Winter Park, FL 55+ active adult communities & homes for sale - Page 5

2,259 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

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

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

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 (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)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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

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.

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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

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Questions? Call us: (888) 625-4885

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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 (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

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Questions? Call us: (888) 625-4885

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 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 Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 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

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 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

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

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

Questions? Call us: (888) 625-4885

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

1 2...3

Venetian Bay

3121 PORTOFINO BLVD, ,, FL, 32168, ,, FL 32168

$489,900

4 beds

4 baths

2,338 sq ft

House

3121 PORTOFINO BLVD, ,, FL, 32168

Community: Venetian Bay

Kings Ridge

2275 ADDISON AVE, CLERMONT, FL, 34711, Clermont, FL 34711

$359,000

2 beds

2 baths

1,975 sq ft

House

2275 ADDISON AVE, CLERMONT, FL, 34711

204 GRAND CANAL DR, KISSIMMEE, FL, 34759

House

704 PINNACLE DR, HAINES CITY, FL, 33844

228 PALM SPARROW CT, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

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

Questions? Call us: (888) 625-4885

Summer Trees

114 HICKORY LN, PORT ORANGE, FL, 32128, Port Orange, FL 32128

$285,000

2 beds

2 baths

1,403 sq ft

House

114 HICKORY LN, PORT ORANGE, FL, 32128

Community: Summer Trees

Venetian Bay

3255 TIGER PALM WAY, NEW SMYRNA BEACH, F..., New Smyrna Beach, FL 32168

$439,990

4 beds

3 baths

2,081 sq ft

House

3255 TIGER PALM WAY, NEW SMYRNA BEACH, F...

Community: Venetian Bay

Halifax Plantation

3063 SILVERMINES AVE, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$619,000

4 beds

3 baths

2,127 sq ft

House

3063 SILVERMINES AVE, ORMOND BEACH, FL, ...

Community: Halifax Plantation

Sullivan Ranch

30136 JUTLAND CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$589,900

6 beds

5 baths

3,997 sq ft

House

30136 JUTLAND CT, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Plantation Bay Golf & Country Club

18 MAGNOLIA DR S, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$289,900

2 beds

2 baths

1,300 sq ft

Condo

18 MAGNOLIA DR S, ORMOND BEACH, FL, 3217...

Community: Plantation Bay Golf & Country Club

Pennbrooke Fairways

830 OLD OAKS LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$379,247

3 beds

2 baths

1,976 sq ft

House

830 OLD OAKS LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$275,000

2 beds

2 baths

1,156 sq ft

Villa

2301 WHISPER ST, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$584,599

3 beds

2 baths

1,957 sq ft

House

632 CORONACA CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Lakes at Harmony

3485 MIDDLEBROOK PL, HARMONY, FL, 34773, Harmony, FL 34773

$424,999

4 beds

2 baths

2,064 sq ft

House

3485 MIDDLEBROOK PL, HARMONY, FL, 34773

Community: The Lakes at Harmony

Plantation Bay Golf & Country Club

1274 ROYAL POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$534,900

3 beds

2 baths

2,032 sq ft

House

1274 ROYAL POINTE LN, ORMOND BEACH, FL, ...

Community: Plantation Bay Golf & Country Club

Grand Haven

45 SAINT ANDREWS CT, PALM COAST, FL, 321..., Palm Coast, FL 32137

$559,000

4 beds

3 baths

2,514 sq ft

House

45 SAINT ANDREWS CT, PALM COAST, FL, 321...

Community: Grand Haven

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

Questions? Call us: (888) 625-4885

The Villages®

$429,900

3 beds

2 baths

1,500 sq ft

House

2790 CARYTOWN LOOP, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$550,000

3 beds

2 baths

1,906 sq ft

House

16846 SE 80TH BELLAVISTA CIR, THE VILLAG...

Community: The Villages®

Latitude Margaritaville

202 SUMMERTIME PL, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$474,000

2 beds

3 baths

1,748 sq ft

House

202 SUMMERTIME PL, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

The Savannahs

4304 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$398,000

3 beds

2 baths

1,812 sq ft

House

4304 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

Breakaway Trails

3 ECHO WOODS WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$599,900

4 beds

3 baths

2,506 sq ft

House

3 ECHO WOODS WAY, ORMOND BEACH, FL, 3217...

Community: Breakaway Trails

Plantation Bay Golf & Country Club

735 COBBLESTONE DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$535,000

2 beds

3 baths

2,181 sq ft

Townhouse

735 COBBLESTONE DR, ORMOND BEACH, FL, 32...

Community: Plantation Bay Golf & Country Club

Solivita

3420 FALLBROOK DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$295,000

2 beds

2 baths

1,499 sq ft

House

3420 FALLBROOK DR, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

12416 NE 48TH LOOP, OXFORD, FL, 34484, Oxford, FL 34484

$333,000

3 beds

2 baths

1,662 sq ft

House

12416 NE 48TH LOOP, OXFORD, FL, 34484

Community: The Villages®

The Country Club of Mount Dora

7029 PINE HOLLOW DR, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$469,000

3 beds

2 baths

2,160 sq ft

House

7029 PINE HOLLOW DR, MOUNT DORA, FL, 327...

Community: The Country Club of Mount Dora

The Villages®

$519,000

3 beds

2 baths

1,851 sq ft

House

1294 ALLAIRE LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

The Country Club of Mount Dora

8031 ARCADIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$396,500

3 beds

2 baths

1,611 sq ft

House

8031 ARCADIAN CT, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

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

Questions? Call us: (888) 625-4885

The Villages®

911 MEDIRA DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$317,900

2 beds

2 baths

1,268 sq ft

Villa

911 MEDIRA DR, LADY LAKE, FL, 32159

Community: The Villages®

Trilogy® Orlando

228 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$415,000

2 beds

2 baths

2,197 sq ft

House

228 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

1 2 3 4 5 6 7 8 9 10 11 12 13 14…57

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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2,259 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 5

95 communities near Winter Park

2,259 homes near Winter Park

4 beds

4 baths

2,338 sq ft

House

2 beds

2 baths

1,975 sq ft

House

2 beds

2 baths

1,655 sq ft

House

3 beds

2 baths

2,719 sq ft

House

2 beds

2 baths

1,548 sq ft

House

3 beds

2 baths

2,526 sq ft

House

2 beds

2 baths

1,300 sq ft

Condo

3 beds

2 baths

1,857 sq ft

House

3 beds

2 baths

1,653 sq ft

House

3 beds

2 baths

1,788 sq ft

House

3 beds

2 baths

1,512 sq ft

House

3 beds

2 baths

1,759 sq ft

House

2 beds

2 baths

1,532 sq ft

House

3 beds

2 baths

1,327 sq ft

House

3 beds

2 baths

1,900 sq ft

House

3 beds

2 baths

1,648 sq ft

House

2 beds

2 baths

1,403 sq ft

House

4 beds

3 baths

2,081 sq ft

House

4 beds

3 baths

2,127 sq ft

House

6 beds