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Winter Park, FL 55+ active adult communities & homes for sale - Page 44

2,259 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
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
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
Want to learn more about 55+ communities in Winter Park? 55places can help!
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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
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) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
Grand Haven
$200ks - $800ks
Grand Haven, Palm Coast, FL
New and Resale | Age-targeted | Built 1997 - present | 1,901 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.
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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 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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 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 (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
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
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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.
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
5 rating (1 reviews) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
Foxwood Lake Estates
$100ks - $200ks
Foxwood Lake Estates, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes
5 rating (2 reviews) Bridgewater at Viera
$300ks - $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes
Gatherings of Lake Nona
$300ks - $400ks
Gatherings of Lake Nona, Orlando, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 216 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
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (1 reviews) VillageWalk at Lake Nona
$300ks - $700ks
VillageWalk at Lake Nona, Orlando, FL
Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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.
12...3
Latitude Margaritaville 333 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124
$379,900

2 beds

|

2 baths

|

1,308 sq ft

|

House

333 POP TOP LN, DAYTONA BEACH, FL, 32124
Sandpiper Golf & Country Club 5888 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$349,900

2 beds

|

2 baths

|

1,852 sq ft

|

House

5888 SANDPIPERS DR, LAKELAND, FL, 33809
Breakaway Trails 175 DEEP WOODS WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174
$640,000

5 beds

|

3 baths

|

2,959 sq ft

|

House

175 DEEP WOODS WAY, ORMOND BEACH, FL, 32...
Community: Breakaway Trails
Spruce Creek Country Club 11728 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$299,500

2 beds

|

2 baths

|

1,575 sq ft

|

House

11728 SE 91ST CIR, SUMMERFIELD, FL, 3449...
The Villages® 17723 SE 81ST TIMBERWOOD TER, THE VILLAG..., The Villages, FL 32162
$360,000

3 beds

|

2 baths

|

2,027 sq ft

|

House

17723 SE 81ST TIMBERWOOD TER, THE VILLAG...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
The Villages® 16672 SE 78TH LIVE OAK AVE, THE VILLAGES..., The Villages, FL 32162
$399,000

3 beds

|

2 baths

|

1,850 sq ft

|

House

16672 SE 78TH LIVE OAK AVE, THE VILLAGES...
Community: The Villages®
Venetian Bay 3218 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$779,000

3 beds

|

2 baths

|

2,269 sq ft

|

House

3218 MODENA WAY, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
Highland Lakes 5932 MCENROE CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$230,000

2 beds

|

2 baths

|

1,210 sq ft

|

Villa

5932 MCENROE CT, LEESBURG, FL, 34748
Community: Highland Lakes
Royal Highlands 21849 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$425,000

3 beds

|

2 baths

|

2,074 sq ft

|

House

21849 TARTAN ST, LEESBURG, FL, 34748
Community: Royal Highlands
The Villages® 9711 SE 171ST ARGYLL ST, THE VILLAGES, F..., The Villages, FL 32162
$335,000

3 beds

|

2 baths

|

1,392 sq ft

|

House

9711 SE 171ST ARGYLL ST, THE VILLAGES, F...
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.
American Village 29 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164
$349,900

3 beds

|

2 baths

|

1,604 sq ft

|

House

29 GREEN CIR, PALM COAST, FL, 32164
Community: American Village
Scottish Highlands 822 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788
$220,000

2 beds

|

2 baths

|

1,414 sq ft

|

House

822 DUNDEE CIR, LEESBURG, FL, 34788
Community: Scottish Highlands
Pennbrooke Fairways 752 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,247

3 beds

|

2 baths

|

1,620 sq ft

|

House

752 OLD OAKS LN, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Lakes of Mount Dora 8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$489,500

3 beds

|

2 baths

|

1,823 sq ft

|

House

8301 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Halifax Plantation 3145 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174
$365,000

3 beds

|

3 baths

|

2,384 sq ft

|

House

3145 CONNEMARA DR, ORMOND BEACH, FL, 321...
Community: Halifax Plantation
Spruce Creek South 9826 SE 178TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$249,900

2 beds

|

2 baths

|

1,312 sq ft

|

House

9826 SE 178TH LN, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Latitude Margaritaville 298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124
$588,900

2 beds

|

3 baths

|

2,139 sq ft

|

House

298 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...
Plantation at Leesburg 4721 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$307,900

3 beds

|

2 baths

|

1,979 sq ft

|

House

4721 TARA VIEW RD, LEESBURG, FL, 34748
Heritage Hills 3538 FAIRWATERS CT B, CLERMONT, FL, 3471..., Clermont, FL 34711
$290,000

2 beds

|

2 baths

|

1,374 sq ft

|

Villa

3538 FAIRWATERS CT B, CLERMONT, FL, 3471...
Community: Heritage Hills
Royal Highlands 4741 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$344,999

3 beds

|

2 baths

|

1,902 sq ft

|

House

4741 INVERNESS DR, LEESBURG, FL, 34748
Community: Royal Highlands
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® 670 WOODBRIDGE WAY, THE VILLAGES, FL, 32..., The Villages, FL 32163
$884,900

3 beds

|

2 baths

|

2,299 sq ft

|

House

670 WOODBRIDGE WAY, THE VILLAGES, FL, 32...
Community: The Villages®
Foxwood Lake Estates 1679 FOXWAY DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$149,900

2 beds

|

2 baths

|

1,248 sq ft

|

Manufactured Home

1679 FOXWAY DR, LAKELAND, FL, 33810
Pennbrooke Fairways 32747 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,247

2 beds

|

2 baths

|

1,192 sq ft

|

House

32747 WESTWOOD LOOP, LEESBURG, FL, 34748
Community: Pennbrooke Fairways
Halifax Plantation 1346 MIDDLE LAKE DR, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174
$349,000

3 beds

|

2 baths

|

1,672 sq ft

|

House

1346 MIDDLE LAKE DR, ORMOND BEACH, FL, 3...
Community: Halifax Plantation
Twin Lakes 5043 VANTAGE CT, ST. CLOUD, FL, 34772, St. Cloud, FL 34772
$479,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

5043 VANTAGE CT, ST. CLOUD, FL, 34772
Community: Twin Lakes
Twin Lakes 5043 VANTAGE CT, ST CLOUD, FL, 34772, St Cloud, FL 34772
$479,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

5043 VANTAGE CT, ST CLOUD, FL, 34772
Community: Twin Lakes
Plantation Bay Golf & Country Club 60 KINGSLEY CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$385,000

3 beds

|

2 baths

|

2,144 sq ft

|

House

60 KINGSLEY CIR, ORMOND BEACH, FL, 32174
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Indian River Colony Club 1311 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940
$359,000

4 beds

|

3 baths

|

1,859 sq ft

|

House

1311 INDEPENDENCE AVE, MELBOURNE, FL, 32...
Plantation Bay Golf & Country Club 13 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174
$849,900

3 beds

|

4 baths

|

3,596 sq ft

|

House

13 BAY POINTE DR, ORMOND BEACH, FL, 3217...
The Country Club of Mount Dora 5039 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757
$679,900

4 beds

|

3 baths

|

2,509 sq ft

|

House

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327...
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.
Westhaven at Ovation - Townes Collection 13953 EASDALE ALY, WINTER GARDEN, FL, 34..., Winter Garden, FL 34787
$509,900

3 beds

|

3 baths

|

1,770 sq ft

|

Townhouse

13953 EASDALE ALY, WINTER GARDEN, FL, 34...
Lakes of Mount Dora 1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757
$588,800

3 beds

|

3 baths

|

2,330 sq ft

|

House

1990 WALLINGFORD LOOP, MOUNT DORA, FL, 3...
Community: Lakes of Mount Dora
The Villages® 1504 LYNCHBURG LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,550 sq ft

|

House

1504 LYNCHBURG LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
Del Webb Orlando 329 ALICANTE CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$425,000

3 beds

|

2 baths

|

2,000 sq ft

|

House

329 ALICANTE CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
Solivita 116 GLENDALE CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$309,000

2 beds

|

2 baths

|

1,655 sq ft

|

House

116 GLENDALE CT, KISSIMMEE, FL, 34759
Community: Solivita
Plantation at Leesburg 25239 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748
$249,900

2 beds

|

2 baths

|

1,563 sq ft

|

House

25239 CRANES ROOST CIR, LEESBURG, FL, 34...
Solivita 362 VIA TORRENTE DR, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$379,000

2 beds

|

2 baths

|

1,705 sq ft

|

House

362 VIA TORRENTE DR, KISSIMMEE, FL, 3475...
Community: Solivita
Del Webb Sunbridge 2499 CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$455,000

3 beds

|

2 baths

|

1,650 sq ft

|

House

2499 CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
Legacy of Leesburg 5922 SAGE LEAF PL, LEESBURG, FL, 34748, Leesburg, FL 34748
$324,000

3 beds

|

2 baths

|

1,913 sq ft

|

House

5922 SAGE LEAF PL, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Highland Lakes 5636 LAVER ST, LEESBURG, FL, 34748, Leesburg, FL 34748
$259,900

2 beds

|

2 baths

|

1,497 sq ft

|

House

5636 LAVER 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.

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2,259 homes
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