR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$259,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

1649 CAMPOS DR, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 12900 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$399,000

3 beds

|

2 baths

|

2,149 sq ft

|

House

12900 SE 97TH TERRACE RD, SUMMERFIELD, F...
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 17577 SE 112TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$375,000

3 beds

|

2 baths

|

1,543 sq ft

|

House

17577 SE 112TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
Sun City Center 611 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$334,900

2 beds

|

2 baths

|

1,668 sq ft

|

Townhouse

611 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Sun City Center 1348 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$369,000

3 beds

|

2 baths

|

1,860 sq ft

|

Condo

1348 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
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
On Top of the World 9880 SW 88TH TER B, OCALA, FL, 34481, Ocala, FL 34481
$255,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

9880 SW 88TH TER B, OCALA, FL, 34481
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
Trilogy® Orlando 100 FLAME VINE WAY, GROVELAND, FL, 34736, Groveland, FL 34736
$325,000

2 beds

|

2 baths

|

1,808 sq ft

|

House

100 FLAME VINE WAY, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Lake Jovita Golf and Country Club 13217 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525
$695,000

4 beds

|

3 baths

|

2,601 sq ft

|

House

13217 THOROUGHBRED DR, DADE CITY, FL, 33...
Del Webb Oasis 13846 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787
$699,000

2 beds

|

3 baths

|

2,108 sq ft

|

House

13846 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
The Villages® 2498 YALAHA AVE, THE VILLAGES, FL, 32162, The Villages, FL 32162
$375,000

2 beds

|

2 baths

|

1,210 sq ft

|

Villa

2498 YALAHA AVE, THE VILLAGES, FL, 32162
Community: The Villages®
Spruce Creek Country Club 13184 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$549,900

2 beds

|

3 baths

|

2,423 sq ft

|

House

13184 SE 97TH TERRACE RD, SUMMERFIELD, F...

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3,631 homes near Winter Garden
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