Winter Park, FL 55+ active adult communities & homes for sale - Page 4

2,377 homes near Winter Park

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4 rating (17 reviews)

The Villages®

<$100k - $2Ms

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

Download the Ultimate 55+ Homebuying Guide Whether you’re searching for a 55+ community, downsizing, or exploring other housing options, our free-to-download guide will assist you in finding the ideal home for your needs.

Grand Haven

$300Ks - $1Ms

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 homes

Pelican Bay Daytona Beach

$100Ks - $400Ks

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 - $400Ks

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

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Questions? Call us: (888) 625-4885

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

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 - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (8 reviews)

Royal Highlands

$200Ks - $400Ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

Del Webb at Viera

$400Ks - $1Ms

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

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Questions? Call us: (888) 625-4885

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

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 - $800Ks

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

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Questions? Call us: (888) 625-4885

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 - $800Ks

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

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

$300Ks - $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

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

Questions? Call us: (888) 625-4885

1 rating (1 reviews)

Sullivan Ranch

$200Ks - $700Ks

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

The Savannahs

4464 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$399,900

4 beds

2 baths

2,051 sq ft

House

4464 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

Venetian Bay

3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$680,000

3 beds

3 baths

2,472 sq ft

House

3555 MARIBELLA DR, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

The Villages®

$412,990

3 beds

2 baths

1,647 sq ft

Villa

2467 ROGERS RD, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$395,000

3 beds

2 baths

1,644 sq ft

House

294 MATISSE AVE, THE VILLAGES, FL, 32162

Community: The Villages®

New Trilogy® Orlando

383 ALCOVE DR, GROVELAND, FL, 34736, Groveland, FL 34736

$357,000

2 beds

2 baths

1,568 sq ft

Villa

383 ALCOVE DR, GROVELAND, FL, 34736

House

109 FALLING ACORN AVE, GROVELAND, FL, 34...

Community: Trilogy® Orlando

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Questions? Call us: (888) 625-4885

The Villages®

$683,000

3 beds

3 baths

2,252 sq ft

Villa

17487 SE 84TH FOXGROVE AVE, THE VILLAGES...

Community: The Villages®

The Villages®

$715,000

3 beds

2 baths

1,922 sq ft

House

5835 TUPPER CT, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$234,900

2 beds

2 baths

1,143 sq ft

Villa

1611 CAMPOS DR, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$575,000

3 beds

3 baths

1,911 sq ft

House

4528 HAYWARD PATH, THE VILLAGES, FL, 321...

Community: The Villages®

Halifax Plantation

3205 BAILEY ANN DR, ORMOND BEACH, FL, 32..., Ormond Beach, FL 32174

$389,900

3 beds

2 baths

1,695 sq ft

House

3205 BAILEY ANN DR, ORMOND BEACH, FL, 32...

Community: Halifax Plantation

The Villages®

$177,504

2 beds

2 baths

1,092 sq ft

Manufactured Home

817 HIBISCUS DR, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$499,999

3 beds

2 baths

1,416 sq ft

Villa

431 JARQUIN WAY, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$329,900

3 beds

2 baths

1,495 sq ft

House

934 ORCHID ST, THE VILLAGES, FL, 32159

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Lakeside Landings

10069 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484

$429,990

3 beds

2 baths

2,059 sq ft

House

10069 LAKE MIONA WAY, OXFORD, FL, 34484

Community: Lakeside Landings

The Villages®

$539,900

3 beds

2 baths

1,924 sq ft

House

4216 BALCHARAN TER, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$274,900

2 beds

2 baths

1,143 sq ft

Villa

1615 NAVIDAD ST, THE VILLAGES, FL, 32162

Community: The Villages®

New Halifax Plantation

3324 WESTMEATH DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$675,000

4 beds

3 baths

2,724 sq ft

House

3324 WESTMEATH DR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

New Solivita

405 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$375,000

3 beds

3 baths

2,350 sq ft

House

405 BALBOA DR, KISSIMMEE, FL, 34759

Community: Solivita

New The Villages®

2429 HOPESPRING LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162

$349,000

2 beds

2 baths

1,367 sq ft

House

2429 HOPESPRING LOOP, THE VILLAGES, FL, ...

Community: The Villages®

New Spruce Creek Country Club

9345 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$479,000

2 beds

2 baths

1,989 sq ft

House

9345 SE 136TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Royal Highlands

5309 CORNWALL CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$375,000

3 beds

3 baths

2,337 sq ft

House

5309 CORNWALL CT, LEESBURG, FL, 34748

Community: Royal Highlands

Tohoqua Reserve

1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$489,000

3 beds

3 baths

2,175 sq ft

House

1974 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

House

12135 SE 172ND LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

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

Questions? Call us: (888) 625-4885

Traditions at Lake Ruby

3738 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$329,000

2 beds

2 baths

1,797 sq ft

House

3738 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

The Villages®

$299,000

2 beds

2 baths

1,156 sq ft

Villa

930 MARGAUX TRL, THE VILLAGES, FL, 32162

Community: The Villages®

1 2 3 4 5 6 7 8 9 10 11 12 13 14…60

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2,377 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 4

90 communities near Winter Park

2,377 homes near Winter Park

4 beds

2 baths

2,051 sq ft

House

3 beds

3 baths

2,472 sq ft

House

3 beds

2 baths

1,647 sq ft

Villa

3 beds

2 baths

1,644 sq ft

House

2 beds

2 baths

1,568 sq ft

Villa

3 beds

2 baths

1,537 sq ft

Villa

3 beds

2 baths

1,820 sq ft

House

4 beds

2 baths

3,865 sq ft

House

3 beds

2 baths

1,993 sq ft

House

3 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

2,000 sq ft

House

3 beds

2 baths

1,918 sq ft

House

3 beds

2 baths

1,780 sq ft

House

3 beds

3 baths

2,252 sq ft

Villa

3 beds

2 baths

1,922 sq ft

House

2 beds

2 baths

1,143 sq ft

Villa

3 beds

3 baths

1,911 sq ft

House

3 beds

2 baths

1,695 sq ft

House

2 beds

2 baths

1,092 sq ft

Manufactured Home

3 beds