Winter Park, FL 55+ active adult communities & homes for sale - Page 20

2,702 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

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

4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

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

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

$200ks - $800ks

Grand Haven, Palm Coast, FL

New and Resale | Age-targeted | Built 1997 - present | 1,901 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 (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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Questions? Call us: (888) 625-4885

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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 (1 reviews)

Cresswind at Victoria Gar...

$300ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

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

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

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

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

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

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

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

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

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

$200ks - $500ks

The Timbers at Everlands, Palm Bay, FL

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

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

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

Questions? Call us: (888) 625-4885

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

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

1 2...3

Ridgehaven

1312 OAKHAVEN AVE, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$414,410

4 beds

3 baths

2,190 sq ft

House

1312 OAKHAVEN AVE, ORMOND BEACH, FL, 321...

3580 CASALTA CIR, NEW SMYRNA BEACH, FL, ...

30173 EMERALD FOREST DR, MOUNT DORA, FL,...

Esplanade at McKinnon Groves

17742 SEDONA ST, WINTER GARDEN, FL, 3478..., Winter Garden, FL 34787

$916,028

3 beds

3 baths

2,475 sq ft

House

17742 SEDONA ST, WINTER GARDEN, FL, 3478...

Community: Esplanade at McKinnon Groves

Latitude Margaritaville

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

$648,000

3 beds

3 baths

2,110 sq ft

House

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

Community: Latitude Margaritaville

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Questions? Call us: (888) 625-4885

The Villages®

$330,000

2 beds

2 baths

1,332 sq ft

Villa

7618 SE 171ST SUN VALLEY PL, THE VILLAGE...

Community: The Villages®

The Villages®

$489,000

3 beds

3 baths

2,402 sq ft

House

823 SAN SALVADOR DR, THE VILLAGES, FL, 3...

Community: The Villages®

Pennbrooke Fairways

228 GRAND VISTA TRL, LEESBURG, FL, 34748, Leesburg, FL 34748

$270,000

2 beds

2 baths

1,568 sq ft

House

228 GRAND VISTA TRL, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Solivita

766 CARMEL LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$430,000

3 beds

3 baths

2,320 sq ft

House

766 CARMEL LN, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

8420 COUNTY RD A1, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$299,900

3 beds

2 baths

2,176 sq ft

Manufactured Home

8420 COUNTY RD A1, LADY LAKE, FL, 32159

Community: The Villages®

The Villages®

$950,000

3 beds

3 baths

2,192 sq ft

House

3452 BOSIE RUN, THE VILLAGES, FL, 32163

Community: The Villages®

Huntington at Hunter's Ridge

5 SHEAR WATER TRL, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$379,000

3 beds

2 baths

1,826 sq ft

House

5 SHEAR WATER TRL, ORMOND BEACH, FL, 321...

Community: Huntington at Hunter's Ridge

The Villages®

$650,000

3 beds

2 baths

2,000 sq ft

House

745 DOWDING WAY, THE VILLAGES, FL, 32162

Community: The Villages®

Stonecrest

17879 SE 125TH CIR, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$425,000

3 beds

3 baths

2,071 sq ft

House

17879 SE 125TH CIR, SUMMERFIELD, FL, 344...

Community: Stonecrest

Cindy Certified

1809 HAZELTON ST, PALM BAY, FL, 32907, Palm Bay, FL 32907

$355,650

4 beds

2 baths

1,755 sq ft

House

1809 HAZELTON ST, PALM BAY, FL, 32907

The Timbers at Everlands

1029 CAVAILIAN PL, PALM BAY, FL, 32907, Palm Bay, FL 32907

$397,000

3 beds

3 baths

2,032 sq ft

House

1029 CAVAILIAN PL, PALM BAY, FL, 32907

Community: The Timbers at Everlands

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Questions? Call us: (888) 625-4885

The Villages®

$525,000

3 beds

2 baths

1,685 sq ft

Villa

1134 SOUTHERN SUN DR, THE VILLAGES, FL, ...

Community: The Villages®

The Villages®

$450,000

3 beds

2 baths

1,731 sq ft

House

3602 PEPPERIDGE CIR, THE VILLAGES, FL, 3...

Community: The Villages®

Esplanade at McKinnon Groves

11341 BOURBON ROSE CIR, WINTER GARDEN, F..., Winter Garden, FL 34787

$936,063

4 beds

5 baths

2,974 sq ft

House

11341 BOURBON ROSE CIR, WINTER GARDEN, F...

Community: Esplanade at McKinnon Groves

Sandpiper Golf & Country Club

6031 SANDERLING DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$265,000

2 beds

2 baths

1,520 sq ft

House

6031 SANDERLING DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Cindy Certified

1947 ALTAVISTA CIR, LAKELAND, FL, 33810, Lakeland, FL 33810

$410,000

3 beds

2 baths

2,107 sq ft

2716 LYALL LOOP, THE VILLAGES, FL, 32163

Community: The Villages®

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

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Esplanade at McKinnon Groves

11275 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787

$420,000

2 beds

2 baths

1,515 sq ft

Villa

11275 SILVER TRUMPET LOOP, WINTER GARDEN...

Community: Esplanade at McKinnon Groves

Esplanade at McKinnon Groves

11279 SILVER TRUMPET LOOP, WINTER GARDEN..., Winter Garden, FL 34787

$432,318

2 beds

2 baths

1,515 sq ft

Villa

11279 SILVER TRUMPET LOOP, WINTER GARDEN...

Community: Esplanade at McKinnon Groves

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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.

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2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 20

98 communities near Winter Park

2,702 homes near Winter Park

4 beds

3 baths

2,190 sq ft

House

3 beds

2 baths

1,823 sq ft

House

4 beds

2 baths

2,521 sq ft

House

3 beds

2 baths

1,892 sq ft

House

3 beds

2 baths

1,891 sq ft

Townhouse

3 beds

2 baths

2,145 sq ft

House

3 beds

2 baths

2,202 sq ft

House

3 beds

2 baths

1,437 sq ft

Villa

3 beds

2 baths

1,839 sq ft

House

2 beds

2 baths

1,100 sq ft

House

4 beds

2 baths

1,850 sq ft

House

3 beds

2 baths

2,121 sq ft

House

3 beds

3 baths

1,718 sq ft

House

3 beds

2 baths

2,066 sq ft

House

3 beds

3 baths

2,475 sq ft

House

3 beds

3 baths

2,110 sq ft

House

2 beds

2 baths

1,332 sq ft

Villa

3 beds

3 baths

2,402 sq ft

House

2 beds

2 baths

1,568 sq ft

House

3 beds