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

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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

13320 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

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Questions? Call us: (888) 625-4885

Spruce Creek South

9948 SE 175TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$279,900

2 beds

2 baths

1,878 sq ft

House

9948 SE 175TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

Esplanade at Highland Ranch

1339 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715

$630,000

3 beds

3 baths

2,449 sq ft

House

1339 ZEEK RIDGE ST, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

The Villages®

$329,000

2 beds

2 baths

1,203 sq ft

Villa

3021 BEARD RD, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek South

9499 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$249,500

2 beds

2 baths

1,678 sq ft

House

9499 SE 174TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

Latitude Margaritaville

206 ST SOMEWHERE DR, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$475,000

2 beds

2 baths

1,606 sq ft

Villa

206 ST SOMEWHERE DR, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

The Lakes at Harmony

3116 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773

$434,000

3 beds

2 baths

1,924 sq ft

House

3116 OXBOW CT, HARMONY, FL, 34773

Community: The Lakes at Harmony

Spruce Creek Country Club

9033 SE 135TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$274,900

3 beds

2 baths

1,726 sq ft

House

9033 SE 135TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Highland Lakes

26126 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$289,900

3 beds

2 baths

1,890 sq ft

House

26126 NEWCOMBE CIR, LEESBURG, FL, 34748

Community: Highland Lakes

Spruce Creek Country Club

11864 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$369,500

2 beds

2 baths

2,270 sq ft

House

11864 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Cresswind at Victoria Gardens

1011 CLAYMONT BLVD, DELAND, FL, 32724, Deland, FL 32724

$347,047

3 beds

2 baths

1,541 sq ft

House

1011 CLAYMONT BLVD, DELAND, FL, 32724

House

3987 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

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

Questions? Call us: (888) 625-4885

Trilogy® Orlando

626 CONSERVATION BLVD, GROVELAND, FL, 34..., Groveland, FL 34736

$438,000

3 beds

2 baths

1,905 sq ft

House

626 CONSERVATION BLVD, GROVELAND, FL, 34...

Community: Trilogy® Orlando

Trilogy® Orlando

243 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$400,000

3 beds

2 baths

1,838 sq ft

House

243 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Latitude Margaritaville

613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$359,900

2 beds

2 baths

1,204 sq ft

House

613 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

Trilogy® Orlando

126 BAYOU BEND RD, GROVELAND, FL, 34736, Groveland, FL 34736

$325,000

2 beds

2 baths

1,269 sq ft

House

126 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

Sullivan Ranch

30442 LIPIZZAN TER, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$315,000

3 beds

2 baths

1,663 sq ft

Villa

30442 LIPIZZAN TER, MOUNT DORA, FL, 3275...

Community: Sullivan Ranch

Ridgehaven

1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$423,800

4 beds

3 baths

2,190 sq ft

House

1340 OAKHAVEN AVE, ORMOND BEACH, FL, 321...

Community: Ridgehaven

Ridgehaven

1320 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$420,510

4 beds

2 baths

1,908 sq ft

House

1320 OAKHAVEN AVE, ORMOND BEACH, FL, 321...

Community: Ridgehaven

Solivita

100 MERIDIAN AVE, POINCIANA, FL, 34759, Poinciana, FL 34759

$305,000

2 beds

2 baths

1,840 sq ft

House

100 MERIDIAN AVE, POINCIANA, FL, 34759

Community: Solivita

Archers Mill

3361 ARCH AVE, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$450,990

4 beds

4 baths

3,004 sq ft

House

3361 ARCH AVE, ORMOND BEACH, FL, 32174

Community: Archers Mill

Stonecrest

12103 SE 176TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$374,000

3 beds

2 baths

1,822 sq ft

House

12103 SE 176TH LOOP, SUMMERFIELD, FL, 34...

House

1524 CONWAY CT, THE VILLAGES, FL, 32162

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

2,004 sq ft

House

3 beds

2 baths

1,863 sq ft

House

3 beds

3 baths

2,208 sq ft

House

3 beds

2 baths

2,031 sq ft

House

2 beds

3 baths

2,346 sq ft

House

2 beds

2 baths

1,878 sq ft

House

3 beds

3 baths

2,449 sq ft

House

2 beds

2 baths

1,203 sq ft

Villa

2 beds

2 baths

1,678 sq ft

House

2 beds

2 baths

1,606 sq ft

Villa

3 beds

2 baths

1,924 sq ft

House

3 beds

2 baths

1,726 sq ft

House

3 beds

2 baths

1,890 sq ft

House

2 beds

2 baths

2,270 sq ft

House

3 beds

2 baths

1,541 sq ft

House

2 beds

2 baths

1,520 sq ft

House

2 beds

2 baths

1,473 sq ft

House

2 beds

2 baths

1,356 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds