Winter Park, FL 55+ active adult communities & homes for sale - Page 16

2,702 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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 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

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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

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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

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)

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.

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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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)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

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Questions? Call us: (888) 625-4885

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 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 Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

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

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Questions? Call us: (888) 625-4885

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

1 2...3

Royal Highlands

20554 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748

$488,000

3 beds

2 baths

2,583 sq ft

House

20554 QUEEN ALEXANDRA DR, LEESBURG, FL, ...

Community: Royal Highlands

Plantation at Leesburg

4755 TARA VIEW RD, LEESBURG, FL, 34748, Leesburg, FL 34748

$320,000

2 beds

2 baths

2,035 sq ft

House

4755 TARA VIEW RD, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Cindy Certified

2380 VOLUNTEER AVE, KISSIMMEE, FL, 34744, Kissimmee, FL 34744

$411,000

3 beds

2 baths

2,068 sq ft

House

2380 VOLUNTEER AVE, KISSIMMEE, FL, 34744

Cindy Certified

2844 ARMSTRONG AVE, CLERMONT, FL, 34714, Clermont, FL 34714

$589,760

3 beds

2 baths

2,214 sq ft

House

2844 ARMSTRONG AVE, CLERMONT, FL, 34714

Latitude Margaritaville

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

$629,000

2 beds

2 baths

1,922 sq ft

House

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

Community: Latitude Margaritaville

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Questions? Call us: (888) 625-4885

Cindy Certified

5123 BUTTONSAGE DR, ST CLOUD, FL, 34772, St Cloud, FL 34772

$540,132

4 beds

3 baths

2,174 sq ft

House

5123 BUTTONSAGE DR, ST CLOUD, FL, 34772

Cindy Certified

5127 BUTTONSAGE DR, ST CLOUD, FL, 34772, St Cloud, FL 34772

$504,013

3 beds

2 baths

1,742 sq ft

House

5127 BUTTONSAGE DR, ST CLOUD, FL, 34772

Cindy Certified

105 E CHERRY PL, DELAND, FL, 32724, Deland, FL 32724

$475,000

4 beds

2 baths

2,457 sq ft

House

105 E CHERRY PL, DELAND, FL, 32724

Scottish Highlands

70 STONE HAVEN CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$269,000

2 beds

3 baths

2,146 sq ft

House

70 STONE HAVEN CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Cindy Certified

2940 AVALONIA DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$489,900

3 beds

2 baths

1,731 sq ft

Townhouse

2940 AVALONIA DR, MELBOURNE, FL, 32940

Latitude Margaritaville

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

$359,900

2 beds

2 baths

1,308 sq ft

House

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

Community: Latitude Margaritaville

Breakaway Trails

15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3..., Ormond Beach, FL 32174

$449,900

3 beds

2 baths

1,875 sq ft

House

15 CIRCLE CREEK WAY, ORMOND BEACH, FL, 3...

Community: Breakaway Trails

Venetian Bay

3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168

$489,900

4 beds

4 baths

2,338 sq ft

House

3121 PORTOFINO BLVD, NEW SMYRNA BEACH, F...

Community: Venetian Bay

Plantation Bay Golf & Country Club

13 JASMINE RUN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$325,000

2 beds

3 baths

2,087 sq ft

House

13 JASMINE RUN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Huntington at Hunter's Ridge

6 FOX LAIR CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$357,500

3 beds

2 baths

1,637 sq ft

House

6 FOX LAIR CT, ORMOND BEACH, FL, 32174

Community: Huntington at Hunter's Ridge

Plantation Bay Golf & Country Club

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

$368,000

2 beds

2 baths

1,526 sq ft

Townhouse

817 PINEWOOD DR, ORMOND BEACH, FL, 32174

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

Bridgewater at Viera

1012 GREAT BELT CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940

$635,000

3 beds

3 baths

2,325 sq ft

House

1012 GREAT BELT CIR, MELBOURNE, FL, 3294...

Community: Bridgewater at Viera

Heritage Hills

3641 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711

$277,000

2 beds

2 baths

1,374 sq ft

Villa

3641 SOLANA CIR B, CLERMONT, FL, 34711

Community: Heritage Hills

Palms at Serenoa

17762 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714

$459,000

4 beds

2 baths

2,034 sq ft

House

17762 BLAZING STAR CIR, CLERMONT, FL, 34...

Community: Palms at Serenoa

Cindy Certified

151 PERGOLA PL, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$299,000

3 beds

2 baths

1,537 sq ft

House

151 PERGOLA PL, ORMOND BEACH, FL, 32174

Cindy Certified

765 GREENWAY BLVD, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$275,990

4 beds

2 baths

1,498 sq ft

House

765 GREENWAY BLVD, LAKE WALES, FL, 33859

Legacy of Leesburg

5615 CELEBRATION WAY, LEESBURG, FL, 3474..., Leesburg, FL 34748

$350,000

3 beds

2 baths

1,766 sq ft

House

5615 CELEBRATION WAY, LEESBURG, FL, 3474...

Community: Legacy of Leesburg

The Villages®

$285,000

2 beds

2 baths

1,564 sq ft

House

710 CORTEZ AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Breakaway Trails

8 BLACK WATER WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$455,000

3 beds

2 baths

1,705 sq ft

House

8 BLACK WATER WAY, ORMOND BEACH, FL, 321...

Community: Breakaway Trails

Cindy Certified

761 GREENWAY BLVD, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$276,900

5 beds

2 baths

1,708 sq ft

House

761 GREENWAY BLVD, LAKE WALES, FL, 33859

The Villages®

$449,900

3 beds

2 baths

1,492 sq ft

Villa

3501 CONNOR WAY, THE VILLAGES, FL, 32163

Community: The Villages®

Stonecrest

11932 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$330,000

3 beds

3 baths

2,118 sq ft

House

11932 SE 179TH ST, SUMMERFIELD, FL, 3449...

Community: Stonecrest

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

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The Villages®

$520,000

3 beds

2 baths

1,535 sq ft

House

1427 GAYLE MILL DR, THE VILLAGES, FL, 32...

Community: The Villages®

Twin Lakes

2495 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772

$330,000

2 beds

2 baths

1,464 sq ft

Villa

2495 DATURA LOOP, ST CLOUD, FL, 34772

Community: Twin Lakes

The Timbers at Everlands

1443 BLESSED ISLES DR, PALM BAY, FL, 329..., Palm Bay, FL 32907

$530,000

4 beds

3 baths

2,640 sq ft

House

1443 BLESSED ISLES DR, PALM BAY, FL, 329...

Community: The Timbers at Everlands

Cindy Certified

3830 SALT MARSH CIR, WEST MELBOURNE, FL,..., West Melbourne, FL 32904

$580,000

4 beds

4 baths

2,800 sq ft

House

3830 SALT MARSH CIR, WEST MELBOURNE, FL,...

Arlington Ridge

$305,000

2 beds

2 baths

1,649 sq ft

House

3601 ARLINGTON RIDGE BLVD, LEESBURG, FL,...

Community: Arlington Ridge

Pelican Bay Daytona Beach

725 SEA DUCK DR, DAYTONA BEACH, FL, 3211..., Daytona Beach, FL 32119

$565,000

4 beds

3 baths

2,673 sq ft

House

725 SEA DUCK DR, DAYTONA BEACH, FL, 3211...

Community: Pelican Bay Daytona Beach

Lake Henry Estates

472 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844

$240,000

2 beds

2 baths

1,117 sq ft

House

472 SWEETWATER WAY, HAINES CITY, FL, 338...

Community: Lake Henry Estates

The Villages®

$254,900

2 beds

2 baths

1,100 sq ft

House

897 LIVINGSTON LOOP, THE VILLAGES, FL, 3...

Community: The Villages®

Cindy Certified

1258 TURTLE ISLAND RD, LADY LAKE, FL, 32..., Lady Lake, FL 32159

$274,990

3 beds

2 baths

1,509 sq ft

Villa

1258 TURTLE ISLAND RD, LADY LAKE, FL, 32...

Cindy Certified

384 BALI ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$266,990

3 beds

2 baths

1,509 sq ft

Villa

384 BALI ST, LADY LAKE, FL, 32159

Cindy Certified

344 BALI ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$259,990

3 beds

2 baths

1,509 sq ft

Villa

344 BALI ST, LADY LAKE, FL, 32159

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

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Cindy Certified

1079 OCEAN LODGE RD, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$331,990

3 beds

2 baths

2,021 sq ft

House

1079 OCEAN LODGE RD, LADY LAKE, FL, 3215...

Cindy Certified

1039 OCEAN LODGE RD, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$371,990

3 beds

2 baths

2,384 sq ft

House

1039 OCEAN LODGE RD, LADY LAKE, FL, 3215...

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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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2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 16

98 communities near Winter Park

2,702 homes near Winter Park

3 beds

2 baths

2,583 sq ft

House

2 beds

2 baths

2,035 sq ft

House

3 beds

2 baths

2,068 sq ft

House

3 beds

2 baths

2,214 sq ft

House

2 beds

2 baths

1,922 sq ft

House

4 beds

3 baths

2,174 sq ft

House

3 beds

2 baths

1,742 sq ft

House

4 beds

2 baths

2,457 sq ft

House

2 beds

3 baths

2,146 sq ft

House

3 beds

2 baths

1,731 sq ft

Townhouse

2 beds

2 baths

1,308 sq ft

House

3 beds

2 baths

1,875 sq ft

House

4 beds

4 baths

2,338 sq ft

House

2 beds

3 baths

2,087 sq ft

House

3 beds

2 baths

1,637 sq ft

House

2 beds

2 baths

1,526 sq ft

Townhouse

3 beds

3 baths

2,325 sq ft

House

2 beds

2 baths

1,374 sq ft

Villa

4 beds

2 baths

2,034 sq ft

House

3 beds