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Winter Park, FL 55+ active adult communities & homes for sale - Page 60

2,513 homes near Winter Park

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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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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
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
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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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes
5 rating (1 reviews) Plantation Bay Golf &...
$400ks - $2Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 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
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 (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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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Questions? Call us: (888) 625-4885
Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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.
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
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
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Questions? Call us: (888) 625-4885
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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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.
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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
Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $600ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
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Questions? Call us: (888) 625-4885
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
3.8 rating (5 reviews) Traditions at Lake Ruby
$200ks - $300ks
Traditions at Lake Ruby, Winter Haven, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes
4.4 rating (16 reviews) Del Webb Orlando
$200ks - $500ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
4.1 rating (9 reviews) Indian River Colony Club
$200ks - $400ks
Indian River Colony Club, Melbourne, FL
New and Resale | 55+ age-restricted | Built 1986 - present | 777 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.
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes
12...3
Sandpiper Golf & Country Club 5976 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5976 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5970 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5970 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5992 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5992 TEAL TRL, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5987 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5987 TEAL TRL, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5982 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5982 CORMORANT CT, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Sandpiper Golf & Country Club 5914 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5914 CORMORANT CT, LAKELAND, FL, 33809
Kings Ridge 2131 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$289,499

2 beds

|

2 baths

|

1,394 sq ft

|

House

2131 BURLEY AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Bridgewater at Viera 1563 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$445,900

3 beds

|

2 baths

|

1,598 sq ft

|

House

1563 GREAT BELT CIR, MELBOURNE, FL, 3294...
Solivita 726 IRVINE RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$449,900

3 beds

|

3 baths

|

2,427 sq ft

|

House

726 IRVINE RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
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.
Sandpiper Golf & Country Club 5920 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5920 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5927 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5927 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5926 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5926 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5933 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5933 CORMORANT CT, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Sandpiper Golf & Country Club 5921 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5921 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5909 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5909 CORMORANT CT, LAKELAND, FL, 33809
Venetian Bay 2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168
$979,000

3 beds

|

3 baths

|

2,034 sq ft

|

House

2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
Spruce Creek Country Club 13863 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,000

3 beds

|

2 baths

|

1,844 sq ft

|

House

13863 SE 85TH CIR, SUMMERFIELD, FL, 3449...
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.
Pennbrooke Fairways 751 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$309,900

3 beds

|

2 baths

|

1,753 sq ft

|

House

751 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
American Village 43 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$334,990

3 beds

|

2 baths

|

1,604 sq ft

|

House

43 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
American Village 79 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$329,990

3 beds

|

2 baths

|

1,585 sq ft

|

House

79 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Del Webb Sunbridge 2793 NATURE VIEW RD, ST CLOUD, FL, 34771, St Cloud, FL 34771
$665,000

4 beds

|

3 baths

|

2,761 sq ft

|

House

2793 NATURE VIEW RD, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Kings Ridge 3525 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711
$344,900

2 beds

|

2 baths

|

1,548 sq ft

|

House

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
Four Seasons at Orlando 2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$515,000

3 beds

|

2 baths

|

2,042 sq ft

|

House

2233 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Plantation at Leesburg 25243 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$350,000

3 beds

|

3 baths

|

2,529 sq ft

|

House

25243 RIVER CREST DR, LEESBURG, FL, 3474...
Del Webb Sunbridge 6129 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$519,900

3 beds

|

3 baths

|

2,077 sq ft

|

House

6129 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
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.
Venetian Bay 2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$350,000

3 beds

|

3 baths

|

1,754 sq ft

|

House

2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Spruce Creek Country Club 14004 SE 94TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$324,999

3 beds

|

2 baths

|

1,718 sq ft

|

House

14004 SE 94TH AVE, SUMMERFIELD, FL, 3449...
Halifax Plantation 2840 MONAGHAN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$450,000

4 beds

|

3 baths

|

2,106 sq ft

|

House

2840 MONAGHAN DR, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
Solivita 780 MYSTIC HILL CT, POINCIANA, FL, 34759, Poinciana, FL 34759
$389,000

2 beds

|

3 baths

|

2,053 sq ft

|

House

780 MYSTIC HILL CT, POINCIANA, FL, 34759
Community: Solivita
American Village 71 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$359,990

4 beds

|

2 baths

|

1,986 sq ft

|

House

71 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Lakes of Mount Dora 3975 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$379,990

2 beds

|

2 baths

|

1,402 sq ft

|

House

3975 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Highland Fairways 3245 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$234,500

2 beds

|

2 baths

|

1,045 sq ft

|

House

3245 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Pelican Bay Daytona Beach 102 BLUE HERON DR A, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$198,000

2 beds

|

2 baths

|

1,237 sq ft

|

Condo

102 BLUE HERON DR A, DAYTONA BEACH, FL, ...
Four Seasons at Orlando 7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747
$699,950

3 beds

|

3 baths

|

2,754 sq ft

|

House

7748 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...
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 913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$464,800

2 beds

|

2 baths

|

1,558 sq ft

|

House

913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
Heritage Isle 6858 TOLAND DR 304, MELBOURNE, FL, 32940, Melbourne, FL 32940
$292,500

2 beds

|

2 baths

|

1,194 sq ft

|

Condo

6858 TOLAND DR 304, MELBOURNE, FL, 32940
Community: Heritage Isle
Colonnades 4846 COLONNADES CLUB BLVD, LAKELAND, FL,..., Lakeland, FL 33811
$257,000

2 beds

|

2 baths

|

1,534 sq ft

|

House

4846 COLONNADES CLUB BLVD, LAKELAND, FL,...
Community: Colonnades
Lake Ashton 4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$200,000

2 beds

|

2 baths

|

1,083 sq ft

|

House

4488 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Latitude Margaritaville 786 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$699,900

3 beds

|

3 baths

|

2,392 sq ft

|

House

786 JOLLYMON WAY, DAYTONA BEACH, FL, 321...
Solivita 619 TAPATIO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$519,000

5 beds

|

5 baths

|

2,881 sq ft

|

House

619 TAPATIO LN, KISSIMMEE, FL, 34759
Community: Solivita

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2,513 homes
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