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

Halifax Plantation

3158 CONNEMARA DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$428,000

3 beds

2 baths

1,741 sq ft

House

3158 CONNEMARA DR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

Palms at Serenoa

3441 MEADOW BEAUTY WAY, CLERMONT, FL, 34..., Clermont, FL 34714

$350,000

2 beds

2 baths

1,646 sq ft

Villa

3441 MEADOW BEAUTY WAY, CLERMONT, FL, 34...

Community: Palms at Serenoa

New Kings Ridge

1990 FARMINGTON CT, CLERMONT, FL, 34711, Clermont, FL 34711

$440,000

3 beds

2 baths

2,148 sq ft

House

1990 FARMINGTON CT, CLERMONT, FL, 34711

Community: Kings Ridge

Venetian Bay

422 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$653,702

4 beds

3 baths

2,542 sq ft

House

422 JUNONIA BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Plantation at Leesburg

25243 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$350,000

3 beds

3 baths

2,529 sq ft

House

25243 RIVER CREST DR, LEESBURG, FL, 3474...

Villa

220 ESTRADA PL, THE VILLAGES, FL, 32159

361 PARROT LN, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

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Questions? Call us: (888) 625-4885

The Villages®

$265,000

3 beds

2 baths

1,404 sq ft

House

3049 GLENWOOD PL, THE VILLAGES, FL, 3216...

Community: The Villages®

Venetian Bay

426 VENETIAN PALMS BLVD, NEW SMYRNA BEAC..., New Smyrna Beach, FL 32168

$356,800

3 beds

3 baths

1,779 sq ft

House

426 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

Kings Ridge

2292 EDMONTON CT, CLERMONT, FL, 34711, Clermont, FL 34711

$349,000

2 beds

2 baths

1,554 sq ft

House

2292 EDMONTON CT, CLERMONT, FL, 34711

Community: Kings Ridge

Ridgehaven

1348 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$419,990

4 beds

3 baths

2,190 sq ft

House

1348 OAKHAVEN AVE, ORMOND BEACH, FL, 321...

Community: Ridgehaven

The Villages®

$599,999

3 beds

2 baths

2,050 sq ft

House

527 BEVILLE PL, THE VILLAGES, FL, 32163

Community: The Villages®

Ridgehaven

171 PARKHAVEN DR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$311,000

3 beds

2 baths

1,572 sq ft

House

171 PARKHAVEN DR, ORMOND BEACH, FL, 3217...

Community: Ridgehaven

The Villages®

$350,000

3 beds

2 baths

1,392 sq ft

House

2196 KERWOOD LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

Venetian Bay

2913 N ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$1,099,000

4 beds

3 baths

3,148 sq ft

House

2913 N ASCIANO CT, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

The Villages®

$267,500

3 beds

2 baths

1,262 sq ft

House

17930 SE 83RD MELODY AVE, THE VILLAGES, ...

Community: The Villages®

The Villages®

$870,000

3 beds

2 baths

3,215 sq ft

House

1078 LAKEVIEW LN, THE VILLAGES, FL, 3216...

Community: The Villages®

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Questions? Call us: (888) 625-4885

The Villages®

$569,000

3 beds

2 baths

1,602 sq ft

House

1757 FLAGSTONE TER, THE VILLAGES, FL, 32...

Community: The Villages®

Spruce Creek South

17533 SE 96TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$254,900

2 beds

2 baths

1,534 sq ft

House

17533 SE 96TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Arlington Ridge

4513 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748

$439,777

3 beds

3 baths

2,138 sq ft

House

4513 ANTIETAM CREEK TRL, LEESBURG, FL, 3...

Community: Arlington Ridge

Huntington at Hunter's Ridge

15 SHEAR WATER TRL, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$384,000

3 beds

2 baths

2,105 sq ft

House

15 SHEAR WATER TRL, ORMOND BEACH, FL, 32...

Community: Huntington at Hunter's Ridge

Spruce Creek Country Club

11977 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$289,900

3 beds

2 baths

1,720 sq ft

House

11977 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

The Villages®

$359,000

2 beds

2 baths

1,094 sq ft

Villa

627 DELGADO AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Archers Mill

3305 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$469,990

4 beds

4 baths

2,787 sq ft

House

3305 ARCH AVE, ORMOND BEACH, FL, 32174

Community: Archers Mill

Archers Mill

3211 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$402,795

4 beds

3 baths

2,361 sq ft

House

3211 ARCH AVE, ORMOND BEACH, FL, 32174

Community: Archers Mill

Legacy of Leesburg

27238 STONEY BROOK DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$440,000

4 beds

2 baths

2,585 sq ft

House

27238 STONEY BROOK DR, LEESBURG, FL, 347...

Community: Legacy of Leesburg

Heritage - The Cottages of Sanders Grove

28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F..., Okahumpka, FL 34762

$293,000

4 beds

2 baths

1,617 sq ft

House

28026 CYPRESS SPRINGS LOOP, OKAHUMPKA, F...

House

157 WOODCOCK CT, DAYTONA BEACH, FL, 3211...

Community: Pelican Bay Daytona Beach

Breakaway Trails

45 WINDING CREEK WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$614,900

3 beds

2 baths

2,366 sq ft

House

45 WINDING CREEK WAY, ORMOND BEACH, FL, ...

Community: Breakaway Trails

Halifax Plantation

3787 CARRICK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$599,000

3 beds

2 baths

2,459 sq ft

House

3787 CARRICK DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

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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

1,741 sq ft

House

2 beds

2 baths

1,646 sq ft

Villa

3 beds

2 baths

2,148 sq ft

House

4 beds

3 baths

2,542 sq ft

House

3 beds

3 baths

2,529 sq ft

House

3 beds

2 baths

1,663 sq ft

House

3 beds

2 baths

1,584 sq ft

House

4 beds

3 baths

2,106 sq ft

House

2 beds

2 baths

1,860 sq ft

House

2 beds

2 baths

1,121 sq ft

Villa

2 beds

2 baths

1,321 sq ft

House

3 beds

2 baths

1,494 sq ft

House

2 beds

2 baths

1,274 sq ft

Manufactured Home

2 beds

2 baths

1,596 sq ft

House

2 beds

2 baths

1,204 sq ft

House

3 beds

2 baths

1,404 sq ft

House

3 beds

3 baths

1,779 sq ft

House

2 beds

2 baths

1,554 sq ft

House

4 beds

3 baths

2,190 sq ft

House

3 beds