Winter Garden, FL 55+ active adult communities & homes for sale

3,958 homes near Winter Garden

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Del Webb Oasis

$400Ks - $1Ms

Del Webb Oasis, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2020 - present | 422 homes

4 rating (17 reviews)

The Villages®

<$100k - $1Ms

The Villages®, The Villages, FL

New and Resale | 55+ age-restricted | Built 1978 - present | 70,000 homes

4.1 rating (55 reviews)

On Top of the World

<$100k - $600Ks

On Top of the World, Ocala, FL

New and Resale | 55+ age-restricted | Built 1981 - present | 10,000 homes

3.8 rating (14 reviews)

Sun City Center

<$100k - $600Ks

Sun City Center, Sun City Center, FL

Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes

4.7 rating (18 reviews)

Solivita

$200Ks - $700Ks

Solivita, Kissimmee, FL

New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 homes

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

Questions? Call us: (689) 407-5757

3.6 rating (46 reviews)

Latitude Margaritaville

$300Ks - $700Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

4.2 rating (10 reviews)

Stone Creek

$200Ks - $800Ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.1 rating (29 reviews)

Oak Run

$100Ks - $300Ks

Oak Run, Ocala, FL

Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes

4.5 rating (11 reviews)

Spruce Creek Country Club

$200Ks - $500Ks

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 - $400Ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 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.

5 rating (3 reviews)

Stonecrest

$200Ks - $600Ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

5 rating (7 reviews)

Kings Ridge

$200Ks - $400Ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

5 rating (3 reviews)

Twin Lakes

$200Ks - $1Ms

Twin Lakes, St. Cloud, FL

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

No reviews yet

Pelican Bay Daytona Beach

<$100k - $600Ks

Pelican Bay Daytona Beach, Daytona Beach, FL

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

4.6 rating (5 reviews)

Ocala Preserve

$200Ks - $600Ks

Ocala Preserve, Ocala, FL

New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 homes

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

Questions? Call us: (689) 407-5757

4.7 rating (3 reviews)

Spruce Creek South

$200Ks - $300Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $900Ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes

5 rating (1 reviews)

Cypress Lakes

$200Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $900Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

No reviews yet

Venetian Bay

$200Ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

5 rating (8 reviews)

Royal Highlands

$200Ks - $400Ks

Royal Highlands, Leesburg, FL

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

3.8 rating (6 reviews)

Trilogy® Orlando

$200Ks - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

3.8 rating (6 reviews)

Tampa Bay Golf and Countr...

$200Ks - $400Ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes

5 rating (1 reviews)

Del Webb Sunbridge

$300Ks - $1Ms

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$400Ks - $1Ms

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 Garden? 55places can help!

Questions? Call us: (689) 407-5757

5 rating (8 reviews)

Pennbrooke Fairways

$100Ks - $300Ks

Pennbrooke Fairways, Leesburg, FL

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

3.6 rating (5 reviews)

Heritage Hills

$300Ks - $500Ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

5 rating (1 reviews)

Ocala Palms

$100Ks - $400Ks

Ocala Palms, Ocala, FL

Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes

5 rating (1 reviews)

Cresswind at Victoria Gar...

$300Ks - $600Ks

Cresswind at Victoria Gar..., DeLand, FL

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

5 rating (5 reviews)

SummerGlen

$200Ks - $500Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,029 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

No reviews yet

Breakaway Trails

$400Ks - $700Ks

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$200Ks - $800Ks

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

$200Ks - $800Ks

Harbor Hills Country Club, Lady Lake, FL

New and Resale | Age-targeted | Built 1989 - present | 940 homes

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

Questions? Call us: (689) 407-5757

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $300Ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $500Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

No reviews yet

Pine Run Estates

$100Ks - $400Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

No reviews yet

Lake Jovita Golf and Coun...

$400Ks - $1Ms

Lake Jovita Golf and Coun..., Dade City, FL

New and Resale | Age-targeted | Built 1999 - present | 875 homes

No reviews yet

Esplanade at Wiregrass Ra...

$400Ks - $900Ks

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

1 2 3

Tampa Bay Golf and Country Club

29408 PRINCEVILLE DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576

$299,900

3 beds

2 baths

1,593 sq ft

House

29408 PRINCEVILLE DR, SAN ANTONIO, FL, 3...

Community: Tampa Bay Golf and Country Club

Latitude Margaritaville

418 GOOD LIFE WAY, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$629,900

3 beds

3 baths

2,083 sq ft

House

418 GOOD LIFE WAY, DAYTONA BEACH, FL, 32...

Community: Latitude Margaritaville

Southshore Bay

5328 STOIC VALE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$300,000

2 beds

2 baths

1,636 sq ft

Villa

5328 STOIC VALE DR, WIMAUMA, FL, 33598

Community: Southshore Bay

The Villages®

1717 LILLY LN, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$274,900

2 beds

2 baths

1,856 sq ft

Manufactured Home

1717 LILLY LN, LADY LAKE, FL, 32159

Community: The Villages®

Scottish Highlands

610 FANNICH CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$224,900

2 beds

2 baths

1,086 sq ft

House

610 FANNICH CT, LEESBURG, FL, 34788

Community: Scottish Highlands

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

Questions? Call us: (689) 407-5757

Highland Lakes

6435 BORG ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$350,000

3 beds

2 baths

2,186 sq ft

House

6435 BORG ST, LEESBURG, FL, 34748

Community: Highland Lakes

Colonnades

1618 BIRCHWOOD LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811

$259,900

2 beds

2 baths

1,579 sq ft

House

1618 BIRCHWOOD LOOP, LAKELAND, FL, 33811

Community: Colonnades

Traditions at Lake Ruby

3912 BALDWIN LN, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884

$305,000

2 beds

2 baths

1,719 sq ft

House

3912 BALDWIN LN, WINTER HAVEN, FL, 33884

Community: Traditions at Lake Ruby

Stone Creek

6184 SW 89TH CT, OCALA, FL, 34481, Ocala, FL 34481

$549,000

3 beds

3 baths

2,110 sq ft

House

6184 SW 89TH CT, OCALA, FL, 34481

Community: Stone Creek

Heritage - The Cottages of Sanders Grove

28023 CYPRESS SPRINGS LOOP, OKAHUMPKA, F..., Okahumpka, FL 34762

$305,000

3 beds

2 baths

1,601 sq ft

House

28023 CYPRESS SPRINGS LOOP, OKAHUMPKA, F...

Community: Heritage - The Cottages of Sanders Grove

Plantation at Leesburg

24515 BOCAGE WAY, LEESBURG, FL, 34748, Leesburg, FL 34748

$379,999

3 beds

3 baths

2,204 sq ft

House

24515 BOCAGE WAY, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Quail Meadow

5003 NW 32ND ST, OCALA, FL, 34482, Ocala, FL 34482

$284,900

3 beds

2 baths

1,441 sq ft

House

5003 NW 32ND ST, OCALA, FL, 34482

Community: Quail Meadow

Harbor Hills Country Club

39601 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$599,000

4 beds

2 baths

2,889 sq ft

House

39601 HARBOR HILLS BLVD, LADY LAKE, FL, ...

Community: Harbor Hills Country Club

Liberty Village

7727 SW 74TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$289,500

2 beds

2 baths

1,548 sq ft

House

7727 SW 74TH LOOP, OCALA, FL, 34481

Community: Liberty Village

Spruce Creek Country Club

12024 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$319,000

2 beds

2 baths

1,488 sq ft

House

12024 SE 91ST CIR, SUMMERFIELD, FL, 3449...

House

406 TISBURY CT, DELAND, FL, 32724

House

368 ALCOVE DR, GROVELAND, FL, 34736

Community: Trilogy® Orlando

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

Questions? Call us: (689) 407-5757

Trilogy® Orlando

135 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736

$380,000

2 beds

2 baths

1,651 sq ft

House

135 CREPE MYRTLE DR, GROVELAND, FL, 3473...

Community: Trilogy® Orlando

El Dorado

2130 SW 37TH STREET RD, OCALA, FL, 34471, Ocala, FL 34471

$794,500

5 beds

3 baths

4,333 sq ft

House

2130 SW 37TH STREET RD, OCALA, FL, 34471

Community: El Dorado

Harbor Hills Country Club

5746 CRESTVIEW DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$787,000

4 beds

4 baths

4,058 sq ft

House

5746 CRESTVIEW DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Harbor Hills Country Club

5072 GREENS DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$795,000

3 beds

3 baths

2,712 sq ft

House

5072 GREENS DR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Summer Trees

41 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$275,000

2 beds

2 baths

1,495 sq ft

House

41 CROOKED PINE RD, PORT ORANGE, FL, 321...

Community: Summer Trees

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Frequently Asked Questions

What size 55+ communities are there in Winter Garden?

In Winter Garden, there are no large communities, no medium communities, and 2 small communities with less than 500 homes.

How many homes are there in the smallest, largest, and average 55+ communities in Winter Garden?

The smallest 55+ communities in Winter Garden has 163 homes, the largest has 422 homes, and the average communities consists of 292 homes.

Are there new 55+ homes available in Winter Garden?

Yes, there are new 55+ homes available in Winter Garden. The most recent communities started in Winter Garden include Overture Hamlin, Del Webb Oasis. There are also 2 communities in Winter Garden that offer new construction homes, including Overture Hamlin, Del Webb Oasis.

Are there gated 55+ communities in Winter Garden?

Yes, there is gated 55+ communities in Winter Garden. Approximately 50.0% of 55+ communities in the area are gated. For instance, Del Webb Oasis is a gated communities with 422 homes.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 143 days. The average price of homes for sale in these communities is approximately $502,460, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $502,460.

Want more information about active adult communities around Winter Garden?

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3,958 homes near Winter Garden

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Winter Garden, FL 55+ active adult communities & homes for sale

106 communities near Winter Garden

3,958 homes near Winter Garden

3 beds

2 baths

1,593 sq ft

House

3 beds

3 baths

2,083 sq ft

House

2 beds

2 baths

1,636 sq ft

Villa

2 beds

2 baths

1,856 sq ft

Manufactured Home

2 beds

2 baths

1,086 sq ft

House

3 beds

2 baths

2,186 sq ft

House

2 beds

2 baths

1,579 sq ft

House

2 beds

2 baths

1,719 sq ft

House

3 beds

3 baths

2,110 sq ft

House

3 beds

2 baths

1,601 sq ft

House

3 beds

3 baths

2,204 sq ft

House

3 beds

2 baths

1,441 sq ft

House

4 beds

2 baths

2,889 sq ft

House

2 beds

2 baths

1,548 sq ft

House

2 beds

2 baths

1,488 sq ft

House

2 beds

2 baths

1,008 sq ft

Manufactured Home

3 beds

2 baths

1,776 sq ft

House

2 beds

2 baths

1,374 sq ft

Villa

2 beds

2 baths

1,672 sq ft

House

2 beds