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Winter Garden, FL 55+ active adult communities & homes for sale - Page 42

3,497 homes near Winter Garden

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4 rating (17 reviews) The Villages®
$100ks - $1Ms
The Villages®, The Villages, FL
New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes
3.8 rating (14 reviews) Sun City Center
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4 rating (56 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
4.2 rating (10 reviews) Stone Creek
$200ks - $500ks
Stone Creek, Ocala, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes
4.7 rating (18 reviews) Solivita
$300ks - $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
4.5 rating (11 reviews) Spruce Creek Country Club
$100ks - $400ks
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 - $300ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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
3.6 rating (48 reviews) Latitude Margaritaville
$300ks - $800ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
Venetian Bay
$300ks - $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.
4.6 rating (5 reviews) Ocala Preserve
$100ks - $500ks
Ocala Preserve, Ocala, FL
New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 homes
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
4 rating (7 reviews) Tampa Bay Golf and Countr...
$200ks - $500ks
Tampa Bay Golf and Countr..., San Antonio, FL
Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes
3.8 rating (4 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4 rating (2 reviews) Harbor Hills Country Club
$300ks - $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 homes
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
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 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.
3.6 rating (5 reviews) Heritage Hills
$200ks - $400ks
Heritage Hills, Clermont, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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.
12...3
SummerGlen 1690 SW 158TH LN, OCALA, FL, 34473, Ocala, FL 34473
$279,900

3 beds

|

2 baths

|

1,647 sq ft

|

House

1690 SW 158TH LN, OCALA, FL, 34473
Community: SummerGlen
The Villages® 2679 LANTANA AVE, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$539,000

3 beds

|

2 baths

|

1,966 sq ft

|

House

2679 LANTANA AVE, THE VILLAGES, FL, 3216...
Community: The Villages®
The Villages® 258 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$298,000

2 beds

|

2 baths

|

1,130 sq ft

|

House

258 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Latitude Margaritaville 227 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$489,900

2 beds

|

2 baths

|

1,778 sq ft

|

House

227 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Venetian Bay 656 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$779,576

5 beds

|

4 baths

|

3,221 sq ft

|

House

656 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Jovita Golf and Country Club 12442 FOREST HIGHLANDS DR, DADE CITY, FL..., Dade City, FL 33525
$449,900

3 beds

|

2 baths

|

2,230 sq ft

|

House

12442 FOREST HIGHLANDS DR, DADE CITY, FL...
Sun City Center 656 FORT DUQUESNA DR, SUN CITY CENTER, F..., Sun City Center, FL 33573
$235,000

2 beds

|

2 baths

|

1,408 sq ft

|

House

656 FORT DUQUESNA DR, SUN CITY CENTER, F...
Community: Sun City Center
Tampa Bay Golf and Country Club 10504 MOSHIE LN, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$299,900

3 beds

|

2 baths

|

1,645 sq ft

|

House

10504 MOSHIE LN, SAN ANTONIO, FL, 33576
Tampa Bay Golf and Country Club 29407 SNAP HOOK DR, SAN ANTONIO, FL, 335..., San Antonio, FL 33576
$338,600

2 beds

|

2 baths

|

1,489 sq ft

|

House

29407 SNAP HOOK DR, SAN ANTONIO, FL, 335...
The Villages® 2454 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162
$235,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2454 SOUTHERN OAK ST, THE VILLAGES, FL, ...
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.
The Villages® 2311 CRESTVIEW ST, THE VILLAGES, FL, 321..., The Villages, FL 32162
$415,000

3 beds

|

2 baths

|

1,602 sq ft

|

Villa

2311 CRESTVIEW ST, THE VILLAGES, FL, 321...
Community: The Villages®
Twin Lakes 4918 DRAWDY CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$479,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

4918 DRAWDY CT, ST CLOUD, FL, 34772
Community: Twin Lakes
Southshore Bay 17551 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598
$289,000

2 beds

|

3 baths

|

1,737 sq ft

|

Villa

17551 HOLLY WELL AVE, WIMAUMA, FL, 33598
Community: Southshore Bay
The Villages® 8108 SE 169TH TWEEDSIDE LOOP, THE VILLAG..., The Villages, FL 32162
$309,900

3 beds

|

3 baths

|

1,352 sq ft

|

Villa

8108 SE 169TH TWEEDSIDE LOOP, THE VILLAG...
Community: The Villages®
Legacy of Leesburg 27106 GREENFLY ORCHID LN, LEESBURG, FL, ..., Leesburg, FL 34748
$289,900

3 beds

|

2 baths

|

1,541 sq ft

|

House

27106 GREENFLY ORCHID LN, LEESBURG, FL, ...
Community: Legacy of Leesburg
Stone Creek 7868 SW 97TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$569,300

3 beds

|

3 baths

|

2,508 sq ft

|

House

7868 SW 97TH CIR, 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
Sun City Center 737 MCCALLISTER AVE 265, SUN CITY CENTER..., Sun City Center, FL 33573
$255,000

2 beds

|

2 baths

|

1,546 sq ft

|

Condo

737 MCCALLISTER AVE 265, SUN CITY CENTER...
Community: Sun City Center
On Top of the World 9662 SW 93RD LOOP, OCALA, FL, 34481, Ocala, FL 34481
$229,000

2 beds

|

2 baths

|

2,035 sq ft

|

House

9662 SW 93RD LOOP, OCALA, FL, 34481
Community: On Top of the World
JB Ranch 6053 SW 93RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$309,900

4 beds

|

2 baths

|

2,034 sq ft

|

House

6053 SW 93RD LOOP, OCALA, FL, 34476
Community: JB Ranch
Stonecrest 17776 SE 114TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,000

3 beds

|

3 baths

|

1,646 sq ft

|

Villa

17776 SE 114TH AVE, SUMMERFIELD, FL, 344...
Community: Stonecrest
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.
Latitude Margaritaville 538 DAIQUIRI PL, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$374,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

538 DAIQUIRI PL, DAYTONA BEACH, FL, 3212...
SummerGlen 15691 SW 11TH COURT RD, OCALA, FL, 34473, Ocala, FL 34473
$279,999

3 beds

|

2 baths

|

1,646 sq ft

|

House

15691 SW 11TH COURT RD, OCALA, FL, 34473
Community: SummerGlen
Archers Mill 3295 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$584,900

4 beds

|

4 baths

|

2,787 sq ft

|

House

3295 ARCH AVE, ORMOND BEACH, FL, 32174
Community: Archers Mill
Palm Cay 8417 SW 106TH ST, OCALA, FL, 34481, Ocala, FL 34481
$179,900

2 beds

|

2 baths

|

1,080 sq ft

|

House

8417 SW 106TH ST, OCALA, FL, 34481
Community: Palm Cay
Majestic Oaks Ocala 5402 SW 85TH ST, OCALA, FL, 34476, Ocala, FL 34476
$340,000

3 beds

|

2 baths

|

2,099 sq ft

|

House

5402 SW 85TH ST, OCALA, FL, 34476
Community: Majestic Oaks Ocala
On Top of the World 8061 SW 81ST LOOP, OCALA, FL, 34476, Ocala, FL 34476
$244,000

3 beds

|

2 baths

|

1,654 sq ft

|

House

8061 SW 81ST LOOP, OCALA, FL, 34476
Community: On Top of the World
On Top of the World 9646 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$210,000

2 beds

|

2 baths

|

1,517 sq ft

|

House

9646 SW 92ND PLACE RD, 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
Latitude Margaritaville 1068 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$609,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

1068 SEA SHELL CT, DAYTONA BEACH, FL, 32...
Legacy of Leesburg 5154 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$345,000

3 beds

|

2 baths

|

2,045 sq ft

|

House

5154 AURORA DR, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Royal Harbor 5481 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$319,900

3 beds

|

2 baths

|

1,513 sq ft

|

House

5481 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
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 Country Club 9435 SE 124TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$319,900

2 beds

|

2 baths

|

1,720 sq ft

|

House

9435 SE 124TH PL, SUMMERFIELD, FL, 34491
Venetian Bay 365 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$375,000

3 beds

|

2 baths

|

1,614 sq ft

|

House

365 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Del Webb Orlando 715 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837
$419,900

2 beds

|

2 baths

|

2,056 sq ft

|

House

715 ASTURIAS RD, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Royal Highlands 21325 ROYAL TROON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$379,900

2 beds

|

2 baths

|

2,333 sq ft

|

House

21325 ROYAL TROON DR, LEESBURG, FL, 3474...
Community: Royal Highlands
Venetian Bay 3446 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$420,000

4 beds

|

4 baths

|

2,379 sq ft

|

Townhouse

3446 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Cresswind at Victoria Gardens 215 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724
$585,000

3 beds

|

3 baths

|

2,792 sq ft

|

House

215 AVENHAM DR, DELAND, FL, 32724
Sun City Center 2512 LANCASTER DR 2512, SUN CITY CENTER,..., Sun City Center, FL 33573
$220,000

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

2512 LANCASTER DR 2512, SUN CITY CENTER,...
Community: Sun City Center
Spruce Creek Country Club 13720 SE 97TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$439,000

2 beds

|

2 baths

|

1,888 sq ft

|

House

13720 SE 97TH AVE, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Latitude Margaritaville 281 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$629,000

2 beds

|

2 baths

|

1,922 sq ft

|

House

281 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Sun City Center 205 ANDOVER PL 119, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$114,799

1 beds

|

2 baths

|

800 sq ft

|

Condo

205 ANDOVER PL 119, SUN CITY CENTER, FL,...
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.

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3,497 homes
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