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Winter Park, FL 55+ active adult communities & homes for sale - Page 42

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
Latitude Margaritaville 103 FLIP FLOP CT, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124
$645,000

2 beds

|

2 baths

|

1,681 sq ft

|

House

103 FLIP FLOP CT, DAYTONA BEACH, FL, 321...
The Villages® 18101 SANDALWOOD DR, WILDWOOD, FL, 34785, Wildwood, FL 34785
$94,900

1 beds

|

1 baths

|

872 sq ft

|

Condo

18101 SANDALWOOD DR, WILDWOOD, FL, 34785
Community: The Villages®
Heritage Hills 3547 FAIRWATERS CT A, CLERMONT, FL, 3471..., Clermont, FL 34711
$324,500

2 beds

|

2 baths

|

1,503 sq ft

|

Villa

3547 FAIRWATERS CT A, CLERMONT, FL, 3471...
Community: Heritage Hills
Venetian Bay 3617 CASELLO DR, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$340,000

2 beds

|

3 baths

|

1,824 sq ft

|

Townhouse

3617 CASELLO DR, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Venetian Bay 3403 TORRE BLVD, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$410,000

2 beds

|

2 baths

|

1,916 sq ft

|

Villa

3403 TORRE BLVD, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 915 RAMOS DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$449,900

3 beds

|

2 baths

|

2,022 sq ft

|

House

915 RAMOS DR, THE VILLAGES, FL, 32159
Community: The Villages®
Palms at Serenoa 17478 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$380,000

2 beds

|

2 baths

|

1,822 sq ft

|

House

17478 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Plantation at Leesburg 3639 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,900

2 beds

|

2 baths

|

1,709 sq ft

|

House

3639 WESTOVER CIR, LEESBURG, FL, 34748
Kings Ridge 2535 NEW CASTLE CT, CLERMONT, FL, 34711, Clermont, FL 34711
$379,000

2 beds

|

2 baths

|

1,930 sq ft

|

House

2535 NEW CASTLE CT, CLERMONT, FL, 34711
Community: Kings Ridge
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 Landings 2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$395,000

6 beds

|

3 baths

|

2,696 sq ft

|

House

2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
Lakes at Laurel Highlands 2651 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$395,000

6 beds

|

3 baths

|

2,696 sq ft

|

House

2651 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Twin Lakes 2458 DREAM HOME CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$887,000

3 beds

|

3 baths

|

2,966 sq ft

|

House

2458 DREAM HOME CT, ST CLOUD, FL, 34772
Community: Twin Lakes
The Villages® 602 JUANITA CT, THE VILLAGES, FL, 32159, The Villages, FL 32159
$425,000

3 beds

|

2 baths

|

1,776 sq ft

|

House

602 JUANITA CT, THE VILLAGES, FL, 32159
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 17353 SE 78TH HARMONY CIR, THE VILLAGES,..., The Villages, FL 32162
$259,000

1 beds

|

1 baths

|

955 sq ft

|

Villa

17353 SE 78TH HARMONY CIR, THE VILLAGES,...
Community: The Villages®
The Villages® 631 ENCONTO ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$319,000

2 beds

|

2 baths

|

1,128 sq ft

|

House

631 ENCONTO ST, LADY LAKE, FL, 32159
Community: The Villages®
Heritage Hills 3557 BELLAND CIR D, CLERMONT, FL, 34711, Clermont, FL 34711
$289,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3557 BELLAND CIR D, CLERMONT, FL, 34711
Community: Heritage Hills
Spruce Creek Country Club 13103 SE 86TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$415,960

3 beds

|

2 baths

|

2,413 sq ft

|

House

13103 SE 86TH CT, SUMMERFIELD, FL, 34491
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.
Venetian Bay 354 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$349,990

3 beds

|

2 baths

|

1,520 sq ft

|

House

354 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Lakeside Landings 5318 EDGEWATER WAY 10, OXFORD, FL, 34484, Oxford, FL 34484
$223,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5318 EDGEWATER WAY 10, OXFORD, FL, 34484
Community: Lakeside Landings
Solivita 677 VIA CORSO CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$480,000

3 beds

|

3 baths

|

2,235 sq ft

|

House

677 VIA CORSO CT, KISSIMMEE, FL, 34759
Community: Solivita
Harbor Hills Country Club 39819 GROVE HEIGHTS, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$520,000

3 beds

|

2 baths

|

2,504 sq ft

|

House

39819 GROVE HEIGHTS, LADY LAKE, FL, 3215...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 17824 SE 114TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$225,000

3 beds

|

2 baths

|

1,483 sq ft

|

House

17824 SE 114TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
The Villages® 1568 BLACK LAKE DR, THE VILLAGES, FL, 32..., The Villages, FL 32162
$2,250,000

4 beds

|

5 baths

|

4,654 sq ft

|

House

1568 BLACK LAKE DR, THE VILLAGES, FL, 32...
Community: The Villages®
Lakeside Landings 10158 JULIA ISLES AVE, OXFORD, FL, 34484, Oxford, FL 34484
$369,000

3 beds

|

2 baths

|

1,889 sq ft

|

House

10158 JULIA ISLES AVE, OXFORD, FL, 34484
Community: Lakeside Landings
Twin Lakes 2454 DREAM HOME CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$680,000

3 beds

|

3 baths

|

2,208 sq ft

|

House

2454 DREAM HOME CT, ST CLOUD, FL, 34772
Community: Twin 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.
Solivita 2472 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$294,900

3 beds

|

2 baths

|

1,539 sq ft

|

Villa

2472 PALM TREE DR, KISSIMMEE, FL, 34759
Community: Solivita
The Villages® 3499 AUBURNDALE AVE, THE VILLAGES, FL, 3..., The Villages, FL 32162
$329,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

3499 AUBURNDALE AVE, THE VILLAGES, FL, 3...
Community: The Villages®
Sandpiper Golf & Country Club 6043 CONDOR DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$299,000

2 beds

|

2 baths

|

1,786 sq ft

|

House

6043 CONDOR DR, LAKELAND, FL, 33809
Tohoqua Reserve 1881 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$355,000

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

1881 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
Heritage Hills 3550 FAIRWATERS CT C, CLERMONT, FL, 3471..., Clermont, FL 34711
$304,900

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3550 FAIRWATERS CT C, CLERMONT, FL, 3471...
Community: Heritage Hills
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Stonecrest 11351 SE 175TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$274,900

3 beds

|

2 baths

|

1,717 sq ft

|

House

11351 SE 175TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Four Seasons at Orlando 7916 HANSON BAY PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747
$499,000

3 beds

|

3 baths

|

2,470 sq ft

|

House

7916 HANSON BAY PL, KISSIMMEE, FL, 34747
Spruce Creek Country Club 13324 SE 91ST COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491
$348,000

3 beds

|

2 baths

|

1,870 sq ft

|

House

13324 SE 91ST COURT RD, SUMMERFIELD, FL,...
Stonecrest 17187 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$479,900

3 beds

|

3 baths

|

2,026 sq ft

|

House

17187 SE 116TH COURT RD, SUMMERFIELD, FL...
Community: Stonecrest
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.
Alhambra Villas Condominiums 249 N HILL AVE 30, DELAND, FL, 32724, Deland, FL 32724
$199,500

2 beds

|

2 baths

|

1,043 sq ft

|

Condo

249 N HILL AVE 30, DELAND, FL, 32724
The Villages® 2306 OAK BEND PL, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$275,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2306 OAK BEND PL, THE VILLAGES, FL, 3216...
Community: The Villages®
Grand Isle 1444 BOCA RIO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$489,900

3 beds

|

2 baths

|

2,011 sq ft

|

House

1444 BOCA RIO DR, MELBOURNE, FL, 32940
Community: Grand Isle
Traditions at Lake Ruby 2925 DAYTON DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$299,900

3 beds

|

2 baths

|

2,109 sq ft

|

House

2925 DAYTON DR, WINTER HAVEN, FL, 33884
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Lakes of Mount Dora 2389 PAWTUCKET PASS, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$538,000

3 beds

|

2 baths

|

2,048 sq ft

|

House

2389 PAWTUCKET PASS, MOUNT DORA, FL, 327...
Community: Lakes of Mount Dora
Plantation Bay Golf & Country Club 503 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$1,325,000

5 beds

|

4 baths

|

3,067 sq ft

|

House

503 WINGSPAN DR, ORMOND BEACH, FL, 32174

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2,513 homes
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