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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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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 (2 reviews) Heritage Isle
$200Ks - $500Ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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
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 (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.
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 (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
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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 - $600Ks
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
Spruce Creek Country Club 14004 SE 94TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$329,000

3 beds

|

2 baths

|

1,718 sq ft

|

House

14004 SE 94TH AVE, SUMMERFIELD, FL, 3449...
Latitude Margaritaville 391 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$419,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

391 LOST SHAKER WAY, DAYTONA BEACH, FL, ...
Lake Henry Estates 543 CLUBHILL DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$269,900

2 beds

|

2 baths

|

1,868 sq ft

|

House

543 CLUBHILL DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Summit Greens 1083 MESA VERDE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$374,900

2 beds

|

2 baths

|

1,908 sq ft

|

House

1083 MESA VERDE CT, CLERMONT, FL, 34711
Community: Summit Greens
Huntington at Hunter's Ridge 19 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$349,900

3 beds

|

2 baths

|

1,837 sq ft

|

House

19 HUNTINGTON PL, ORMOND BEACH, FL, 3217...
Want to learn more about 55+ communities in Winter Park? 55places can help!
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Venetian Bay 349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$389,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Del Webb Orlando 507 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837
$426,900

4 beds

|

3 baths

|

2,616 sq ft

|

House

507 CADIZ DR, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Spruce Creek Country Club 11735 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$419,900

3 beds

|

2 baths

|

2,413 sq ft

|

House

11735 SE 91ST CIR, SUMMERFIELD, FL, 3449...
Indian River Colony Club 1144 IRONSIDES AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$359,700

4 beds

|

2 baths

|

1,840 sq ft

|

House

1144 IRONSIDES AVE, MELBOURNE, FL, 32940
Plantation Bay Golf & Country Club 1111 HANSBERRY CT, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$424,500

2 beds

|

2 baths

|

1,542 sq ft

|

Townhouse

1111 HANSBERRY CT, ORMOND BEACH, 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.
Pelican Bay Daytona Beach 5 SKIMMER CIR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$337,900

3 beds

|

3 baths

|

2,086 sq ft

|

House

5 SKIMMER CIR, DAYTONA BEACH, FL, 32119
Solivita 145 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$224,999

2 beds

|

2 baths

|

1,102 sq ft

|

House

145 PALAZZO LN, KISSIMMEE, FL, 34759
Community: Solivita
Royal Highlands 21122 LIONHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$269,900

3 beds

|

2 baths

|

1,453 sq ft

|

House

21122 LIONHEART DR, LEESBURG, FL, 34748
Community: Royal Highlands
Halifax Plantation 3751 CARRICK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$679,900

3 beds

|

2 baths

|

2,163 sq ft

|

House

3751 CARRICK DR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Grand Haven 200 RIVERFRONT DR B103, PALM COAST, FL, ..., Palm Coast, FL 32137
$375,000

3 beds

|

2 baths

|

1,762 sq ft

|

Condo

200 RIVERFRONT DR B103, PALM COAST, FL, ...
Community: Grand Haven
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Carillon Lakes 4220 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$335,000

3 beds

|

2 baths

|

1,735 sq ft

|

House

4220 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
Plantation at Leesburg 3909 RIVER CREST CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,690 sq ft

|

House

3909 RIVER CREST CIR, LEESBURG, FL, 3474...
Kings Ridge 4202 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$325,000

2 beds

|

3 baths

|

1,722 sq ft

|

House

4202 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Trilogy® Orlando 404 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$349,900

2 beds

|

2 baths

|

1,613 sq ft

|

House

404 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Cresswind DeLand 1322 SAVOY LN, DELAND, FL, 32724, Deland, FL 32724
$493,990

3 beds

|

3 baths

|

2,289 sq ft

|

House

1322 SAVOY LN, DELAND, FL, 32724
Community: Cresswind DeLand
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.
Cresswind DeLand 1304 CLUB CRESSWIND WAY, DELAND, FL, 327..., Deland, FL 32724
$473,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

1304 CLUB CRESSWIND WAY, DELAND, FL, 327...
Community: Cresswind DeLand
Carmel Condominium 1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ..., Rockledge, FL 32955
$225,000

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ...
Community: Carmel Condominium
The Timbers at Everlands 2552 ANTARUS DR NW, PALM BAY, FL, 32907, Palm Bay, FL 32907
$326,455

3 beds

|

3 baths

|

1,963 sq ft

|

House

2552 ANTARUS DR NW, PALM BAY, FL, 32907
Bridgewater at Viera 1143 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$714,900

3 beds

|

3 baths

|

2,468 sq ft

|

House

1143 GREAT BELT CIR, MELBOURNE, FL, 3294...
Alamanda Key 4310 ALAMANDA KEY DR, MELBOURNE, FL, 329..., Melbourne, FL 32901
$475,000

3 beds

|

2 baths

|

1,787 sq ft

|

House

4310 ALAMANDA KEY DR, MELBOURNE, FL, 329...
Community: Alamanda Key
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Carmel Condominium 1410 HUNTINGTON LN APT 1204, ROCKLEDGE, ..., Rockledge, FL 32955
$154,900

2 beds

|

2 baths

|

1,008 sq ft

|

Condo

1410 HUNTINGTON LN APT 1204, ROCKLEDGE, ...
Community: Carmel Condominium
Royal Palm 5408 DAYLILLY ST, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$374,929

4 beds

|

2 baths

|

1,871 sq ft

|

House

5408 DAYLILLY ST, PORT ORANGE, FL, 32128
Community: Royal Palm
Latitude Margaritaville 913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$479,500

2 beds

|

2 baths

|

1,558 sq ft

|

House

913 BAMA BREEZE DR, DAYTONA BEACH, FL, 3...
Plantation Bay Golf & Country Club 46 LONGRIDGE LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$435,000

2 beds

|

2 baths

|

1,529 sq ft

|

Townhouse

46 LONGRIDGE LN, ORMOND BEACH, FL, 32174
Halifax Plantation 1141 GLENGAD RUN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$325,000

3 beds

|

2 baths

|

1,627 sq ft

|

House

1141 GLENGAD RUN, ORMOND BEACH, FL, 3217...
Community: Halifax Plantation
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 2460 PROMENADE DR, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$425,000

3 beds

|

2 baths

|

1,863 sq ft

|

House

2460 PROMENADE DR, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
The Villages® 1117 PARADISE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$195,000

2 beds

|

2 baths

|

1,383 sq ft

|

Manufactured Home

1117 PARADISE DR, LADY LAKE, FL, 32159
Community: The Villages®
Solivita 253 SAND PIPER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$319,900

2 beds

|

2 baths

|

2,038 sq ft

|

House

253 SAND PIPER DR, KISSIMMEE, FL, 34759
Community: Solivita
Venetian Bay 118 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$399,990

3 beds

|

2 baths

|

1,900 sq ft

|

House

118 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
Pelican Bay Daytona Beach 133 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$215,000

2 beds

|

2 baths

|

1,242 sq ft

|

Condo

133 BLUE HERON DR C, DAYTONA BEACH, FL, ...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 8905 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$299,500

2 beds

|

2 baths

|

1,488 sq ft

|

House

8905 SE 130TH LOOP, SUMMERFIELD, FL, 344...
Del Webb Oasis 13846 FRESH IVY ST, WINTER GARDEN, FL, 3..., Winter Garden, FL 34787
$689,000

2 beds

|

3 baths

|

2,108 sq ft

|

House

13846 FRESH IVY ST, WINTER GARDEN, FL, 3...
Community: Del Webb Oasis
Spruce Creek Country Club 9543 SE 137TH STREET RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$529,000

3 beds

|

2 baths

|

2,806 sq ft

|

House

9543 SE 137TH STREET RD, SUMMERFIELD, FL...
Twin Lakes 5026 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772
$560,000

3 beds

|

3 baths

|

2,208 sq ft

|

House

5026 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...
Community: Twin Lakes
Venetian Bay 3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168
$700,000

3 beds

|

3 baths

|

2,472 sq ft

|

House

3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,...
Community: Venetian Bay

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2,487 homes near Winter Park
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