Winter Park, FL 55+ active adult communities & homes for sale - Page 42

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

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

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

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

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

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Questions? Call us: (888) 625-4885

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Del Webb at Viera

$400ks - $1Ms

Del Webb at Viera, Melbourne, FL

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

Plantation Bay Golf & Country Club

908 WOODSTREAM LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$339,000

3 beds

2 baths

1,627 sq ft

House

908 WOODSTREAM LN, ORMOND BEACH, FL, 321...

Community: Plantation Bay Golf & Country Club

The Villages®

13718 COUNTY RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$285,000

5 beds

3 baths

2,176 sq ft

Manufactured Home

13718 COUNTY RD, LADY LAKE, FL, 32159

Community: The Villages®

Cindy Certified

2173 RAGLAN CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$379,000

3 beds

2 baths

1,712 sq ft

House

2173 RAGLAN CIR, ORMOND BEACH, FL, 32174

Solivita

278 ANASTASIA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$223,000

2 beds

2 baths

1,317 sq ft

Halfplex

278 ANASTASIA DR, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

5217 CAMBRIDGE CT, WILDWOOD, FL, 34785, Wildwood, FL 34785

$170,000

2 beds

2 baths

1,352 sq ft

Manufactured Home

5217 CAMBRIDGE CT, WILDWOOD, FL, 34785

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Scottish Highlands

1117 BEN HOPE DR, LEESBURG, FL, 34788, Leesburg, FL 34788

$315,000

2 beds

3 baths

2,280 sq ft

House

1117 BEN HOPE DR, LEESBURG, FL, 34788

Community: Scottish Highlands

The Villages®

1012 DIEGO CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$414,900

3 beds

2 baths

1,976 sq ft

House

1012 DIEGO CT, LADY LAKE, FL, 32159

Community: The Villages®

Cindy Certified

4065 NEGAL CIR, MELBOURNE, FL, 32901, Melbourne, FL 32901

$570,000

4 beds

2 baths

2,191 sq ft

House

4065 NEGAL CIR, MELBOURNE, FL, 32901

Colonnades

4860 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$213,000

2 beds

2 baths

1,350 sq ft

House

4860 GOLDENVIEW LN, LAKELAND, FL, 33811

Community: Colonnades

Cindy Certified

2991 CASTERTON DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$535,000

3 baths

2,555 sq ft

House

3851 MANOR OAKS CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

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Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

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

$850,000

5 beds

5 baths

3,523 sq ft

House

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

Community: Pelican Bay Daytona Beach

Cindy Certified

1218 SOLEWAY AVE, PALM BAY, FL, 32907, Palm Bay, FL 32907

$362,175

2 baths

1,600 sq ft

House

25 PRINCE MICHAEL LN, PALM COAST, FL, 32...

Grand Haven

63 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$1,560,000

3 beds

4 baths

3,296 sq ft

House

63 FRONT ST, PALM COAST, FL, 32137

Community: Grand Haven

Pelican Bay Daytona Beach

176 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$245,000

2 beds

2 beds

2 baths

1,565 sq ft

House

2361 PRAIRIE DUNES, CLERMONT, FL, 34711

Community: Summit Greens

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

Questions? Call us: (888) 625-4885

Halifax Plantation

3412 REXFORD CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$585,000

4 beds

3 baths

2,250 sq ft

House

3412 REXFORD CIR, ORMOND BEACH, FL, 3217...

Community: Halifax Plantation

Indian River Colony Club

1649 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940

$349,000

3 beds

2 baths

2,026 sq ft

House

1649 INDEPENDENCE AVE, MELBOURNE, FL, 32...

Community: Indian River Colony Club

Royal Highlands

4646 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$289,900

3 beds

2 baths

2,020 sq ft

House

4646 INVERNESS DR, LEESBURG, FL, 34748

Community: Royal Highlands

Cindy Certified

1932 CHICKASAW BLVD, DAVENPORT, FL, 3383..., Davenport, FL 33837

$379,900

4 beds

2 baths

1,928 sq ft

House

1932 CHICKASAW BLVD, DAVENPORT, FL, 3383...

The Villages®

$545,000

3 beds

$258,500

3 beds

2 baths

1,436 sq ft

Townhouse

1887 CERULEAN DR, PALM BAY, FL, 32907

Community: The Timbers at Everlands

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

Questions? Call us: (888) 625-4885

Twin Lakes

5038 DANCY LN, ST CLOUD, FL, 34772, St Cloud, FL 34772

$424,990

2 beds

2 baths

1,707 sq ft

House

5038 DANCY LN, ST CLOUD, FL, 34772

Community: Twin Lakes

The Timbers at Everlands

1916 CERULEAN DR, PALM BAY, FL, 32907, Palm Bay, FL 32907

$250,000

2 beds

2 baths

1,308 sq ft

House

1916 CERULEAN DR, PALM BAY, FL, 32907

Community: The Timbers at Everlands

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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 42

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,627 sq ft

House

5 beds

3 baths

2,176 sq ft

Manufactured Home

3 beds

2 baths

1,712 sq ft

House

2 beds

2 baths

1,317 sq ft

Halfplex

2 beds

2 baths

1,352 sq ft

Manufactured Home

2 beds

3 baths

2,280 sq ft

House

3 beds

2 baths

1,976 sq ft

House

4 beds

2 baths

2,191 sq ft

House

2 beds

2 baths

1,350 sq ft

House

3 beds

3 baths

1,938 sq ft

House

3 beds

2 baths

2,886 sq ft

House

3 beds

3 baths

2,777 sq ft

House

4 beds

2 baths

2,164 sq ft

House

3 beds

2 baths

1,842 sq ft

House

2 beds

2 baths

1,806 sq ft

House

3 beds

3 baths

2,555 sq ft

House

5 beds

5 baths

3,523 sq ft

House

4 beds

2 baths

1,820 sq ft

House

2 beds

2 baths

1,528 sq ft

House

3 beds