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

93 communities 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
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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 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 (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
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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.
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
Trilogy® Orlando, Groveland, FL
Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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
2.8 rating (6 reviews) Arlington Ridge
$200ks - $500ks
Arlington Ridge, Leesburg, FL
New and Resale | 55+ age-restricted | Built 2005 - present | 629 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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Questions? Call us: (888) 625-4885
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) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
Halifax Plantation
$300ks - $1Ms
Halifax Plantation, Ormond Beach, FL
New and Resale | Age-targeted | Built 1980 - present | 1,000 homes
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
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 (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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 (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
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
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Summer Trees
$200ks - $400ks
Summer Trees, Port Orange, FL
Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes
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Four Seasons at Orlando
$300ks - $600ks
Four Seasons at Orlando, Kissimmee, FL
New Construction | 55+ age-restricted | Built 2017 - present | 557 homes
4.8 rating (6 reviews) Highland Lakes
$100ks - $200ks
Highland Lakes, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes
Ridgehaven
$300ks - $600ks
Ridgehaven, Ormond Beach, FL
New Construction | 55+ age-restricted
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) 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
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
1 rating (1 reviews) Sullivan Ranch
$200ks - $500ks
Sullivan Ranch, Mount Dora, FL
Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
The Timbers at Everlands
$200ks - $500ks
The Timbers at Everlands, Palm Bay, FL
New Construction | 55+ age-restricted | Built 2023 - present | 450 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
5 rating (2 reviews) Bridgewater at Viera
$300ks - $800ks
Bridgewater at Viera, Melbourne, FL
Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
5 rating (2 reviews) Heritage Isle
$300ks - $500ks
Heritage Isle, Viera, FL
Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes
4 rating (4 reviews) High Vista at Ridgewood L...
$200ks - $300ks
High Vista at Ridgewood L..., Davenport, FL
Resale Only | 55+ age-restricted | Built 1995 - 2005 | 623 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
New The Villages® 3189 DARIEN WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162
$895,000

3 beds

|

2 baths

|

1,727 sq ft

|

House

3189 DARIEN WAY, THE VILLAGES, FL, 32162
Community: The Villages®
New Del Webb Orlando 418 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837
$346,500

3 beds

|

2 baths

|

1,713 sq ft

|

House

418 DEL SOL AVE, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Sullivan Ranch 30115 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$434,900

3 beds

|

2 baths

|

2,164 sq ft

|

House

30115 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
New Kings Ridge 3422 CHESSINGTON ST, CLERMONT, FL, 34711, Clermont, FL 34711
$409,900

3 beds

|

2 baths

|

2,031 sq ft

|

House

3422 CHESSINGTON ST, CLERMONT, FL, 34711
Community: Kings Ridge
New The Villages® 712 SHELTON ST, THE VILLAGES, FL, 32163, The Villages, FL 32163
$315,000

3 beds

|

2 baths

|

1,352 sq ft

|

House

712 SHELTON ST, THE VILLAGES, FL, 32163
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Heritage Landings 2778 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$334,900

3 beds

|

2 baths

|

1,685 sq ft

|

House

2778 CANYON CREST DR, LAKELAND, FL, 3381...
Community: Heritage Landings
New Lakes at Laurel Highlands 2778 CANYON CREST DR, LAKELAND, FL, 3381..., Lakeland, FL 33811
$334,900

3 beds

|

2 baths

|

1,685 sq ft

|

House

2778 CANYON CREST DR, LAKELAND, FL, 3381...
New The Villages® 1120 BERNARDO BLVD, THE VILLAGES, FL, 32..., The Villages, FL 32159
$395,000

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

1120 BERNARDO BLVD, THE VILLAGES, FL, 32...
Community: The Villages®
New The Villages® 2741 PERSIMMON LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32162
$799,900

3 beds

|

2 baths

|

1,978 sq ft

|

House

2741 PERSIMMON LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
New Sandpiper Golf & Country Club 6068 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$345,000

2 beds

|

2 baths

|

1,762 sq ft

|

House

6068 SWALLOW DR, LAKELAND, FL, 33809
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 Indian River Colony Club 1618 FRONTIER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$319,321

2 beds

|

2 baths

|

1,664 sq ft

|

House

1618 FRONTIER DR, MELBOURNE, FL, 32940
New Cresswind at Victoria Gardens 203 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724
$415,000

3 beds

|

2 baths

|

1,847 sq ft

|

House

203 HERON POINT WAY, DELAND, FL, 32724
New Highland Lakes 25904 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$337,500

3 beds

|

2 baths

|

2,153 sq ft

|

House

25904 NEWCOMBE CIR, LEESBURG, FL, 34748
Community: Highland Lakes
New Del Webb Orlando 344 ALICANTE CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$485,000

4 beds

|

3 baths

|

2,643 sq ft

|

House

344 ALICANTE CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
New Lakes of Mount Dora 2003 BAYSIDE AVE, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$525,000

3 beds

|

2 baths

|

1,864 sq ft

|

House

2003 BAYSIDE AVE, MOUNT DORA, FL, 32757
Community: Lakes of Mount Dora
New Pelican Bay Daytona Beach 340 BOB WHITE CT 3400, DAYTONA BEACH, FL..., Daytona Beach, FL 32119
$169,900

2 beds

|

2 baths

|

1,093 sq ft

|

Condo

340 BOB WHITE CT 3400, DAYTONA BEACH, FL...
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Lake Ashton 4072 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859
$280,000

2 beds

|

2 baths

|

1,530 sq ft

|

House

4072 DUNMORE DR, LAKE WALES, FL, 33859
Community: Lake Ashton
New Stonecrest 11081 SE 167TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$439,000

3 beds

|

3 baths

|

2,068 sq ft

|

House

11081 SE 167TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
New Bridgewater at Viera 9503 ALISTER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940
$370,000

3 beds

|

2 baths

|

1,565 sq ft

|

House

9503 ALISTER DR, MELBOURNE, FL, 32940
New Lake James 7835 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$479,000

3 beds

|

2 baths

|

2,175 sq ft

|

House

7835 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
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 Grand Haven 4 CHINIER ST, PALM COAST, FL, 32137, Palm Coast, FL 32137
$600,000

3 beds

|

2 baths

|

1,906 sq ft

|

House

4 CHINIER ST, PALM COAST, FL, 32137
Community: Grand Haven
New Spring Lake Towers 700 MIRROR TER 507, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881
$164,900

2 beds

|

2 baths

|

1,351 sq ft

|

Condo

700 MIRROR TER 507, WINTER HAVEN, FL, 33...
Community: Spring Lake Towers
New Lake Ashton 5312 NICKLAUS DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884
$334,900

3 beds

|

2 baths

|

1,700 sq ft

|

House

5312 NICKLAUS DR, WINTER HAVEN, FL, 3388...
Community: Lake Ashton
New Stonecrest 17808 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$349,500

3 beds

|

3 baths

|

2,282 sq ft

|

Villa

17808 SE 115TH CT, SUMMERFIELD, FL, 3449...
Community: Stonecrest
New The Villages® 401 CALHOUN CT, THE VILLAGES, FL, 32162, The Villages, FL 32162
$400,000

3 beds

|

2 baths

|

1,663 sq ft

|

Villa

401 CALHOUN CT, THE VILLAGES, FL, 32162
Community: The Villages®
New Royal Highlands 20618 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$324,900

3 beds

|

2 baths

|

1,945 sq ft

|

House

20618 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
New The Villages® 897 FOLKSTONE WAY, THE VILLAGES, FL, 321..., The Villages, FL 32162
$449,900

3 beds

|

2 baths

|

1,939 sq ft

|

House

897 FOLKSTONE WAY, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Royal Harbor 5190 CHINA SEA DR, TAVARES, FL, 32778, Tavares, FL 32778
$300,000

3 beds

|

2 baths

|

1,442 sq ft

|

House

5190 CHINA SEA DR, TAVARES, FL, 32778
Community: Royal Harbor
New Silver Lakes 6257 SILVER LAKES DR, LAKELAND, FL, 3381..., Lakeland, FL 33810
$319,000

3 beds

|

2 baths

|

1,759 sq ft

|

House

6257 SILVER LAKES DR, LAKELAND, FL, 3381...
Community: Silver Lakes
New Trilogy® Orlando 603 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736
$500,000

2 beds

|

2 baths

|

1,918 sq ft

|

House

603 CONSERVATION BLVD, GROVELAND, FL, 34...
Community: Trilogy® Orlando
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 Pelican Bay Daytona Beach 108 LOON CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119
$314,900

3 beds

|

2 baths

|

1,661 sq ft

|

House

108 LOON CT, DAYTONA BEACH, FL, 32119
New Venetian Bay 3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168
$449,900

3 beds

|

2 baths

|

2,174 sq ft

|

House

3455 PEGASO AVE, NEW SMYRNA BEACH, FL, 3...
Community: Venetian Bay
New Royal Highlands 5745 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,000

2 beds

|

2 baths

|

1,280 sq ft

|

House

5745 KING JAMES AVE, LEESBURG, FL, 34748
Community: Royal Highlands
New The Villages® 2378 YOUNGMANN LOOP, THE VILLAGES, FL, 3..., The Villages, FL 32163
$399,900

3 beds

|

2 baths

|

1,611 sq ft

|

House

2378 YOUNGMANN LOOP, THE VILLAGES, FL, 3...
Community: The Villages®
New The Villages® 4258 WIDMANN PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$527,000

3 beds

|

2 baths

|

1,959 sq ft

|

House

4258 WIDMANN PL, THE VILLAGES, FL, 32163
Community: The Villages®
New Grand Haven 200 RIVERFRONT DR D103, PALM COAST, FL, ..., Palm Coast, FL 32137
$375,000

3 beds

|

2 baths

|

1,762 sq ft

|

Condo

200 RIVERFRONT DR D103, PALM COAST, FL, ...
Community: Grand Haven
New Spruce Creek South 9565 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491
$249,900

3 beds

|

2 baths

|

1,704 sq ft

|

House

9565 SE 173RD PL, SUMMERFIELD, FL, 34491
Community: Spruce Creek South
New Summer Trees 125 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128
$289,900

2 beds

|

2 baths

|

1,180 sq ft

|

House

125 CROOKED PINE RD, PORT ORANGE, FL, 32...
Community: Summer Trees
Want to learn more about 55+ communities in Winter Park? 55places can help!
Questions? Call us: (888) 625-4885
New Plantation Bay Golf & Country Club 814 WESTLAKE DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174
$750,000

4 beds

|

3 baths

|

2,619 sq ft

|

House

814 WESTLAKE DR, ORMOND BEACH, FL, 32174
New Breakaway Trails 38 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174
$999,000

5 beds

|

5 baths

|

3,802 sq ft

|

House

38 WINDING CREEK WAY, ORMOND BEACH, FL, ...
Community: Breakaway Trails
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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