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

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 (2 reviews)

Heritage Isle

$200Ks - $500Ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 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

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 (1 reviews)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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 (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 - $600Ks

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

4950 GLEN COE ST, LEESBURG, FL, 34748

Community: Royal Highlands

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Questions? Call us: (888) 625-4885

Park Place

$379,000

3 beds

2 baths

1,878 sq ft

House

21 PARK PLACE CIR, PALM COAST, FL, 32164

Community: Park Place

Halifax Plantation

3169 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$399,000

3 beds

2 baths

1,919 sq ft

House

3169 CONNEMARA DR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

Spruce Creek South

17925 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$239,000

2 beds

2 baths

1,248 sq ft

House

17925 SE 100TH TER, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

Solivita

217 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$455,000

3 beds

3 baths

2,319 sq ft

House

217 SORRENTO RD, KISSIMMEE, FL, 34759

Community: Solivita

Latitude Margaritaville

553 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$655,000

3 beds

3 baths

2,161 sq ft

House

553 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

The Villages®

$314,500

2 beds

2 baths

1,142 sq ft

House

2109 HARSTON TRL, THE VILLAGES, FL, 3216...

Community: The Villages®

Del Webb Orlando

336 DEL SOL AVE, DAVENPORT, FL, 33837, Davenport, FL 33837

$429,900

3 beds

3 baths

2,086 sq ft

House

336 DEL SOL AVE, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Lake Ashton

4232 ROEBELENII DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$347,400

3 beds

2 baths

1,941 sq ft

House

4232 ROEBELENII DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Royal Highlands

21902 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748

$264,900

2 beds

2 baths

1,447 sq ft

House

21902 KING HENRY AVE, LEESBURG, FL, 3474...

Community: Royal Highlands

Royal Highlands

4701 INVERNESS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$383,900

3 beds

2 baths

1,929 sq ft

House

4701 INVERNESS DR, LEESBURG, FL, 34748

House

21144 ROYAL ST GEORGES LN, LEESBURG, FL,...

Community: Royal Highlands

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

Questions? Call us: (888) 625-4885

The Villages®

5092 NE 81ST BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$1,177,000

3 beds

3 baths

3,407 sq ft

House

5092 NE 81ST BLVD, WILDWOOD, FL, 34785

Community: The Villages®

Royal Highlands

5004 SAINT ANDREWS ARC, LEESBURG, FL, 34..., Leesburg, FL 34748

$269,000

2 beds

2 baths

1,483 sq ft

House

5004 SAINT ANDREWS ARC, LEESBURG, FL, 34...

Community: Royal Highlands

Royal Highlands

21815 TARTAN ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$375,000

3 beds

3 baths

2,369 sq ft

House

21815 TARTAN ST, LEESBURG, FL, 34748

Community: Royal Highlands

The Villages®

$355,000

3 beds

2 baths

1,623 sq ft

House

1273 FORT LAWN LOOP, THE VILLAGES, FL, 3...

Community: The Villages®

Plantation at Leesburg

5053 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$279,000

3 beds

2 baths

1,720 sq ft

House

5053 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$659,900

3 beds

3 baths

2,409 sq ft

House

1092 INCORVAIA WAY, THE VILLAGES, FL, 32...

Community: The Villages®

Grand Haven

6 SCARLET OAK CIR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$829,000

3 beds

3 baths

2,465 sq ft

House

6 SCARLET OAK CIR, PALM COAST, FL, 32137

Community: Grand Haven

Spruce Creek South

17551 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$264,900

3 beds

2 baths

1,498 sq ft

House

17551 SE 96TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Latitude Margaritaville

962 ATTITUDE AVE, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$559,900

3 beds

2 baths

1,771 sq ft

House

962 ATTITUDE AVE, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Spruce Creek South

10185 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$259,000

2 beds

3 baths

1,982 sq ft

House

10185 SE 175TH LN, SUMMERFIELD, FL, 3449...

House

20505 QUEEN ALEXANDRA DR, LEESBURG, FL, ...

Community: Royal Highlands

Carmel Condominium

1420 HUNTINGTON LN 2101, ROCKLEDGE, FL, ..., Rockledge, FL 32955

$209,000

2 beds

2 baths

1,228 sq ft

Condo

1420 HUNTINGTON LN 2101, ROCKLEDGE, FL, ...

Community: Carmel Condominium

Royal Harbor

3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778

$399,999

3 beds

3 baths

2,012 sq ft

House

3257 BALTIC SEA BLVD, TAVARES, FL, 32778

Community: Royal Harbor

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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

1,856 sq ft

House

2 beds

2 baths

1,008 sq ft

House

3 beds

2 baths

1,876 sq ft

House

2 beds

2 baths

1,702 sq ft

House

3 beds

2 baths

2,065 sq ft

House

3 beds

2 baths

1,878 sq ft

House

3 beds

2 baths

1,919 sq ft

House

2 beds

2 baths

1,248 sq ft

House

3 beds

3 baths

2,319 sq ft

House

3 beds

3 baths

2,161 sq ft

House

2 beds

2 baths

1,142 sq ft

House

3 beds

3 baths

2,086 sq ft

House

3 beds

2 baths

1,941 sq ft

House

2 beds

2 baths

1,447 sq ft

House

3 beds

2 baths

1,929 sq ft

House

3 beds

2 baths

1,469 sq ft

House

3 beds

2 baths

1,469 sq ft

House

3 beds

3 baths

2,355 sq ft

House

3 beds

2 baths

2,636 sq ft

House

3 beds