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, FL? 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, FL? 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

3.8 rating (6 reviews)

Trilogy® Orlando

$200Ks - $600Ks

Trilogy® Orlando, Groveland, FL

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

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, FL? 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, FL? 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

Latitude Margaritaville

1024 SEA SHELL CT, DAYTONA BEACH, FL, 32..., Daytona Beach, FL 32124

$448,999

2 beds

2 baths

1,563 sq ft

House

1024 SEA SHELL CT, DAYTONA BEACH, FL, 32...

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

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

Windermere

751 INVERIE DR, INVERNESS, FL, 34453, Inverness, FL 34453

$239,000

3 beds

3 baths

1,912 sq ft

Townhouse

751 INVERIE DR, INVERNESS, FL, 34453

Community: Windermere

Valencia Lakes

16232 AMETHYST KEY DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$285,000

3 beds

2 baths

1,517 sq ft

Villa

16232 AMETHYST KEY DR, WIMAUMA, FL, 3359...

Community: Valencia Lakes

Solivita

672 SAN JOAQUIN RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$435,000

3 beds

3 baths

2,190 sq ft

House

672 SAN JOAQUIN RD, KISSIMMEE, FL, 34759

Community: Solivita

Marco Polo Village

5323 SW 111TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476

$449,000

4 beds

3 baths

2,592 sq ft

House

5323 SW 111TH LANE RD, OCALA, FL, 34476

Community: Marco Polo Village

The Villages®

$829,000

3 beds

2 baths

2,575 sq ft

House

960 PICKERING PATH, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$329,000

3 beds

2 baths

1,392 sq ft

House

965 EASTMONT CT, THE VILLAGES, FL, 32162

Community: The Villages®

New JB Ranch

6318 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476

$249,988

3 beds

2 baths

1,505 sq ft

House

6318 SW 89TH LANE RD, OCALA, FL, 34476

Community: JB Ranch

Pennbrooke Fairways

701 COTTAGE PARK LN, LEESBURG, FL, 34748, Leesburg, FL 34748

$175,000

2 beds

1 baths

636 sq ft

House

701 COTTAGE PARK LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

The Villages®

$799,000

3 beds

3 baths

2,019 sq ft

House

3219 ORANGEDALE TER, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$425,000

3 beds

2 baths

2,175 sq ft

House

2738 MORVEN PARK WAY, THE VILLAGES, FL, ...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Stone Creek

9818 SW 63RD LOOP, OCALA, FL, 34481, Ocala, FL 34481

$329,900

3 beds

2 baths

1,938 sq ft

House

9818 SW 63RD LOOP, OCALA, FL, 34481

Community: Stone Creek

Stonecrest

17490 SE 110TH TER, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$330,000

3 beds

2 baths

1,471 sq ft

House

17490 SE 110TH TER, SUMMERFIELD, FL, 344...

Community: Stonecrest

The Villages®

$1,530,000

4 beds

3 baths

3,897 sq ft

House

1721 SUNSET RIDGE DR, THE VILLAGES, FL, ...

Community: The Villages®

New Tampa Bay Golf and Country Club

10232 BUNCOMBE WAY, SAN ANTONIO, FL, 335..., San Antonio, FL 33576

$375,000

3 beds

2 baths

1,397 sq ft

House

10232 BUNCOMBE WAY, SAN ANTONIO, FL, 335...

Community: Tampa Bay Golf and Country Club

Esplanade at Wiregrass Ranch

4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33..., Wesley Chapel, FL 33543

$909,900

3 beds

3 baths

3,087 sq ft

House

4795 FRECCIA LOOP, WESLEY CHAPEL, FL, 33...

Community: Esplanade at Wiregrass Ranch

Palms at Serenoa

3371 YELLOWTOP LOOP, CLERMONT, FL, 34714, Clermont, FL 34714

$392,990

2 beds

2 baths

1,700 sq ft

House

3371 YELLOWTOP LOOP, CLERMONT, FL, 34714

Community: Palms at Serenoa

The Villages®

5107 NE 122ND BLVD, OXFORD, FL, 34484, Oxford, FL 34484

$418,000

4 beds

3 baths

2,180 sq ft

House

5107 NE 122ND BLVD, OXFORD, FL, 34484

Community: The Villages®

Venetian Bay

266 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$459,000

5 beds

3 baths

2,508 sq ft

House

266 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

On Top of the World

8166 SW 80TH TER, OCALA, FL, 34476, Ocala, FL 34476

$265,000

3 beds

2 baths

1,487 sq ft

House

8166 SW 80TH TER, OCALA, FL, 34476

Community: On Top of the World

Venetian Bay

610 MURA CT, NEW SMYRNA BEACH, FL, 32168, New Smyrna Beach, FL 32168

$987,900

5 beds

5 baths

3,535 sq ft

House

610 MURA CT, NEW SMYRNA BEACH, FL, 32168

House

17848 SE 87TH BOURNE AVE, THE VILLAGES, ...

House

3810 COSMOS WAY, THE VILLAGES, FL, 32163

Community: The Villages®

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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.

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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

2 beds

2 baths

1,563 sq ft

House

3 beds

2 baths

1,701 sq ft

House

3 beds

2 baths

2,045 sq ft

House

2 beds

2 baths

1,347 sq ft

House

2 beds

2 baths

1,205 sq ft

House

3 beds

3 baths

1,912 sq ft

Townhouse

3 beds

2 baths

1,517 sq ft

Villa

3 beds

3 baths

2,190 sq ft

House

4 beds

3 baths

2,592 sq ft

House

3 beds

2 baths

2,575 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,505 sq ft

House

2 beds

1 baths

636 sq ft

House

3 beds

3 baths

2,019 sq ft

House

3 beds

2 baths

2,175 sq ft

House

3 beds

2 baths

1,938 sq ft

House

3 beds

2 baths

1,471 sq ft

House

4 beds

3 baths

3,897 sq ft

House

3 beds

2 baths

1,397 sq ft

House

3 beds