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Winter Park, FL 55+ active adult communities & homes for sale - Page 5

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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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
New Fountain View 1348 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$416,490

4 beds

|

3 baths

|

2,336 sq ft

|

House

1348 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
New Sullivan Ranch 30231 HACKNEY LOOP, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757
$474,900

4 beds

|

2 baths

|

2,426 sq ft

|

House

30231 HACKNEY LOOP, MOUNT DORA, FL, 3275...
Community: Sullivan Ranch
New The Lakes at Harmony 3399 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$370,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

3399 SAGEBRUSH ST, HARMONY, FL, 34773
New Highland Lakes 5618 ROSEWALL CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$215,000

2 beds

|

2 baths

|

1,306 sq ft

|

House

5618 ROSEWALL CIR, LEESBURG, FL, 34748
Community: Highland Lakes
New Spruce Creek Country Club 13875 SE 94TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,900

2 beds

|

2 baths

|

1,575 sq ft

|

House

13875 SE 94TH AVE, SUMMERFIELD, FL, 3449...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New The Villages® 1088 GENNESSE LN, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$300,000

2 beds

|

2 baths

|

1,240 sq ft

|

House

1088 GENNESSE LN, THE VILLAGES, FL, 3216...
Community: The Villages®
New The Villages® 2149 ESCOBAR AVE, THE VILLAGES, FL, 3215..., The Villages, FL 32159
$250,000

2 beds

|

2 baths

|

1,121 sq ft

|

Villa

2149 ESCOBAR AVE, THE VILLAGES, FL, 3215...
Community: The Villages®
New Stonecrest 17180 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491
$349,900

3 beds

|

2 baths

|

1,796 sq ft

|

House

17180 SE 115TH TERRACE RD, SUMMERFIELD, ...
Community: Stonecrest
New Heritage Hills 2888 SANDY CAY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$559,000

4 beds

|

3 baths

|

2,562 sq ft

|

House

2888 SANDY CAY ST, CLERMONT, FL, 34711
Community: Heritage Hills
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.
New Plantation Bay Golf & Country Club 830 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$343,000

2 beds

|

2 baths

|

1,510 sq ft

|

Townhouse

830 ALDENHAM LN, ORMOND BEACH, FL, 32174
New Traditions at Lake Ruby 3832 TRADITIONS BLVD, WINTER HAVEN, FL, ..., Winter Haven, FL 33884
$250,000

3 beds

|

2 baths

|

2,109 sq ft

|

House

3832 TRADITIONS BLVD, WINTER HAVEN, FL, ...
New Lakeside Landings 10396 SILVER MAPLE AVE, OXFORD, FL, 3448..., Oxford, FL 34484
$339,000

3 beds

|

2 baths

|

1,658 sq ft

|

House

10396 SILVER MAPLE AVE, OXFORD, FL, 3448...
Community: Lakeside Landings
Del Webb at Viera 8984 NIXIE AVE, MELBOURNE, FL, 32940, Melbourne, FL 32940
$695,000

3 beds

|

2 baths

|

1,919 sq ft

|

House

8984 NIXIE AVE, MELBOURNE, FL, 32940
Community: Del Webb at Viera
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Pelican Bay Daytona Beach 107 GREY WIDGEON CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119
$265,000

2 beds

|

3 baths

|

1,657 sq ft

|

House

107 GREY WIDGEON CT, DAYTONA BEACH, FL, ...
Summer Trees 120 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$304,995

2 beds

|

2 baths

|

1,245 sq ft

|

House

120 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Halifax Plantation 1352 ARKLOW CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$810,000

4 beds

|

4 baths

|

2,721 sq ft

|

House

1352 ARKLOW CIR, ORMOND BEACH, FL, 32174
Community: Halifax Plantation
Indian River Colony Club 1427 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$299,000

3 beds

|

2 baths

|

2,016 sq ft

|

House

1427 PATRIOT DR, MELBOURNE, FL, 32940
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.
Latitude Margaritaville 852 CORAL REEF WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$539,000

2 beds

|

3 baths

|

1,748 sq ft

|

House

852 CORAL REEF WAY, DAYTONA BEACH, FL, 3...
Latitude Margaritaville 303 LATITUDE DR, DAYTONA BEACH, FL, 3212..., Daytona Beach, FL 32124
$397,500

2 beds

|

2 baths

|

1,308 sq ft

|

House

303 LATITUDE DR, DAYTONA BEACH, FL, 3212...
Latitude Margaritaville 825 MARGARITAVILLE AVE, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$549,900

2 beds

|

3 baths

|

1,748 sq ft

|

House

825 MARGARITAVILLE AVE, DAYTONA BEACH, F...
Bridgewater at Viera 2013 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$515,000

2 beds

|

2 baths

|

1,876 sq ft

|

House

2013 GREAT BELT CIR, MELBOURNE, FL, 3294...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Fountain View 1356 FOUNTAIN VIEW ST, ORMOND BEACH, FL,..., Ormond Beach, FL 32174
$415,990

4 beds

|

3 baths

|

2,336 sq ft

|

House

1356 FOUNTAIN VIEW ST, ORMOND BEACH, FL,...
Community: Fountain View
Heritage Isle 6957 FLORISTANA DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$459,900

3 beds

|

2 baths

|

2,253 sq ft

|

House

6957 FLORISTANA DR, MELBOURNE, FL, 32940
Community: Heritage Isle
Trilogy® Orlando 108 MIST FLOWER LN, GROVELAND, FL, 34736, Groveland, FL 34736
$450,000

2 beds

|

2 baths

|

1,900 sq ft

|

House

108 MIST FLOWER LN, GROVELAND, FL, 34736
Community: Trilogy® Orlando
Summit Chase Villas 12449 ORANGEWOOD CIR 17, TAVARES, FL, 32..., Tavares, FL 32778
$179,000

2 beds

|

2 baths

|

918 sq ft

|

Condo

12449 ORANGEWOOD CIR 17, TAVARES, FL, 32...
Community: Summit Chase Villas
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.
Summit Greens 2197 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$345,000

3 beds

|

2 baths

|

1,703 sq ft

|

House

2197 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Venetian Bay 3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$525,000

3 beds

|

2 baths

|

1,764 sq ft

|

House

3615 MARISOL CT, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Kings Ridge 4124 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711
$367,000

2 beds

|

2 baths

|

1,802 sq ft

|

House

4124 KINGSLEY ST, CLERMONT, FL, 34711
Community: Kings Ridge
Scottish Highlands 2218 ORKNEY DR, LEESBURG, FL, 34788, Leesburg, FL 34788
$229,000

2 beds

|

2 baths

|

1,500 sq ft

|

House

2218 ORKNEY DR, LEESBURG, FL, 34788
Community: Scottish Highlands
The Villages® 403 MCLEOD LN, THE VILLAGES, FL, 32162, The Villages, FL 32162
$387,000

3 beds

|

2 baths

|

1,512 sq ft

|

House

403 MCLEOD LN, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1712 CARRERA DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$335,000

3 beds

|

2 baths

|

1,440 sq ft

|

House

1712 CARRERA DR, THE VILLAGES, FL, 32159
Community: The Villages®
Heritage Isle 6770 RINGOLD ST, MELBOURNE, FL, 32940, Melbourne, FL 32940
$435,000

4 beds

|

3 baths

|

2,032 sq ft

|

House

6770 RINGOLD ST, MELBOURNE, FL, 32940
Community: Heritage Isle
Lake Henry Estates 558 PINNACLE DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$253,000

2 beds

|

2 baths

|

1,273 sq ft

|

House

558 PINNACLE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Traditions at Lake Ruby 2708 ATTWATER LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884
$269,999

3 beds

|

2 baths

|

1,561 sq ft

|

House

2708 ATTWATER LOOP, WINTER HAVEN, FL, 33...
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.
Kings Ridge 3828 AVON CT, CLERMONT, FL, 34711, Clermont, FL 34711
$409,000

3 beds

|

2 baths

|

2,026 sq ft

|

House

3828 AVON CT, CLERMONT, FL, 34711
Community: Kings Ridge
The Villages® 3283 CANDLEBROOK ST, THE VILLAGES, FL, 3..., The Villages, FL 32162
$278,750

2 beds

|

2 baths

|

1,142 sq ft

|

House

3283 CANDLEBROOK ST, THE VILLAGES, FL, 3...
Community: The Villages®
The Lakes at Harmony 3464 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$315,000

2 beds

|

2 baths

|

1,404 sq ft

|

House

3464 SAGEBRUSH ST, HARMONY, FL, 34773
Arlington Ridge 27118 ROANOKE DR 516, LEESBURG, FL, 3474..., Leesburg, FL 34748
$379,900

3 beds

|

2 baths

|

1,713 sq ft

|

House

27118 ROANOKE DR 516, LEESBURG, FL, 3474...
Community: Arlington Ridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 14160 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$236,000

2 beds

|

2 baths

|

1,238 sq ft

|

Villa

14160 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Venetian Bay 3605 ROMEA CIR, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$295,000

2 beds

|

3 baths

|

1,664 sq ft

|

Townhouse

3605 ROMEA CIR, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay

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2,513 homes
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