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

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

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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

219 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

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Questions? Call us: (888) 625-4885

Royal Palm

1419 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$400,000

3 beds

2 baths

2,038 sq ft

House

1419 ARECA PALM DR, PORT ORANGE, FL, 321...

Community: Royal Palm

Pennbrooke Fairways

730 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$135,247

2 beds

2 baths

850 sq ft

Manufactured Home

730 COTTAGE PARK LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Sandpiper Golf & Country Club

550 EAGLE RUN, LAKELAND, FL, 33809, Lakeland, FL 33809

$325,000

2 beds

2 baths

1,627 sq ft

House

550 EAGLE RUN, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

The Villages®

$214,500

2 beds

2 baths

1,300 sq ft

Manufactured Home

1619 W SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

$419,900

3 beds

2 baths

1,559 sq ft

House

3394 RIDGEWOOD PATH, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$384,000

3 beds

2 baths

1,635 sq ft

Villa

16820 SE 74 SOULLIERE AVE, THE VILLAGES,...

Community: The Villages®

Cresswind at Victoria Gardens

1631 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724

$439,900

3 beds

2 baths

2,240 sq ft

House

1631 VICTORIA GARDENS DR, DELAND, FL, 32...

Community: Cresswind at Victoria Gardens

Pelican Bay Daytona Beach

965 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$399,000

3 beds

2 baths

2,485 sq ft

House

965 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

Grand Haven

17 SANDPIPER CT, PALM COAST, FL, 32137, Palm Coast, FL 32137

$875,000

4 beds

3 baths

3,196 sq ft

House

17 SANDPIPER CT, PALM COAST, FL, 32137

Community: Grand Haven

The Villages®

$450,000

3 beds

2 baths

1,850 sq ft

House

8617 SE 168TH KITTREDGE LOOP, THE VILLAG...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Lakes at Harmony

3426 SAGEBRUSH ST, HARMONY, FL, 34773, Harmony, FL 34773

$322,000

2 beds

2 baths

1,534 sq ft

House

3426 SAGEBRUSH ST, HARMONY, FL, 34773

Community: The Lakes at Harmony

The Villages®

1124 AVENIDA DE LAS CASAS # 1124, LADY L..., Lady Lake, FL 32159

$450,000

2 beds

3 baths

1,780 sq ft

Villa

1124 AVENIDA DE LAS CASAS # 1124, LADY L...

Community: The Villages®

Pelican Bay Daytona Beach

116 DUCK HAWK CIR 3040, DAYTONA BEACH, F..., Daytona Beach, FL 32119

$227,000

2 beds

2 baths

1,467 sq ft

Halfplex

116 DUCK HAWK CIR 3040, DAYTONA BEACH, F...

Community: Pelican Bay Daytona Beach

The Villages®

$799,900

3 beds

2 baths

1,971 sq ft

House

5647 KEY DEER PATH, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

1507 E SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159

$223,000

2 beds

2 baths

1,040 sq ft

Manufactured Home

1507 E SCHWARTZ BLVD, LADY LAKE, FL, 321...

Community: The Villages®

The Villages®

$271,900

2 beds

2 baths

1,163 sq ft

House

16938 SE 94TH SUNNYBROOK CIR, THE VILLAG...

Community: The Villages®

The Villages®

$730,000

3 beds

2 baths

1,927 sq ft

House

445 SOCIETY HILL CIR, THE VILLAGES, FL, ...

Community: The Villages®

Grand Haven

30 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$550,000

4 beds

4 baths

2,204 sq ft

House

30 FRONT ST, PALM COAST, FL, 32137

Community: Grand Haven

Stonecrest

17415 SE 116TH COURT RD, SUMMERFIELD, FL..., Summerfield, FL 34491

$375,000

2 beds

3 baths

1,686 sq ft

House

17415 SE 116TH COURT RD, SUMMERFIELD, FL...

Community: Stonecrest

Del Webb Orlando

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

$474,000

3 beds

2 baths

2,365 sq ft

House

280 DEL SOL AVE, DAVENPORT, FL, 33837

House

5 CRANE FIELD RD, ORMOND BEACH, FL, 3217...

House

8023 SAINT ANDREWS WAY, MOUNT DORA, FL, ...

Community: The Country Club of Mount Dora

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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

1,657 sq ft

House

3 beds

2 baths

2,183 sq ft

House

3 beds

2 baths

2,120 sq ft

House

2 beds

2 baths

1,561 sq ft

House

4 beds

3 baths

2,196 sq ft

House

3 beds

2 baths

2,038 sq ft

House

2 beds

2 baths

850 sq ft

Manufactured Home

2 beds

2 baths

1,627 sq ft

House

2 beds

2 baths

1,300 sq ft

Manufactured Home

3 beds

2 baths

1,559 sq ft

House

3 beds

2 baths

1,635 sq ft

Villa

3 beds

2 baths

2,240 sq ft

House

3 beds

2 baths

2,485 sq ft

House

4 beds

3 baths

3,196 sq ft

House

3 beds

2 baths

1,850 sq ft

House

2 beds

2 baths

1,534 sq ft

House

2 beds

3 baths

1,780 sq ft

Villa

2 beds

2 baths

1,467 sq ft

Halfplex

3 beds

2 baths

1,971 sq ft

House

2 beds