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

3,953 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 - $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
$200Ks - $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 - $1Ms
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...
$100Ks - $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 - $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
Spruce Creek Country Club 12592 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$490,000

3 beds

|

2 baths

|

2,413 sq ft

|

House

12592 SE 97TH TERRACE RD, SUMMERFIELD, F...
Oak Run 10829 SW 83RD AVE, OCALA, FL, 34481, Ocala, FL 34481
$185,000

2 beds

|

2 baths

|

1,328 sq ft

|

House

10829 SW 83RD AVE, OCALA, FL, 34481
Community: Oak Run
Summer Trees 120 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$294,501

2 beds

|

2 baths

|

1,245 sq ft

|

House

120 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Spruce Creek Country Club 8633 SE 133RD LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$269,900

2 beds

|

2 baths

|

1,346 sq ft

|

House

8633 SE 133RD LN, SUMMERFIELD, FL, 34491
The Villages® 1313 LA ESTRELLITA WAY, THE VILLAGES, FL..., The Villages, FL 32162
$315,500

2 beds

|

2 baths

|

1,248 sq ft

|

House

1313 LA ESTRELLITA WAY, THE VILLAGES, FL...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sandpiper Golf & Country Club 6064 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$299,900

2 beds

|

2 baths

|

1,645 sq ft

|

House

6064 CONDOR DR, LAKELAND, FL, 33809
The Country Club of Mount Dora 8019 ARCADIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$374,000

3 beds

|

2 baths

|

1,501 sq ft

|

House

8019 ARCADIAN CT, MOUNT DORA, FL, 32757
Lakes of Mount Dora 1010 NANTUCKET SOUND, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$459,000

3 beds

|

2 baths

|

1,806 sq ft

|

House

1010 NANTUCKET SOUND, MOUNT DORA, FL, 32...
Community: Lakes of Mount Dora
Spruce Creek Country Club 13944 SE 96TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$449,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

13944 SE 96TH CIR, SUMMERFIELD, FL, 3449...
The Villages® 2968 WOTRING WAY, THE VILLAGES, FL, 3216..., The Villages, FL 32163
$375,000

3 beds

|

2 baths

|

1,739 sq ft

|

Villa

2968 WOTRING WAY, THE VILLAGES, FL, 3216...
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.
Oak Run 11696 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476
$200,000

2 beds

|

2 baths

|

1,218 sq ft

|

House

11696 SW 71ST CIR, OCALA, FL, 34476
Community: Oak Run
The Villages® 3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$419,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ...
Community: The Villages®
Solivita 112 SEVILLA CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$485,900

3 beds

|

3 baths

|

2,450 sq ft

|

House

112 SEVILLA CT, POINCIANA, FL, 34759
Community: Solivita
The Villages® 2564 RED CEDAR LN, THE VILLAGES, FL, 321..., The Villages, FL 32162
$299,000

2 beds

|

2 baths

|

1,188 sq ft

|

Villa

2564 RED CEDAR LN, THE VILLAGES, FL, 321...
Community: The Villages®
Plantation at Leesburg 5436 ASTOR ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$180,000

2 beds

|

2 baths

|

1,542 sq ft

|

House

5436 ASTOR ST, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 705 PRADO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$274,900

2 beds

|

2 baths

|

1,383 sq ft

|

House

705 PRADO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Spruce Creek Country Club 12485 SE 90TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$279,000

2 beds

|

2 baths

|

1,812 sq ft

|

House

12485 SE 90TH TER, SUMMERFIELD, FL, 3449...
On Top of the World 9530 SW 85TH AVE B, OCALA, FL, 34481, Ocala, FL 34481
$155,000

2 beds

|

2 baths

|

1,294 sq ft

|

Villa

9530 SW 85TH AVE B, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 3331 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$424,900

3 beds

|

2 baths

|

2,002 sq ft

|

Halfplex

3331 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Spruce Creek Country Club 13096 SE 93RD TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$419,000

2 beds

|

2 baths

|

2,075 sq ft

|

House

13096 SE 93RD 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.
Pelican Bay Daytona Beach 573 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$364,900

3 beds

|

2 baths

|

1,882 sq ft

|

House

573 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
On Top of the World 8890 SW 104TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$372,000

3 beds

|

2 baths

|

1,651 sq ft

|

House

8890 SW 104TH CIR, OCALA, FL, 34481
Community: On Top of the World
On Top of the World 9607 SW 79TH LANE RD, OCALA, FL, 34481, Ocala, FL 34481
$675,000

3 beds

|

3 baths

|

2,893 sq ft

|

House

9607 SW 79TH LANE RD, OCALA, FL, 34481
Community: On Top of the World
Sun City Center 1201 PERIDOT LN, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$439,900

3 beds

|

2 baths

|

1,951 sq ft

|

House

1201 PERIDOT LN, SUN CITY CENTER, FL, 33...
Community: Sun City Center
Spruce Creek Country Club 9029 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$279,900

2 beds

|

2 baths

|

1,445 sq ft

|

House

9029 SE 135TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 10082 SW 82ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$685,000

3 beds

|

3 baths

|

2,907 sq ft

|

House

10082 SW 82ND PLACE RD, OCALA, FL, 34481
Community: On Top of the World
Venetian Bay 3136 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$390,000

3 beds

|

3 baths

|

1,916 sq ft

|

House

3136 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
The Villages® 1311 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159
$164,900

2 beds

|

2 baths

|

1,092 sq ft

|

Manufactured Home

1311 E SCHWARTZ BLVD, LADY LAKE, FL, 321...
Community: The Villages®
Del Webb Orlando 265 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$349,900

2 beds

|

2 baths

|

1,819 sq ft

|

House

265 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Sun City Center 2004 BERRY ROBERTS DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$359,000

2 beds

|

2 baths

|

1,944 sq ft

|

House

2004 BERRY ROBERTS 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 607 FOX HILLS DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$299,990

2 beds

|

2 baths

|

1,852 sq ft

|

House

607 FOX HILLS DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
The Villages® 2337 ST GEORGE AVE, THE VILLAGES, FL, 32..., The Villages, FL 32162
$379,900

3 beds

|

2 baths

|

1,518 sq ft

|

House

2337 ST GEORGE AVE, THE VILLAGES, FL, 32...
Community: The Villages®
Mirada 31675 CANNON RUSH DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$325,000

2 beds

|

2 baths

|

1,683 sq ft

|

House

31675 CANNON RUSH DR, SAN ANTONIO, FL, 3...
Community: Mirada
The Villages® 8294 SE 177TH WINTERTHUR LOOP, THE VILLA..., The Villages, FL 32162
$389,900

3 beds

|

2 baths

|

1,918 sq ft

|

House

8294 SE 177TH WINTERTHUR LOOP, THE VILLA...
Community: The Villages®
Arlington Ridge 27103 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$502,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

27103 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Venetian Bay 3066 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$594,800

3 beds

|

4 baths

|

1,847 sq ft

|

Townhouse

3066 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
The Villages® 1715 LILLY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$269,000

2 beds

|

2 baths

|

1,756 sq ft

|

Modular

1715 LILLY LN, LADY LAKE, FL, 32159
Community: The Villages®
Ocala Palms 2478 NW 53RD AVENUE RD, OCALA, FL, 34482, Ocala, FL 34482
$347,000

3 beds

|

2 baths

|

2,217 sq ft

|

House

2478 NW 53RD AVENUE RD, OCALA, FL, 34482
Community: Ocala Palms
On Top of the World 8737 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$419,000

3 beds

|

2 baths

|

2,280 sq ft

|

House

8737 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
The Villages® 144 COSTA MESA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$374,900

3 beds

|

2 baths

|

2,046 sq ft

|

House

144 COSTA MESA DR, LADY LAKE, FL, 32159
Community: The Villages®

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3,953 homes near Winter Garden
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