Winter Park, FL 55+ active adult communities & homes for sale - Page 36

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

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

802 GRAND PARK CT, DELAND, FL, 32724, Deland, FL 32724

$310,000

3 beds

2 baths

1,575 sq ft

House

802 GRAND PARK CT, DELAND, FL, 32724

The Villages®

$299,900

2 beds

2 baths

1,128 sq ft

Villa

631 ENCONTO ST, THE VILLAGES, FL, 32159

Community: The Villages®

Venetian Bay

2909 N ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$1,099,000

3 beds

3 baths

2,866 sq ft

House

2909 N ASCIANO CT, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

The Villages®

413 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785

$124,900

2 beds

2 baths

1,092 sq ft

Manufactured Home

413 S TIMBER TRL, WILDWOOD, FL, 34785

Community: The Villages®

Cindy Certified

4566 LIVE OAK LN, OXFORD, FL, 34484, Oxford, FL 34484

$398,990

4 beds

3 baths

2,165 sq ft

House

4566 LIVE OAK LN, OXFORD, FL, 34484

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

Questions? Call us: (888) 625-4885

Cindy Certified

73 FLAGSTICK LN, BUNNELL, FL, 32110, Bunnell, FL 32110

$296,465

3 beds

2 baths

1,459 sq ft

House

73 FLAGSTICK LN, BUNNELL, FL, 32110

Cindy Certified

5 PORTER LN, PALM COAST, FL, 32164, Palm Coast, FL 32164

$391,800

4 beds

3 baths

2,265 sq ft

House

5 PORTER LN, PALM COAST, FL, 32164

Royal Highlands

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

$459,900

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

$295,000

2 beds

2 beds

3 beds

3 baths

2,146 sq ft

House

70 STONE HAVEN CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Grand Haven

10 RIVER PARK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$440,000

2 beds

2 baths

1,828 sq ft

Townhouse

10 RIVER PARK 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

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

Breakaway Trails

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

$399,995

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

$478,990

4 beds

4 baths

2,338 sq ft

House

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

761 GREENWAY BLVD, LAKE WALES, FL, 33859

The Villages®

$435,000

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

$305,000

3 beds

3 baths

2,118 sq ft

House

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

Community: Stonecrest

The Timbers at Everlands

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

$515,000

4 beds

3 baths

2,640 sq ft

House

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

Community: The Timbers at Everlands

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

Questions? Call us: (888) 625-4885

Arlington Ridge

$300,000

2 beds

2 baths

1,649 sq ft

House

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

Community: Arlington Ridge

Lake Henry Estates

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

$240,000

2 beds

3 beds

2 baths

1,776 sq ft

House

5619 PRINCE ANDREW CT, LEESBURG, FL, 347...

Community: Royal Highlands

Cindy Certified

6430 ROVER WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771

$484,990

2 baths

1,457 sq ft

House

11426 LAKEVIEW DR, LEESBURG, FL, 34788

Foxwood Lake Estates

5083 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$208,000

2 beds

2 baths

1,272 sq ft

Manufactured Home

5083 LODGEWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

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

Questions? Call us: (888) 625-4885

The Villages®

$325,000

3 beds

2 baths

1,392 sq ft

House

970 KENOVA AVE, THE VILLAGES, FL, 32162

Community: The Villages®

Cindy Certified

4578 TROVITA CIR, WEST MELBOURNE, FL, 32..., West Melbourne, FL 32904

$489,000

3 beds

2 baths

1,998 sq ft

House

4578 TROVITA CIR, WEST MELBOURNE, FL, 32...

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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 36

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

1,575 sq ft

House

2 beds

2 baths

1,128 sq ft

Villa

3 beds

3 baths

2,866 sq ft

House

2 beds

2 baths

1,092 sq ft

Manufactured Home

4 beds

3 baths

2,165 sq ft

House

3 beds

2 baths

1,459 sq ft

House

4 beds

3 baths

2,265 sq ft

House

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

4 beds

3 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

3 beds

3 baths

2,146 sq ft

House

2 beds

2 baths

1,828 sq ft

Townhouse

3 beds

2 baths

1,731 sq ft

Townhouse

3 beds

2 baths

1,875 sq ft

House

4 beds

4 baths

2,338 sq ft

House

2 beds