Winter Park, FL 55+ active adult communities & homes for sale - Page 27

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

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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

4590 BROOKSHIRE PL, LAKE WALES, FL, 3389..., Lake Wales, FL 33898

$369,000

2 baths

1,504 sq ft

House

8310 PONCE DE LEON ST, LAKELAND, FL, 338...

Heritage Hills

2823 MAYPORT ST, CLERMONT, FL, 34711, Clermont, FL 34711

$495,000

3 beds

3 baths

2,573 sq ft

House

2823 MAYPORT ST, CLERMONT, FL, 34711

Community: Heritage Hills

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Questions? Call us: (888) 625-4885

Tohoqua Reserve

2756 SUMMER RETREAT LN, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$310,000

3 beds

2 baths

1,559 sq ft

Villa

2756 SUMMER RETREAT LN, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

Spruce Creek Country Club

13740 SE 86TH TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$239,000

2 beds

2 baths

1,736 sq ft

House

13740 SE 86TH TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Del Webb Oasis

15000 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787

$849,990

3 beds

4 baths

2,861 sq ft

House

15000 CANOPY COVER DR, WINTER GARDEN, FL...

Community: Del Webb Oasis

Del Webb Orlando

672 CORDOBA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$369,900

2 beds

2 baths

1,956 sq ft

House

672 CORDOBA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Harbor Hills Country Club

39407 TREELINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$589,000

4 beds

4 baths

2,502 sq ft

House

39407 TREELINE DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Royal Highlands

5925 BAG PIPE PL, LEESBURG, FL, 34748, Leesburg, FL 34748

$319,000

3 beds

2 baths

2,251 sq ft

House

5925 BAG PIPE PL, LEESBURG, FL, 34748

Community: Royal Highlands

Spruce Creek South

10337 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$225,000

3 beds

2 baths

1,526 sq ft

House

10337 SE 176TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Plantation at Leesburg

5047 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$185,000

2 beds

2 baths

1,296 sq ft

Manufactured Home

5047 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Harbor Hills Country Club

39905 BAYVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$279,900

2 beds

2 baths

1,598 sq ft

Villa

39905 BAYVIEW DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

The Villages®

$600,000

3 beds

2 baths

2,035 sq ft

House

1451 LUCKETT CT, THE VILLAGES, FL, 32163

Community: The Villages®

Grand Haven

54 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$479,000

3 beds

2 baths

1,506 sq ft

House

54 SHINNECOCK DR, PALM COAST, FL, 32137

Community: Grand Haven

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

Questions? Call us: (888) 625-4885

The Country Club of Mount Dora

8034 ARCADIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$365,000

2 beds

2 baths

1,603 sq ft

House

8034 ARCADIAN CT, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Stonecrest

17399 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491

$319,000

3 beds

2 baths

1,751 sq ft

House

17399 SE 116TH COURT RD, SUMMERFIELD, FL...

Community: Stonecrest

Gatherings of Lake Nona

7545 LAUREATE BLVD 7404, ORLANDO, FL, 32..., Orlando, FL 32827

$414,990

2 beds

2 baths

1,486 sq ft

Condo

7545 LAUREATE BLVD 7404, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Gatherings of Lake Nona

7545 LAUREATE BLVD 7408, ORLANDO, FL, 32..., Orlando, FL 32827

$389,990

2 beds

2 baths

1,368 sq ft

Condo

7545 LAUREATE BLVD 7408, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Grand Haven

206 WILLOW OAK WAY, PALM COAST, FL, 3213..., Palm Coast, FL 32137

$1,299,000

3 beds

3 baths

3,025 sq ft

House

206 WILLOW OAK WAY, PALM COAST, FL, 3213...

Community: Grand Haven

Cindy Certified

30273 RUSTIC MILL ST, MOUNT DORA, FL, 32..., Mount Dora, FL 32757

$475,390

3 beds

3 baths

2,035 sq ft

Villa

2952 KRAMER CT, THE VILLAGES, FL, 32163

Community: The Villages®

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Spruce Creek Country Club

11728 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$279,300

2 beds

2 baths

1,575 sq ft

House

11728 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

The Villages®

$259,000

2 beds

1 baths

1,040 sq ft

House

1023 AVALON AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Esplanade at Highland Ranch

1197 ESPERANZA RIDGE RD, CLERMONT, FL, 3..., Clermont, FL 34715

$620,000

3 beds

3 baths

2,333 sq ft

House

1197 ESPERANZA RIDGE RD, CLERMONT, FL, 3...

Community: Esplanade at Highland Ranch

Pelican Bay Daytona Beach

150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$224,900

3 beds

2 baths

1,365 sq ft

Condo

150 BLUE HERON DR B, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

The Villages®

$539,900

3 beds

2 baths

1,918 sq ft

House

575 RANDALL RD, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$710,000

3 beds

3 baths

1,945 sq ft

House

1078 MAYNARD PATH, THE VILLAGES, FL, 321...

Community: The Villages®

Plantation Bay Golf & Country Club

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

$633,000

5 beds

4 baths

4,274 sq ft

House

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

Community: Plantation Bay Golf & Country Club

The Villages®

$349,900

3 beds

2 baths

1,392 sq ft

House

1276 NORTHBROOK PL, THE VILLAGES, FL, 32...

Community: The Villages®

Cindy Certified

2889 MILLENNIUM CIR, MELBOURNE, FL, 3294..., Melbourne, FL 32940

$589,900

4 beds

4 baths

2,399 sq ft

House

2889 MILLENNIUM CIR, MELBOURNE, FL, 3294...

The Villages®

$290,000

2 beds

2 baths

1,529 sq ft

House

1532 E SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

$229,000

2 beds

2 baths

1,148 sq ft

House

9533 SE 168TH MAPLESONG LN, THE VILLAGES...

Community: The Villages®

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The Villages®

$315,000

2 beds

2 baths

1,066 sq ft

House

1426 JUAREZ PL, THE VILLAGES, FL, 32159

Community: The Villages®

Lakes of Mount Dora

8595 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$409,560

3 beds

2 baths

1,732 sq ft

House

8595 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes 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.

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 27

98 communities near Winter Park

2,698 homes near Winter Park

5 beds

3 baths

2,302 sq ft

House

2 beds

2 baths

1,878 sq ft

House

3 beds

2 baths

1,700 sq ft

House

3 beds

2 baths

1,504 sq ft

House

3 beds

3 baths

2,573 sq ft

House

3 beds

2 baths

1,559 sq ft

Villa

2 beds

2 baths

1,736 sq ft

House

3 beds

4 baths

2,861 sq ft

House

2 beds

2 baths

1,956 sq ft

House

4 beds

4 baths

2,502 sq ft

House

3 beds

2 baths

2,251 sq ft

House

3 beds

2 baths

1,526 sq ft

House

2 beds

2 baths

1,296 sq ft

Manufactured Home

2 beds

2 baths

1,598 sq ft

Villa

3 beds

2 baths

2,035 sq ft

House

3 beds

2 baths

1,506 sq ft

House

2 beds

2 baths

1,603 sq ft

House

3 beds

2 baths

1,751 sq ft

House

2 beds

2 baths

1,486 sq ft

Condo

2 beds