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

90 communities near Winter Park

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4 rating (17 reviews)

The Villages®

$100ks - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

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3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 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 (3 reviews)

Lake Ashton

$200ks - $500ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

4.7 rating (3 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 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.

5 rating (1 reviews)

Plantation Bay Golf &...

$400ks - $2Ms

Plantation Bay Golf &..., Ormond Beach, FL

New and Resale | Age-targeted | Built 1988 - present | 3,500 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

New and Resale | Age-targeted | Built 1980 - present | 1,000 homes

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Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

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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 (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 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

$200ks - $800ks

Grand Haven, Palm Coast, FL

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

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

5 rating (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

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5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

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5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $600ks

Cresswind at Victoria Gar..., DeLand, FL

Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200ks - $300ks

Traditions at Lake Ruby, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes

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Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

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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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

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Questions? Call us: (888) 625-4885

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

1 2...3

New Lakes at Laurel Highlands

2788 GRANDBURY GROVE RD, LAKELAND, FL, 3..., Lakeland, FL 33811

$314,000

3 beds

2 baths

1,711 sq ft

House

Community: Highland Fairways

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New Solivita

531 VILLA PARK RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$399,000

3 beds

3 baths

2,307 sq ft

House

531 VILLA PARK RD, KISSIMMEE, FL, 34759

Community: Solivita

New Venetian Bay

452 VENETIAN VILLA DR, NEW SMYRNA BEACH,..., New Smyrna Beach, FL 32168

$519,900

2 beds

2 baths

2,267 sq ft

House

452 VENETIAN VILLA DR, NEW SMYRNA BEACH,...

Community: Venetian Bay

New Royal Harbor

6210 SAILBOAT AVE, TAVARES, FL, 32778, Tavares, FL 32778

$315,000

3 beds

2 baths

1,594 sq ft

House

6210 SAILBOAT AVE, TAVARES, FL, 32778

Community: Royal Harbor

New The Villages®

2074 BILLER CIR, THE VILLAGES, FL, 32163, The Villages, FL 32163

$929,000

3 beds

3 baths

2,013 sq ft

House

2074 BILLER CIR, THE VILLAGES, FL, 32163

Community: The Villages®

New Trilogy® Orlando

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

$450,000

2 beds

2 baths

2,197 sq ft

House

163 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

New Trilogy® Orlando

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

$319,000

2 beds

2 baths

1,568 sq ft

House

95 BAYOU BEND RD, GROVELAND, FL, 34736

Community: Trilogy® Orlando

New The Villages®

2083 JASPER WAY, THE VILLAGES, FL, 32162, The Villages, FL 32162

$339,900

3 beds

2 baths

1,397 sq ft

Villa

2083 JASPER WAY, THE VILLAGES, FL, 32162

Community: The Villages®

New Solivita

521 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$249,000

2 beds

2 baths

1,258 sq ft

House

521 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

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New The Villages®

2405 KINGSTREE PL, THE VILLAGES, FL, 321..., The Villages, FL 32162

$278,000

2 beds

2 baths

1,188 sq ft

House

2405 KINGSTREE PL, THE VILLAGES, FL, 321...

Community: The Villages®

New Grand Isle

1575 BOCA RIO DR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$439,999

3 beds

2 baths

1,764 sq ft

House

1575 BOCA RIO DR, MELBOURNE, FL, 32940

House

3976 IRONWOOD LN, THE VILLAGES, FL, 3216...

Community: The Villages®

New Summer Trees

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$275,000

2 beds

2 baths

1,370 sq ft

House

102 UNDERBRUSH TRL, PORT ORANGE, FL, 321...

Community: Summer Trees

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New Del Webb Sunbridge

6362 SHIMMERING SHORES LN, ST CLOUD, FL,..., St Cloud, FL 34771

$724,900

3 beds

3 baths

2,249 sq ft

House

6362 SHIMMERING SHORES LN, ST CLOUD, FL,...

Community: Del Webb Sunbridge

New Latitude Margaritaville

672 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$775,000

3 beds

4 baths

2,542 sq ft

House

672 HANG LOOSE WAY, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

New Harbor Hills Country Club

39545 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$639,000

4 beds

3 baths

2,954 sq ft

House

39545 HARBOR HILLS BLVD, LADY LAKE, FL, ...

Community: Harbor Hills Country Club

New The Villages®

5186 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484

$280,000

3 beds

4 baths

1,929 sq ft

House

5186 NE 122ND BLVD, OXFORD, FL, 34484

House

47 CROOKED PINE RD, PORT ORANGE, FL, 321...

Community: Summer Trees

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New The Villages®

9041 SE 166TH KATHY LOOP, THE VILLAGES, ..., The Villages, FL 32162

$520,000

3 beds

2 baths

1,808 sq ft

Villa

9041 SE 166TH KATHY LOOP, THE VILLAGES, ...

Community: The Villages®

New Highland Fairways

3202 OTTER CREEK CT, LAKELAND, FL, 33810, Lakeland, FL 33810

$169,900

2 beds

2 baths

1,274 sq ft

Manufactured Home

3202 OTTER CREEK CT, LAKELAND, FL, 33810

Community: Highland Fairways

New Lakeside Landings

5076 NEPTUNE CIR, OXFORD, FL, 34484, Oxford, FL 34484

$262,500

3 beds

2 baths

1,404 sq ft

House

5076 NEPTUNE CIR, OXFORD, FL, 34484

Community: Lakeside Landings

New Sullivan Ranch

30337 GIDRAN TER, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$544,000

4 beds

3 baths

2,307 sq ft

House

30337 GIDRAN TER, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

New Bridgewater at Viera

1765 VELKY LN, MELBOURNE, FL, 32940, Melbourne, FL 32940

$425,000

2 beds

2 baths

1,565 sq ft

House

1765 VELKY LN, MELBOURNE, FL, 32940

Condo

134 BLUE HERON DR C, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

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New The Villages®

2004 FLOWERSVILLE PL, THE VILLAGES, FL, ..., The Villages, FL 32163

$429,850

3 beds

2 baths

1,589 sq ft

House

2004 FLOWERSVILLE PL, THE VILLAGES, FL, ...

Community: The Villages®

New The Villages®

5837 STORMS AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163

$710,000

3 beds

2 baths

1,933 sq ft

House

5837 STORMS AVE, THE VILLAGES, FL, 32163

Community: The Villages®

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90 communities

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

90 communities near Winter Park

2,540 homes near Winter Park

3 beds

2 baths

1,711 sq ft

House

3 beds

2 baths

1,711 sq ft

House

3 beds

2 baths

1,827 sq ft

House

3 beds

2 baths

1,887 sq ft

House

3 beds

2 baths

2,213 sq ft

House

3 beds

3 baths

2,307 sq ft

House

2 beds

2 baths

2,267 sq ft

House

3 beds

2 baths

1,594 sq ft

House

3 beds

3 baths

2,013 sq ft

House

2 beds

2 baths

2,197 sq ft

House

2 beds

2 baths

1,568 sq ft

House

3 beds

2 baths

1,397 sq ft

Villa

2 beds

2 baths

1,258 sq ft

House

2 beds

2 baths

1,188 sq ft

House

3 beds

2 baths

1,764 sq ft

House

3 beds

2 baths

1,842 sq ft

House

4 beds

2 baths

2,204 sq ft

House

3 beds

2 baths

1,526 sq ft

House

3 beds

2 baths

1,925 sq ft

House

3 beds