Winter Park, FL 55+ active adult communities & homes for sale - Page 58

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

1 2...3

Lakes at Laurel Highlands

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: Lakes at Laurel Highlands

Grand Haven

32 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$389,000

3 beds

2 baths

1,594 sq ft

House

32 SHINNECOCK DR, PALM COAST, FL, 32137

Community: Grand Haven

Cindy Certified

1574 HEARTWELLVILLE ST, PALM BAY, FL, 32..., Palm Bay, FL 32907

$320,000

4 beds

2 baths

1,830 sq ft

House

1574 HEARTWELLVILLE ST, PALM BAY, FL, 32...

Solivita

1317 LOMBARDI CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$259,000

2 beds

2 baths

1,363 sq ft

House

1317 LOMBARDI CT, KISSIMMEE, FL, 34759

Community: Solivita

Venetian Bay

3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$720,000

3 beds

2 baths

1,918 sq ft

House

3338 BELLINO BLVD, NEW SMYRNA BEACH, FL,...

House

260 JACKSON LOOP, DELAND, FL, 32724

Latitude Margaritaville

218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F..., Daytona Beach, FL 32124

$384,900

2 beds

2 baths

1,303 sq ft

Villa

218 OCEAN HAMMOCK LOOP, DAYTONA BEACH, F...

Community: Latitude Margaritaville

The Villages®

$325,000

3 beds

2 baths

1,392 sq ft

House

1609 BLOSSOM TER, THE VILLAGES, FL, 3216...

118 HURST CT, DELAND, FL, 32724

Solivita

130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$364,000

3 beds

2 baths

2,141 sq ft

House

130 PRIMA DR, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$349,900

3 beds

2 baths

1,527 sq ft

House

1521 HOLLYBERRY PL, THE VILLAGES, FL, 32...

Community: The Villages®

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Questions? Call us: (888) 625-4885

The Villages®

8331 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$283,000

4 beds

2 baths

2,240 sq ft

Manufactured Home

8331 COUNTY RD 109, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$377,500

3 beds

2 baths

1,527 sq ft

House

3135 BURNS DR, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek South

17990 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$299,900

3 beds

2 baths

1,870 sq ft

House

17990 SE 100TH TER, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

Colonnades

$219,000

2 beds

2 baths

1,317 sq ft

House

1690 COLONNADES CIR, LAKELAND, FL, 33811

Community: Colonnades

Cindy Certified

588 AUTUMN ASH DR, CLERMONT, FL, 34715, Clermont, FL 34715

$585,000

4 beds

3 baths

2,827 sq ft

7809 SE 171ST HARLESTON ST, THE VILLAGES...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Plantation at Leesburg

4960 HERON RUN CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$234,900

2 beds

2 baths

1,289 sq ft

House

4960 HERON RUN CIR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Cindy Certified

1208 TURTLE ISLAND RD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$299,000

3 beds

2 baths

1,509 sq ft

Halfplex

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

Questions? Call us: (888) 625-4885

Cindy Certified

142 TRANQUIL MIRROR LAKE CT 18, CLERMONT..., Clermont, FL 34711

$1,492,545

4 beds

3 baths

2,974 sq ft

House

142 TRANQUIL MIRROR LAKE CT 18, CLERMONT...

Plantation at Leesburg

25312 GREEN HERON DR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$220,000

2 beds

2 baths

1,289 sq ft

House

25312 GREEN HERON DR, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

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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.

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2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 58

98 communities near Winter Park

2,698 homes near Winter Park

4 beds

2 baths

1,867 sq ft

House

3 beds

2 baths

1,594 sq ft

House

4 beds

2 baths

1,830 sq ft

House

2 beds

2 baths

1,363 sq ft

House

3 beds

2 baths

1,918 sq ft

House

3 beds

2 baths

1,483 sq ft

House

2 beds

2 baths

918 sq ft

Villa

3 beds

2 baths

2,090 sq ft

House

2 beds

2 baths

1,303 sq ft

Villa

3 beds

2 baths

1,392 sq ft

House

4 beds

3 baths

2,499 sq ft

House

3 beds

3 baths

2,270 sq ft

House

2 beds

2 baths

1,528 sq ft

House

3 beds

2 baths

1,318 sq ft

House

3 beds

2 baths

2,141 sq ft

House

3 beds

2 baths

1,527 sq ft

House

4 beds

2 baths

2,240 sq ft

Manufactured Home

3 beds

2 baths

1,527 sq ft

House

3 beds

2 baths

1,870 sq ft

House

2 beds