Winter Park, FL 55+ active adult communities & homes for sale - Page 52

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

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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

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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

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

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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

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

552 CARO CT, NEW SMYRNA BEACH, FL, 32168

Community: Venetian Bay

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Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

102 BOB WHITE CT 102C, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$184,500

2 beds

2 baths

1,165 sq ft

Condo

102 BOB WHITE CT 102C, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

Pelican Bay Daytona Beach

102 BOB WHITE CT C, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$184,500

2 beds

2 baths

1,165 sq ft

Condo

102 BOB WHITE CT C, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Heritage Hills

3542 FAIRWATERS CT D, CLERMONT, FL, 3471..., Clermont, FL 34711

$265,000

2 beds

2 baths

1,374 sq ft

Villa

3542 FAIRWATERS CT D, CLERMONT, FL, 3471...

Community: Heritage Hills

Pelican Bay Daytona Beach

257 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$299,000

2 beds

2 baths

1,900 sq ft

House

257 GULL DR, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

Ridgehaven

1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$394,310

4 beds

3 baths

2,190 sq ft

House

1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321...

Community: Ridgehaven

The Villages®

$460,000

3 beds

2 baths

1,836 sq ft

House

903 RAMOS DR, THE VILLAGES, FL, 32159

Community: The Villages®

Spruce Creek Country Club

13520 SE 87TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$340,000

2 beds

2 baths

1,554 sq ft

House

13520 SE 87TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Latitude Margaritaville

472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$405,000

2 beds

2 baths

1,464 sq ft

House

472 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Grand Haven

17 SANDPIPER CT, PALM COAST, FL, 32137, Palm Coast, FL 32137

$825,000

4 beds

3 baths

3,196 sq ft

House

17 SANDPIPER CT, PALM COAST, FL, 32137

Community: Grand Haven

The Villages®

$309,900

2 beds

2 baths

1,206 sq ft

House

2845 CHARITY LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

Summer Trees

109 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$270,809

2 beds

2 baths

1,259 sq ft

House

109 UNDERBRUSH TRL, PORT ORANGE, FL, 321...

Community: Summer Trees

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Four Seasons at Orlando

2074 FLORA PASS PL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$595,000

3 beds

2 baths

2,130 sq ft

House

2074 FLORA PASS PL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Twin Lakes

4921 CATALPA DR, ST CLOUD, FL, 34772, St Cloud, FL 34772

$539,900

3 beds

3 baths

2,365 sq ft

House

4921 CATALPA DR, ST CLOUD, FL, 34772

Community: Twin Lakes

Royal Harbor

3592 TROPICAL SEAS LOOP, TAVARES, FL, 32..., Tavares, FL 32778

$309,000

2 beds

2 baths

1,452 sq ft

House

3592 TROPICAL SEAS LOOP, TAVARES, FL, 32...

Community: Royal Harbor

Spruce Creek South

10339 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$194,000

2 beds

2 baths

1,008 sq ft

House

10339 SE 179TH ST, SUMMERFIELD, FL, 3449...

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347...

Community: The Villages®

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Venetian Bay

2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$315,000

4 beds

3 baths

2,070 sq ft

House

2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Spruce Creek Country Club

9330 SE 132ND PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$379,900

3 beds

3 baths

2,333 sq ft

House

9330 SE 132ND PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Plantation Bay Golf & Country Club

1047 KILKENNY LN, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$355,000

3 beds

3 baths

2,081 sq ft

Townhouse

1047 KILKENNY LN, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Twin Lakes

2600 MEADOWEDGE LOOP, ST CLOUD, FL, 3477..., St Cloud, FL 34772

$638,800

3 beds

3 baths

2,935 sq ft

House

2600 MEADOWEDGE LOOP, ST CLOUD, FL, 3477...

Community: Twin Lakes

Stonecrest

17306 SE 112TH CT RD, SUMMERFIELD, FL, 3..., Summerfield, FL 34491

$399,000

3 beds

2 baths

1,955 sq ft

House

17306 SE 112TH CT RD, SUMMERFIELD, FL, 3...

Community: Stonecrest

Lakes of Mount Dora

8860 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$399,995

3 beds

2 baths

1,671 sq ft

House

8860 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

Halifax Plantation

3078 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$465,000

3 beds

2 baths

1,914 sq ft

House

3078 SILVERMINES AVE, ORMOND BEACH, FL, ...

Community: Halifax Plantation

Solivita

1305 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$240,000

2 beds

2 baths

1,365 sq ft

House

1305 LOMBARDI CT, KISSIMMEE, FL, 34759

Community: Solivita

Pennbrooke Fairways

127 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$153,000

2 beds

2 baths

1,086 sq ft

Manufactured Home

127 WESTWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Lake Ashton

4004 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$529,900

4 beds

3 baths

2,937 sq ft

House

4004 SABLE LOOP DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Venetian Bay

3106 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$359,900

3 beds

2 baths

1,505 sq ft

House

3106 BORASSUS DR, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Want to learn more about 55+ communities in Winter Park? 55places can help!

Questions? Call us: (888) 625-4885

Arlington Ridge

26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,..., Leesburg, FL 34748

$475,000

4 beds

3 baths

2,318 sq ft

House

26812 AUGUSTA SPRINGS CIR, LEESBURG, FL,...

Community: Arlington Ridge

Solivita

915 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759

$590,000

4 beds

3 baths

3,110 sq ft

House

915 SAN RAPHAEL ST, POINCIANA, FL, 34759

Community: Solivita

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Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

Want more information about active adult communities around Winter Park?

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2,259 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 52

95 communities near Winter Park

2,259 homes near Winter Park

3 beds

2 baths

1,453 sq ft

House

3 beds

2 baths

2,312 sq ft

House

3 beds

2 baths

1,588 sq ft

House

3 beds

2 baths

2,056 sq ft

House

3 beds

2 baths

1,728 sq ft

House

2 beds

2 baths

1,165 sq ft

Condo

2 beds

2 baths

1,165 sq ft

Condo

2 beds

2 baths

1,374 sq ft

Villa

2 beds

2 baths

1,900 sq ft

House

4 beds

3 baths

2,190 sq ft

House

3 beds

2 baths

1,836 sq ft

House

2 beds

2 baths

1,554 sq ft

House

2 beds

2 baths

1,464 sq ft

House

4 beds

3 baths

3,196 sq ft

House

2 beds

2 baths

1,206 sq ft

House

2 beds

2 baths

1,259 sq ft

House

3 beds

2 baths

2,130 sq ft

House

3 beds

3 baths

2,365 sq ft

House

2 beds

2 baths

1,452 sq ft

House

2 beds