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

3,551 homes near Winter Garden

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5 rating (1 reviews)

Del Webb Oasis

$400Ks - $900Ks

Del Webb Oasis, Winter Garden, FL

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

4 rating (17 reviews)

The Villages®

<$100k - $2Ms

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

$100Ks - $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 - $500Ks

Sun City Center, Sun City Center, FL

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

4.7 rating (18 reviews)

Solivita

$100Ks - $600Ks

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 (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

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 - $500Ks

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 - $500Ks

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 - $500Ks

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 - $600Ks

Twin Lakes, St. Cloud, FL

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

Pelican Bay Daytona Beach

$100Ks - $400Ks

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

$100Ks - $400Ks

Spruce Creek South, Summerfield, FL

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

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $700Ks

Valencia Lakes, Wimauma, FL

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

5 rating (1 reviews)

Cypress Lakes

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

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

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

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

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 - $500Ks

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)

VillageWalk at Lake Nona

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 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

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

<$100k - $300Ks

Pennbrooke Fairways, Leesburg, FL

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

5 rating (1 reviews)

Sandpiper Golf & Coun...

$200Ks - $400Ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

3.6 rating (5 reviews)

Heritage Hills

$200Ks - $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 - $400Ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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

Breakaway Trails

$400Ks - $800Ks

Breakaway Trails, Ormond Beach, FL

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

4 rating (4 reviews)

Lakes of Mount Dora

$400Ks - $900Ks

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 - $1Ms

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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

Pine Run Estates

$100Ks - $300Ks

Pine Run Estates, Ocala, FL

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

Lake Jovita Golf and Coun...

$300Ks - $1Ms

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

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

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

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

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

1062 UMBRIA DR, KISSIMMEE, FL, 34759

House

6126 MULLIGAN RUN, THE VILLAGES, FL, 321...

2136 KERWOOD LOOP, THE VILLAGES, FL, 321...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Pine Run Estates

9230 SW 101ST LN, OCALA, FL, 34481, Ocala, FL 34481

$170,000

2 beds

2 baths

1,459 sq ft

House

9230 SW 101ST LN, OCALA, FL, 34481

Community: Pine Run Estates

Del Webb Sunbridge

3122 VANGUARD CT, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$1,275,000

5 beds

4 baths

3,460 sq ft

House

3122 VANGUARD CT, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

New Foxwood Lake Estates

4928 FOXDALE DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$159,777

2 beds

2 baths

1,200 sq ft

Manufactured Home

4928 FOXDALE DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Marion Landing

8695 SW 60TH CIR, OCALA, FL, 34476, Ocala, FL 34476

$208,800

3 beds

2 baths

1,303 sq ft

House

8695 SW 60TH CIR, OCALA, FL, 34476

Community: Marion Landing

Lake Ashton

2204 ASHTON PALMS DR # 2204, LAKE WALES,..., Lake Wales, FL 33859

$225,000

3 beds

2 baths

1,362 sq ft

Condo

2204 ASHTON PALMS DR # 2204, LAKE WALES,...

Community: Lake Ashton

The Villages®

$275,000

2 beds

2 baths

1,156 sq ft

Villa

2671 COLLINGTON DR, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$434,500

3 beds

2 baths

1,796 sq ft

House

1709 MADERO DR, THE VILLAGES, FL, 32159

Community: The Villages®

Ocala Palms

2083 NW 57TH CT, OCALA, FL, 34482, Ocala, FL 34482

$259,000

2 beds

2 baths

1,731 sq ft

House

2083 NW 57TH CT, OCALA, FL, 34482

Community: Ocala Palms

The Villages®

$589,000

3 beds

2 baths

1,678 sq ft

House

512 AINSWORTH CIR, THE VILLAGES, FL, 321...

Community: The Villages®

Poinsettia Heights

1822 NICARAGUA WAY, WINTER HAVEN, FL, 33..., Winter Haven, FL 33881

$219,500

2 beds

2 baths

1,165 sq ft

House

1822 NICARAGUA WAY, WINTER HAVEN, FL, 33...

Community: Poinsettia Heights

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

Questions? Call us: (689) 407-5757

The Villages®

$324,900

3 beds

2 baths

1,490 sq ft

House

7326 SE 173RD ARLINGTON LOOP, THE VILLAG...

Community: The Villages®

The Villages®

$760,000

4 beds

3 baths

2,248 sq ft

House

3031 HICKS PL, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$685,500

3 beds

2 baths

2,312 sq ft

House

2054 PALO ALTO AVE, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$539,000

3 beds

2 baths

2,013 sq ft

House

3338 QUEENSWAY TER, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$549,000

3 beds

2 baths

2,096 sq ft

House

825 ULELAH ST, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$277,000

2 beds

2 baths

1,156 sq ft

Villa

2023 THURMOND AVE, THE VILLAGES, FL, 321...

Community: The Villages®

Majestic Oaks Ocala

8761 SW 52ND CT, OCALA, FL, 34476, Ocala, FL 34476

$360,000

3 beds

2 baths

2,496 sq ft

House

8761 SW 52ND CT, OCALA, FL, 34476

Community: Majestic Oaks Ocala

Pennbrooke Fairways

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

$142,900

1 beds

1 baths

588 sq ft

House

738 COTTAGE PARK LN, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New Spruce Creek Country Club

12762 SE 92ND TER, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$279,900

2 beds

2 baths

1,274 sq ft

House

12762 SE 92ND TER, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Plantation at Leesburg

25633 LAUREL VALLEY RD, LEESBURG, FL, 34..., Leesburg, FL 34748

$429,900

3 beds

2 baths

2,410 sq ft

House

25633 LAUREL VALLEY RD, LEESBURG, FL, 34...

Condo

1305 SPRY CT, SUN CITY CENTER, FL, 33573

Community: Sun City Center

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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.

Want more information about active adult communities around Winter Garden?

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Want to learn more about 55+ communities in Winter Garden?

Call us: (689) 407-5757

3,551 homes near Winter Garden

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

109 communities near Winter Garden

3,551 homes near Winter Garden

3 beds

2 baths

2,120 sq ft

House

2 beds

2 baths

1,614 sq ft

Villa

2 beds

2 baths

2,162 sq ft

House

2 beds

2 baths

1,831 sq ft

House

2 beds

2 baths

1,655 sq ft

House

3 beds

2 baths

2,059 sq ft

House

2 beds

2 baths

1,467 sq ft

Halfplex

2 beds

2 baths

1,889 sq ft

House

3 beds

2 baths

1,634 sq ft

House

2 beds

2 baths

1,561 sq ft

House

3 beds

2 baths

1,552 sq ft

House

3 beds

2 baths

2,930 sq ft

House

2 beds

2 baths

1,799 sq ft

Villa

2 beds

2 baths

1,748 sq ft

Villa

2 beds

2 baths

1,135 sq ft

House

2 beds

2 baths

1,459 sq ft

House

5 beds

4 baths

3,460 sq ft

House

2 beds

2 baths

1,200 sq ft

Manufactured Home

3 beds

2 baths

1,303 sq ft

House

3 beds