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

2,487 homes near Winter Park

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4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$100Ks - $600Ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

3.6 rating (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

5 rating (1 reviews)

Plantation Bay Golf &...

$200Ks - $4Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

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5 rating (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

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

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

5 rating (7 reviews)

Kings Ridge

$200Ks - $400Ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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

Grand Haven

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

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Pelican Bay Daytona Beach

$100Ks - $500Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $300Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

5 rating (1 reviews)

Cypress Lakes

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

Venetian Bay

$200Ks - $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)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 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)

Royal Highlands

$200Ks - $500Ks

Royal Highlands, Leesburg, FL

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

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

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

Del Webb at Viera

$300Ks - $800Ks

Del Webb at Viera, Melbourne, FL

New Construction | 55+ age-restricted | Built 2021 - present | 1,300 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300Ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

5 rating (1 reviews)

Sandpiper Golf & Coun...

$200Ks - $400Ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $500Ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300Ks - $600Ks

Cresswind at Victoria Gar..., DeLand, FL

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

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Questions? Call us: (888) 625-4885

Halifax Plantation

$200Ks - $700Ks

Halifax Plantation, Ormond Beach, FL

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

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $900Ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

4 rating (2 reviews)

Harbor Hills Country Club

$200Ks - $1Ms

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

5 rating (2 reviews)

Bridgewater at Viera

$300Ks - $600Ks

Bridgewater at Viera, Melbourne, FL

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

4.1 rating (9 reviews)

Indian River Colony Club

$200Ks - $400Ks

Indian River Colony Club, Melbourne, FL

New and Resale | 55+ age-restricted | Built 1986 - present | 777 homes

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Questions? Call us: (888) 625-4885

3.9 rating (7 reviews)

Summit Greens

$300Ks - $400Ks

Summit Greens, Clermont, FL

Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes

5 rating (1 reviews)

Royal Harbor

$200Ks - $400Ks

Royal Harbor, Tavares, FL

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

Lakeside Landings

$200Ks - $500Ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $600Ks

Sullivan Ranch, Mount Dora, FL

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

Highland Fairways

$100Ks - $300Ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

1 2...3

Lake Ashton

1336 OAKMONT DR, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$695,000

3 beds

2 baths

2,773 sq ft

House

1336 OAKMONT DR, WINTER HAVEN, FL, 33884

Community: Lake Ashton

Harbor Hills Country Club

39640 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$529,900

3 beds

3 baths

2,531 sq ft

House

39640 HARBOR HILLS BLVD, LADY LAKE, FL, ...

1505 CHESAPEAKE CT, MELBOURNE, FL, 32940

House

3446 EBBING LN, MELBOURNE, FL, 32940

9049 SAINT ANDREWS WAY, MOUNT DORA, FL, ...

Community: The Country Club of Mount Dora

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Questions? Call us: (888) 625-4885

Plantation Bay Golf & Country Club

14 MAGNOLIA DR S # 14, ORMOND BEACH, FL,..., Ormond Beach, FL 32174

$259,000

2 beds

2 baths

1,300 sq ft

Condo

14 MAGNOLIA DR S # 14, ORMOND BEACH, FL,...

Community: Plantation Bay Golf & Country Club

Plantation Bay Golf & Country Club

3 TREETOP TRL, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$358,900

2 beds

3 baths

2,156 sq ft

House

3 TREETOP TRL, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

VillageWalk at Lake Nona

12287 REGAL LILY LN, ORLANDO, FL, 32827, Orlando, FL 32827

$725,000

3 beds

2 baths

2,316 sq ft

House

12287 REGAL LILY LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Plantation Bay Golf & Country Club

842 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$365,000

2 beds

2 baths

1,562 sq ft

Townhouse

842 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Plantation Bay Golf & Country Club

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

$259,000

2 beds

2 baths

1,300 sq ft

Condo

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

Community: Plantation Bay Golf & Country Club

Stonecrest

11041 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$315,000

3 beds

2 baths

1,417 sq ft

House

11041 SE 169TH PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Park Place

$400,000

2 beds

2 baths

1,887 sq ft

House

86 PARK PLACE CIR, PALM COAST, FL, 32164

Community: Park Place

Pelican Bay Daytona Beach

220 SURF SCOOTER DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$279,900

2 beds

2 baths

1,760 sq ft

Townhouse

220 SURF SCOOTER DR, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

Solivita

501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34..., Kissimmee, FL 34759

$320,000

2 beds

2 baths

1,574 sq ft

House

501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34...

Community: Solivita

Halifax Plantation

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

$649,000

4 beds

3 baths

2,127 sq ft

House

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

Community: Halifax Plantation

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

Questions? Call us: (888) 625-4885

Royal Palm

1383 COCONUT PALM CIR, PORT ORANGE, FL, ..., Port Orange, FL 32128

$449,900

3 beds

2 baths

2,360 sq ft

House

1383 COCONUT PALM CIR, PORT ORANGE, FL, ...

Community: Royal Palm

Grand Haven

23 CREEKSIDE DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$899,000

4 beds

3 baths

2,633 sq ft

House

23 CREEKSIDE DR, PALM COAST, FL, 32137

Community: Grand Haven

The Villages®

$289,900

2 beds

2 baths

1,156 sq ft

House

889 ALLAGASH AVE, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$320,000

3 beds

2 baths

1,392 sq ft

House

1819 CAPTIVA CT, THE VILLAGES, FL, 32162

Community: The Villages®

The Lakes at Harmony

3204 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773

$469,000

4 beds

3 baths

2,361 sq ft

House

3204 OXBOW CT, HARMONY, FL, 34773

Community: The Lakes at Harmony

Grand Haven

16 VILLAGE VIEW WAY, PALM COAST, FL, 321..., Palm Coast, FL 32137

$535,000

3 beds

3 baths

1,980 sq ft

House

16 VILLAGE VIEW WAY, PALM COAST, FL, 321...

Community: Grand Haven

Sandpiper Golf & Country Club

5992 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809

$370,000

3 beds

2 baths

1,478 sq ft

House

5992 TEAL TRL, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Sandpiper Golf & Country Club

5970 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809

$375,000

3 beds

2 baths

1,582 sq ft

House

5970 CORMORANT CT, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Sandpiper Golf & Country Club

5987 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809

$370,000

3 beds

2 baths

1,478 sq ft

House

5987 TEAL TRL, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Sandpiper Golf & Country Club

5976 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809

$370,000

3 beds

2 baths

1,478 sq ft

House

5976 CORMORANT CT, LAKELAND, FL, 33809

House

5921 CORMORANT CT, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

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2,487 homes near Winter Park

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

90 communities near Winter Park

2,487 homes near Winter Park

3 beds

2 baths

2,773 sq ft

House

3 beds

3 baths

2,531 sq ft

House

4 beds

2 baths

2,424 sq ft

House

3 beds

2 baths

1,717 sq ft

House

3 beds

2 baths

1,885 sq ft

House

3 beds

2 baths

1,764 sq ft

House

2 beds

2 baths

1,498 sq ft

House

2 beds

2 baths

2,182 sq ft

House

3 beds

2 baths

1,918 sq ft

House

2 beds

2 baths

1,655 sq ft

House

4 beds

2 baths

2,620 sq ft

House

2 beds

2 baths

1,370 sq ft

House

3 beds

3 baths

3,296 sq ft

House

2 beds

2 baths

1,703 sq ft

House

2 beds

2 baths

1,978 sq ft

House

2 beds

2 baths

1,300 sq ft

Condo

2 beds

3 baths

2,156 sq ft

House

3 beds

2 baths

2,316 sq ft

House

2 beds

2 baths

1,562 sq ft

Townhouse

2 beds