Winter Park, FL 55+ active adult communities & homes for sale - Page 29

2,414 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

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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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

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 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 (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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.

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

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

Twin Lakes

$200ks - $600ks

Twin Lakes, St. Cloud, FL

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

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

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

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Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

Halifax Plantation

$300ks - $1Ms

Halifax Plantation, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $1Ms

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 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)

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)

Cresswind at Victoria Gar...

$200ks - $500ks

Cresswind at Victoria Gar..., DeLand, FL

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

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 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)

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 (2 reviews)

Heritage Isle

$300ks - $500ks

Heritage Isle, Viera, FL

Resale Only | 55+ age-restricted | Built 2005 - 2017 | 1,500 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

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

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 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

The Country Club of Mount...

$200ks - $1Ms

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

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

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

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

Questions? Call us: (888) 625-4885

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

5 rating (2 reviews)

Bridgewater at Viera

$300ks - $800ks

Bridgewater at Viera, Melbourne, FL

Resale Only | 55+ age-restricted | Built 2017 - 2023 | 870 homes

1 2...3

Solivita

144 SORRENTO RD, POINCIANA, FL, 34759, Poinciana, FL 34759

$265,000

2 beds

2 baths

1,467 sq ft

House

144 SORRENTO RD, POINCIANA, FL, 34759

Community: Solivita

The Villages®

$615,000

3 beds

2 baths

2,228 sq ft

House

2983 SAINT THOMAS LN, THE VILLAGES, FL, ...

1144 BEN MORE DR, LEESBURG, FL, 34788

Community: Scottish Highlands

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Questions? Call us: (888) 625-4885

Arlington Ridge

26657 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$430,000

3 beds

2 baths

1,832 sq ft

House

26657 MANASSAS DR, LEESBURG, FL, 34748

Community: Arlington Ridge

Royal Highlands

21811 KING HENRY AVE, LEESBURG, FL, 3474..., Leesburg, FL 34748

$334,900

3 beds

2 baths

1,918 sq ft

House

21811 KING HENRY AVE, LEESBURG, FL, 3474...

2952 BODDINGTON WAY, MELBOURNE, FL, 3294...

Community: Heritage Isle

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

Questions? Call us: (888) 625-4885

Solivita

112 SEVILLA CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$465,000

3 beds

3 baths

2,450 sq ft

House

112 SEVILLA CT, KISSIMMEE, FL, 34759

Community: Solivita

Royal Highlands

5729 KING JAMES AVE, LEESBURG, FL, 34748, Leesburg, FL 34748

$436,900

3 beds

3 baths

2,402 sq ft

House

5729 KING JAMES AVE, LEESBURG, FL, 34748

Community: Royal Highlands

The Villages®

$250,000

2 beds

2 baths

1,160 sq ft

Villa

17385 SE 78TH DRAUGHTON CT, THE VILLAGES...

Community: The Villages®

The Villages®

$279,000

2 beds

2 baths

1,258 sq ft

Villa

5719 SPARTINA TER, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$309,900

2 beds

2 baths

1,203 sq ft

House

3552 GROUBY RD, THE VILLAGES, FL, 32163

Community: The Villages®

Park Place

$365,000

3 beds

2 baths

1,879 sq ft

House

133 PARK PLACE CIR, PALM COAST, FL, 3216...

Community: Park Place

The Villages®

$370,000

3 beds

2 baths

1,669 sq ft

House

2129 ZARAGOZA PL, THE VILLAGES, FL, 3215...

Community: The Villages®

Four Seasons at Orlando

7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747

$685,000

3 beds

2 baths

1,969 sq ft

House

7774 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...

Community: Four Seasons at Orlando

Kings Ridge

2282 FENTON AVE, CLERMONT, FL, 34711, Clermont, FL 34711

$350,000

3 beds

2 baths

1,896 sq ft

House

2282 FENTON AVE, CLERMONT, FL, 34711

Community: Kings Ridge

The Villages®

$329,000

2 beds

2 baths

1,214 sq ft

Villa

1717 FRANCISCO ST, THE VILLAGES, FL, 321...

Community: The Villages®

Summer Trees

6034 WINDING RIDGE LN, PORT ORANGE, FL, ..., Port Orange, FL 32128

$499,900

4 beds

2 baths

1,880 sq ft

House

6034 WINDING RIDGE LN, PORT ORANGE, FL, ...

Community: Summer Trees

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

Questions? Call us: (888) 625-4885

The Villages®

$280,000

2 beds

2 baths

1,203 sq ft

Villa

2747 DYSON LOOP, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$499,500

3 beds

2 baths

1,950 sq ft

House

4362 WATCH HILL ST, THE VILLAGES, FL, 32...

Community: The Villages®

Solivita

524 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$218,000

2 beds

2 baths

1,159 sq ft

Halfplex

524 GLENDORA RD, KISSIMMEE, FL, 34759

Community: Solivita

Plantation Bay Golf & Country Club

1234 CROWN POINTE LN, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$550,000

3 beds

2 baths

1,926 sq ft

House

1234 CROWN POINTE LN, ORMOND BEACH, FL, ...

Community: Plantation Bay Golf & Country Club

Venetian Bay

3377 CATERINA DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$860,000

4 beds

4 baths

3,882 sq ft

House

3377 CATERINA DR, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Plantation Bay Golf & Country Club

534 WINGSPAN DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$1,650,000

4 beds

4 baths

3,713 sq ft

House

534 WINGSPAN DR, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

Plantation Bay Golf & Country Club

409 SEABROOK RD, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$479,900

3 beds

2 baths

2,153 sq ft

House

409 SEABROOK RD, ORMOND BEACH, FL, 32174

Community: Plantation Bay Golf & Country Club

The Villages®

$399,999

3 beds

2 baths

2,088 sq ft

House

1271 WHEELING WAY, THE VILLAGES, FL, 321...

Community: The Villages®

The Villages®

$305,000

2 beds

2 baths

1,275 sq ft

House

771 FENWICK LOOP, THE VILLAGES, FL, 3216...

Community: The Villages®

Gatherings of Lake Nona

7521 LAUREATE BLVD 5306, ORLANDO, FL, 32..., Orlando, FL 32827

$444,900

2 beds

2 baths

1,549 sq ft

Condo

7521 LAUREATE BLVD 5306, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

The Villages®

$220,000

2 beds

2 baths

1,344 sq ft

Manufactured Home

529 RAINBOW BLVD, THE VILLAGES, FL, 3215...

Community: The Villages®

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

Questions? Call us: (888) 625-4885

Heritage Hills

4052 SERENA LN, CLERMONT, FL, 34711, Clermont, FL 34711

$400,000

3 beds

2 baths

1,672 sq ft

House

4052 SERENA LN, CLERMONT, FL, 34711

Community: Heritage Hills

The Villages®

$289,900

2 beds

2 baths

1,156 sq ft

Villa

2558 CARRINGTON CT, THE VILLAGES, FL, 32...

Community: The Villages®

1…23 24 25 26 27 28 29 30 31 32 33 34 35…61

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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2,414 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 29

93 communities near Winter Park

2,414 homes near Winter Park

2 beds

2 baths

1,467 sq ft

House

3 beds

2 baths

2,228 sq ft

House

2 beds

2 baths

1,937 sq ft

House

3 beds

2 baths

1,712 sq ft

House

2 beds

2 baths

1,213 sq ft

House

3 beds

2 baths

1,832 sq ft

House

3 beds

2 baths

1,918 sq ft

House

3 beds

2 baths

1,814 sq ft

House

3 beds

2 baths

1,999 sq ft

House

2 beds

2 baths

1,808 sq ft

House

3 beds

2 baths

1,860 sq ft

House

2 beds

2 baths

1,040 sq ft

Manufactured Home

2 beds

2 baths

1,922 sq ft

House

3 beds

2 baths

1,392 sq ft

House

2 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

2,034 sq ft

House

3 beds

3 baths

2,450 sq ft

House

3 beds

3 baths

2,402 sq ft

House

2 beds

2 baths

1,160 sq ft

Villa

2 beds