Winter Park, FL 55+ active adult communities & homes for sale - Page 51

2,259 homes 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

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

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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

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

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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

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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

Grand Haven

$200ks - $800ks

Grand Haven, Palm Coast, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 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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Questions? Call us: (888) 625-4885

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 (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

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

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

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

5 rating (1 reviews)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 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 (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

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Questions? Call us: (888) 625-4885

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

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

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 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

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 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

The Timbers at Everlands

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

New Construction | 55+ age-restricted | Built 2023 - present | 450 homes

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

Questions? Call us: (888) 625-4885

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

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

1 2...3

Spruce Creek Country Club

8789 SE 136TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$312,000

3 beds

2 baths

2,029 sq ft

House

8789 SE 136TH LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

Solivita

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

$239,239

2 beds

2 baths

1,258 sq ft

House

601 GRAND CANAL DR, KISSIMMEE, FL, 34759

Community: Solivita

VillageWalk at Lake Nona

7991 ESTA LN, ORLANDO, FL, 32827, Orlando, FL 32827

$950,000

4 beds

5 baths

3,454 sq ft

House

7991 ESTA LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

Scottish Highlands

2105 GREENLAW CT 2105, LEESBURG, FL, 347..., Leesburg, FL 34788

$175,000

2 beds

2 baths

932 sq ft

Condo

2105 GREENLAW CT 2105, LEESBURG, FL, 347...

Community: Scottish Highlands

Cresswind at Victoria Gardens

322 BELLINGRATH TER, DELAND, FL, 32724, Deland, FL 32724

$550,000

3 beds

3 baths

2,708 sq ft

House

322 BELLINGRATH TER, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

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Questions? Call us: (888) 625-4885

Cresswind DeLand

1213 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724

$499,990

3 beds

3 baths

1,983 sq ft

House

1213 CRESSWIND BLVD, DELAND, FL, 32724

Community: Cresswind DeLand

Cresswind DeLand

1235 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724

$574,990

3 beds

4 baths

2,496 sq ft

House

1235 CRESSWIND BLVD, DELAND, FL, 32724

Community: Cresswind DeLand

Solivita

806 EBB TIDE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$414,000

3 beds

3 baths

2,011 sq ft

House

806 EBB TIDE LN, KISSIMMEE, FL, 34759

Community: Solivita

Summer Trees

127 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$247,900

3 beds

2 baths

1,426 sq ft

House

127 CYPRESS POND RD, PORT ORANGE, FL, 32...

Community: Summer Trees

Foxwood Lake Estates

4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381..., Lakeland, FL 33810

$179,900

2 beds

2 baths

1,456 sq ft

Manufactured Home

4969 FOXWOOD LAKE DR, LAKELAND, FL, 3381...

Community: Foxwood Lake Estates

Lake James

$399,000

2 beds

2 baths

1,925 sq ft

House

7914 LAKE JAMES BLVD, LAKELAND, FL, 3381...

Community: Lake James

Plantation at Leesburg

4704 RIVER RIDGE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$399,900

3 beds

2 baths

2,155 sq ft

House

4704 RIVER RIDGE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Sullivan Ranch

21632 HIDDEN CRK, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$679,000

4 beds

4 baths

3,853 sq ft

House

21632 HIDDEN CRK, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Spruce Creek South

10767 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$225,000

3 beds

2 baths

1,690 sq ft

House

10767 SE 174TH LOOP, SUMMERFIELD, FL, 34...

Community: Spruce Creek South

Stonecrest

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

$299,900

3 beds

2 baths

1,326 sq ft

House

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

Community: Stonecrest

Del Webb Oasis

15162 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787

$865,000

2 beds

2 baths

2,049 sq ft

House

15162 CANOPY COVER DR, WINTER GARDEN, FL...

Community: Del Webb Oasis

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

Questions? Call us: (888) 625-4885

The Villages®

$262,900

2 beds

2 baths

1,120 sq ft

House

8065 SE 175TH COLUMBIA PL, THE VILLAGES,...

Community: The Villages®

Twin Lakes

2557 YELLOW BRICK RD, ST CLOUD, FL, 3477..., St Cloud, FL 34772

$319,900

2 beds

2 baths

1,464 sq ft

Villa

2557 YELLOW BRICK RD, ST CLOUD, FL, 3477...

Community: Twin Lakes

Lakes of Mount Dora

8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$475,000

3 beds

2 baths

2,081 sq ft

House

8852 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

Latitude Margaritaville

280 LAST MANGO, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$389,000

2 beds

2 baths

1,456 sq ft

Villa

280 LAST MANGO, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

Foxwood Lake Estates

5079 LODGEWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$179,000

2 beds

2 baths

1,144 sq ft

Manufactured Home

5079 LODGEWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Pennbrooke Fairways

32819 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$185,700

2 beds

2 baths

1,162 sq ft

House

32819 TIMBERWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Venetian Bay

3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$299,000

3 beds

3 baths

1,614 sq ft

Townhouse

3009 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Halifax Plantation

3034 ADRIAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$545,000

4 beds

3 baths

2,641 sq ft

House

3034 ADRIAN DR, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Lakeside Landings

4846 AUDREY MARIE CT, OXFORD, FL, 34484, Oxford, FL 34484

$399,980

3 beds

2 baths

2,200 sq ft

House

4846 AUDREY MARIE CT, OXFORD, FL, 34484

Community: Lakeside Landings

Arlington Ridge

27343 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$327,000

3 beds

2 baths

1,607 sq ft

House

27343 ROANOKE DR, LEESBURG, FL, 34748

Community: Arlington Ridge

Del Webb Orlando

536 ARENA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$309,000

3 beds

2 baths

1,508 sq ft

House

536 ARENA DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

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5133 LINKS LN, LEESBURG, FL, 34748

Community: Royal Highlands

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

Questions? Call us: (888) 625-4885

The Villages®

$352,829

2 beds

2 baths

1,270 sq ft

Villa

1067 CARVER CT, THE VILLAGES, FL, 32163

Community: The Villages®

Highland Lakes

26209 NEWCOMBE CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$249,000

2 beds

2 baths

1,514 sq ft

House

26209 NEWCOMBE CIR, LEESBURG, FL, 34748

Community: Highland Lakes

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Frequently Asked Questions

What size 55+ communities are there in Winter Park?

In Winter Park, there is 1 small community with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Park?

The smallest 55+ community in Winter Park has 178 homes, the largest has 178 homes, and the average community consists of 178 homes.

Are there new 55+ homes available in Winter Park?

Yes, there is new 55+ home available in Winter Park. The most recent community started in Winter Park include Rosalia Winter Park. There is also 1 community in Winter Park that offers new construction homes, including Rosalia Winter Park.

Are there gated 55+ communities in Winter Park?

Yes, there is gated 55+ community in Winter Park. The only 55+ community in Winter Park is gated. For instance, Rosalia Winter Park is a gated community with 178 homes.

Want more information about active adult communities around Winter Park?

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Call us: (888) 625-4885

2,259 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 51

95 communities near Winter Park

2,259 homes near Winter Park

3 beds

2 baths

2,029 sq ft

House

2 beds

2 baths

1,258 sq ft

House

4 beds

5 baths

3,454 sq ft

House

2 beds

2 baths

932 sq ft

Condo

3 beds

3 baths

2,708 sq ft

House

3 beds

3 baths

1,983 sq ft

House

3 beds

4 baths

2,496 sq ft

House

3 beds

3 baths

2,011 sq ft

House

3 beds

2 baths

1,426 sq ft

House

2 beds

2 baths

1,456 sq ft

Manufactured Home

2 beds

2 baths

1,925 sq ft

House

3 beds

2 baths

2,155 sq ft

House

4 beds

4 baths

3,853 sq ft

House

3 beds

2 baths

1,690 sq ft

House

3 beds

2 baths

1,326 sq ft

House

2 beds

2 baths

2,049 sq ft

House

2 beds

2 baths

1,120 sq ft

House

2 beds

2 baths

1,464 sq ft

Villa

3 beds

2 baths

2,081 sq ft

House

2 beds