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

519 CADIZ DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

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Questions? Call us: (888) 625-4885

Summit Greens

2503 SQUAW CRK, CLERMONT, FL, 34711, Clermont, FL 34711

$389,900

3 beds

2 baths

1,919 sq ft

House

2503 SQUAW CRK, CLERMONT, FL, 34711

Community: Summit Greens

Heritage Isle

3035 SAVOY DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$299,000

2 beds

2 baths

1,531 sq ft

Townhouse

3035 SAVOY DR, MELBOURNE, FL, 32940

Community: Heritage Isle

Plantation at Leesburg

25749 WHISPER OAKS RD, LEESBURG, FL, 347..., Leesburg, FL 34748

$299,000

3 beds

2 baths

1,967 sq ft

House

25749 WHISPER OAKS RD, LEESBURG, FL, 347...

Community: Plantation at Leesburg

Esplanade at Highland Ranch

2342 CLEMBLUE RD, CLERMONT, FL, 34715, Clermont, FL 34715

$430,000

3 beds

3 baths

1,847 sq ft

House

2342 CLEMBLUE RD, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

Venetian Bay

3454 VELONA AVE, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$450,000

3 beds

2 baths

2,211 sq ft

House

3454 VELONA AVE, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Arlington Ridge

4415 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748

$420,000

2 beds

2 baths

2,076 sq ft

House

4415 ANTIETAM CREEK TRL, LEESBURG, FL, 3...

Community: Arlington Ridge

Plantation at Leesburg

4514 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$289,900

3 beds

2 baths

1,785 sq ft

House

4514 RIVER RIDGE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Halifax Plantation

3026 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$549,900

3 beds

3 baths

2,232 sq ft

House

3026 ADRIAN DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Plantation Bay Golf & Country Club

596 ALDENHAM LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$724,900

3 beds

2 baths

2,608 sq ft

House

596 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Lake James

$495,000

2 beds

2 baths

1,911 sq ft

House

7898 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

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Questions? Call us: (888) 625-4885

Kings Ridge

2131 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711

$299,999

2 beds

2 baths

1,394 sq ft

House

2131 BURLEY AVE, CLERMONT, FL, 34711

Community: Kings Ridge

Kings Ridge

3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711

$329,900

3 beds

2 baths

1,552 sq ft

House

3684 EVERSHOLT ST, CLERMONT, FL, 34711

Community: Kings Ridge

Solivita

469 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$499,000

3 beds

4 baths

2,616 sq ft

House

469 SORRENTO RD, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$309,900

3 beds

3 baths

1,830 sq ft

House

1833 W SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

Cresswind at Victoria Gardens

1677 VICTORIA GARDENS DR, DELAND, FL, 32..., Deland, FL 32724

$335,000

3 beds

2 baths

1,512 sq ft

House

1677 VICTORIA GARDENS DR, DELAND, FL, 32...

Community: Cresswind at Victoria Gardens

Latitude Margaritaville

244 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$429,900

2 beds

2 baths

1,466 sq ft

House

244 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Foxwood Lake Estates

5082 FOX CLIFF DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$204,990

2 beds

2 baths

1,352 sq ft

Manufactured Home

5082 FOX CLIFF DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Sullivan Ranch

21846 BELGIAN CT, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$300,000

2 beds

2 baths

1,437 sq ft

House

21846 BELGIAN CT, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Plantation at Leesburg

26234 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$274,900

3 beds

2 baths

1,761 sq ft

House

26234 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Spruce Creek Country Club

9385 SE 125TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$430,000

2 beds

2 baths

1,870 sq ft

House

9385 SE 125TH ST, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

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Spruce Creek South

10339 SE 179TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$209,000

2 beds

2 baths

1,008 sq ft

House

10339 SE 179TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Harbor Hills Country Club

5528 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$699,900

4 beds

3 baths

3,639 sq ft

House

5528 CITATION CT, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Huntington at Hunter's Ridge

23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$425,000

3 beds

3 baths

1,852 sq ft

House

23 FAWN HAVEN TRL, ORMOND BEACH, FL, 321...

Community: Huntington at Hunter's Ridge

Lakes at Laurel Highlands

1829 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811

$335,000

4 beds

2 baths

1,867 sq ft

House

1829 PRISTINE LOOP, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

The Country Club of Mount Dora

1741 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$1,575,000

5 beds

5 baths

5,573 sq ft

House

1741 EDGEWATER DR, MOUNT DORA, FL, 32757

Community: The Country Club of Mount Dora

Royal Highlands

5430 SIR CHURCHILL DR, LEESBURG, FL, 347..., Leesburg, FL 34748

$292,000

3 beds

2 baths

1,986 sq ft

House

5430 SIR CHURCHILL DR, LEESBURG, FL, 347...

Community: Royal Highlands

Kings Ridge

2225 ELVERSON AVE, CLERMONT, FL, 34711, Clermont, FL 34711

$389,000

3 beds

2 baths

1,892 sq ft

House

2225 ELVERSON AVE, CLERMONT, FL, 34711

Community: Kings Ridge

Ormond Renaissance

799 STERTHAUS DR 207, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$399,000

3 beds

2 baths

1,523 sq ft

Condo

799 STERTHAUS DR 207, ORMOND BEACH, FL, ...

Community: Ormond Renaissance

Indian River Colony Club

1469 PATRIOT DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$430,000

4 beds

3 baths

1,963 sq ft

House

1469 PATRIOT DR, MELBOURNE, FL, 32940

Community: Indian River Colony Club

Trilogy® Orlando

363 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736

$325,000

2 beds

2 baths

1,568 sq ft

House

363 ALCOVE DR, GROVELAND, FL, 34736

Villa

1253 ZYDECO CT, THE VILLAGES, FL, 32163

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

2 beds

2 baths

1,537 sq ft

Villa

2 beds

2 baths

1,100 sq ft

House

3 beds

2 baths

1,730 sq ft

House

3 beds

2 baths

1,993 sq ft

House

2 beds

2 baths

1,358 sq ft

House

3 beds

2 baths

1,919 sq ft

House

2 beds

2 baths

1,531 sq ft

Townhouse

3 beds

2 baths

1,967 sq ft

House

3 beds

3 baths

1,847 sq ft

House

3 beds

2 baths

2,211 sq ft

House

2 beds

2 baths

2,076 sq ft

House

3 beds

2 baths

1,785 sq ft

House

3 beds

3 baths

2,232 sq ft

House

3 beds

2 baths

2,608 sq ft

House

2 beds

2 baths

1,911 sq ft

House

2 beds

2 baths

1,394 sq ft

House

3 beds

2 baths

1,552 sq ft

House

3 beds

4 baths

2,616 sq ft

House

3 beds

3 baths

1,830 sq ft

House

3 beds