Winter Park, FL 55+ active adult communities & homes for sale - Page 28

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

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

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4.7 rating (18 reviews)

Solivita

$300ks - $700ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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 (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 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

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

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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

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

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

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

The Country Club of Mount...

$200ks - $1Ms

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

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

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

Heritage - The Cottages o...

$300ks

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

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

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

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

4.8 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

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

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

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

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

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

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

1 2...3

The Villages®

$429,900

3 beds

2 baths

1,500 sq ft

House

2790 CARYTOWN LOOP, THE VILLAGES, FL, 32...

Community: The Villages®

Cindy Certified

2146 RIDGE POINTE LN, CLERMONT, FL, 3471..., Clermont, FL 34715

$599,900

4 beds

3 baths

2,373 sq ft

House

2146 RIDGE POINTE LN, CLERMONT, FL, 3471...

The Villages®

$550,000

3 beds

2 baths

1,906 sq ft

House

16846 SE 80TH BELLAVISTA CIR, THE VILLAG...

Community: The Villages®

Latitude Margaritaville

202 SUMMERTIME PL, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$469,900

2 beds

3 baths

1,748 sq ft

House

202 SUMMERTIME PL, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

The Savannahs

4304 CALADIUM CIR, WEST MELBOURNE, FL, 3..., West Melbourne, FL 32904

$389,900

3 beds

2 baths

1,812 sq ft

House

4304 CALADIUM CIR, WEST MELBOURNE, FL, 3...

Community: The Savannahs

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

Questions? Call us: (888) 625-4885

Breakaway Trails

3 ECHO WOODS WAY, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$599,900

4 beds

2 beds

2 baths

1,268 sq ft

Villa

911 MEDIRA DR, LADY LAKE, FL, 32159

Community: The Villages®

Trilogy® Orlando

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

$400,000

2 beds

2 baths

2,197 sq ft

House

228 BAYOU BEND RD, GROVELAND, FL, 34736

3737 ASTRAL RD, MELBOURNE, FL, 32901

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

Questions? Call us: (888) 625-4885

Cindy Certified

806 GRAND PARK CT, DELAND, FL, 32724, Deland, FL 32724

$339,900

4 beds

2 baths

1,830 sq ft

House

806 GRAND PARK CT, DELAND, FL, 32724

Plantation Bay Golf & Country Club

1025 SUDBURY LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$3,750,000

4 beds

5 baths

5,547 sq ft

Villa

1025 SUDBURY LN, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

The Villages®

$570,000

3 beds

2 baths

2,033 sq ft

House

595 RANDALL RD, THE VILLAGES, FL, 32163

Community: The Villages®

Silver Lakes

$414,990

3 beds

3 baths

1,902 sq ft

House

6323 SILVER LAKES DR, LAKELAND, FL, 3381...

Community: Silver Lakes

Royal Highlands

4808 KILT CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$305,000

2 beds

2 baths

2,213 sq ft

House

4808 KILT CT, LEESBURG, FL, 34748

Community: Royal Highlands

Summit Chase Villas

12520 ORANGEWOOD CT, TAVARES, FL, 32778, Tavares, FL 32778

$185,000

2 beds

2 baths

918 sq ft

Villa

12520 ORANGEWOOD CT, TAVARES, FL, 32778

Community: Summit Chase Villas

The Villages®

$599,900

3 beds

2 baths

2,666 sq ft

House

542 LOMA PASEO DR, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$359,900

3 beds

2 baths

1,559 sq ft

House

2007 YEARLING WAY, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$864,000

3 beds

2 baths

2,523 sq ft

House

8481 SE 168TH KITTREDGE LOOP, THE VILLAG...

Community: The Villages®

Cindy Certified

14 POWDER HILL LN, PALM COAST, FL, 32164, Palm Coast, FL 32164

$399,900

4 beds

2 baths

1,800 sq ft

House

14 POWDER HILL LN, PALM COAST, FL, 32164

Plantation at Leesburg

3701 PLANTATION BLVD, LEESBURG, FL, 3474..., Leesburg, FL 34748

$305,000

3 beds

2 baths

1,802 sq ft

House

3701 PLANTATION BLVD, LEESBURG, FL, 3474...

3124 REPOSE DR, CLERMONT, FL, 34714

The Villages®

$535,000

3 beds

2 baths

1,959 sq ft

House

522 LOMA PASEO DR, THE VILLAGES, FL, 321...

Community: The Villages®

Cindy Certified

5203 HAVEN VIEW DR, CLERMONT, FL, 34714, Clermont, FL 34714

$359,490

2 beds

2 baths

1,580 sq ft

House

5203 HAVEN VIEW DR, CLERMONT, FL, 34714

The Villages®

$325,000

3 beds

2 baths

1,392 sq ft

House

1911 DEL NORTE DR, THE VILLAGES, FL, 321...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Grand Haven

42 SHINNECOCK DR, PALM COAST, FL, 32137, Palm Coast, FL 32137

$399,900

3 beds

2 baths

1,883 sq ft

House

42 SHINNECOCK DR, PALM COAST, FL, 32137

Community: Grand Haven

Venetian Bay

3320 MARSILI AVE, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$354,900

4 beds

2 baths

1,662 sq ft

House

3320 MARSILI AVE, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

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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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2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 28

98 communities near Winter Park

2,702 homes near Winter Park

3 beds

2 baths

1,500 sq ft

House

4 beds

3 baths

2,373 sq ft

House

3 beds

2 baths

1,906 sq ft

House

2 beds

3 baths

1,748 sq ft

House

3 beds

2 baths

1,812 sq ft

House

4 beds

3 baths

2,506 sq ft

House

4 beds

2 baths

1,707 sq ft

House

4 beds

3 baths

2,471 sq ft

House

2 beds

2 baths

1,268 sq ft

Villa

2 beds

2 baths

2,197 sq ft

House

3 beds

2 baths

1,702 sq ft

House

3 beds

3 baths

1,909 sq ft

House

3 beds

2 baths

1,579 sq ft

House

2 beds

2 baths

1,266 sq ft

Villa

3 beds

3 baths

2,171 sq ft

House

3 beds

2 baths

1,429 sq ft

House

4 beds

2 baths

1,830 sq ft

House

4 beds

5 baths

5,547 sq ft

Villa

3 beds

2 baths

2,033 sq ft

House

3 beds