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Winter Park, FL 55+ active adult communities & homes for sale - Page 61

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
Halifax Plantation 3070 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$495,000

4 beds

|

3 baths

|

2,111 sq ft

|

House

3070 SILVERMINES AVE, ORMOND BEACH, FL, ...
Community: Halifax Plantation
Venetian Bay 3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$599,000

3 beds

|

2 baths

|

1,916 sq ft

|

House

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Lakes of Mount Dora 8167 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$340,000

3 beds

|

2 baths

|

1,613 sq ft

|

House

8167 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$539,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Plantation at Leesburg 25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$235,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

25800 BELLE HELENE, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Summit Greens 2503 SQUAW CRK, CLERMONT, FL, 34711, Clermont, FL 34711
$357,900

3 beds

|

2 baths

|

1,919 sq ft

|

House

2503 SQUAW CRK, CLERMONT, FL, 34711
Community: Summit Greens
Indian River Colony Club 1423 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940
$295,000

3 beds

|

2 baths

|

1,832 sq ft

|

House

1423 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Stonecrest 17471 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$369,900

2 beds

|

2 baths

|

1,993 sq ft

|

House

17471 SE 110TH TER, SUMMERFIELD, FL, 344...
Community: Stonecrest
The Villages® 1482 AZTECA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$342,000

2 beds

|

2 baths

|

1,499 sq ft

|

Villa

1482 AZTECA LOOP, THE VILLAGES, FL, 3216...
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.
American Village 73 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$334,990

2 beds

|

2 baths

|

1,799 sq ft

|

House

73 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Spring Lake Towers 700 MIRROR TER 303, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$109,900

2 beds

|

2 baths

|

1,029 sq ft

|

Condo

700 MIRROR TER 303, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
Lakes of Mount Dora 2435 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$544,900

3 beds

|

2 baths

|

2,080 sq ft

|

House

2435 PAWTUCKET PASS, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Colonnades 4965 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$233,500

2 beds

|

2 baths

|

1,350 sq ft

|

House

4965 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Lakes at Harmony 3144 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773
$370,000

3 beds

|

2 baths

|

1,852 sq ft

|

House

3144 SONGBIRD CIR, HARMONY, FL, 34773
Venetian Bay 3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$479,000

3 beds

|

2 baths

|

2,174 sq ft

|

House

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Stonecrest 17816 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$260,000

3 beds

|

3 baths

|

1,741 sq ft

|

House

17816 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Plantation at Leesburg 25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748
$260,000

3 beds

|

2 baths

|

1,737 sq ft

|

House

25333 RIVER CREST DR, LEESBURG, FL, 3474...
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 429 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$467,000

2 beds

|

3 baths

|

2,345 sq ft

|

House

429 VILLA PARK RD, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 772 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$564,900

3 beds

|

4 baths

|

2,616 sq ft

|

House

772 SAN RAPHAEL ST, KISSIMMEE, FL, 34759
Community: Solivita
Twin Lakes 2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477..., Saint Cloud, FL 34772
$525,000

3 beds

|

3 baths

|

2,365 sq ft

|

House

2789 SOUTHLAND ST, SAINT CLOUD, FL, 3477...
Community: Twin Lakes
Stonecrest 11799 SE 173RD LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$470,000

3 beds

|

2 baths

|

2,008 sq ft

|

House

11799 SE 173RD LANE RD, SUMMERFIELD, FL,...
Community: Stonecrest
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Indian River Colony Club 1375 MAYFLOWER AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$330,000

3 beds

|

2 baths

|

2,010 sq ft

|

House

1375 MAYFLOWER AVE, MELBOURNE, FL, 32940
Plantation at Leesburg 25339 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$296,900

3 beds

|

2 baths

|

1,765 sq ft

|

House

25339 CRESTWATER DR, LEESBURG, FL, 34748
Latitude Margaritaville 1082 CASTAWAY CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$530,000

2 beds

|

2 baths

|

1,684 sq ft

|

House

1082 CASTAWAY CT, DAYTONA BEACH, FL, 321...
The Villages® 17238 SE 94TH COULTS CIR, THE VILLAGES, ..., The Villages, FL 32162
$325,000

3 beds

|

2 baths

|

1,558 sq ft

|

House

17238 SE 94TH COULTS CIR, THE VILLAGES, ...
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.
Vienna Square 1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$185,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Latitude Margaritaville 710 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$549,900

2 beds

|

3 baths

|

1,743 sq ft

|

House

710 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 914 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$454,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

914 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Highland Lakes 6419 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$260,000

3 beds

|

2 baths

|

1,964 sq ft

|

House

6419 BORG ST, LEESBURG, FL, 34748
Community: Highland Lakes
Plantation Bay Golf & Country Club 1009 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$2,799,900

4 beds

|

5 baths

|

3,927 sq ft

|

House

1009 SUDBURY LN, ORMOND BEACH, FL, 32174
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Indian River Colony Club 1551 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940
$298,900

3 beds

|

2 baths

|

1,816 sq ft

|

House

1551 INDEPENDENCE AVE, MELBOURNE, FL, 32...
The Villages® 3203 ISLAWILD WAY, THE VILLAGES, FL, 321..., The Villages, FL 32163
$355,000

3 beds

|

2 baths

|

1,542 sq ft

|

House

3203 ISLAWILD WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Royal Highlands 20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748
$355,000

3 beds

|

2 baths

|

2,070 sq ft

|

House

20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
The Villages® 1307 GALINDO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$335,000

3 beds

|

2 baths

|

1,872 sq ft

|

House

1307 GALINDO PL, THE VILLAGES, FL, 32159
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 1124 SAWGRASS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$360,000

3 beds

|

2 baths

|

2,113 sq ft

|

House

1124 SAWGRASS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
Kings Ridge 3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$329,900

3 beds

|

2 baths

|

1,552 sq ft

|

House

3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Spruce Creek Country Club 9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$399,900

3 beds

|

2 baths

|

2,126 sq ft

|

House

9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Lake Ashton 4063 BIRKDALE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$294,500

2 beds

|

2 baths

|

1,530 sq ft

|

House

4063 BIRKDALE DR, 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
Spruce Creek Country Club 13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$255,000

3 beds

|

2 baths

|

1,760 sq ft

|

House

13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
The Wellington 689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,..., Winter Haven, FL 33880
$124,000

2 beds

|

2 baths

|

1,050 sq ft

|

Townhouse

689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,...
Community: The Wellington

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2,513 homes
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