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Winter Garden, FL 55+ active adult communities & homes for sale - Page 92

3,683 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
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
$100ks - $800ks
Sun City Center, Sun City Center, FL
Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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
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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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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
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
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
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
4.6 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
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Questions? Call us: (689) 407-5757
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
4.7 rating (3 reviews) Spruce Creek South
$100ks - $200ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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
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
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
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 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
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $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
$300ks - $900ks
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 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
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
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) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 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.
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes
5 rating (4 reviews) Highlands Ridge
<$100k - $300ks
Highlands Ridge, Avon Park, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 850 homes
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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
12...3
Sun City Center 1715 S PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$310,000

2 beds

|

2 baths

|

1,618 sq ft

|

House

1715 S PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
Sun City Center 1120 EMERALD DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573
$399,000

2 beds

|

2 baths

|

1,885 sq ft

|

House

1120 EMERALD DUNES DR, SUN CITY CENTER, ...
Community: Sun City Center
Harbor Hills Country Club 6042 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$364,900

3 beds

|

2 baths

|

2,190 sq ft

|

House

6042 TOPSAIL RD, LADY LAKE, FL, 32159
Alhambra Villas Condominiums 201 N HILL AVE 150, DELAND, FL, 32724, Deland, FL 32724
$194,900

2 beds

|

2 baths

|

1,090 sq ft

|

Condo

201 N HILL AVE 150, DELAND, FL, 32724
Sun City Center 2403 NANTUCKET GREEN CT, SUN CITY CENTER..., Sun City Center, FL 33573
$165,000

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2403 NANTUCKET GREEN CT, SUN CITY CENTER...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cherrywood 6008 SW 103RD LOOP, OCALA, FL, 34476, Ocala, FL 34476
$349,900

3 beds

|

2 baths

|

1,763 sq ft

|

House

6008 SW 103RD LOOP, OCALA, FL, 34476
Community: Cherrywood
Oak Run 11447 SW 69TH CIR, OCALA, FL, 34476, Ocala, FL 34476
$234,900

2 beds

|

2 baths

|

1,687 sq ft

|

House

11447 SW 69TH CIR, OCALA, FL, 34476
Community: Oak Run
Trilogy® Orlando 119 CRESCENT MOON DR, GROVELAND, FL, 347..., Groveland, FL 34736
$315,000

2 beds

|

2 baths

|

1,556 sq ft

|

House

119 CRESCENT MOON DR, GROVELAND, FL, 347...
Community: Trilogy® Orlando
Colonnades 1618 BIRCHWOOD LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811
$239,900

2 beds

|

2 baths

|

1,579 sq ft

|

House

1618 BIRCHWOOD LOOP, LAKELAND, FL, 33811
Community: Colonnades
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 1529 ALLEGHENY DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$239,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

1529 ALLEGHENY DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Pelican Bay Daytona Beach 129 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$205,000

3 beds

|

2 baths

|

1,347 sq ft

|

Condo

129 BLUE HERON DR A, DAYTONA BEACH, FL, ...
Stone Creek 6094 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$330,000

3 beds

|

2 baths

|

1,587 sq ft

|

House

6094 SW 93RD CIR, OCALA, FL, 34481
Community: Stone Creek
Carlsberg Estates on Lake Suzanne 4189 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$240,000

3 beds

|

2 baths

|

1,385 sq ft

|

House

4189 CANNES AVE, LAKE WALES, FL, 33859
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Ocala Preserve 4086 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$248,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4086 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
Traditions at Lake Ruby 3832 TRADITIONS BLVD, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$290,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3832 TRADITIONS BLVD, WINTER HAVEN, FL, ...
Colonnades 4829 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$249,900

2 beds

|

2 baths

|

1,182 sq ft

|

House

4829 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
The Villages® 3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ..., The Villages, FL 32163
$415,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

3812 NOTTINGHAM LOOP, 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.
Lake Ashton 4432 WATERFORD DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$279,900

2 beds

|

2 baths

|

1,605 sq ft

|

House

4432 WATERFORD DR, LAKE WALES, FL, 33859
Community: Lake Ashton
Sun City Center 401 DORCHESTER PL 58, SUN CITY CENTER, F..., Sun City Center, FL 33573
$123,900

2 beds

|

2 baths

|

984 sq ft

|

Condo

401 DORCHESTER PL 58, SUN CITY CENTER, F...
Community: Sun City Center
On Top of the World 9823 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$289,500

2 beds

|

2 baths

|

1,467 sq ft

|

House

9823 SW 95TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Highland Fairways 1967 LONG BOAT DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$260,000

2 beds

|

2 baths

|

1,955 sq ft

|

House

1967 LONG BOAT DR, LAKELAND, FL, 33810
Community: Highland Fairways
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1119 VILLEROY DR, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$399,900

3 beds

|

2 baths

|

1,924 sq ft

|

House

1119 VILLEROY DR, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Liberty Village 7474 SW 78TH TER, OCALA, FL, 34481, Ocala, FL 34481
$385,000

4 beds

|

3 baths

|

2,292 sq ft

|

House

7474 SW 78TH TER, OCALA, FL, 34481
Community: Liberty Village
The Villages® 892 NASH LOOP, THE VILLAGES, FL, 32162, The Villages, FL 32162
$289,900

2 beds

|

2 baths

|

1,090 sq ft

|

House

892 NASH LOOP, THE VILLAGES, FL, 32162
Community: The Villages®
Royal Highlands 20505 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$234,300

3 beds

|

2 baths

|

1,396 sq ft

|

House

20505 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
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.
SummerGlen 16292 SW 13TH TER, OCALA, FL, 34473, Ocala, FL 34473
$349,000

3 beds

|

2 baths

|

2,297 sq ft

|

House

16292 SW 13TH TER, OCALA, FL, 34473
Community: SummerGlen
Foxwood Lake Estates 5013 FOXWOOD BLVD, LAKELAND, FL, 33810, Lakeland, FL 33810
$170,000

2 beds

|

2 baths

|

1,056 sq ft

|

Manufactured Home

5013 FOXWOOD BLVD, LAKELAND, FL, 33810
Solivita 729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$509,900

4 beds

|

4 baths

|

2,616 sq ft

|

House

729 SAN RAPHAEL ST, KISSIMMEE, FL, 34759
Community: Solivita
Pelican Bay Daytona Beach 244 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$325,000

2 beds

|

2 baths

|

1,370 sq ft

|

House

244 PALM SPARROW CT, DAYTONA BEACH, FL, ...
SummerGlen 16026 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473
$266,654

3 beds

|

2 baths

|

1,800 sq ft

|

House

16026 SW 14TH AVENUE RD, OCALA, FL, 3447...
Community: SummerGlen
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Twin Lakes 2323 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$355,000

2 beds

|

2 baths

|

1,449 sq ft

|

Villa

2323 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
On Top of the World 8678 SW 83RD CIR, OCALA, FL, 34481, Ocala, FL 34481
$319,000

3 beds

|

2 baths

|

1,695 sq ft

|

House

8678 SW 83RD CIR, OCALA, FL, 34481
Community: On Top of the World
Pennbrooke Fairways 32525 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$285,000

2 beds

|

3 baths

|

1,643 sq ft

|

House

32525 OAK PARK DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Lakes at Laurel Highlands 1823 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811
$330,000

3 beds

|

2 baths

|

1,711 sq ft

|

House

1823 PRISTINE LOOP, LAKELAND, FL, 33811
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.
Twin Lakes 2410 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772
$369,000

2 beds

|

2 baths

|

1,464 sq ft

|

Villa

2410 DATURA LOOP, SAINT CLOUD, FL, 34772
Community: Twin Lakes
High Vista at Ridgewood Lakes 100 MOSS LN, DAVENPORT, FL, 33837, Davenport, FL 33837
$399,000

3 beds

|

2 baths

|

2,051 sq ft

|

House

100 MOSS LN, DAVENPORT, FL, 33837
Alhambra Villas Condominiums 217 N HILL AVE 20, DELAND, FL, 32724, Deland, FL 32724
$234,900

2 beds

|

2 baths

|

1,066 sq ft

|

Condo

217 N HILL AVE 20, DELAND, FL, 32724
Ocala Palms 5247 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482
$219,900

2 beds

|

2 baths

|

1,161 sq ft

|

House

5247 NW 18TH ST, OCALA, FL, 34482
Community: Ocala Palms
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates 10300 SW 98TH TER, OCALA, FL, 34481, Ocala, FL 34481
$145,000

2 beds

|

2 baths

|

960 sq ft

|

House

10300 SW 98TH TER, OCALA, FL, 34481
Community: Pine Run Estates
Quail Meadow 4773 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482
$359,990

3 beds

|

2 baths

|

2,152 sq ft

|

House

4773 NW 32ND ST, OCALA, FL, 34482
Community: Quail Meadow

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