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Winter Park, FL 55+ active adult communities & homes for sale - Page 22

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 (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 (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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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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
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
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 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.
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
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
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
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
Tohoqua Reserve
$300ks - $600ks
Tohoqua Reserve, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2021 - present | 258 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
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 (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
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
Royal Highlands 21516 CASTLE VIEW CT, LEESBURG, FL, 3474..., Leesburg, FL 34748
$259,900

3 beds

|

2 baths

|

1,798 sq ft

|

House

21516 CASTLE VIEW CT, LEESBURG, FL, 3474...
Community: Royal Highlands
Heritage Isle 3725 GURRERO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$469,900

3 beds

|

2 baths

|

1,901 sq ft

|

House

3725 GURRERO DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Latitude Margaritaville 215 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$365,000

2 beds

|

2 baths

|

1,204 sq ft

|

House

215 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Four Seasons at Orlando 2101 ANTILLES CLUB DR, KISSIMMEE, FL, 34..., Kissimmee, FL 34747
$725,000

3 beds

|

3 baths

|

2,360 sq ft

|

House

2101 ANTILLES CLUB DR, KISSIMMEE, FL, 34...
Latitude Margaritaville 488 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$719,900

2 beds

|

3 baths

|

2,139 sq ft

|

House

488 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Isle 6218 VAN NESS DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$445,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

6218 VAN NESS DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Grand Isle 1574 TIMACUAN DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$390,000

3 beds

|

2 baths

|

1,781 sq ft

|

House

1574 TIMACUAN DR, MELBOURNE, FL, 32940
Community: Grand Isle
Venetian Bay 3361 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$449,500

3 beds

|

2 baths

|

2,440 sq ft

|

House

3361 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Venetian Bay 3365 LUNA BELLA LN, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$509,900

4 beds

|

3 baths

|

2,467 sq ft

|

House

3365 LUNA BELLA LN, NEW SMYRNA BEACH, FL...
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.
The Villages® 954 AVALON AVE, THE VILLAGES, FL, 32159, The Villages, FL 32159
$268,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

954 AVALON AVE, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 1625 PINEHURST DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$255,000

3 beds

|

2 baths

|

1,590 sq ft

|

Manufactured Home

1625 PINEHURST DR, LADY LAKE, FL, 32159
Community: The Villages®
Latitude Margaritaville 485 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$385,900

2 beds

|

2 baths

|

1,308 sq ft

|

Villa

485 MARGARITAVILLE AVE, DAYTONA BEACH, F...
The Lakes at Harmony 3403 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$389,000

3 beds

|

2 baths

|

1,876 sq ft

|

House

3403 SAGEBRUSH ST, HARMONY, FL, 34773
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Arlington Ridge 27014 CAMERONS RUN, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

2 baths

|

2,256 sq ft

|

House

27014 CAMERONS RUN, LEESBURG, FL, 34748
Community: Arlington Ridge
Latitude Margaritaville 925 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$469,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

925 MARGARITAVILLE AVE, DAYTONA BEACH, F...
The Villages® 17109 SE 93RD YONDEL CIR, THE VILLAGES, ..., The Villages, FL 32162
$314,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

17109 SE 93RD YONDEL CIR, THE VILLAGES, ...
Community: The Villages®
The Villages® 640 SAN MARINO DR, THE VILLAGES, FL, 321..., The Villages, FL 32159
$327,000

3 beds

|

2 baths

|

1,494 sq ft

|

House

640 SAN MARINO DR, 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 Villages® 3559 WYNGATE PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$425,000

3 beds

|

2 baths

|

1,559 sq ft

|

House

3559 WYNGATE PL, THE VILLAGES, FL, 32163
Community: The Villages®
The Villages® 533 INNER CIR, THE VILLAGES, FL, 32162, The Villages, FL 32162
$699,900

3 beds

|

3 baths

|

2,171 sq ft

|

House

533 INNER CIR, THE VILLAGES, FL, 32162
Community: The Villages®
Plantation at Leesburg 25113 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

3 beds

|

2 baths

|

2,084 sq ft

|

House

25113 RIVERWALK DR, LEESBURG, FL, 34748
Spruce Creek South 17945 SE 104TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$209,900

2 beds

|

2 baths

|

1,134 sq ft

|

House

17945 SE 104TH TER, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Tohoqua Reserve 1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$474,000

3 beds

|

2 baths

|

2,056 sq ft

|

House

1994 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Vienna Square 2452 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$332,452

2 beds

|

2 baths

|

1,729 sq ft

|

House

2452 SALZBURG LOOP, WINTER HAVEN, FL, 33...
Community: Vienna Square
The Villages® 1301 FONTANA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$474,900

3 beds

|

2 baths

|

2,106 sq ft

|

House

1301 FONTANA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Highland Lakes 26441 EVERT ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$265,000

3 beds

|

2 baths

|

1,580 sq ft

|

House

26441 EVERT ST, LEESBURG, FL, 34748
Community: Highland Lakes
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® 1137 SANTA CRUZ DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$292,000

2 beds

|

2 baths

|

1,214 sq ft

|

Villa

1137 SANTA CRUZ DR, THE VILLAGES, FL, 32...
Community: The Villages®
The Villages® 3768 INFINITY RUN, THE VILLAGES, FL, 321..., The Villages, FL 32163
$369,900

3 beds

|

2 baths

|

1,521 sq ft

|

House

3768 INFINITY RUN, THE VILLAGES, FL, 321...
Community: The Villages®
Traditions at Lake Ruby 3363 LIVINGSTON WAY, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884
$245,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

3363 LIVINGSTON WAY, WINTER HAVEN, FL, 3...
Breakaway Trails 3 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$425,000

3 beds

|

2 baths

|

2,737 sq ft

|

House

3 FOREST VIEW WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Compass Pointe 958 DANVILLE CIR, MELBOURNE, FL, 32904, Melbourne, FL 32904
$349,500

3 beds

|

2 baths

|

1,919 sq ft

|

House

958 DANVILLE CIR, MELBOURNE, FL, 32904
Community: Compass Pointe
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Plantation at Leesburg 4532 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$320,000

3 beds

|

2 baths

|

1,882 sq ft

|

House

4532 RIVER RIDGE DR, LEESBURG, FL, 34748
Baytree 138 BAYTREE BLVD, TAVARES, FL, 32778, Tavares, FL 32778
$225,000

2 beds

|

2 baths

|

1,339 sq ft

|

Villa

138 BAYTREE BLVD, TAVARES, FL, 32778
Community: Baytree
Spruce Creek Country Club 12747 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$339,900

2 beds

|

2 baths

|

1,575 sq ft

|

House

12747 SE 97TH TERRACE RD, SUMMERFIELD, F...
The Villages® 3024 PAYNES PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$649,900

3 beds

|

2 baths

|

2,222 sq ft

|

House

3024 PAYNES PL, THE VILLAGES, FL, 32162
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.
Solivita 396 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$229,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

396 GRAND CANAL DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 5288 HURTT ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$648,000

3 beds

|

2 baths

|

1,642 sq ft

|

Villa

5288 HURTT ST, THE VILLAGES, FL, 32163
Community: The Villages®
Huntington at Hunter's Ridge 35 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$409,900

3 beds

|

2 baths

|

1,850 sq ft

|

House

35 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...
Solivita 899 BELLA VIANA RD, POINCIANA, FL, 34759, Poinciana, FL 34759
$460,000

3 beds

|

3 baths

|

2,307 sq ft

|

House

899 BELLA VIANA RD, POINCIANA, FL, 34759
Community: Solivita
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Alhambra Villas Condominiums 151 N HILL AVE 100, DELAND, FL, 32724, Deland, FL 32724
$145,000

2 beds

|

2 baths

|

979 sq ft

|

Condo

151 N HILL AVE 100, DELAND, FL, 32724
The Villages® 977 CARIBOU WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$420,000

2 beds

|

2 baths

|

1,825 sq ft

|

House

977 CARIBOU WAY, THE VILLAGES, FL, 32162
Community: The Villages®

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2,513 homes
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