Winter Park, FL 55+ active adult communities & homes for sale - Page 28

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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Questions? Call us: (888) 625-4885

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

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

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

896 BARCELONA DR, POINCIANA, FL, 34759

Community: Solivita

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

Questions? Call us: (888) 625-4885

Lakes of Mount Dora

3945 KENNEBUNK LOOP, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$403,140

3 beds

2 baths

1,614 sq ft

House

3945 KENNEBUNK LOOP, MOUNT DORA, FL, 327...

Community: Lakes of Mount Dora

The Country Club of Mount Dora

7004 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$450,000

2 beds

2 baths

2,205 sq ft

House

7004 PINE HOLLOW DR, MOUNT DORA, FL, 327...

Community: The Country Club of Mount Dora

Venetian Bay

424 LUNA BELLA LN 332, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$270,000

3 beds

2 baths

1,659 sq ft

Condo

424 LUNA BELLA LN 332, NEW SMYRNA BEACH,...

Community: Venetian Bay

The Villages®

208 ARAGON LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$225,000

2 beds

2 baths

1,383 sq ft

House

208 ARAGON LN, LADY LAKE, FL, 32159

Community: The Villages®

Pennbrooke Fairways

815 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748

$259,900

3 beds

2 baths

1,538 sq ft

House

815 GRAND VISTA TRL, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Spruce Creek Country Club

9215 SE 118TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$324,999

3 beds

2 baths

1,720 sq ft

House

9215 SE 118TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Del Webb Orlando

442 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$424,900

3 beds

3 baths

2,581 sq ft

House

442 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$699,000

3 beds

2 baths

2,092 sq ft

House

1209 BARCELONA DR, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$349,000

3 beds

2 baths

1,397 sq ft

House

1695 VINEWOOD AVE, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$425,000

3 beds

2 baths

1,887 sq ft

House

490 LITTLE RIVER PATH, THE VILLAGES, FL,...

Community: The Villages®

The Villages®

$480,000

3 beds

2 baths

1,726 sq ft

Villa

583 ARTEAGA WAY, THE VILLAGES, FL, 32162

House

13361 SE 101ST AVE, BELLEVIEW, FL, 34420

Spruce Creek Country Club

14179 SE 88TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$338,800

2 beds

2 baths

1,699 sq ft

House

14179 SE 88TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Grand Haven

4 CROSSBAR WAY, PALM COAST, FL, 32137, Palm Coast, FL 32137

$339,000

2 beds

2 baths

1,637 sq ft

House

4 CROSSBAR WAY, PALM COAST, FL, 32137

Community: Grand Haven

The Timbers at Everlands

1251 MIRAFLORES TRL, PALM BAY, FL, 32907, Palm Bay, FL 32907

$249,000

2 beds

2 baths

1,310 sq ft

Townhouse

1251 MIRAFLORES TRL, PALM BAY, FL, 32907

Community: The Timbers at Everlands

Royal Highlands

5704 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748

$259,900

2 beds

2 baths

1,245 sq ft

House

5704 KING JAMES AVE, LEESBURG, FL, 34748

House

11137 SE 174TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Halifax Plantation

1309 MUNSTER CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$425,000

3 beds

2 baths

2,120 sq ft

House

1309 MUNSTER CIR, ORMOND BEACH, FL, 3217...

Community: Halifax Plantation

Cindy Certified

7068 LANIER FALLS RD, DELAND, FL, 32724, Deland, FL 32724

$325,000

2 baths

1,415 sq ft

House

30539 LIPIZZAN TER, MOUNT DORA, FL, 3275...

Community: Sullivan Ranch

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

Questions? Call us: (888) 625-4885

Cindy Certified

2524 RAPOLLO DR, KISSIMMEE, FL, 34741, Kissimmee, FL 34741

$414,990

3 beds

2 baths

1,706 sq ft

House

2524 RAPOLLO DR, KISSIMMEE, FL, 34741

The Country Club of Mount Dora

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$659,900

3 beds

3 baths

2,509 sq ft

House

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327...

Community: The Country Club of Mount Dora

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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 28

98 communities near Winter Park

2,698 homes near Winter Park

2 beds

2 baths

1,977 sq ft

House

3 beds

2 baths

1,787 sq ft

House

2 beds

2 baths

1,143 sq ft

Villa

3 beds

2 baths

2,095 sq ft

House

2 beds

3 baths

1,935 sq ft

House

3 beds

2 baths

1,614 sq ft

House

2 beds

2 baths

2,205 sq ft

House

3 beds

2 baths

1,659 sq ft

Condo

2 beds

2 baths

1,383 sq ft

House

3 beds

2 baths

1,538 sq ft

House

3 beds

2 baths

1,720 sq ft

House

3 beds

3 baths

2,581 sq ft

House

3 beds

2 baths

2,092 sq ft

House

3 beds

2 baths

1,397 sq ft

House

3 beds

2 baths

1,887 sq ft

House

3 beds

2 baths

1,726 sq ft

Villa

3 beds

2 baths

2,192 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

2,065 sq ft

House

2 beds