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Winter Park, FL 55+ active adult communities & homes for sale - Page 20

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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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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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
The Villages® 4788 ROSTAS WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$559,000

3 beds

|

2 baths

|

1,516 sq ft

|

House

4788 ROSTAS WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Plantation Bay Golf & Country Club 673 ELK RIVER DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$419,900

3 beds

|

2 baths

|

2,271 sq ft

|

House

673 ELK RIVER DR, ORMOND BEACH, FL, 3217...
The Villages® 307 DEL MAR DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$499,307

3 beds

|

2 baths

|

1,776 sq ft

|

House

307 DEL MAR DR, LADY LAKE, FL, 32159
Community: The Villages®
Gatherings of Lake Nona 7521 LAUREATE BLVD 5308, ORLANDO, FL, 32..., Orlando, FL 32827
$349,000

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7521 LAUREATE BLVD 5308, ORLANDO, FL, 32...
Del Webb Minneola 2522 DEL WEBB DR, MINNEOLA, FL, 34715, Minneola, FL 34715
$565,330

2 beds

|

2 baths

|

1,917 sq ft

|

House

2522 DEL WEBB DR, MINNEOLA, FL, 34715
Community: Del Webb Minneola
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Questions? Call us: (888) 625-4885
Del Webb Minneola 1120 CANOPY VIEW WAY, MINNEOLA, FL, 3471..., Minneola, FL 34715
$414,000

2 beds

|

2 baths

|

1,471 sq ft

|

House

1120 CANOPY VIEW WAY, MINNEOLA, FL, 3471...
Community: Del Webb Minneola
Del Webb Minneola 1597 SKYLINE HEIGHTS CIR, MINNEOLA, FL, ..., Minneola, FL 34715
$799,480

3 beds

|

3 baths

|

2,653 sq ft

|

House

1597 SKYLINE HEIGHTS CIR, MINNEOLA, FL, ...
Community: Del Webb Minneola
The Villages® 520 SAINT ANDREWS BLVD, LADY LAKE, FL, 3..., Lady Lake, FL 32159
$219,900

2 beds

|

2 baths

|

1,040 sq ft

|

Manufactured Home

520 SAINT ANDREWS BLVD, LADY LAKE, FL, 3...
Community: The Villages®
Spruce Creek South 10689 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491
$222,900

2 beds

|

2 baths

|

1,008 sq ft

|

House

10689 SE 174TH LOOP, SUMMERFIELD, FL, 34...
Community: Spruce Creek South
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® 1710 LILLY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$174,900

2 beds

|

2 baths

|

1,256 sq ft

|

Manufactured Home

1710 LILLY LN, LADY LAKE, FL, 32159
Community: The Villages®
Cresswind at Victoria Gardens 307 STONINGTON WAY, DELAND, FL, 32724, Deland, FL 32724
$289,000

3 beds

|

2 baths

|

1,480 sq ft

|

House

307 STONINGTON WAY, DELAND, FL, 32724
Latitude Margaritaville 781 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$827,900

3 beds

|

3 baths

|

2,415 sq ft

|

House

781 ATTITUDE AVE, DAYTONA BEACH, FL, 321...
Summit Chase Villas 12435 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778
$219,900

2 beds

|

2 baths

|

986 sq ft

|

House

12435 ORANGEWOOD CIR, TAVARES, FL, 32778
Community: Summit Chase Villas
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Hills 3825 QUAINT LN F, CLERMONT, FL, 34711, Clermont, FL 34711
$319,999

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3825 QUAINT LN F, CLERMONT, FL, 34711
Community: Heritage Hills
Plantation Bay Golf & Country Club 1020 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$1,625,000

4 beds

|

4 baths

|

3,411 sq ft

|

House

1020 SUDBURY LN, ORMOND BEACH, FL, 32174
Solivita 1166 CAMBRIA BND, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$649,000

3 beds

|

3 baths

|

2,442 sq ft

|

House

1166 CAMBRIA BND, KISSIMMEE, FL, 34759
Community: Solivita
Summer Trees 10 OAK LN, PORT ORANGE, FL, 32128, Port Orange, FL 32128
$295,000

3 beds

|

2 baths

|

1,602 sq ft

|

House

10 OAK LN, PORT ORANGE, FL, 32128
Community: Summer Trees
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.
Esplanade at Highland Ranch 1159 ESPERANZA RIDGE RD, CLERMONT, FL, 3..., Clermont, FL 34715
$440,000

3 beds

|

2 baths

|

1,874 sq ft

|

House

1159 ESPERANZA RIDGE RD, CLERMONT, FL, 3...
The Villages® 2924 BONIFAY PATH, THE VILLAGES, FL, 321..., The Villages, FL 32163
$1,950,000

3 beds

|

2 baths

|

3,320 sq ft

|

House

2924 BONIFAY PATH, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 3094 BRINE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$385,000

3 beds

|

2 baths

|

1,580 sq ft

|

House

3094 BRINE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Spruce Creek Country Club 8739 SE 140TH PLACE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$242,000

3 beds

|

2 baths

|

2,046 sq ft

|

House

8739 SE 140TH PLACE RD, SUMMERFIELD, FL,...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
American Village 35 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$357,990

3 beds

|

2 baths

|

1,604 sq ft

|

House

35 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Grand Haven 9 SAINT ANDREWS CT, PALM COAST, FL, 3213..., Palm Coast, FL 32137
$475,000

4 beds

|

2 baths

|

1,986 sq ft

|

House

9 SAINT ANDREWS CT, PALM COAST, FL, 3213...
Community: Grand Haven
Plantation Bay Golf & Country Club 1204 SUNNINGDALE LN, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$475,000

3 beds

|

2 baths

|

1,912 sq ft

|

House

1204 SUNNINGDALE LN, ORMOND BEACH, FL, 3...
Esplanade at Highland Ranch 1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715
$429,500

2 beds

|

2 baths

|

1,710 sq ft

|

House

1282 ZEEK RIDGE ST, CLERMONT, FL, 34715
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 at Victoria Gardens 109 AVENHAM DR, DELAND, FL, 32724, Deland, FL 32724
$317,999

2 beds

|

2 baths

|

1,508 sq ft

|

House

109 AVENHAM DR, DELAND, FL, 32724
Breakaway Trails 35 CARRIAGE CREEK WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$389,900

3 beds

|

2 baths

|

1,803 sq ft

|

House

35 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...
Community: Breakaway Trails
Plantation at Leesburg 25741 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$264,900

2 beds

|

2 baths

|

1,531 sq ft

|

House

25741 BELLE HELENE, LEESBURG, FL, 34748
Latitude Margaritaville 118 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$374,000

2 beds

|

2 baths

|

1,308 sq ft

|

House

118 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Spruce Creek Country Club 9375 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$629,900

2 beds

|

2 baths

|

1,958 sq ft

|

House

9375 SE 125TH ST, SUMMERFIELD, FL, 34491
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 3283 WISE WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163
$594,000

3 beds

|

2 baths

|

1,942 sq ft

|

House

3283 WISE WAY, THE VILLAGES, FL, 32163
Community: The Villages®
Sullivan Ranch 30207 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$429,000

4 beds

|

3 baths

|

2,590 sq ft

|

House

30207 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Alamanda Key 3720 ALAMANDA KEY DR DRIVE, MELBOURNE, F..., Melbourne, FL 32901
$425,000

3 beds

|

2 baths

|

1,729 sq ft

|

House

3720 ALAMANDA KEY DR DRIVE, MELBOURNE, F...
Community: Alamanda Key
Grand Haven 200 RIVERFRONT DR A301, PALM COAST, FL, ..., Palm Coast, FL 32137
$549,000

3 beds

|

3 baths

|

2,167 sq ft

|

Condo

200 RIVERFRONT DR A301, PALM COAST, FL, ...
Community: Grand Haven
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.
Heritage Isle 6717 SUTRO HEIGHTS LN, MELBOURNE, FL, 32..., Melbourne, FL 32940
$385,000

3 beds

|

2 baths

|

1,825 sq ft

|

House

6717 SUTRO HEIGHTS LN, MELBOURNE, FL, 32...
Community: Heritage Isle
Carillon Lakes 3943 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$378,000

3 beds

|

2 baths

|

1,906 sq ft

|

House

3943 WINDCHIME LN, LAKELAND, FL, 33811
Community: Carillon Lakes
The Villages® 1220 AVENIDA DE LAS CASAS, THE VILLAGES,..., The Villages, FL 32159
$447,900

3 beds

|

3 baths

|

1,820 sq ft

|

House

1220 AVENIDA DE LAS CASAS, THE VILLAGES,...
Community: The Villages®
Plantation at Leesburg 5535 TANGELO ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$275,000

3 beds

|

2 baths

|

2,040 sq ft

|

House

5535 TANGELO ST, LEESBURG, FL, 34748
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 4714 WIGHTMAN CIR, THE VILLAGES, FL, 321..., The Villages, FL 32163
$648,000

3 beds

|

3 baths

|

1,869 sq ft

|

House

4714 WIGHTMAN CIR, THE VILLAGES, FL, 321...
Community: The Villages®
The Villages® 1972 ASHWOOD RUN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$369,000

3 beds

|

2 baths

|

1,467 sq ft

|

House

1972 ASHWOOD RUN, THE VILLAGES, FL, 3216...
Community: The Villages®

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2,513 homes
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