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

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

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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

Indian River Colony Club

1198 CONTINENTAL AVE, MELBOURNE, FL, 329..., Melbourne, FL 32940

$360,000

3 beds

3 baths

2,304 sq ft

House

1198 CONTINENTAL AVE, MELBOURNE, FL, 329...

290 JEFFERSON LN, THE VILLAGES, FL, 3216...

House

1069 AVERY MEADOWS WAY, DELAND, FL, 3272...

Community: Cresswind at Victoria Gardens

Latitude Margaritaville

901 BARNACLE BAY CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$639,900

3 beds

3 baths

2,394 sq ft

House

901 BARNACLE BAY CT, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Venetian Bay

513 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$774,999

4 beds

3 baths

2,900 sq ft

House

513 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Del Webb Orlando

372 TOLDEDO RD, DAVENPORT, FL, 33837, Davenport, FL 33837

$390,000

2 beds

2 baths

1,836 sq ft

House

372 TOLDEDO RD, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Spruce Creek Country Club

12771 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$289,000

2 beds

2 baths

1,237 sq ft

House

12771 SE 92ND TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Pelican Bay Daytona Beach

517 BROWN PELICAN DR, DAYTONA BEACH, FL,..., Daytona Beach, FL 32119

$204,900

3 beds

2 baths

1,520 sq ft

Townhouse

517 BROWN PELICAN DR, DAYTONA BEACH, FL,...

Community: Pelican Bay Daytona Beach

Venetian Bay

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

$526,000

3 beds

3 baths

2,040 sq ft

House

206 VENETIAN PALMS BLVD, NEW SMYRNA BEAC...

Community: Venetian Bay

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

Questions? Call us: (888) 625-4885

The Villages®

$409,000

3 beds

2 baths

1,766 sq ft

House

3102 SWEETGUM ST, THE VILLAGES, FL, 3216...

Community: The Villages®

Spruce Creek Country Club

9244 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$359,000

2 beds

2 baths

2,130 sq ft

House

9244 SE 128TH ST, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Spruce Creek Country Club

13089 SE 86TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$321,000

2 beds

2 baths

1,870 sq ft

House

13089 SE 86TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

The Villages®

$465,000

3 beds

2 baths

1,956 sq ft

House

791 ENISGROVE WAY, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$265,000

2 beds

2 baths

1,583 sq ft

House

1208 TARPON LN, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$337,500

3 beds

2 baths

1,392 sq ft

House

17937 SE 83RD PINELAND TER, THE VILLAGES...

Community: The Villages®

The Villages®

$349,900

3 beds

2 baths

1,472 sq ft

House

2573 CARIBE DR, THE VILLAGES, FL, 32162

Community: The Villages®

Lake Ashton

5384 HOGAN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$371,900

2 beds

2 baths

1,682 sq ft

House

5384 HOGAN LN, WINTER HAVEN, FL, 33884

Community: Lake Ashton

Pelican Bay Daytona Beach

101 BOB WHITE CT APT 1, DAYTONA BEACH, F..., Daytona Beach, FL 32119

$199,900

3 beds

3 baths

1,527 sq ft

Condo

101 BOB WHITE CT APT 1, DAYTONA BEACH, F...

Community: Pelican Bay Daytona Beach

The Villages®

$384,900

3 beds

2 baths

1,684 sq ft

House

17065 SE 79TH MCLAWREN TER, THE VILLAGES...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Venetian Bay

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$459,500

3 beds

3 baths

2,203 sq ft

Townhouse

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Vienna Square

2343 SALZBURG LOOP, WINTER HAVEN, FL, 33..., Winter Haven, FL 33884

$327,500

3 beds

2 baths

1,948 sq ft

House

2343 SALZBURG LOOP, WINTER HAVEN, FL, 33...

Community: Vienna Square

Stonecrest

11381 SE 175TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$250,000

2 beds

2 baths

1,504 sq ft

House

11381 SE 175TH LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

The Villages®

$299,000

2 beds

2 baths

1,623 sq ft

Villa

1019 AVALON AVE, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$495,000

3 beds

2 baths

2,109 sq ft

House

3814 FELLOWSHIP AVE, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$499,900

3 beds

2 baths

1,998 sq ft

House

1096 STRADINGER ST, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$750,000

3 beds

2 baths

1,813 sq ft

House

959 FISH CAMP RD, THE VILLAGES, FL, 3216...

Community: The Villages®

Arlington Ridge

26689 OTTER CREEK LN, LEESBURG, FL, 3474..., Leesburg, FL 34748

$384,999

3 beds

2 baths

1,725 sq ft

House

26689 OTTER CREEK LN, LEESBURG, FL, 3474...

Community: Arlington Ridge

Indian River Colony Club

1317 INDEPENDENCE AVE, MELBOURNE, FL, 32..., Melbourne, FL 32940

$360,000

2 beds

2 baths

1,852 sq ft

House

1317 INDEPENDENCE AVE, MELBOURNE, FL, 32...

Community: Indian River Colony Club

Del Webb Oasis

15514 ORCHID ROSE CT, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$707,070

2 beds

2 baths

1,943 sq ft

House

15514 ORCHID ROSE CT, WINTER GARDEN, FL,...

House

2291 MONTBROOK PL, THE VILLAGES, FL, 321...

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

3 beds

3 baths

2,304 sq ft

House

3 beds

2 baths

1,607 sq ft

House

2 beds

2 baths

1,143 sq ft

Villa

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

1,527 sq ft

House

3 beds

2 baths

1,652 sq ft

House

3 beds

2 baths

1,656 sq ft

Villa

2 beds

2 baths

1,393 sq ft

House

2 beds

2 baths

1,651 sq ft

House

3 beds

3 baths

2,394 sq ft

House

4 beds

3 baths

2,900 sq ft

House

2 beds

2 baths

1,836 sq ft

House

2 beds

2 baths

1,237 sq ft

House

3 beds

2 baths

1,520 sq ft

Townhouse

3 beds

3 baths

2,040 sq ft

House

3 beds

2 baths

1,766 sq ft

House

2 beds

2 baths

2,130 sq ft

House

2 beds

2 baths

1,870 sq ft

House

3 beds

2 baths

1,956 sq ft

House

2 beds