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

2,487 homes near Winter Park

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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
4.7 rating (18 reviews) Solivita
$100Ks - $600Ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes
3.6 rating (48 reviews) Latitude Margaritaville
$300Ks - $900Ks
Latitude Margaritaville, Daytona Beach, FL
Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes
5 rating (1 reviews) Plantation Bay Golf &...
$200Ks - $4Ms
Plantation Bay Golf &..., Ormond Beach, FL
New and Resale | Age-targeted | Built 1988 - present | 3,500 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
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5 rating (2 reviews) Plantation at Leesburg
$100Ks - $500Ks
Plantation at Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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 (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 - $600Ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Grand Haven
$300Ks - $1Ms
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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.
Pelican Bay Daytona Beach
$100Ks - $500Ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
4.7 rating (3 reviews) Spruce Creek South
$100Ks - $300Ks
Spruce Creek South, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes
5 rating (1 reviews) Cypress Lakes
$100Ks - $200Ks
Cypress Lakes, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes
5 rating (3 reviews) Lake Ashton
$200Ks - $800Ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
Venetian Bay
$200Ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
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5 rating (2 reviews) Heritage Isle
$200Ks - $500Ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 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 - $500Ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
5 rating (1 reviews) VillageWalk at Lake Nona
$300Ks - $1Ms
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 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.
Del Webb at Viera
$300Ks - $800Ks
Del Webb at Viera, Melbourne, FL
New Construction | 55+ age-restricted | Built 2021 - present | 1,300 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) Sandpiper Golf & Coun...
$200Ks - $400Ks
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) Cresswind at Victoria Gar...
$300Ks - $600Ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
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Halifax Plantation
$200Ks - $700Ks
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 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
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
$400Ks - $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
$200Ks - $1Ms
Harbor Hills Country Club, Lady Lake, FL
New and Resale | Age-targeted | Built 1989 - present | 940 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 - $300Ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
4.4 rating (16 reviews) Del Webb Orlando
$300Ks - $400Ks
Del Webb Orlando, Davenport, FL
Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes
5 rating (2 reviews) Bridgewater at Viera
$300Ks - $600Ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
3.9 rating (7 reviews) Summit Greens
$300Ks - $400Ks
Summit Greens, Clermont, FL
Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes
5 rating (1 reviews) Royal Harbor
$200Ks - $400Ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
Lakeside Landings
$200Ks - $500Ks
Lakeside Landings, Oxford, FL
New and Resale | Age-targeted | Built 2005 - present | 700 homes
1 rating (1 reviews) Sullivan Ranch
$300Ks - $600Ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Highland Fairways
$100Ks - $300Ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Cresswind at Victoria Gardens 1547 LAMBROOK DR, DELAND, FL, 32724, Deland, FL 32724
$379,000

2 beds

|

2 baths

|

1,651 sq ft

|

House

1547 LAMBROOK DR, DELAND, FL, 32724
High Vista at Ridgewood Lakes 117 RIDGE VIEW DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$279,000

2 beds

|

2 baths

|

2,013 sq ft

|

House

117 RIDGE VIEW DR, DAVENPORT, FL, 33837
Royal Harbor 5837 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$315,000

3 beds

|

2 baths

|

1,900 sq ft

|

House

5837 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Pennbrooke Fairways 32218 SWEET BRIAR CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$239,900

2 beds

|

2 baths

|

1,272 sq ft

|

House

32218 SWEET BRIAR CT, LEESBURG, FL, 3474...
Community: Pennbrooke Fairways
Royal Highlands 5433 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

1,995 sq ft

|

House

5433 SIR CHURCHILL DR, LEESBURG, FL, 347...
Community: Royal Highlands
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Halifax Plantation 3132 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$319,900

3 beds

|

2 baths

|

1,670 sq ft

|

Townhouse

3132 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
Summer Trees 6065 SPRUCE POINT CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128
$629,900

4 beds

|

3 baths

|

2,806 sq ft

|

House

6065 SPRUCE POINT CIR, PORT ORANGE, FL, ...
Community: Summer Trees
Spruce Creek South 10462 SE 177TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$230,900

2 beds

|

2 baths

|

1,144 sq ft

|

House

10462 SE 177TH PL, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Harbor Hills Country Club 5132 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$749,500

3 beds

|

2 baths

|

2,466 sq ft

|

House

5132 GREENS DR, LADY LAKE, FL, 32159
Arlington Ridge 26807 BULL RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

2 beds

|

2 baths

|

1,962 sq ft

|

House

26807 BULL RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
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.
Solivita 861 BELLA VIANA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$429,000

2 beds

|

3 baths

|

2,379 sq ft

|

House

861 BELLA VIANA RD, KISSIMMEE, FL, 34759
Community: Solivita
Del Webb Sunbridge 2928 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771
$429,000

3 beds

|

3 baths

|

1,854 sq ft

|

Townhouse

2928 VOYAGER AVE, SAINT CLOUD, FL, 34771
Community: Del Webb Sunbridge
Lake Ashton 4128 ABERDEEN LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$250,000

3 beds

|

2 baths

|

1,503 sq ft

|

House

4128 ABERDEEN LN, LAKE WALES, FL, 33859
Community: Lake Ashton
Plantation at Leesburg 5057 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$169,000

2 beds

|

2 baths

|

1,170 sq ft

|

Manufactured Home

5057 EL DESTINO DR, LEESBURG, FL, 34748
Harbor Hills Country Club 5235 ISLAND TERRACE CT, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$599,900

3 beds

|

3 baths

|

2,446 sq ft

|

House

5235 ISLAND TERRACE CT, LADY LAKE, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Kings Ridge 4003 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711
$350,000

3 beds

|

3 baths

|

1,722 sq ft

|

House

4003 HAMMERSMITH DR, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 12347 NE 52ND LOOP, OXFORD, FL, 34484, Oxford, FL 34484
$349,000

4 beds

|

4 baths

|

2,092 sq ft

|

House

12347 NE 52ND LOOP, OXFORD, FL, 34484
Community: The Villages®
Grand Isle 1692 KEYS GATE DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$349,000

2 beds

|

2 baths

|

1,422 sq ft

|

House

1692 KEYS GATE DR, MELBOURNE, FL, 32940
Community: Grand Isle
Carillon Lakes 4249 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$308,900

3 beds

|

2 baths

|

1,784 sq ft

|

House

4249 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
The Villages® 1041 REIDVILLE RD, THE VILLAGES, FL, 321..., The Villages, FL 32162
$379,000

2 beds

|

2 baths

|

1,196 sq ft

|

Villa

1041 REIDVILLE RD, THE VILLAGES, FL, 321...
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.
Del Webb Orlando 503 VIGO ST, DAVENPORT, FL, 33837, Davenport, FL 33837
$323,000

2 beds

|

2 baths

|

1,468 sq ft

|

House

503 VIGO ST, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Foxwood Lake Estates 1785 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$220,000

2 beds

|

2 baths

|

1,344 sq ft

|

Manufactured Home

1785 QUAIL HILL DR, LAKELAND, FL, 33810
Highland Fairways 1957 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$315,900

2 beds

|

2 baths

|

1,637 sq ft

|

House

1957 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Lake Henry Estates 669 WATERFORD DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$242,000

3 beds

|

2 baths

|

1,741 sq ft

|

House

669 WATERFORD DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Solivita 772 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$589,900

3 beds

|

4 baths

|

2,616 sq ft

|

House

772 SAN RAPHAEL ST, KISSIMMEE, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Carlsberg Estates on Lake Suzanne 260 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$229,900

2 beds

|

2 baths

|

1,321 sq ft

|

House

260 LAKE SUZANNE DR, LAKE WALES, FL, 338...
Lakes of Mount Dora 3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$549,990

3 beds

|

2 baths

|

2,180 sq ft

|

House

3951 KENNEBUNK LOOP, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Lake Ashton 4004 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859
$579,900

4 beds

|

3 baths

|

2,937 sq ft

|

House

4004 SABLE LOOP DR, LAKE WALES, FL, 3385...
Community: Lake Ashton
Venetian Bay 545 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$414,900

3 beds

|

2 baths

|

1,916 sq ft

|

House

545 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Venetian Bay 3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$395,000

2 beds

|

2 baths

|

1,003 sq ft

|

Townhouse

3069 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
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.
Colonnades 4829 COLONNADES CIR, LAKELAND, FL, 33811, Lakeland, FL 33811
$262,500

2 beds

|

2 baths

|

1,182 sq ft

|

House

4829 COLONNADES CIR, LAKELAND, FL, 33811
Community: Colonnades
VillageWalk at Lake Nona 12048 TALITHA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$480,000

3 beds

|

3 baths

|

1,830 sq ft

|

Townhouse

12048 TALITHA LN, ORLANDO, FL, 32827
The Villages® 1508 GIFFORD CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$410,000

3 beds

|

2 baths

|

1,554 sq ft

|

House

1508 GIFFORD CT, THE VILLAGES, FL, 32162
Community: The Villages®
Solivita 417 LAKE BUTLER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$324,900

3 beds

|

2 baths

|

2,728 sq ft

|

House

417 LAKE BUTLER DR, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168
$524,999

4 beds

|

3 baths

|

2,338 sq ft

|

House

3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Solivita 1305 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$283,000

2 beds

|

2 baths

|

1,365 sq ft

|

House

1305 LOMBARDI CT, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 487 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$329,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

487 MONTEREY ST, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 1604 KILEY CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$349,900

2 beds

|

2 baths

|

1,456 sq ft

|

Manufactured Home

1604 KILEY CT, LADY LAKE, FL, 32159
Community: The Villages®
Spruce Creek Country Club 8924 SE 118TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$399,000

3 beds

|

2 baths

|

2,120 sq ft

|

House

8924 SE 118TH LN, SUMMERFIELD, FL, 34491
Plantation Bay Golf & Country Club 1223 CROWN POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$449,900

3 beds

|

2 baths

|

1,950 sq ft

|

House

1223 CROWN POINTE LN, ORMOND BEACH, FL, ...

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2,487 homes near Winter Park
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