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

3,573 homes near Winter Garden

Sort by:

Relevance

No reviews yet

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 - $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 - $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

$100Ks - $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 - $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 - $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 - $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 - $900Ks

Twin Lakes, St. Cloud, FL

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

No reviews yet

Pelican Bay Daytona Beach

$100Ks - $500Ks

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

$100Ks - $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 - $500Ks

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

$300Ks - $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 - $900Ks

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...

$200Ks - $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

$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

No reviews yet

Breakaway Trails

$300Ks - $1Ms

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? 55places can help!

Questions? Call us: (689) 407-5757

4.8 rating (6 reviews)

Highland Lakes

$200Ks - $300Ks

Highland Lakes, Leesburg, FL

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

4.3 rating (15 reviews)

Del Webb Orlando

$200Ks - $400Ks

Del Webb Orlando, Davenport, FL

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

No reviews yet

Pine Run Estates

<$100k - $400Ks

Pine Run Estates, Ocala, FL

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

No reviews yet

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

No reviews yet

Esplanade at Wiregrass Ra...

$400Ks - $1Ms

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

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

1 2...3

Summit Greens

807 WOLF CREEK ST, CLERMONT, FL, 34711, Clermont, FL 34711

$339,000

2 beds

2 baths

1,717 sq ft

House

807 WOLF CREEK ST, CLERMONT, FL, 34711

Community: Summit Greens

Sun City Center

$175,000

2 beds

2 baths

984 sq ft

Condo

1906 CANTERBURY LN 20, SUN CITY CENTER, ...

Community: Sun City Center

Highland Lakes

6033 WADE ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$249,900

2 beds

2 baths

1,632 sq ft

House

6033 WADE ST, LEESBURG, FL, 34748

Community: Highland Lakes

El Dorado

2065 SW 37TH STREET RD, OCALA, FL, 34471, Ocala, FL 34471

$889,500

4 beds

3 baths

4,092 sq ft

House

2065 SW 37TH STREET RD, OCALA, FL, 34471

Community: El Dorado

Four Seasons at Orlando

7790 FOUR SEASONS BLVD, KISSIMMEE, FL, 3..., Kissimmee, FL 34747

$765,000

3 beds

3 baths

2,470 sq ft

House

7790 FOUR SEASONS BLVD, KISSIMMEE, FL, 3...

Community: Four Seasons at Orlando

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

Questions? Call us: (689) 407-5757

Spruce Creek South

9488 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$300,000

2 beds

2 baths

1,884 sq ft

House

9488 SE 174TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek South

Sun City Center

$255,000

3 beds

10 baths

1,429 sq ft

Condo

1226 LYNDHURST GREENS DR, SUN CITY CENTE...

Community: Sun City Center

Spruce Creek Country Club

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491

$439,000

3 beds

2 baths

2,267 sq ft

House

9894 SE 138TH LOOP, SUMMERFIELD, FL, 344...

Community: Spruce Creek Country Club

Highland Lakes

27141 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$239,900

2 beds

2 baths

1,564 sq ft

House

27141 RACQUET CIR, LEESBURG, FL, 34748

Community: Highland Lakes

Sun City Center

$219,000

2 beds

2 baths

1,298 sq ft

Condo

1015 RADISON LAKE CT # 65, SUN CITY CENT...

Community: Sun City Center

The Villages®

$479,900

3 beds

2 baths

1,865 sq ft

House

2895 APACHE CT, THE VILLAGES, FL, 32163

Community: The Villages®

Solivita

789 CIELO TRL, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$496,000

3 beds

3 baths

2,427 sq ft

House

789 CIELO TRL, KISSIMMEE, FL, 34759

Community: Solivita

Plantation at Leesburg

3646 WESTOVER CIR, LEESBURG, FL, 34748, Leesburg, FL 34748

$390,000

2 beds

2 baths

2,400 sq ft

House

3646 WESTOVER CIR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

Sun City Center

$154,900

2 beds

2 baths

1,100 sq ft

Condo

404 FULHAM CT A, SUN CITY CENTER, FL, 33...

Community: Sun City Center

The Villages®

$359,900

3 beds

2 baths

1,631 sq ft

House

2297 MONTBROOK PL, THE VILLAGES, FL, 321...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Legacy of Leesburg

5352 TREASURE VIEW WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$299,000

3 beds

2 baths

2,241 sq ft

House

5352 TREASURE VIEW WAY, LEESBURG, FL, 34...

Community: Legacy of Leesburg

Venetian Bay

2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA..., New Smyrna Beach, FL 32168

$855,000

3 beds

3 baths

2,536 sq ft

House

2816 E VENETIAN LAKE CIR, NEW SMYRNA BEA...

Community: Venetian Bay

Breakaway Trails

33 COQUINA RIDGE WAY, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$699,000

4 beds

3 baths

2,602 sq ft

House

33 COQUINA RIDGE WAY, ORMOND BEACH, FL, ...

Community: Breakaway Trails

Sullivan Ranch

30245 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$350,000

4 beds

2 baths

1,670 sq ft

House

30245 CHEVAL ST, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

Sun City Center

$350,000

3 beds

3 baths

2,218 sq ft

House

2113 E DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

Traditions at Lake Ruby

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$399,900

4 beds

3 baths

2,404 sq ft

House

3686 PLYMOUTH DR, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Valencia Lakes

16135 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$535,000

2 beds

2 baths

2,074 sq ft

House

16135 CAPE CORAL DR, WIMAUMA, FL, 33598

Community: Valencia Lakes

Lakes of Mount Dora

8456 NORWICH WAY, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$648,999

4 beds

3 baths

2,460 sq ft

House

8456 NORWICH WAY, MOUNT DORA, FL, 32757

Community: Lakes of Mount Dora

Ocala Preserve

4040 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$269,990

2 beds

2 baths

1,614 sq ft

House

4040 NW 44TH CIR, OCALA, FL, 34482

Community: Ocala Preserve

Twin Lakes

5014 E FOUNTAINWOOD DR, SAINT CLOUD, FL,..., Saint Cloud, FL 34772

$479,800

3 beds

3 baths

2,208 sq ft

House

5014 E FOUNTAINWOOD DR, SAINT CLOUD, FL,...

House

7732 SW 86TH CT, OCALA, FL, 34481

Condo

2028 ACADIA GREENS DR, SUN CITY CENTER, ...

Community: Sun City Center

1…68 69 70 71 72 73 74 75 76 77 78 79 80…90

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

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

Call us: (689) 407-5757

3,573 homes near Winter Garden

Remove Boundaries ×

Map Satellite

Call Us Call Us

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

106 communities near Winter Garden

3,573 homes near Winter Garden

2 beds

2 baths

1,717 sq ft

House

2 beds

2 baths

984 sq ft

Condo

2 beds

2 baths

1,632 sq ft

House

4 beds

3 baths

4,092 sq ft

House

3 beds

3 baths

2,470 sq ft

House

2 beds

2 baths

1,884 sq ft

House

3 beds

10 baths

1,429 sq ft

Condo

3 beds

2 baths

2,267 sq ft

House

2 beds

2 baths

1,564 sq ft

House

2 beds

2 baths

1,298 sq ft

Condo

3 beds

2 baths

1,865 sq ft

House

3 beds

3 baths

2,427 sq ft

House

2 beds

2 baths

2,400 sq ft

House

2 beds

2 baths

1,100 sq ft

Condo

3 beds

2 baths

1,631 sq ft

House

3 beds

2 baths

2,241 sq ft

House

3 beds

3 baths

2,536 sq ft

House

4 beds

3 baths

2,602 sq ft

House

4 beds

2 baths

1,670 sq ft

House

3 beds