Winter Park, FL 55+ active adult communities & homes for sale - Page 11

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

Esplanade at Westview

4364 CURACAO PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758

$770,000

3 beds

3 baths

3,004 sq ft

House

4364 CURACAO PL, KISSIMMEE, FL, 34758

Community: Esplanade at Westview

The Villages®

$425,000

3 beds

2 baths

1,476 sq ft

Villa

8975 SE 168TH TAILFER ST, THE VILLAGES, ...

Community: The Villages®

Carillon Lakes

3007 BELLFLOWER WAY, LAKELAND, FL, 33811, Lakeland, FL 33811

$379,900

3 beds

3 baths

1,846 sq ft

House

3007 BELLFLOWER WAY, LAKELAND, FL, 33811

Community: Carillon Lakes

Venetian Bay

477 LUNA BELLA LN, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$675,000

5 beds

4 baths

3,002 sq ft

House

477 LUNA BELLA LN, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Four Seasons at Orlando

1667 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$339,500

2 beds

2 baths

1,437 sq ft

Villa

1667 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

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

Questions? Call us: (888) 625-4885

Lake Henry Estates

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

$274,900

3 beds

2 baths

1,835 sq ft

House

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

Community: Lake Henry Estates

Plantation at Leesburg

25120 CLIFFORD HL, LEESBURG, FL, 34748, Leesburg, FL 34748

$191,000

2 beds

2 baths

1,349 sq ft

Manufactured Home

25120 CLIFFORD HL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Halifax Plantation

1384 ALEUT LN, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$620,000

3 beds

2 baths

2,068 sq ft

House

1384 ALEUT LN, ORMOND BEACH, FL, 32174

Community: Halifax Plantation

Lake Ashton

1102 ASHTON PALMS DR, LAKE WALES, FL, 33..., Lake Wales, FL 33859

$225,000

2 beds

2 baths

1,196 sq ft

Condo

1102 ASHTON PALMS DR, LAKE WALES, FL, 33...

Community: Lake Ashton

Plantation at Leesburg

25201 CLIFFORD HL, LEESBURG, FL, 34748, Leesburg, FL 34748

$169,900

2 beds

2 baths

1,173 sq ft

Manufactured Home

25201 CLIFFORD HL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

112 LYONIA LN, WILDWOOD, FL, 34785, Wildwood, FL 34785

$197,000

2 beds

2 baths

1,664 sq ft

Manufactured Home

112 LYONIA LN, WILDWOOD, FL, 34785

Community: The Villages®

Royal Harbor

3204 ANTIGUA BAY LN, TAVARES, FL, 32778, Tavares, FL 32778

$339,900

3 beds

2 baths

1,785 sq ft

House

3204 ANTIGUA BAY LN, TAVARES, FL, 32778

Community: Royal Harbor

Carillon Lakes

3833 WHISTLEWOOD CIR, LAKELAND, FL, 3381..., Lakeland, FL 33811

$325,000

3 beds

2 baths

1,706 sq ft

House

3833 WHISTLEWOOD CIR, LAKELAND, FL, 3381...

Community: Carillon Lakes

Legacy of Leesburg

27028 OLD ENGLISH CT, LEESBURG, FL, 3474..., Leesburg, FL 34748

$550,000

3 beds

3 baths

3,067 sq ft

House

27028 OLD ENGLISH CT, LEESBURG, FL, 3474...

Community: Legacy of Leesburg

Kings Ridge

4075 KINGSLEY ST, CLERMONT, FL, 34711, Clermont, FL 34711

$349,900

3 beds

2 baths

1,782 sq ft

House

4075 KINGSLEY ST, CLERMONT, FL, 34711

Community: Kings Ridge

Cindy Certified

1362 CORK DR, ORMOND BEACH, FL, 32174, Ormond Beach, FL 32174

$345,000

3 beds

2 baths

1,373 sq ft

House

1362 CORK DR, ORMOND BEACH, FL, 32174

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

Questions? Call us: (888) 625-4885

Pelican Bay Daytona Beach

168 BERMUDA PETREL CT, DAYTONA BEACH, FL..., Daytona Beach, FL 32119

$235,000

2 beds

2 baths

1,260 sq ft

House

168 BERMUDA PETREL CT, DAYTONA BEACH, FL...

Community: Pelican Bay Daytona Beach

Esplanade at Westview

4536 OCHOS RIOS PL, KISSIMMEE, FL, 34758, Kissimmee, FL 34758

$299,900

3 beds

2 baths

1,553 sq ft

House

4536 OCHOS RIOS PL, KISSIMMEE, FL, 34758

Community: Esplanade at Westview

Venetian Bay

354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$289,999

2 beds

3 baths

1,837 sq ft

Townhouse

354 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Del Webb Orlando

519 VIGO ST, DAVENPORT, FL, 33837, Davenport, FL 33837

$449,000

3 beds

2 baths

2,320 sq ft

House

519 VIGO ST, DAVENPORT, FL, 33837

Community: Del Webb Orlando

The Villages®

$248,000

2 beds

2 baths

1,198 sq ft

House

16970 SE 94TH SUNNYBROOK CIR, THE VILLAG...

Community: The Villages®

Spruce Creek South

10298 SE 176TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$185,000

2 beds

2 baths

1,248 sq ft

House

10298 SE 176TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Plantation at Leesburg

25333 RIVER CREST DR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$259,000

3 beds

2 baths

1,737 sq ft

House

25333 RIVER CREST DR, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

Stonecrest

10982 SE 169TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$395,000

3 beds

2 baths

1,727 sq ft

House

10982 SE 169TH PL, SUMMERFIELD, FL, 3449...

Community: Stonecrest

The Villages®

$239,000

2 beds

1 baths

1,034 sq ft

Villa

483 HILDALGO DR, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$299,900

2 beds

2 baths

1,370 sq ft

House

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

Community: The Villages®

The Wellington

689 LAKE HOWARD DR 213, WINTER HAVEN, FL..., Winter Haven, FL 33880

$149,000

2 beds

2 baths

1,072 sq ft

Condo

689 LAKE HOWARD DR 213, WINTER HAVEN, FL...

Community: The Wellington

Cindy Certified

1930 DEEP CREEK DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$625,000

4 beds

3 baths

2,932 sq ft

House

1930 DEEP CREEK DR, LAKELAND, FL, 33810

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

Questions? Call us: (888) 625-4885

Latitude Margaritaville

243 ISLAND BREEZE AVE, DAYTONA BEACH, FL..., Daytona Beach, FL 32124

$489,000

2 beds

2 baths

1,771 sq ft

House

243 ISLAND BREEZE AVE, DAYTONA BEACH, FL...

Community: Latitude Margaritaville

The Villages®

$435,000

3 beds

2 baths

1,466 sq ft

Villa

16844 SE 91ST PHILLIPS CT, THE VILLAGES,...

Community: The Villages®

1…5 6 7 8 9 10 11 12 13 14 15 16 17…68

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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Call us: (888) 625-4885

2,702 homes

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Winter Park, FL 55+ active adult communities & homes for sale - Page 11

98 communities near Winter Park

2,702 homes near Winter Park

3 beds

3 baths

3,004 sq ft

House

3 beds

2 baths

1,476 sq ft

Villa

3 beds

3 baths

1,846 sq ft

House

5 beds

4 baths

3,002 sq ft

House

2 beds

2 baths

1,437 sq ft

Villa

3 beds

2 baths

1,835 sq ft

House

2 beds

2 baths

1,349 sq ft

Manufactured Home

3 beds

2 baths

2,068 sq ft

House

2 beds

2 baths

1,196 sq ft

Condo

2 beds

2 baths

1,173 sq ft

Manufactured Home

2 beds

2 baths

1,664 sq ft

Manufactured Home

3 beds

2 baths

1,785 sq ft

House

3 beds

2 baths

1,706 sq ft

House

3 beds

3 baths

3,067 sq ft

House

3 beds

2 baths

1,782 sq ft

House

3 beds

2 baths

1,373 sq ft

House

2 beds

2 baths

1,260 sq ft

House

3 beds

2 baths

1,553 sq ft

House

2 beds

3 baths

1,837 sq ft

Townhouse

3 beds