Winter Park, FL 55+ active adult communities & homes for sale - Page 48

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

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.

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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Questions? Call us: (888) 625-4885

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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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

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

9495 SE 130TH PLACE RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

Latitude Margaritaville

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

$619,900

2 beds

3 baths

2,158 sq ft

House

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

Community: Latitude Margaritaville

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Questions? Call us: (888) 625-4885

Solivita

801 GLENDORA RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$539,000

3 beds

2 baths

2,719 sq ft

House

801 GLENDORA RD, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

5092 NE 81ST BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$925,000

3 beds

3 baths

3,407 sq ft

House

5092 NE 81ST BLVD, WILDWOOD, FL, 34785

Community: The Villages®

Del Webb Orlando

799 ASTURIAS RD, DAVENPORT, FL, 33837, Davenport, FL 33837

$279,900

2 beds

2 baths

1,281 sq ft

House

799 ASTURIAS RD, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$400,000

3 beds

2 baths

1,569 sq ft

House

2454 YOUNGMANN LOOP, THE VILLAGES, FL, 3...

Community: The Villages®

Plantation at Leesburg

25100 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748

$165,000

2 beds

2 baths

1,144 sq ft

Manufactured Home

25100 PINE HL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$289,900

2 beds

2 baths

1,192 sq ft

House

1405 W SCHWARTZ BLVD, THE VILLAGES, FL, ...

Community: The Villages®

Heritage Hills

3464 EMBERS LN, CLERMONT, FL, 34711, Clermont, FL 34711

$435,000

3 beds

3 baths

2,032 sq ft

House

3464 EMBERS LN, CLERMONT, FL, 34711

Community: Heritage Hills

Colonnades

$225,900

2 beds

2 baths

1,188 sq ft

House

4938 COLONNADES CIR, LAKELAND, FL, 33811

Community: Colonnades

The Villages®

$585,000

3 beds

2 baths

1,934 sq ft

House

16816 SE 85TH SAPELO CT, THE VILLAGES, F...

Community: The Villages®

Scottish Highlands

1409 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788

$214,999

2 beds

2 baths

1,482 sq ft

House

1409 NEW ABBEY AVE, LEESBURG, FL, 34788

Community: Scottish Highlands

Lake Henry Estates

477 SWEETWATER WAY, HAINES CITY, FL, 338..., Haines City, FL 33844

$278,900

3 beds

2 baths

1,835 sq ft

House

477 SWEETWATER WAY, HAINES CITY, FL, 338...

Community: Lake Henry Estates

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Questions? Call us: (888) 625-4885

The Villages®

$329,000

3 beds

2 baths

1,667 sq ft

Villa

1928 PEACHTREE AVE, THE VILLAGES, FL, 32...

8017 SE 175TH COLUMBIA PL, THE VILLAGES,...

Community: The Villages®

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Four Seasons at Orlando

1998 KEY BAY TRL 524, KISSIMMEE, FL, 347..., Kissimmee, FL 34747

$365,000

2 beds

2 baths

1,583 sq ft

Villa

1998 KEY BAY TRL 524, KISSIMMEE, FL, 347...

Community: Four Seasons at Orlando

Lake Ashton

6308 PINEHURST LOOP, WINTER HAVEN, FL, 3..., Winter Haven, FL 33884

$456,900

3 beds

2 baths

2,045 sq ft

House

6308 PINEHURST LOOP, WINTER HAVEN, FL, 3...

Community: Lake Ashton

Solivita

176 CAPE FLORIDA DR, POINCIANA, FL, 3475..., Poinciana, FL 34759

$299,000

2 beds

2 baths

1,440 sq ft

House

176 CAPE FLORIDA DR, POINCIANA, FL, 3475...

Community: Solivita

Lakes of Mount Dora

3054 NEW HAVEN PL, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$489,900

3 beds

2 baths

2,227 sq ft

House

3054 NEW HAVEN PL, MOUNT DORA, FL, 32757

Community: Lakes of Mount Dora

The Villages®

109 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785

$75,000

2 beds

2 baths

1,152 sq ft

Manufactured Home

109 LYONIA LN, WILDWOOD, FL, 34785

Community: The Villages®

Solivita

661 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759

$413,990

2 beds

2 baths

2,130 sq ft

House

661 CARMEL LN, POINCIANA, FL, 34759

Community: Solivita

Esplanade at Highland Ranch

1284 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715

$399,000

2 beds

2 baths

1,722 sq ft

House

1284 ZEEK RIDGE ST, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

The Villages®

$359,000

2 beds

2 baths

1,300 sq ft

House

1069 BURNETTOWN PL, THE VILLAGES, FL, 32...

Community: The Villages®

The Lakes at Harmony

3212 OXBOW CT, HARMONY, FL, 34773, Harmony, FL 34773

$370,000

3 beds

2 baths

1,580 sq ft

House

3212 OXBOW CT, HARMONY, FL, 34773

Community: The Lakes at Harmony

Enclave at VillageWalk

10938 SAVONA WAY, ORLANDO, FL, 32827, Orlando, FL 32827

$1,599,000

6 beds

6 baths

5,334 sq ft

House

10938 SAVONA WAY, ORLANDO, FL, 32827

Community: Enclave at VillageWalk

Del Webb Sunbridge

2745 NATURE VIEW RD, ST CLOUD, FL, 34771, St Cloud, FL 34771

$874,900

3 beds

4 baths

2,806 sq ft

House

2745 NATURE VIEW RD, ST CLOUD, FL, 34771

Community: Del Webb Sunbridge

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

Questions? Call us: (888) 625-4885

Heritage Isle

2700 CAMBERLY CIR, MELBOURNE, FL, 32940, Melbourne, FL 32940

$290,000

2 beds

2 baths

1,394 sq ft

Townhouse

2700 CAMBERLY CIR, MELBOURNE, FL, 32940

Community: Heritage Isle

Plantation at Leesburg

25735 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$299,250

3 beds

2 baths

1,652 sq ft

House

25735 GLEN EAGLE DR, 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.

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 48

95 communities near Winter Park

2,259 homes near Winter Park

2 beds

2 baths

1,390 sq ft

Villa

3 beds

2 baths

2,594 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

3 beds

2 baths

2,003 sq ft

House

2 beds

3 baths

2,158 sq ft

House

3 beds

2 baths

2,719 sq ft

House

3 beds

3 baths

3,407 sq ft

House

2 beds

2 baths

1,281 sq ft

House

3 beds

2 baths

1,569 sq ft

House

2 beds

2 baths

1,144 sq ft

Manufactured Home

2 beds

2 baths

1,192 sq ft

House

3 beds

3 baths

2,032 sq ft

House

2 beds

2 baths

1,188 sq ft

House

3 beds

2 baths

1,934 sq ft

House

2 beds

2 baths

1,482 sq ft

House

3 beds

2 baths

1,835 sq ft

House

3 beds

2 baths

1,667 sq ft

Villa

2 beds

2 baths

1,228 sq ft

Condo

3 beds

2 baths

2,087 sq ft

House

2 beds