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Winter Park, FL 55+ active adult communities & homes for sale - Page 13

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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Questions? Call us: (888) 625-4885
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
The Villages® 1706 EL NINO ST, THE VILLAGES, FL, 32162, The Villages, FL 32162
$244,999

2 beds

|

2 baths

|

1,143 sq ft

|

Villa

1706 EL NINO ST, THE VILLAGES, FL, 32162
Community: The Villages®
Scottish Highlands 828 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$269,900

3 beds

|

2 baths

|

2,189 sq ft

|

Condo

828 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
Palms at Serenoa 17750 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714
$429,800

3 beds

|

2 baths

|

1,822 sq ft

|

House

17750 BLAZING STAR CIR, CLERMONT, FL, 34...
Community: Palms at Serenoa
Breakaway Trails 3 SLOW STREAM WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$479,900

3 beds

|

2 baths

|

1,966 sq ft

|

House

3 SLOW STREAM WAY, ORMOND BEACH, FL, 321...
Community: Breakaway Trails
Spruce Creek South 10475 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$225,000

2 beds

|

2 baths

|

1,248 sq ft

|

House

10475 SE 178TH ST, SUMMERFIELD, FL, 3449...
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Bridgewater at Viera 1262 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940
$749,624

3 beds

|

3 baths

|

2,457 sq ft

|

House

1262 GREAT BELT CIR, MELBOURNE, FL, 3294...
Sandpiper Golf & Country Club 6236 RAVEN RUN, LAKELAND, FL, 33809, Lakeland, FL 33809
$245,000

2 beds

|

2 baths

|

1,179 sq ft

|

House

6236 RAVEN RUN, LAKELAND, FL, 33809
Stonecrest 11972 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491
$340,000

3 beds

|

2 baths

|

1,738 sq ft

|

House

11972 SE 176TH PLACE RD, SUMMERFIELD, FL...
Community: Stonecrest
Spruce Creek Country Club 9003 SE 118TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$349,900

2 beds

|

2 baths

|

1,850 sq ft

|

House

9003 SE 118TH LN, 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.
Grand Haven 10 RIVER POINT DR, PALM COAST, FL, 32137, Palm Coast, FL 32137
$469,000

2 beds

|

2 baths

|

1,828 sq ft

|

Townhouse

10 RIVER POINT DR, PALM COAST, FL, 32137
Community: Grand Haven
The Villages® 1106 SOUTHERN SUN DR, THE VILLAGES, FL, ..., The Villages, FL 32162
$585,000

3 beds

|

2 baths

|

1,837 sq ft

|

Villa

1106 SOUTHERN SUN DR, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 309 CHULA VISTA AVE, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$349,000

3 beds

|

2 baths

|

1,550 sq ft

|

House

309 CHULA VISTA AVE, LADY LAKE, FL, 3215...
Community: The Villages®
Pennbrooke Fairways 62 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$212,000

2 beds

|

2 baths

|

1,192 sq ft

|

House

62 WESTWOOD DR, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Heritage Isle 6456 KLEIN LN, MELBOURNE, FL, 32940, Melbourne, FL 32940
$314,900

2 beds

|

2 baths

|

1,529 sq ft

|

Townhouse

6456 KLEIN LN, MELBOURNE, FL, 32940
Community: Heritage Isle
The Lakes at Harmony 3383 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773
$349,500

4 beds

|

2 baths

|

1,853 sq ft

|

House

3383 SAGEBRUSH ST, HARMONY, FL, 34773
Halifax Plantation 1128 KILLARNEY DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$499,900

3 beds

|

2 baths

|

2,159 sq ft

|

House

1128 KILLARNEY DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
The Villages® 17353 SE 76TH FLINTLOCK TER, THE VILLAGE..., The Villages, FL 32162
$284,900

2 beds

|

2 baths

|

1,388 sq ft

|

House

17353 SE 76TH FLINTLOCK TER, THE VILLAGE...
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.
Latitude Margaritaville 223 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124
$415,000

2 beds

|

2 baths

|

1,464 sq ft

|

House

223 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...
Heritage Isle 6604 PICO ST, MELBOURNE, FL, 32940, Melbourne, FL 32940
$359,900

3 beds

|

2 baths

|

1,594 sq ft

|

House

6604 PICO ST, MELBOURNE, FL, 32940
Community: Heritage Isle
The Villages® 3258 HOLLEY TER, THE VILLAGES, FL, 32163, The Villages, FL 32163
$485,000

4 beds

|

2 baths

|

2,028 sq ft

|

House

3258 HOLLEY TER, THE VILLAGES, FL, 32163
Community: The Villages®
Lakes of Mount Dora 8093 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$329,800

3 beds

|

2 baths

|

1,436 sq ft

|

House

8093 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 1314 CAMERO DR, THE VILLAGES, FL, 32159, The Villages, FL 32159
$529,000

3 beds

|

2 baths

|

2,257 sq ft

|

House

1314 CAMERO DR, THE VILLAGES, FL, 32159
Community: The Villages®
Lakes at Laurel Highlands 2829 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$319,000

3 beds

|

2 baths

|

1,711 sq ft

|

House

2829 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Heritage Landings 2829 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811
$319,000

3 beds

|

2 baths

|

1,711 sq ft

|

House

2829 GRANDBURY GROVE RD, LAKELAND, FL, 3...
Community: Heritage Landings
The Villages® 2906 CANYON AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163
$555,000

3 beds

|

2 baths

|

2,200 sq ft

|

House

2906 CANYON AVE, THE VILLAGES, FL, 32163
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.
Latitude Margaritaville 1002 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124
$509,000

3 beds

|

2 baths

|

1,848 sq ft

|

House

1002 SEA SHELL CT, DAYTONA BEACH, FL, 32...
Latitude Margaritaville 193 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124
$859,900

3 beds

|

3 baths

|

2,415 sq ft

|

House

193 ISLAND BREEZE AVE, DAYTONA BEACH, FL...
Spruce Creek Country Club 12767 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$329,000

3 beds

|

2 baths

|

1,720 sq ft

|

House

12767 SE 97TH TERRACE RD, SUMMERFIELD, F...
Plantation Bay Golf & Country Club 902 BROOKRIDGE LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$575,000

3 beds

|

2 baths

|

2,202 sq ft

|

House

902 BROOKRIDGE LN, ORMOND BEACH, FL, 321...
Harbor Hills Country Club 6053 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$624,900

3 beds

|

3 baths

|

3,024 sq ft

|

House

6053 SPINNAKER LOOP, LADY LAKE, FL, 3215...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 2837 CADE CT, THE VILLAGES, FL, 32163, The Villages, FL 32163
$659,900

3 beds

|

2 baths

|

2,000 sq ft

|

House

2837 CADE CT, THE VILLAGES, FL, 32163
Community: The Villages®
Venetian Bay 538 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168
$334,000

3 beds

|

3 baths

|

1,779 sq ft

|

House

538 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...
Community: Venetian Bay
The Villages® 683 KRIETEMEYER PATH, THE VILLAGES, FL, ..., The Villages, FL 32163
$2,000,000

4 beds

|

3 baths

|

3,345 sq ft

|

House

683 KRIETEMEYER PATH, THE VILLAGES, FL, ...
Community: The Villages®
The Villages® 4515 LESCHAK LN, THE VILLAGES, FL, 32163, The Villages, FL 32163
$434,500

3 beds

|

2 baths

|

1,569 sq ft

|

House

4515 LESCHAK LN, THE VILLAGES, FL, 32163
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.
Venetian Bay 3307 E LOCANDA CIR, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168
$785,000

4 beds

|

3 baths

|

2,250 sq ft

|

House

3307 E LOCANDA CIR, NEW SMYRNA BEACH, FL...
Community: Venetian Bay
Plantation at Leesburg 3544 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

1,856 sq ft

|

House

3544 MOUNT HOPE LOOP, LEESBURG, FL, 3474...
Baytree 240 JUNIPER WAY, TAVARES, FL, 32778, Tavares, FL 32778
$219,900

2 beds

|

2 baths

|

1,200 sq ft

|

Villa

240 JUNIPER WAY, TAVARES, FL, 32778
Community: Baytree
Silver Lakes 6323 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$415,000

3 beds

|

3 baths

|

1,902 sq ft

|

House

6323 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Spruce Creek Country Club 13915 SE 94TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$320,000

2 beds

|

2 baths

|

1,575 sq ft

|

House

13915 SE 94TH AVE, SUMMERFIELD, FL, 3449...
Summer Trees 49 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$265,000

2 beds

|

2 baths

|

1,295 sq ft

|

House

49 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees

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2,513 homes
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