Winter Park, FL 55+ active adult communities & homes for sale - Page 2

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

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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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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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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

New The Villages®

2231 LANDREA LOOP, THE VILLAGES, FL, 321..., The Villages, FL 32163

$775,000

3 beds

3 baths

1,929 sq ft

House

2231 LANDREA LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

New Latitude Margaritaville

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

$375,000

2 beds

2 baths

1,308 sq ft

House

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

Community: Latitude Margaritaville

New Archers Mill

349 ROVER RD, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$449,990

4 beds

4 baths

2,405 sq ft

House

349 ROVER RD, ORMOND BEACH, FL, 32174

Community: Archers Mill

New Latitude Margaritaville

225 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$522,900

2 beds

2 baths

1,778 sq ft

House

225 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

New Tohoqua Reserve

1833 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744

$320,000

3 beds

2 baths

1,559 sq ft

Villa

1833 SPRING SHOWER CIR, KISSIMMEE, FL, 3...

Community: Tohoqua Reserve

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Questions? Call us: (888) 625-4885

New Carillon Lakes

4050 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811

$329,900

3 beds

2 baths

1,814 sq ft

House

4050 WHISTLEWOOD CIR, LAKELAND, FL, 3381...

Community: Carillon Lakes

New The Villages®

1230 DESILVA ST, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$492,000

3 beds

2 baths

1,842 sq ft

House

1230 DESILVA ST, LADY LAKE, FL, 32159

Community: The Villages®

New Kings Ridge

4010 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711

$439,900

2 beds

2 baths

2,102 sq ft

House

4010 HAMMERSMITH DR, CLERMONT, FL, 34711

Community: Kings Ridge

New The Villages®

2581 ERROL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162

$299,900

2 beds

2 baths

1,156 sq ft

Villa

2581 ERROL TER, THE VILLAGES, FL, 32162

Community: The Villages®

New Highland Lakes

27202 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$360,000

3 beds

2 baths

2,833 sq ft

House

27202 RACQUET CIR, LEESBURG, FL, 34748

Community: Highland Lakes

New Lakes of Mount Dora

8113 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757

$449,000

3 beds

2 baths

1,806 sq ft

House

8113 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...

Community: Lakes of Mount Dora

New Plantation at Leesburg

3851 MANOR OAKS CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$350,000

3 beds

3 baths

2,555 sq ft

House

3851 MANOR OAKS CT, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

926 LONG LEAF LN, THE VILLAGES, FL, 3216..., The Villages, FL 32163

$425,000

3 beds

2 baths

1,541 sq ft

House

926 LONG LEAF LN, THE VILLAGES, FL, 3216...

Community: The Villages®

New Heritage Isle

3354 MOONSTONE LN, MELBOURNE, FL, 32940, Melbourne, FL 32940

$350,000

2 beds

2 baths

1,655 sq ft

House

3354 MOONSTONE LN, MELBOURNE, FL, 32940

Community: Heritage Isle

New Pelican Bay Daytona Beach

537 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$900,000

5 beds

5 baths

3,523 sq ft

House

537 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

New The Savannahs

4224 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$434,900

4 beds

2 baths

2,046 sq ft

House

4224 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

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New Pennbrooke Fairways

622 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$44,247

1 beds

1 baths

560 sq ft

Manufactured Home

622 COTTAGE PARK LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New Scottish Highlands

32 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$267,000

2 beds

2 baths

1,528 sq ft

House

32 GORDON CT, LEESBURG, FL, 34788

Community: Scottish Highlands

New Plantation Bay Golf & Country Club

908 WOODSTREAM LN, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$399,000

3 beds

2 baths

1,627 sq ft

House

908 WOODSTREAM LN, ORMOND BEACH, FL, 321...

Community: Plantation Bay Golf & Country Club

New Spruce Creek South

17966 SE 97TH CT, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$279,900

3 beds

2 baths

1,450 sq ft

House

17966 SE 97TH CT, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

New Heritage Isle

3151 ANZA ST, MELBOURNE, FL, 32940, Melbourne, FL 32940

$449,900

3 beds

2 baths

1,861 sq ft

House

3151 ANZA ST, MELBOURNE, FL, 32940

Community: Heritage Isle

New Twin Lakes

2789 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772

$499,900

3 beds

3 baths

2,365 sq ft

House

2789 SOUTHLAND ST, ST CLOUD, FL, 34772

Community: Twin Lakes

New Foxwood Lake Estates

1794 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$139,900

2 beds

2 baths

900 sq ft

Manufactured Home

1794 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Cresswind at Lake Harris

1615 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778

$739,990

3 beds

4 baths

2,776 sq ft

House

1615 BELLAGIO LOOP, TAVARES, FL, 32778

Community: Cresswind at Lake Harris

New Cresswind at Lake Harris

1620 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778

$569,990

3 beds

3 baths

2,289 sq ft

House

1620 BELLAGIO LOOP, TAVARES, FL, 32778

Community: Cresswind at Lake Harris

New Cresswind at Lake Harris

1457 SANTORINI WAY, TAVARES, FL, 32778, Tavares, FL 32778

$449,990

3 beds

2 baths

1,724 sq ft

House

1457 SANTORINI WAY, TAVARES, FL, 32778

Community: Cresswind at Lake Harris

New The Villages®

1787 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159

$165,000

2 beds

2 baths

1,332 sq ft

Manufactured Home

1787 W SCHWARTZ BLVD, LADY LAKE, FL, 321...

Community: The Villages®

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New Cresswind DeLand

1214 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724

$599,990

3 beds

3 baths

2,129 sq ft

House

1214 CRESSWIND BLVD, DELAND, FL, 32724

Community: Cresswind DeLand

New Grand Haven

63 FRONT ST, PALM COAST, FL, 32137, Palm Coast, FL 32137

$1,560,000

3 beds

4 baths

3,296 sq ft

House

63 FRONT ST, PALM COAST, FL, 32137

Community: Grand Haven

New The Villages®

17239 SE 84TH KNIGHT AVE, THE VILLAGES, ..., The Villages, FL 32162

$365,000

3 beds

2 baths

1,660 sq ft

House

17239 SE 84TH KNIGHT AVE, THE VILLAGES, ...

Community: The Villages®

New The Villages®

1442 JOSHUA CT, THE VILLAGES, FL, 32163, The Villages, FL 32163

$349,000

2 beds

2 baths

1,257 sq ft

Villa

1442 JOSHUA CT, THE VILLAGES, FL, 32163

Community: The Villages®

New The Villages®

5415 ZAJAC AVE, THE VILLAGES, FL, 32163, The Villages, FL 32163

$309,000

2 beds

2 baths

1,295 sq ft

Villa

5415 ZAJAC AVE, THE VILLAGES, FL, 32163

Community: The Villages®

New Royal Palm

1444 ARECA PALM DR, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$405,906

3 beds

2 baths

1,624 sq ft

House

1444 ARECA PALM DR, PORT ORANGE, FL, 321...

Community: Royal Palm

New Plantation Bay Golf & Country Club

610 WOODBRIDGE DR, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$1,585,000

3 beds

3 baths

2,806 sq ft

House

610 WOODBRIDGE DR, ORMOND BEACH, FL, 321...

Community: Plantation Bay Golf & Country Club

New Pelican Bay Daytona Beach

176 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$255,000

2 beds

2 baths

1,461 sq ft

House

176 PALM SPARROW CT, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

New The Villages®

17449 SE 81ST NEWBERRY CT, THE VILLAGES,..., The Villages, FL 32162

$155,000

1 beds

1 baths

837 sq ft

House

17449 SE 81ST NEWBERRY CT, THE VILLAGES,...

Community: The Villages®

New Pelican Bay Daytona Beach

149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$179,000

2 beds

2 baths

1,129 sq ft

Condo

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

Community: Pelican Bay Daytona Beach

New Arlington Ridge

4358 ANTIETAM CREEK TRL, LEESBURG, FL, 3..., Leesburg, FL 34748

$354,900

3 beds

2 baths

1,776 sq ft

House

4358 ANTIETAM CREEK TRL, LEESBURG, FL, 3...

Community: Arlington Ridge

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

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New Summit Greens

2361 PRAIRIE DUNES, CLERMONT, FL, 34711, Clermont, FL 34711

$349,000

2 beds

2 baths

1,565 sq ft

House

2361 PRAIRIE DUNES, CLERMONT, FL, 34711

Community: Summit Greens

New Plantation at Leesburg

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$249,999

3 beds

2 baths

1,868 sq ft

House

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

1 2 3 4 5 6 7 8 9 10 11 12 13 14…57

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 2

95 communities near Winter Park

2,259 homes near Winter Park

3 beds

3 baths

1,929 sq ft

House

2 beds

2 baths

1,308 sq ft

House

4 beds

4 baths

2,405 sq ft

House

2 beds

2 baths

1,778 sq ft

House

3 beds

2 baths

1,559 sq ft

Villa

3 beds

2 baths

1,814 sq ft

House

3 beds

2 baths

1,842 sq ft

House

2 beds

2 baths

2,102 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

2,833 sq ft

House

3 beds

2 baths

1,806 sq ft

House

3 beds

3 baths

2,555 sq ft

House

3 beds

2 baths

1,541 sq ft

House

2 beds

2 baths

1,655 sq ft

House

5 beds

5 baths

3,523 sq ft

House

4 beds

2 baths

2,046 sq ft

House

1 beds

1 baths

560 sq ft

Manufactured Home

2 beds

2 baths

1,528 sq ft

House

3 beds

2 baths

1,627 sq ft

House

3 beds