Winter Park, FL 55+ active adult communities & homes for sale - Page 23

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

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

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

The Villages®

$439,000

3 beds

2 baths

1,647 sq ft

Villa

3116 MONUMENT WAY, THE VILLAGES, FL, 321...

Community: The Villages®

Esplanade at Westview

4488 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758

$314,990

2 beds

2 baths

1,872 sq ft

House

4488 OCHOS RIOS PL, KISSIMMEE, FL, 34758

Community: Esplanade at Westview

Plantation Bay Golf & Country Club

13 BAY POINTE DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$839,000

3 beds

4 baths

3,596 sq ft

House

13 BAY POINTE DR, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Esplanade at Westview

4482 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758

$314,990

2 beds

2 baths

1,872 sq ft

House

4482 OCHOS RIOS PL, KISSIMMEE, FL, 34758

Community: Esplanade at Westview

Pelican Bay Daytona Beach

348 BOB WHITE CT 119A, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$165,000

2 beds

2 baths

1,165 sq ft

Condo

348 BOB WHITE CT 119A, DAYTONA BEACH, FL...

House

7953 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

Cindy Certified

2815 DAIRY RD, MELBOURNE, FL, 32904, Melbourne, FL 32904

$949,000

2 baths

2,301 sq ft

House

21526 KING HENRY AVE, LEESBURG, FL, 3474...

Community: Royal Highlands

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

Questions? Call us: (888) 625-4885

Cindy Certified

1656 HAMLIN RIDGE RD, MINNEOLA, FL, 3471..., Minneola, FL 34715

$589,000

4 beds

2 baths

2,103 sq ft

House

1656 HAMLIN RIDGE RD, MINNEOLA, FL, 3471...

Cindy Certified

1069 SANDPIPER LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33881

$379,999

4 beds

3 baths

2,034 sq ft

House

1069 SANDPIPER LOOP, WINTER HAVEN, FL, 3...

Cindy Certified

1150 AMBER WAVES CT, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$261,990

2 baths

1,437 sq ft

House

1987 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

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

Questions? Call us: (888) 625-4885

Stonecrest

11890 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$319,000

2 beds

2 baths

1,673 sq ft

House

11890 SE 178TH ST, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Cindy Certified

3060 KINGSMAN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$500,000

4 beds

4 baths

2,787 sq ft

House

3060 KINGSMAN TRL, ORMOND BEACH, FL, 321...

Venetian Bay

524 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168

$400,000

3 beds

3 baths

1,779 sq ft

House

524 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

Cindy Certified

3064 KINGSMAN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$439,990

4 beds

3 baths

2,361 sq ft

House

3064 KINGSMAN TRL, ORMOND BEACH, FL, 321...

The Villages®

1223 TARPON LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$265,000

2 beds

2 baths

1,545 sq ft

House

1223 TARPON LN, LADY LAKE, FL, 32159

Community: The Villages®

Cindy Certified

128 BRIARGATE LOOK, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$599,900

2 baths

1,330 sq ft

House

17461 SE 110TH CT, SUMMERFIELD, FL, 3449...

Community: Stonecrest

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

Questions? Call us: (888) 625-4885

The Villages®

$320,000

2 beds

2 baths

1,156 sq ft

Villa

2207 JETTA WAY, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$339,000

3 beds

2 baths

1,426 sq ft

House

3250 SHERFINSKI AVE, THE VILLAGES, FL, 3...

Community: The Villages®

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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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Call us: (888) 625-4885

2,698 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 23

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,647 sq ft

Villa

2 beds

2 baths

1,872 sq ft

House

3 beds

4 baths

3,596 sq ft

House

2 beds

2 baths

1,872 sq ft

House

2 beds

2 baths

1,165 sq ft

Condo

2 beds

2 baths

1,245 sq ft

Villa

2 beds

2 baths

1,503 sq ft

Villa

2 beds

2 baths

1,589 sq ft

House

3 beds

2 baths

1,927 sq ft

House

2 beds

2 baths

1,966 sq ft

House

4 beds

3 baths

2,840 sq ft

House

3 beds

3 baths

2,271 sq ft

House

3 beds

2 baths

1,572 sq ft

House

3 beds

2 baths

1,961 sq ft

House

2 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

2,301 sq ft

House

4 beds

2 baths

2,103 sq ft

House

4 beds

3 baths

2,034 sq ft

House

5 beds

2 baths

1,739 sq ft

House

2 beds