Winter Park, FL 55+ active adult communities & homes for sale - Page 34

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

9570 SE 136TH PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$359,999

2 beds

2 baths

1,528 sq ft

House

9570 SE 136TH PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

The Lakes at Harmony

3113 SONGBIRD CIR, ST CLOUD, FL, 34773, St Cloud, FL 34773

$385,000

3 beds

2 baths

1,876 sq ft

House

3113 SONGBIRD CIR, ST CLOUD, FL, 34773

53 HIGH VISTA DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

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

Questions? Call us: (888) 625-4885

Del Webb Orlando

519 CADIZ DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$300,000

2 beds

2 baths

1,358 sq ft

House

519 CADIZ DR, DAVENPORT, FL, 33837

Community: Del Webb Orlando

Solivita

130 PRIMA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$369,000

3 beds

2 baths

2,141 sq ft

House

130 PRIMA DR, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$369,900

3 beds

2 baths

1,527 sq ft

House

1521 HOLLYBERRY PL, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

8331 COUNTY RD 109, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$289,900

4 beds

2 baths

2,240 sq ft

Manufactured Home

8331 COUNTY RD 109, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$379,500

3 beds

2 baths

1,527 sq ft

House

3135 BURNS DR, THE VILLAGES, FL, 32163

Community: The Villages®

Spruce Creek Country Club

9029 SE 130TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$379,900

3 beds

2 baths

2,809 sq ft

House

9029 SE 130TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

The Villages®

$328,500

2 beds

2 baths

1,188 sq ft

Villa

1004 DAVIT PL, THE VILLAGES, FL, 32162

Community: The Villages®

The Villages®

$559,900

3 beds

2 baths

1,969 sq ft

Villa

1411 FRANKLIN CT, THE VILLAGES, FL, 3216...

Community: The Villages®

The Villages®

$294,500

2 beds

2 baths

1,284 sq ft

Villa

9108 SE 177TH BELMONT PL, THE VILLAGES, ...

Community: The Villages®

Scottish Highlands

335 RIVER GLASS CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$269,500

3 beds

3 baths

2,189 sq ft

House

335 RIVER GLASS CT, LEESBURG, FL, 34788

Community: Scottish Highlands

Spruce Creek South

17990 SE 100TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$319,000

3 beds

2 baths

1,870 sq ft

House

17990 SE 100TH TER, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

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

Questions? Call us: (888) 625-4885

Colonnades

$219,000

2 beds

2 baths

1,317 sq ft

House

1690 COLONNADES CIR, LAKELAND, FL, 33811

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...

Community: Twin Lakes

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

Questions? Call us: (888) 625-4885

The Villages®

$700,000

4 beds

3 baths

2,959 sq ft

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

Foxwood Lake Estates

1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$164,900

3 beds

2 baths

1,176 sq ft

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Four Seasons at Orlando

1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$419,000

2 beds

2 baths

1,557 sq ft

Villa

1999 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Lakes at Laurel Highlands

2933 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811

$375,000

5 beds

3 baths

2,696 sq ft

House

2933 IVY LAKE CT, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

High Vista at Ridgewood Lakes

116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$299,000

3 beds

2 baths

1,776 sq ft

House

116 FLEMING LN, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

The Villages®

603 ROBIN LN, WILDWOOD, FL, 34785, Wildwood, FL 34785

$159,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

603 ROBIN LN, WILDWOOD, FL, 34785

Community: The Villages®

The Villages®

$260,000

2 beds

2 baths

1,121 sq ft

Villa

1714 EL NINO ST, THE VILLAGES, FL, 32162

Community: The Villages®

Plantation Bay Golf & Country Club

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

$550,000

3 beds

2 baths

2,090 sq ft

House

608 ALDENHAM LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Plantation at Leesburg

25845 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$325,000

3 beds

2 baths

2,047 sq ft

House

25845 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

717 TANGERINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$215,000

2 beds

2 baths

1,332 sq ft

Manufactured Home

717 TANGERINE DR, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$1,149,000

3 beds

2 baths

3,082 sq ft

House

2254 ISLEWORTH CIR, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Harbor Hills Country Club

5204 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$449,900

3 beds

3 baths

2,248 sq ft

House

5204 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Lake Ashton

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL..., Winter Haven, FL 33884

$579,900

3 beds

2 baths

2,354 sq ft

House

5268 PEBBLE BEACH BLVD, WINTER HAVEN, FL...

Community: Lake Ashton

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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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2,259 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 34

95 communities near Winter Park

2,259 homes near Winter Park

2 beds

2 baths

1,528 sq ft

House

3 beds

2 baths

1,876 sq ft

House

3 beds

3 baths

2,453 sq ft

House

3 beds

2 baths

1,404 sq ft

House

3 beds

2 baths

1,856 sq ft

House

2 beds

2 baths

1,358 sq ft

House

3 beds

2 baths

2,141 sq ft

House

3 beds

2 baths

1,527 sq ft

House

4 beds

2 baths

2,240 sq ft

Manufactured Home

3 beds

2 baths

1,527 sq ft

House

3 beds

2 baths

2,809 sq ft

House

2 beds

2 baths

1,188 sq ft

Villa

3 beds

2 baths

1,969 sq ft

Villa

2 beds

2 baths

1,284 sq ft

Villa

3 beds

3 baths

2,189 sq ft

House

3 beds

2 baths

1,870 sq ft

House

2 beds

2 baths

1,317 sq ft

House

2 beds

2 baths

1,652 sq ft

House

2 beds

2 baths

1,488 sq ft

House

2 beds