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

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.

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

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

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

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

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

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

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

672 CORDOBA DR, DAVENPORT, FL, 33837

Manufactured Home

1717 PALM AIRE DR, LADY LAKE, FL, 32159

1299 CRESSWIND BLVD, DELAND, FL, 32724

Villa

26755 CASH CT, LEESBURG, FL, 34748

Community: Highland Lakes

Latitude Margaritaville

171 CATAMARAN CV, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$929,900

3 beds

3 baths

2,468 sq ft

House

171 CATAMARAN CV, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Del Webb Sunbridge

6514 BARNSTORM WAY, SAINT CLOUD, FL, 347..., Saint Cloud, FL 34771

$539,900

3 beds

2 baths

1,881 sq ft

House

6514 BARNSTORM WAY, SAINT CLOUD, FL, 347...

Community: Del Webb Sunbridge

Heritage Hills

3596 KINLEY BROOKE LN, CLERMONT, FL, 347..., Clermont, FL 34711

$395,900

3 beds

2 baths

1,677 sq ft

House

3596 KINLEY BROOKE LN, CLERMONT, FL, 347...

Community: Heritage Hills

Palms at Serenoa

17581 SUMMERSWEET WAY, CLERMONT, FL, 347..., Clermont, FL 34714

$339,900

2 beds

2 baths

1,627 sq ft

Villa

17581 SUMMERSWEET WAY, CLERMONT, FL, 347...

Community: Palms at Serenoa

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

Questions? Call us: (888) 625-4885

American Village

79 GREEN CIR, PALM COAST, FL, 32164, Palm Coast, FL 32164

$309,990

3 beds

2 baths

1,585 sq ft

House

79 GREEN CIR, PALM COAST, FL, 32164

Community: American Village

The Villages®

$325,000

2 beds

2 baths

1,295 sq ft

House

3349 CLARA CT, THE VILLAGES, FL, 32163

Community: The Villages®

New Harbor Hills Country Club

5524 SADDLEBACK CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$375,000

3 beds

2 baths

2,066 sq ft

House

5524 SADDLEBACK CT, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

The Villages®

$319,900

3 beds

2 baths

1,392 sq ft

House

17985 SE 92ND AMORY AVE, THE VILLAGES, F...

Community: The Villages®

New Kings Ridge

3840 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711

$325,000

2 beds

2 baths

1,705 sq ft

House

3840 EVERSHOLT ST, CLERMONT, FL, 34711

Community: Kings Ridge

The Villages®

$349,000

3 beds

2 baths

1,392 sq ft

House

2469 ELDON PL, THE VILLAGES, FL, 32162

Community: The Villages®

Plantation Bay Golf & Country Club

38 LANDINGS LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$289,899

2 beds

2 baths

1,358 sq ft

Townhouse

38 LANDINGS LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Breakaway Trails

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$499,900

4 beds

3 baths

2,544 sq ft

House

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321...

Community: Breakaway Trails

The Villages®

$189,900

2 beds

2 baths

1,188 sq ft

Manufactured Home

407 TARRSON BLVD, THE VILLAGES, FL, 3215...

Community: The Villages®

Del Webb at Viera

3447 EBBING LN, MELBOURNE, FL, 32940, Melbourne, FL 32940

$599,330

3 beds

2 baths

2,056 sq ft

House

3447 EBBING LN, MELBOURNE, FL, 32940

House

16903 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

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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

4 beds

5 baths

2,917 sq ft

House

3 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

1,240 sq ft

House

3 beds

2 baths

1,699 sq ft

Villa

2 beds

2 baths

1,956 sq ft

House

2 beds

2 baths

1,724 sq ft

House

2 beds

2 baths

1,156 sq ft

House

3 beds

3 baths

2,197 sq ft

House

2 beds

2 baths

1,190 sq ft

Condo

2 beds

2 baths

1,284 sq ft

Manufactured Home

3 beds

2 baths

1,656 sq ft

Detached

2 beds

2 baths

1,385 sq ft

Villa

3 beds

2 baths

1,850 sq ft

House

3 beds

2 baths

1,552 sq ft

House

3 beds

4 baths

2,776 sq ft

House

2 beds

2 baths

1,434 sq ft

House

3 beds

2 baths

1,616 sq ft

House

3 beds

2 baths

1,852 sq ft

House

3 beds

3 baths

2,692 sq ft

House

3 beds