Winter Park, FL 55+ active adult communities & homes for sale - Page 4

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

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

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

2191 SILVER RE DR, LAKELAND, FL, 33810

Community: Silver Lakes

New

Cindy Certified

5349 SANDPINE HAVEN LN, PORT ORANGE, FL,..., Port Orange, FL 32128

$359,900

3 beds

2 baths

1,750 sq ft

House

5349 SANDPINE HAVEN LN, PORT ORANGE, FL,...

New The Lakes at Harmony

3128 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773

$337,500

2 beds

2 baths

1,408 sq ft

House

3128 SONGBIRD CIR, HARMONY, FL, 34773

Community: The Lakes at Harmony

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Questions? Call us: (888) 625-4885

New The Villages®

1479 OLYMPIA ST, THE VILLAGES, FL, 32163, The Villages, FL 32163

$306,900

2 beds

2 baths

1,188 sq ft

Villa

1479 OLYMPIA ST, THE VILLAGES, FL, 32163

Community: The Villages®

New Plantation Bay Golf & Country Club

214 ASHWOOD CT, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$1,275,000

3 beds

3 baths

2,995 sq ft

House

214 ASHWOOD CT, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

New Trilogy® Orlando

312 SALT MARSH LN, GROVELAND, FL, 34736, Groveland, FL 34736

$525,000

2 beds

2 baths

1,948 sq ft

House

312 SALT MARSH LN, GROVELAND, FL, 34736

Community: Trilogy® Orlando

New

Cindy Certified

4440 PAGOSA SPRINGS CIR, MELBOURNE, FL, ..., Melbourne, FL 32901

$359,900

3 beds

2 baths

1,772 sq ft

House

4440 PAGOSA SPRINGS CIR, MELBOURNE, FL, ...

New

Cindy Certified

13361 SE 101ST AVE, BELLEVIEW, FL, 34420, Belleview, FL 34420

$234,900

2 baths

1,310 sq ft

Townhouse

1251 MIRAFLORES TRL, PALM BAY, FL, 32907

Community: The Timbers at Everlands

New

Cindy Certified

769 GRAND RESERVE DR, BUNNELL, FL, 32110, Bunnell, FL 32110

$312,900

3 beds

4 beds

3 baths

2,580 sq ft

House

3722 LONGFORD CIR, ORMOND BEACH, FL, 321...

Community: Halifax Plantation

New

Cindy Certified

2775 MERCY CIR, CLERMONT, FL, 34714, Clermont, FL 34714

$548,990

4 beds

3 baths

2,175 sq ft

House

2775 MERCY CIR, CLERMONT, FL, 34714

New Stonecrest

11137 SE 174TH LOOP, SUMMERFIELD, FL, 34..., Summerfield, FL 34491

$269,000

3 beds

2 baths

1,453 sq ft

House

11137 SE 174TH LOOP, SUMMERFIELD, FL, 34...

Community: Stonecrest

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

Questions? Call us: (888) 625-4885

New Halifax Plantation

1309 MUNSTER CIR, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$425,000

3 beds

2 baths

2,120 sq ft

House

1309 MUNSTER CIR, ORMOND BEACH, FL, 3217...

Community: Halifax Plantation

New

Cindy Certified

7068 LANIER FALLS RD, DELAND, FL, 32724, Deland, FL 32724

$325,000

3 baths

2,302 sq ft

House

3565 SANSOME CIR, MELBOURNE, FL, 32940

Community: Heritage Isle

New

Cindy Certified

2524 RAPOLLO DR, KISSIMMEE, FL, 34741, Kissimmee, FL 34741

$419,990

3 beds

2 baths

1,706 sq ft

House

2524 RAPOLLO DR, KISSIMMEE, FL, 34741

New The Country Club of Mount Dora

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327..., Mount Dora, FL 32757

$659,900

3 beds

2 baths

2,509 sq ft

House

5039 GREENBRIAR TRL, MOUNT DORA, FL, 327...

Community: The Country Club of Mount Dora

New The Villages®

2732 PRIVADA DR, THE VILLAGES, FL, 32162, The Villages, FL 32162

$305,000

3 beds

2 baths

1,392 sq ft

House

2732 PRIVADA DR, THE VILLAGES, FL, 32162

Community: The Villages®

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

Questions? Call us: (888) 625-4885

The Villages®

1532 W SCHWARTZ BLVD, LADY LAKE, FL, 321..., Lady Lake, FL 32159

$224,900

2 beds

2 baths

1,092 sq ft

Modular

1532 W SCHWARTZ BLVD, LADY LAKE, FL, 321...

Community: The Villages®

Plantation at Leesburg

5349 TANGELO ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$250,000

2 beds

2 baths

1,308 sq ft

House

5349 TANGELO ST, LEESBURG, FL, 34748

Community: Plantation at Leesburg

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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 4

98 communities near Winter Park

2,702 homes near Winter Park

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

2,065 sq ft

House

2 beds

2 baths

1,812 sq ft

House

3 beds

2 baths

1,750 sq ft

House

2 beds

2 baths

1,408 sq ft

House

2 beds

2 baths

1,188 sq ft

Villa

3 beds

3 baths

2,995 sq ft

House

2 beds

2 baths

1,948 sq ft

House

3 beds

2 baths

1,772 sq ft

House

3 beds

2 baths

1,285 sq ft

House

2 beds

2 baths

1,699 sq ft

House

2 beds

2 baths

1,637 sq ft

House

3 beds

2 baths

1,718 sq ft

House

3 beds

2 baths

1,937 sq ft

House

2 beds

2 baths

1,310 sq ft

Townhouse

3 beds

2 baths

1,655 sq ft

House

2 beds

2 baths

1,245 sq ft

House

2 beds

2 baths

1,630 sq ft

House

3 beds

2 baths

1,718 sq ft

House

3 beds