Winter Park, FL 55+ active adult communities & homes for sale - Page 21

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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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

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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

Del Webb Sunbridge

2511 PINE PRESERVE CT, ST CLOUD, FL, 347..., St Cloud, FL 34771

$620,000

3 beds

2 baths

2,077 sq ft

House

2511 PINE PRESERVE CT, ST CLOUD, FL, 347...

Community: Del Webb Sunbridge

Summit Chase Villas

12435 ORANGEWOOD CIR, TAVARES, FL, 32778, Tavares, FL 32778

$199,900

2 beds

2 baths

1,105 sq ft

Villa

12435 ORANGEWOOD CIR, TAVARES, FL, 32778

Community: Summit Chase Villas

The Villages®

$525,000

2 beds

2 baths

1,397 sq ft

Villa

1802 PUERTO BELLO DR, THE VILLAGES, FL, ...

Community: The Villages®

Del Webb Sunbridge

2722 RIVER CREEK LN, ST CLOUD, FL, 34771, St Cloud, FL 34771

$1,025,000

3 beds

4 baths

3,778 sq ft

House

2722 RIVER CREEK LN, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

Venetian Bay

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

$888,000

3 beds

3 baths

2,297 sq ft

House

146 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...

Community: Venetian Bay

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Questions? Call us: (888) 625-4885

Latitude Margaritaville

361 PARROT LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$354,444

2 beds

2 baths

1,160 sq ft

House

361 PARROT LN, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

Tohoqua Reserve

1880 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$349,990

2 beds

2 baths

1,559 sq ft

House

1880 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Kings Ridge

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Indian River Colony Club

1461 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$340,000

3 beds

2 baths

1,739 sq ft

House

1461 PATRIOT DR, MELBOURNE, FL, 32940

Community: Indian River Colony Club

Cindy Certified

11 PROSPERITY LN, PALM COAST, FL, 32164, Palm Coast, FL 32164

$325,000

3 beds

2 baths

1,462 sq ft

House

11 PROSPERITY LN, PALM COAST, FL, 32164

Twin Lakes

2344 DATURA LOOP, ST CLOUD, FL, 34772, St Cloud, FL 34772

$347,500

2 beds

2 baths

1,464 sq ft

House

2344 DATURA LOOP, ST CLOUD, FL, 34772

Community: Twin Lakes

Grand Haven

18 N PARK LN, PALM COAST, FL, 32137, Palm Coast, FL 32137

$990,000

4 beds

4 baths

3,804 sq ft

House

18 N PARK LN, PALM COAST, FL, 32137

Community: Grand Haven

Lakeside Landings

5032 NEPTUNE CIR, OXFORD, FL, 34484, Oxford, FL 34484

$349,900

4 beds

3 baths

2,368 sq ft

House

5032 NEPTUNE CIR, OXFORD, FL, 34484

Community: Lakeside Landings

Latitude Margaritaville

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

$365,000

2 beds

2 baths

1,160 sq ft

House

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

Community: Latitude Margaritaville

The Villages®

4913 NE 122ND AVE, OXFORD, FL, 34484, Oxford, FL 34484

$360,000

4 beds

3 baths

2,629 sq ft

House

4913 NE 122ND AVE, OXFORD, FL, 34484

Community: The Villages®

The Villages®

$197,500

2 beds

2 baths

1,040 sq ft

Manufactured Home

1541 DORAL CIR, THE VILLAGES, FL, 32159

Community: The Villages®

The Timbers at Everlands

1652 MIRAFLORES TRL, PALM BAY, FL, 32907, Palm Bay, FL 32907

$249,663

2 beds

2 baths

1,308 sq ft

Townhouse

1652 MIRAFLORES TRL, PALM BAY, FL, 32907

Community: The Timbers at Everlands

The Timbers at Everlands

1632 MIRAFLORES TRL, PALM BAY, FL, 32907, Palm Bay, FL 32907

$249,663

2 beds

2 baths

1,308 sq ft

Townhouse

1632 MIRAFLORES TRL, PALM BAY, FL, 32907

Community: The Timbers at Everlands

The Villages®

1248 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159

$749,900

3 beds

3 baths

2,088 sq ft

Townhouse

1248 AVENIDA DE LAS CASAS, LADY LAKE, FL...

Community: The Villages®

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The Villages®

$395,000

3 beds

2 baths

1,560 sq ft

House

1238 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

Cindy Certified

2095 MAJORELLE DR, PALM BAY, FL, 32907, Palm Bay, FL 32907

$364,550

2 baths

1,830 sq ft

House

1306 GLENDALE AVE, PALM BAY, FL, 32907

VillageWalk at Lake Nona

12064 NAVALE LN, ORLANDO, FL, 32827, Orlando, FL 32827

$766,770

4 beds

3 baths

2,514 sq ft

House

12064 NAVALE LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Ridgehaven

418 BROOKHAVEN TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$600,000

5 beds

5 baths

3,807 sq ft

House

418 BROOKHAVEN TRL, ORMOND BEACH, FL, 32...

Community: Ridgehaven

Latitude Margaritaville

339 COOL WATERS WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$359,500

2 beds

2 baths

1,204 sq ft

House

339 COOL WATERS WAY, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

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

Questions? Call us: (888) 625-4885

Cindy Certified

1633 LAKE RESERVE DR, DELAND, FL, 32724, Deland, FL 32724

$699,990

4 beds

3 baths

2,129 sq ft

House

1633 LAKE RESERVE DR, DELAND, FL, 32724

Cresswind DeLand

1293 TWIN FARMS CT, DELAND, FL, 32724, Deland, FL 32724

$529,990

2 beds

2 baths

2,029 sq ft

House

1293 TWIN FARMS CT, DELAND, FL, 32724

Community: Cresswind DeLand

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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 21

98 communities near Winter Park

2,698 homes near Winter Park

3 beds

2 baths

2,077 sq ft

House

2 beds

2 baths

1,105 sq ft

Villa

2 beds

2 baths

1,397 sq ft

Villa

3 beds

4 baths

3,778 sq ft

House

3 beds

3 baths

2,297 sq ft

House

2 beds

2 baths

1,160 sq ft

House

2 beds

2 baths

1,559 sq ft

House

3 beds

2 baths

1,640 sq ft

House

3 beds

2 baths

1,715 sq ft

Villa

3 beds

2 baths

1,372 sq ft

Villa

2 beds

2 baths

1,732 sq ft

House

2 beds

2 baths

1,345 sq ft

House

3 beds

2 baths

1,888 sq ft

House

2 beds

2 baths

1,575 sq ft

House

2 beds

2 baths

1,200 sq ft

House

2 beds

2 baths

1,722 sq ft

House

3 beds

2 baths

1,739 sq ft

House

3 beds

2 baths

1,462 sq ft

House

2 beds

2 baths

1,464 sq ft

House

4 beds