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Winter Garden, FL 55+ active adult communities & homes for sale - Page 44

3,769 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 (57 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
$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
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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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.
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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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
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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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) Cresswind at Victoria Gar...
$300ks - $500ks
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.
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Cresswind Lakewood Ranch
$400ks - $700ks
Cresswind Lakewood Ranch, Lakewood Ranch, FL
New and Resale | 55+ age-restricted | Built 2018 - present | 648 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
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) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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.
123...4
Twin Lakes 5042 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772
$484,250

3 beds

|

2 baths

|

2,056 sq ft

|

House

5042 DANCY LN, ST CLOUD, FL, 34772
Community: Twin Lakes
Silver Lakes 2258 SILVER RE DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$290,000

3 beds

|

2 baths

|

1,355 sq ft

|

House

2258 SILVER RE DR, LAKELAND, FL, 33810
Community: Silver Lakes
The Villages® 1260 GRANADA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$314,900

2 beds

|

2 baths

|

1,541 sq ft

|

House

1260 GRANADA CT, LADY LAKE, FL, 32159
Community: The Villages®
Sun City Center 1901 ANDOVER WAY 26, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$71,500

1 beds

|

2 baths

|

800 sq ft

|

Condo

1901 ANDOVER WAY 26, SUN CITY CENTER, FL...
Community: Sun City Center
Colonnades 4918 PLEASANT HOLLOW TRL, LAKELAND, FL, ..., Lakeland, FL 33811
$199,900

2 beds

|

2 baths

|

1,123 sq ft

|

House

4918 PLEASANT HOLLOW TRL, LAKELAND, FL, ...
Community: Colonnades
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Solivita 380 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$285,000

3 beds

|

2 baths

|

1,786 sq ft

|

House

380 SORRENTO RD, KISSIMMEE, FL, 34759
Community: Solivita
Arlington Ridge 4834 INDEPENDENCE TRL, LEESBURG, FL, 347..., Leesburg, FL 34748
$299,900

2 beds

|

2 baths

|

1,772 sq ft

|

House

4834 INDEPENDENCE TRL, LEESBURG, FL, 347...
Community: Arlington Ridge
Breakaway Trails 56 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$423,810

3 beds

|

2 baths

|

1,748 sq ft

|

House

56 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3...
Community: Breakaway Trails
Sun City Center 624 LA JOLLA AVE, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573
$299,000

3 beds

|

3 baths

|

2,012 sq ft

|

House

624 LA JOLLA AVE, SUN CITY CENTER, FL, 3...
Community: Sun City Center
Lake James 2356 LAKE JAMES WAY, LAKELAND, FL, 33810, Lakeland, FL 33810
$375,000

2 beds

|

2 baths

|

2,124 sq ft

|

House

2356 LAKE JAMES WAY, LAKELAND, FL, 33810
Community: Lake James
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.
Cindy Certified
4442 SW 111TH PL, OCALA, FL, 34476, Ocala, FL 34476
$409,000

4 beds

|

3 baths

|

2,367 sq ft

|

House

4442 SW 111TH PL, OCALA, FL, 34476
Summit Greens 3003 PINNACLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$349,000

2 beds

|

2 baths

|

1,718 sq ft

|

House

3003 PINNACLE CT, CLERMONT, FL, 34711
Community: Summit Greens
Stone Creek 9407 SW 52ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$389,900

3 beds

|

2 baths

|

1,662 sq ft

|

House

9407 SW 52ND LOOP, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 8707 SW 88TH COURT RD K, OCALA, FL, 3448..., Ocala, FL 34481
$239,000

2 beds

|

2 baths

|

2,015 sq ft

|

Villa

8707 SW 88TH COURT RD K, OCALA, FL, 3448...
Community: On Top of the World
Sun City Center 2017 HAMPSTEAD CIR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$149,900

2 beds

|

2 baths

|

1,448 sq ft

|

Condo

2017 HAMPSTEAD CIR, SUN CITY CENTER, FL,...
Community: Sun City Center
Heritage - The Cottages of Sanders Grove 5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762, Okahumpka, FL 34762
$309,990

3 beds

|

2 baths

|

1,407 sq ft

|

House

5727 HIAWASSEE RD, OKAHUMPKA, FL, 34762
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
On Top of the World 8525 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$299,500

3 beds

|

2 baths

|

1,746 sq ft

|

House

8525 SW 79TH AVE, OCALA, FL, 34476
Community: On Top of the World
JB Ranch 9358 SW 60TH TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476
$292,500

2 beds

|

2 baths

|

1,813 sq ft

|

House

9358 SW 60TH TERRACE RD, OCALA, FL, 3447...
Community: JB Ranch
The Villages® 16581 SE 77TH NORTHRIDGE CT, THE VILLAGE..., The Villages, FL 32162
$479,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

16581 SE 77TH NORTHRIDGE CT, THE VILLAGE...
Community: The Villages®
Cindy Certified
17127 INGRAM BLUFF DR, WINTER GARDEN, FL..., Winter Garden, FL 34787
$721,820

4 beds

|

3 baths

|

2,235 sq ft

|

House

17127 INGRAM BLUFF DR, WINTER GARDEN, FL...
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.
On Top of the World 9041 SW 88TH PL, OCALA, FL, 34481, Ocala, FL 34481
$499,999

3 beds

|

3 baths

|

2,376 sq ft

|

House

9041 SW 88TH PL, OCALA, FL, 34481
Community: On Top of the World
Breakaway Trails 180 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$497,000

3 beds

|

2 baths

|

1,983 sq ft

|

House

180 BLACK HICKORY WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
Lake Ashton 4496 STRATHMORE DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$369,500

3 beds

|

2 baths

|

2,312 sq ft

|

House

4496 STRATHMORE DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Sun City Center 1529 ALLEGHENY DR, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$225,000

2 beds

|

2 baths

|

1,226 sq ft

|

House

1529 ALLEGHENY DR, SUN CITY CENTER, FL, ...
Community: Sun City Center
Spruce Creek Country Club 13260 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$309,900

2 beds

|

2 baths

|

1,498 sq ft

|

House

13260 SE 92ND COURT RD, SUMMERFIELD, FL,...
Heritage - The Cottages of Sanders Grove 6209 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$343,445

4 beds

|

2 baths

|

1,758 sq ft

|

House

6209 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Spruce Creek Country Club 9921 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$286,900

2 beds

|

2 baths

|

1,872 sq ft

|

House

9921 SE 138TH LOOP, SUMMERFIELD, FL, 344...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 803 CHIPPER DR, SUN CITY CENTER, FL, 335..., Sun City Center, FL 33573
$337,900

2 beds

|

2 baths

|

1,854 sq ft

|

Villa

803 CHIPPER DR, SUN CITY CENTER, FL, 335...
Community: Sun City Center
Cindy Certified
225 TRIUMPH DR, SEBRING, FL, 33872, Sebring, FL 33872
$294,900

3 beds

|

2 baths

|

1,492 sq ft

|

House

225 TRIUMPH DR, SEBRING, FL, 33872
Cindy Certified
5123 SW 91ST ST, OCALA, FL, 34476, Ocala, FL 34476
$323,000

4 beds

|

2 baths

|

2,334 sq ft

|

House

5123 SW 91ST ST, OCALA, FL, 34476
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.
Heritage - The Cottages of Sanders Grove 6201 SANDERS GROVE CIR, OKAHUMPKA, FL, 3..., Okahumpka, FL 34762
$341,535

4 beds

|

2 baths

|

1,625 sq ft

|

House

6201 SANDERS GROVE CIR, OKAHUMPKA, FL, 3...
Ocala Palms 5455 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482
$299,900

3 beds

|

2 baths

|

1,858 sq ft

|

House

5455 NW 26TH LN, OCALA, FL, 34482
Community: Ocala Palms
Latitude Margaritaville 500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$399,900

2 beds

|

2 baths

|

1,464 sq ft

|

House

500 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...
Esplanade at Westview 4457 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$325,000

2 beds

|

2 baths

|

1,483 sq ft

|

House

4457 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Esplanade at Westview 4463 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$380,019

2 beds

|

2 baths

|

1,677 sq ft

|

House

4463 OCHOS RIOS PL, KISSIMMEE, FL, 34758
Cindy Certified
2937 DEERBERRY LN, CLERMONT, FL, 34714, Clermont, FL 34714
$449,000

4 beds

|

3 baths

|

2,157 sq ft

|

House

2937 DEERBERRY LN, CLERMONT, FL, 34714
Sun City Center 445 NOBLE FAIRE DR, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$399,900

3 beds

|

3 baths

|

2,637 sq ft

|

House

445 NOBLE FAIRE DR, SUN CITY CENTER, FL,...
Community: Sun City Center
Venetian Bay 3073 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$315,000

3 beds

|

3 baths

|

1,614 sq ft

|

House

3073 MELETO 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
Latitude Margaritaville 424 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$614,900

2 beds

|

3 baths

|

2,116 sq ft

|

House

424 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Cindy Certified
5428 HUTCHINSON ST, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$409,888

4 beds

|

2 baths

|

1,896 sq ft

|

House

5428 HUTCHINSON ST, PORT ORANGE, FL, 321...
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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3,769 homes
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