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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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

284 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

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Carlsberg Estates on Lake Suzanne

4189 CANNES AVE, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$259,900

3 beds

2 baths

1,385 sq ft

House

4189 CANNES AVE, LAKE WALES, FL, 33859

Community: Carlsberg Estates on Lake Suzanne

Carlsberg Estates on Lake Suzanne

341 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$247,000

2 beds

2 baths

1,385 sq ft

House

341 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

Carlsberg Estates on Lake Suzanne

496 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$340,000

2 beds

2 baths

1,637 sq ft

House

496 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

Carlsberg Estates on Lake Suzanne

231 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$259,900

2 beds

2 baths

1,406 sq ft

House

231 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

Plantation at Leesburg

5414 ASTOR ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$244,700

2 beds

2 baths

1,256 sq ft

House

5414 ASTOR ST, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Plantation at Leesburg

25125 BELLEVUE, LEESBURG, FL, 34748, Leesburg, FL 34748

$160,000

2 beds

2 baths

936 sq ft

Manufactured Home

25125 BELLEVUE, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Ridgehaven

1336 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$450,050

4 beds

3 baths

2,337 sq ft

House

1336 OAKHAVEN AVE, ORMOND BEACH, FL, 321...

Community: Ridgehaven

Traditions at Lake Ruby

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$320,000

3 beds

2 baths

2,109 sq ft

House

3614 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

The Villages®

$335,000

3 beds

2 baths

1,392 sq ft

Villa

1762 MEADOWLARK AVE, THE VILLAGES, FL, 3...

Community: The Villages®

Colonnades

4816 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$191,900

2 beds

2 baths

1,066 sq ft

Modular

4816 GOLDENVIEW LN, LAKELAND, FL, 33811

Community: Colonnades

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Questions? Call us: (888) 625-4885

The Villages®

$500,000

3 beds

2 baths

2,085 sq ft

House

1178 BETHUNE WAY, THE VILLAGES, FL, 3216...

202 ESTRADA PL, THE VILLAGES, FL, 32159

Community: The Villages®

Halifax Plantation

1184 ATHLONE WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$284,900

2 beds

2 baths

1,393 sq ft

House

1184 ATHLONE WAY, ORMOND BEACH, FL, 3217...

Community: Halifax Plantation

Venetian Bay

112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL..., New Smyrna Beach, FL 32168

$719,000

3 beds

2 baths

2,372 sq ft

House

112 PORTOFINO BLVD, NEW SMYRNA BEACH, FL...

Community: Venetian Bay

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The Villages®

$468,000

3 beds

2 baths

1,865 sq ft

House

2895 APACHE CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$989,000

3 beds

2 baths

1,871 sq ft

House

1573 NORFOLK AVE, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$229,000

1 beds

1 baths

991 sq ft

Villa

2317 WHISPER ST, THE VILLAGES, FL, 32162

Community: The Villages®

Del Webb Sunbridge

2960 CHERRY BLOSSOM LOOP, SAINT CLOUD, F..., Saint Cloud, FL 34771

$419,900

3 beds

2 baths

1,584 sq ft

Villa

2960 CHERRY BLOSSOM LOOP, SAINT CLOUD, F...

Community: Del Webb Sunbridge

Heritage Hills

3632 SOLANA CIR B, CLERMONT, FL, 34711, Clermont, FL 34711

$300,000

2 beds

2 baths

1,374 sq ft

Villa

3632 SOLANA CIR B, CLERMONT, FL, 34711

Community: Heritage Hills

Heritage Isle

3130 LE CONTE ST, MELBOURNE, FL, 32940, Melbourne, FL 32940

$283,000

2 beds

2 baths

1,394 sq ft

Townhouse

3130 LE CONTE ST, MELBOURNE, FL, 32940

Community: Heritage Isle

Kings Ridge

4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711

$419,900

2 beds

2 baths

1,968 sq ft

House

4202 HAMMERSMITH DR, CLERMONT, FL, 34711

Community: Kings Ridge

Lake Ashton

4488 TURNBERRY LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$217,500

2 beds

2 baths

1,083 sq ft

House

4488 TURNBERRY LN, LAKE WALES, FL, 33859

Community: Lake Ashton

The Savannahs

4344 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$439,900

4 beds

2 baths

2,046 sq ft

House

4344 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

Harbor Hills Country Club

6048 TOPSAIL RD, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$299,900

3 beds

2 baths

2,028 sq ft

House

6048 TOPSAIL RD, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

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Pelican Bay Daytona Beach

348 BOB WHITE CT APT 9, DAYTONA BEACH, F..., Daytona Beach, FL 32119

$240,000

3 beds

3 baths

1,527 sq ft

Condo

348 BOB WHITE CT APT 9, DAYTONA BEACH, F...

Community: Pelican Bay Daytona Beach

Four Seasons at Orlando

1830 ESTUARY LN, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$305,000

2 beds

2 baths

1,557 sq ft

Villa

1830 ESTUARY LN, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

The Villages®

$309,750

3 beds

2 baths

1,231 sq ft

House

8143 SE 175TH COLUMBIA PL, THE VILLAGES,...

Community: The Villages®

Stonecrest

12459 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$309,900

3 beds

2 baths

1,326 sq ft

House

12459 SE 176TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

Plantation at Leesburg

25504 BELLE ALLIANCE, LEESBURG, FL, 3474..., Leesburg, FL 34748

$194,900

2 beds

2 baths

1,674 sq ft

Manufactured Home

25504 BELLE ALLIANCE, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

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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

2,030 sq ft

House

2 beds

2 baths

1,387 sq ft

House

3 beds

2 baths

2,002 sq ft

House

3 beds

2 baths

1,429 sq ft

House

2 beds

2 baths

1,170 sq ft

House

3 beds

2 baths

1,385 sq ft

House

2 beds

2 baths

1,385 sq ft

House

2 beds

2 baths

1,637 sq ft

House

2 beds

2 baths

1,406 sq ft

House

2 beds

2 baths

1,256 sq ft

House

2 beds

2 baths

936 sq ft

Manufactured Home

4 beds

3 baths

2,337 sq ft

House

3 beds

2 baths

2,109 sq ft

House

3 beds

2 baths

1,392 sq ft

Villa

2 beds

2 baths

1,066 sq ft

Modular

3 beds

2 baths

2,085 sq ft

House

3 beds

2 baths

1,363 sq ft

House

3 beds

2 baths

1,634 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds