Winter Park, FL 55+ active adult communities & homes for sale - Page 57

2,698 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

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

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 (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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)

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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 (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

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 (8 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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 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

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

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

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

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

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

Questions? Call us: (888) 625-4885

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

27210 STONEY BROOK DR, LEESBURG, FL, 347...

Community: Legacy of Leesburg

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Questions? Call us: (888) 625-4885

Solivita

477 VILLA PARK RD, POINCIANA, FL, 34759, Poinciana, FL 34759

$450,000

3 beds

3 baths

2,345 sq ft

House

477 VILLA PARK RD, POINCIANA, FL, 34759

Community: Solivita

Plantation at Leesburg

5712 SUMMERBROOKE CT, LEESBURG, FL, 3474..., Leesburg, FL 34748

$525,000

3 beds

3 baths

2,961 sq ft

House

5712 SUMMERBROOKE CT, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

The Country Club of Mount Dora

1741 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$1,280,000

5 beds

5 baths

5,573 sq ft

House

1741 EDGEWATER DR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Arlington Ridge

26921 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$199,000

2 beds

2 baths

1,254 sq ft

Villa

26921 WHITE PLAINS WAY, LEESBURG, FL, 34...

108 VIA ROMA, ORMOND BEACH, FL, 32174

The Villages®

$339,900

3 beds

2 baths

1,392 sq ft

House

17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

The Villages®

$275,000

2 beds

2 baths

1,156 sq ft

Villa

324 EMMALEE PL, THE VILLAGES, FL, 32162

Community: The Villages®

Grand Haven

82 LAGARE ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$650,000

3 beds

4 baths

2,792 sq ft

House

82 LAGARE ST, PALM COAST, FL, 32137

Community: Grand Haven

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

Questions? Call us: (888) 625-4885

The Country Club of Mount Dora

1760 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$724,500

4 beds

3 baths

3,141 sq ft

House

1760 EDGEWATER DR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Pelican Bay Daytona Beach

770 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$795,000

5 beds

4 baths

3,165 sq ft

House

770 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Arlington Ridge

4307 BENT CREEK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$369,900

3 beds

2 baths

1,683 sq ft

House

4307 BENT CREEK LN, LEESBURG, FL, 34748

Community: Arlington Ridge

Kings Ridge

3871 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711

$289,900

2 beds

2 baths

1,327 sq ft

House

3871 EVERSHOLT ST, CLERMONT, FL, 34711

Community: Kings Ridge

Traditions at Lake Ruby

3890 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$395,000

4 beds

3 baths

2,322 sq ft

House

3890 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

The Villages®

$449,900

3 beds

2 baths

1,939 sq ft

House

2033 SALMON WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Stonecrest

17083 SE 115TH TERRACE RD, SUMMERFIELD, ..., Summerfield, FL 34491

$289,900

3 beds

2 baths

1,724 sq ft

House

17083 SE 115TH TERRACE RD, SUMMERFIELD, ...

Community: Stonecrest

Plantation at Leesburg

3719 BELLE ROSE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$445,000

3 beds

3 baths

2,571 sq ft

House

3719 BELLE ROSE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Cindy Certified

1823 SUMMER SERENITY DR, KISSIMMEE, FL, ..., Kissimmee, FL 34744

$375,000

3 beds

3 baths

1,900 sq ft

House

1823 SUMMER SERENITY DR, KISSIMMEE, FL, ...

Indian River Colony Club

1551 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940

$269,000

3 beds

2 baths

1,816 sq ft

House

1551 INDEPENDENCE AVE, MELBOURNE, FL, 32...

Community: Indian River Colony Club

Cindy Certified

3055 ISOLA BELLA BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$870,000

4 beds

3 baths

2,700 sq ft

House

3055 ISOLA BELLA BLVD, MOUNT DORA, FL, 3...

House

6045 MEDITATION DR, CLERMONT, FL, 34714

Breakaway Trails

8 FOX CLIFF WAY, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$469,000

4 beds

3 baths

2,566 sq ft

House

8 FOX CLIFF WAY, ORMOND BEACH, FL, 32174

Community: Breakaway Trails

The Villages®

1314 SANTA ROSA CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$400,000

2 beds

2 baths

1,302 sq ft

Villa

1314 SANTA ROSA CT, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$361,000

3 beds

2 baths

1,539 sq ft

House

4151 BALCHARAN TER, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

23104 SANDALWOOD DR 104, WILDWOOD, FL, 3..., Wildwood, FL 34785

$125,000

2 beds

2 baths

1,110 sq ft

Condo

23104 SANDALWOOD DR 104, WILDWOOD, FL, 3...

Community: The Villages®

Plantation Bay Golf & Country Club

438 LONG COVE RD, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$500,000

3 beds

2 baths

1,820 sq ft

House

438 LONG COVE RD, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

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

Questions? Call us: (888) 625-4885

Cindy Certified

5208 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762

$364,900

4 beds

3 baths

2,291 sq ft

House

5208 MEADOW SONG DR, OKAHUMPKA, FL, 3476...

Heritage Landings

2658 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811

$320,000

4 beds

2 baths

1,867 sq ft

House

2658 GRANDBURY GROVE RD, LAKELAND, FL, 3...

Community: Heritage Landings

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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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2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 57

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

3 baths

2,565 sq ft

House

2 beds

2 baths

1,513 sq ft

Manufactured Home

3 beds

2 baths

2,199 sq ft

House

3 beds

2 baths

2,103 sq ft

House

3 beds

2 baths

1,601 sq ft

House

3 beds

3 baths

2,345 sq ft

House

3 beds

3 baths

2,961 sq ft

House

5 beds

5 baths

5,573 sq ft

House

2 beds

2 baths

1,254 sq ft

Villa

3 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

2,312 sq ft

House

3 beds

2 baths

2,598 sq ft

House

3 beds

2 baths

2,092 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

4 baths

2,792 sq ft

House

4 beds

3 baths

3,141 sq ft

House

5 beds

4 baths

3,165 sq ft

House

3 beds

2 baths

1,683 sq ft

House

2 beds