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Winter Park, FL 55+ active adult communities & homes for sale - Page 53

2,259 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
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
4.5 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
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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
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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
Grand Haven
$200ks - $800ks
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.
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (3 reviews) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 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
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 Park? 55places can help!
Questions? Call us: (888) 625-4885
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
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 (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) Cresswind at Victoria Gar...
$200ks - $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.
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
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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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 (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
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Questions? Call us: (888) 625-4885
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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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.
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 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
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
5 rating (2 reviews) Bridgewater at Viera
$300ks - $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (1 reviews) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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.
12...3
Latitude Margaritaville 280 LAST MANGO DR, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$389,000

2 beds

|

2 baths

|

1,456 sq ft

|

Townhouse

280 LAST MANGO DR, DAYTONA BEACH, FL, 32...
The Villages® 16946 SE 93RD CUTHBERT CIR, THE VILLAGES..., The Villages, FL 32162
$427,000

3 beds

|

2 baths

|

2,002 sq ft

|

House

16946 SE 93RD CUTHBERT CIR, THE VILLAGES...
Community: The Villages®
Sullivan Ranch 30101 BRETTON LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$669,900

4 beds

|

3 baths

|

3,452 sq ft

|

House

30101 BRETTON LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
Grand Haven 455 RIVERFRONT DR A104, PALM COAST, FL, ..., Palm Coast, FL 32137
$974,000

3 beds

|

3 baths

|

2,167 sq ft

|

Condo

455 RIVERFRONT DR A104, PALM COAST, FL, ...
Community: Grand Haven
American Village 31 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$369,795

4 beds

|

2 baths

|

1,986 sq ft

|

House

31 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
Highland Fairways 2137 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810
$274,500

3 beds

|

2 baths

|

1,808 sq ft

|

House

2137 GRAND CYPRESS DR, LAKELAND, FL, 338...
Community: Highland Fairways
Plantation at Leesburg 3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748
$435,000

3 beds

|

3 baths

|

2,664 sq ft

|

House

3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...
The Villages® 939 KOLLER CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$449,999

2 beds

|

2 baths

|

1,880 sq ft

|

House

939 KOLLER CT, THE VILLAGES, FL, 32163
Community: The Villages®
Pennbrooke Fairways 615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$82,999

1 beds

|

1 baths

|

490 sq ft

|

Manufactured Home

615 COTTAGE PARK LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
The Villages® 712 JASON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$210,000

2 beds

|

2 baths

|

1,292 sq ft

|

Manufactured Home

712 JASON DR, LADY LAKE, 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.
The Villages® 870 HENDERSON LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$299,900

3 beds

|

2 baths

|

1,375 sq ft

|

House

870 HENDERSON LN, THE VILLAGES, FL, 3216...
Community: The Villages®
Plantation Bay Golf & Country Club 875 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$388,000

3 beds

|

3 baths

|

2,101 sq ft

|

Townhouse

875 PINEWOOD DR, ORMOND BEACH, FL, 32174
Summer Trees 130 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$279,950

3 beds

|

2 baths

|

1,363 sq ft

|

House

130 CYPRESS POND RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Breakaway Trails 94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$585,000

4 beds

|

3 baths

|

3,261 sq ft

|

House

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
The Villages® 1619 W SCHWARTZ BLVD, THE VILLAGES, FL, ..., The Villages, FL 32159
$204,000

2 beds

|

2 baths

|

1,300 sq ft

|

Manufactured Home

1619 W SCHWARTZ BLVD, THE VILLAGES, FL, ...
Community: The Villages®
Solivita 507 PRESIDO PARK PL, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$269,000

2 beds

|

2 baths

|

1,302 sq ft

|

House

507 PRESIDO PARK PL, KISSIMMEE, FL, 3475...
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1224 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$239,900

2 beds

|

2 baths

|

912 sq ft

|

Manufactured Home

1224 DUSTIN DR, LADY LAKE, FL, 32159
Community: The Villages®
Stonecrest 17209 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$349,500

2 beds

|

2 baths

|

1,695 sq ft

|

House

17209 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
Spruce Creek Country Club 9244 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$339,500

2 beds

|

2 baths

|

2,130 sq ft

|

House

9244 SE 128TH ST, SUMMERFIELD, FL, 34491
The Villages® 3818 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$350,000

3 beds

|

2 baths

|

1,501 sq ft

|

House

3818 INFINITY RUN, 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.
The Reserve at Victoria 1548 LAKE RESERVE DR, DELAND, FL, 32724, Deland, FL 32724
$701,000

4 beds

|

3 baths

|

2,436 sq ft

|

House

1548 LAKE RESERVE DR, DELAND, FL, 32724
Plantation Bay Golf & Country Club 945 STONE LAKE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$699,900

4 beds

|

3 baths

|

2,910 sq ft

|

House

945 STONE LAKE DR, ORMOND BEACH, FL, 321...
Colonnades 4816 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$185,000

2 beds

|

2 baths

|

1,066 sq ft

|

Manufactured Home

4816 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
VillageWalk at Lake Nona 12004 ULETA LN, ORLANDO, FL, 32827, Orlando, FL 32827
$1,100,000

4 beds

|

4 baths

|

4,114 sq ft

|

House

12004 ULETA LN, ORLANDO, FL, 32827
Del Webb Sunbridge 6213 CITRUS GROVE CT, ST CLOUD, FL, 3477..., St Cloud, FL 34771
$899,821

3 beds

|

3 baths

|

2,269 sq ft

|

House

6213 CITRUS GROVE CT, ST CLOUD, FL, 3477...
Community: Del Webb Sunbridge
Plantation Bay Golf & Country Club 998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$3,295,000

5 beds

|

4 baths

|

5,454 sq ft

|

House

998 DOWNSHIRE LN, ORMOND BEACH, FL, 3217...
Grand Haven 200 RIVERFRONT DR B303, PALM COAST, FL, ..., Palm Coast, FL 32137
$369,900

3 beds

|

2 baths

|

1,762 sq ft

|

Condo

200 RIVERFRONT DR B303, 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
Latitude Margaritaville 221 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$419,900

2 beds

|

2 baths

|

1,509 sq ft

|

House

221 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Heritage Hills 3524 LITCHFIELD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$464,990

4 beds

|

3 baths

|

2,293 sq ft

|

House

3524 LITCHFIELD CT, CLERMONT, FL, 34711
Community: Heritage Hills
Del Webb Minneola 2761 TOP HILL CT, MINNEOLA, FL, 34715, Minneola, FL 34715
$578,900

2 beds

|

2 baths

|

1,943 sq ft

|

House

2761 TOP HILL CT, MINNEOLA, FL, 34715
Community: Del Webb Minneola
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 525 SHOREHAVEN DR, POINCIANA, FL, 34759, Poinciana, FL 34759
$310,000

2 beds

|

2 baths

|

2,064 sq ft

|

House

525 SHOREHAVEN DR, POINCIANA, FL, 34759
Community: Solivita
Royal Harbor 5486 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778
$388,000

3 beds

|

3 baths

|

2,284 sq ft

|

House

5486 BOUNTY CIR, TAVARES, FL, 32778
Community: Royal Harbor
Ridgehaven 179 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$299,990

3 beds

|

2 baths

|

1,572 sq ft

|

House

179 PARKHAVEN DR, ORMOND BEACH, FL, 3217...
Community: Ridgehaven
Vienna Square 1709 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$259,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1709 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Highland Fairways 1836 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$230,000

2 beds

|

2 baths

|

1,545 sq ft

|

House

1836 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Royal Harbor 4954 RAINBOW TROUT RD, TAVARES, FL, 3277..., Tavares, FL 32778
$299,000

3 beds

|

2 baths

|

1,489 sq ft

|

House

4954 RAINBOW TROUT RD, TAVARES, FL, 3277...
Community: Royal Harbor
The Villages® 17700 SE 92ND GRANTHAM TER, THE VILLAGES..., The Villages, FL 32162
$299,500

3 beds

|

2 baths

|

1,516 sq ft

|

House

17700 SE 92ND GRANTHAM TER, THE VILLAGES...
Community: The Villages®
Trilogy® Orlando 176 SILVER MAPLE RD, GROVELAND, FL, 3473..., Groveland, FL 34736
$490,000

2 beds

|

3 baths

|

2,074 sq ft

|

House

176 SILVER MAPLE RD, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Arlington Ridge 27106 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$419,900

3 beds

|

2 baths

|

2,436 sq ft

|

House

27106 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
Lake Ashton 4429 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$349,900

3 beds

|

2 baths

|

1,847 sq ft

|

House

4429 TURNBERRY LN, LAKE WALES, FL, 33859
Community: Lake Ashton
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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2,259 homes
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