Winter Park, FL 55+ active adult communities & homes for sale - Page 66

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

Cindy Certified

2170 RAGLAN CIR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$399,999

3 beds

2 baths

1,548 sq ft

House

2170 RAGLAN CIR, ORMOND BEACH, FL, 32174

The Villages®

5371 WARM SPRINGS AVE, WILDWOOD, FL, 347..., Wildwood, FL 34785

$275,000

2 beds

1 baths

696 sq ft

House

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

Community: The Villages®

Plantation Bay Golf & Country Club

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

$340,000

3 beds

3 baths

2,081 sq ft

Townhouse

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

Community: Plantation Bay Golf & Country Club

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

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

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

Questions? Call us: (888) 625-4885

The Villages®

$399,900

3 beds

2 baths

2,002 sq ft

House

16946 SE 93RD CUTHBERT CIR, THE VILLAGES...

Community: The Villages®

Royal Highlands

4528 GLEN COE ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$380,500

2 beds

2 baths

2,200 sq ft

House

4528 GLEN COE ST, LEESBURG, FL, 34748

Community: Royal Highlands

Highland Fairways

2137 GRAND CYPRESS DR, LAKELAND, FL, 338..., Lakeland, FL 33810

$259,900

3 beds

2 baths

1,808 sq ft

House

2137 GRAND CYPRESS DR, LAKELAND, FL, 338...

Community: Highland Fairways

Plantation at Leesburg

3606 MULBERRY GROVE LOOP, LEESBURG, FL, ..., Leesburg, FL 34748

$440,000

3 beds

3 baths

2,664 sq ft

House

3606 MULBERRY GROVE LOOP, LEESBURG, FL, ...

Community: Plantation at Leesburg

The Villages®

$449,999

2 beds

2 baths

1,880 sq ft

House

939 KOLLER CT, THE VILLAGES, FL, 32163

Community: The Villages®

Pennbrooke Fairways

615 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$79,900

1 beds

1 baths

490 sq ft

Manufactured Home

615 COTTAGE PARK LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

712 JASON DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$198,000

2 beds

2 baths

1,292 sq ft

Manufactured Home

712 JASON DR, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$299,900

3 beds

2 baths

1,375 sq ft

House

870 HENDERSON LN, THE VILLAGES, FL, 3216...

Community: The Villages®

Plantation Bay Golf & Country Club

875 PINEWOOD DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$370,000

3 beds

3 baths

2,101 sq ft

Townhouse

875 PINEWOOD DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Summer Trees

130 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$279,950

3 beds

2 baths

1,363 sq ft

House

130 CYPRESS POND RD, PORT ORANGE, FL, 32...

Community: Summer Trees

Breakaway Trails

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$549,900

4 beds

3 baths

3,261 sq ft

House

94 SHADOWCREEK WAY, ORMOND BEACH, FL, 32...

Community: Breakaway Trails

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

Questions? Call us: (888) 625-4885

The Villages®

1224 DUSTIN DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$239,900

2 beds

2 baths

912 sq ft

Manufactured Home

1224 DUSTIN DR, LADY LAKE, FL, 32159

Community: The Villages®

Cindy Certified

855 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$299,000

4 beds

3 baths

1,988 sq ft

House

855 SUNSHOWER DR, LADY LAKE, FL, 32159

Cindy Certified

851 SUNSHOWER DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$294,000

4 beds

2 baths

1,840 sq ft

House

851 SUNSHOWER DR, LADY LAKE, FL, 32159

Spruce Creek Country Club

9244 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$329,000

2 beds

2 baths

2,130 sq ft

House

9244 SE 128TH ST, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Colonnades

4816 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$182,000

2 beds

2 baths

1,066 sq ft

Manufactured Home

4816 GOLDENVIEW LN, LAKELAND, FL, 33811

Community: Colonnades

Cindy Certified

3104 DAMPIER DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$633,930

2 baths

1,328 sq ft

House

25119 CRANES ROOST CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

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

Questions? Call us: (888) 625-4885

Cindy Certified

2866 SUPERMARINE RD, TAVARES, FL, 32778, Tavares, FL 32778

$349,990

4 beds

2 baths

1,758 sq ft

House

2866 SUPERMARINE RD, TAVARES, FL, 32778

Cindy Certified

27 PRINCE KAAREL LN, PALM COAST, FL, 321..., Palm Coast, FL 32164

$353,900

3 beds

2 baths

1,693 sq ft

House

27 PRINCE KAAREL LN, PALM COAST, FL, 321...

Cindy Certified

40 PRESIDENTIAL LN, PALM COAST, FL, 3216..., Palm Coast, FL 32164

$338,900

3 baths

2,343 sq ft

House

313 SANTA BARBARA LN, KISSIMMEE, FL, 347...

Community: Solivita

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

Questions? Call us: (888) 625-4885

Carmel Condominium

1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ..., Rockledge, FL 32955

$179,900

2 beds

2 baths

1,008 sq ft

Condo

1420 HUNTINGTON LN 2105, ROCKLEDGE, FL, ...

Community: Carmel Condominium

The Timbers at Everlands

853 ANTIBES CT, PALM BAY, FL, 32907, Palm Bay, FL 32907

$360,000

3 beds

3 baths

2,182 sq ft

House

853 ANTIBES CT, 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.

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 66

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,548 sq ft

House

2 beds

1 baths

696 sq ft

House

3 beds

3 baths

2,081 sq ft

Townhouse

3 beds

2 baths

1,955 sq ft

House

2 beds

2 baths

1,365 sq ft

House

3 beds

2 baths

2,002 sq ft

House

2 beds

2 baths

2,200 sq ft

House

3 beds

2 baths

1,808 sq ft

House

3 beds

3 baths

2,664 sq ft

House

2 beds

2 baths

1,880 sq ft

House

1 beds

1 baths

490 sq ft

Manufactured Home

2 beds

2 baths

1,292 sq ft

Manufactured Home

3 beds

2 baths

1,375 sq ft

House

3 beds

3 baths

2,101 sq ft

Townhouse

3 beds

2 baths

1,363 sq ft

House

4 beds

3 baths

3,261 sq ft

House

2 beds

2 baths

912 sq ft

Manufactured Home

4 beds

3 baths

1,988 sq ft

House

4 beds

2 baths

1,840 sq ft

House

2 beds