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

3,958 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 - $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

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

Sun City Center

$315,000

2 beds

2 baths

1,503 sq ft

Villa

689 CHIPPER DR, SUN CITY CENTER, FL, 335...

Community: Sun City Center

Solivita

119 VERONA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$379,900

3 beds

2 baths

1,467 sq ft

House

119 VERONA DR, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

678 IRVINE RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759

$535,000

4 beds

3 baths

2,326 sq ft

House

678 IRVINE RANCH RD, KISSIMMEE, FL, 3475...

Community: Solivita

Sun City Center

$419,900

3 beds

2 baths

1,800 sq ft

Condo

2313 NOTTINGHAM GREENS DR # 2313, SUN CI...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Latitude Margaritaville

663 BEACH BUM BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$649,900

3 beds

3 baths

2,110 sq ft

House

663 BEACH BUM BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

Lake Ashton

4088 DUNMORE DR, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$389,000

3 beds

2 baths

1,943 sq ft

House

4088 DUNMORE DR, LAKE WALES, FL, 33859

Community: Lake Ashton

Del Webb Sunbridge

2496 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771

$575,000

2 beds

2 baths

1,670 sq ft

House

2496 PINE PRESERVE CT, SAINT CLOUD, FL, ...

Community: Del Webb Sunbridge

The Villages®

$499,900

3 beds

2 baths

2,198 sq ft

House

304 GONZALES PL, THE VILLAGES, FL, 32159

Community: The Villages®

Solivita

154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347..., Kissimmee, FL 34759

$644,900

3 beds

4 baths

2,616 sq ft

House

154 RANCHO MIRAGE DR, KISSIMMEE, FL, 347...

Community: Solivita

Solivita

243 NEW RIVER DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$290,000

2 beds

2 baths

1,560 sq ft

House

243 NEW RIVER DR, KISSIMMEE, FL, 34759

Community: Solivita

Ocala Palms

5470 NW 26TH LN, OCALA, FL, 34482, Ocala, FL 34482

$288,500

2 beds

2 baths

1,569 sq ft

House

5470 NW 26TH LN, OCALA, FL, 34482

Community: Ocala Palms

Stone Creek

6832 SW 93RD AVE, OCALA, FL, 34481, Ocala, FL 34481

$374,900

3 beds

2 baths

1,714 sq ft

House

6832 SW 93RD AVE, OCALA, FL, 34481

Community: Stone Creek

Del Webb Sunbridge

2590 CLIFF WAY, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$399,000

2 beds

2 baths

1,584 sq ft

Villa

2590 CLIFF WAY, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Latitude Margaritaville

600 HANG LOOSE WAY, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$665,000

2 beds

3 baths

2,158 sq ft

House

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

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

On Top of the World

9117 SW 93RD CIR, OCALA, FL, 34481, Ocala, FL 34481

$229,000

3 beds

2 baths

1,428 sq ft

House

9117 SW 93RD CIR, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

7912 SW 89TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$419,000

3 beds

2 baths

1,958 sq ft

House

7912 SW 89TH CIR, OCALA, FL, 34481

Community: On Top of the World

Venetian Bay

3620 TRESTO ST, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$335,000

2 beds

3 baths

1,827 sq ft

Townhouse

3620 TRESTO ST, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Majestic Oaks Ocala

4961 SW 88TH PL, OCALA, FL, 34476, Ocala, FL 34476

$335,000

4 beds

2 baths

1,827 sq ft

House

4961 SW 88TH PL, OCALA, FL, 34476

Community: Majestic Oaks Ocala

Breakaway Trails

129 BLACK HICKORY WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174

$499,900

3 beds

2 baths

2,081 sq ft

House

129 BLACK HICKORY WAY, ORMOND BEACH, FL,...

Community: Breakaway Trails

Lakes at Laurel Highlands

1823 PRISTINE LOOP, LAKELAND, FL, 33811, Lakeland, FL 33811

$330,000

3 beds

2 baths

1,711 sq ft

House

1823 PRISTINE LOOP, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

Solivita

4311 VIA CAVOUR CT, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$479,000

3 beds

3 baths

2,003 sq ft

House

4311 VIA CAVOUR CT, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

24104 SANDALWOOD DR # 104, WILDWOOD, FL,..., Wildwood, FL 34785

$122,500

1 beds

1 baths

872 sq ft

Condo

24104 SANDALWOOD DR # 104, WILDWOOD, FL,...

Community: The Villages®

Ocala Preserve

3977 NW 46TH TER, OCALA, FL, 34482, Ocala, FL 34482

$300,000

2 beds

2 baths

1,392 sq ft

House

3977 NW 46TH TER, OCALA, FL, 34482

Community: Ocala Preserve

On Top of the World

9085 SW 96TH LN B, OCALA, FL, 34481, Ocala, FL 34481

$199,500

2 beds

2 baths

1,709 sq ft

Villa

9085 SW 96TH LN B, OCALA, FL, 34481

Community: On Top of the World

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

Questions? Call us: (689) 407-5757

Highlands Ridge

2704 E WATERVIEW DR, AVON PARK, FL, 3382..., Avon Park, FL 33825

$98,000

3 beds

2 baths

1,700 sq ft

Mobile Home

2704 E WATERVIEW DR, AVON PARK, FL, 3382...

Community: Highlands Ridge

Pennbrooke Fairways

32218 SWEET BRIAR CT, LEESBURG, FL, 3474..., Leesburg, FL 34748

$269,900

2 beds

2 baths

1,272 sq ft

House

32218 SWEET BRIAR CT, LEESBURG, FL, 3474...

Community: Pennbrooke Fairways

SummerGlen

15092 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$384,900

3 beds

2 baths

2,285 sq ft

House

15092 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

The Lakes at Harmony

3240 SONGBIRD CIR, HARMONY, FL, 34773, Harmony, FL 34773

$550,000

3 beds

3 baths

1,955 sq ft

House

3240 SONGBIRD CIR, HARMONY, FL, 34773

Community: The Lakes at Harmony

Pennbrooke Fairways

32525 OAK PARK DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$285,000

2 beds

3 baths

1,643 sq ft

House

32525 OAK PARK DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Gatherings of Lake Nona

7517 LAUREATE BLVD 4205, ORLANDO, FL, 32..., Orlando, FL 32827

$370,000

2 beds

2 baths

1,486 sq ft

Condo

7517 LAUREATE BLVD 4205, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

Four Seasons at Orlando

7637 SAND PIERRE CT, KISSIMMEE, FL, 3474..., Kissimmee, FL 34747

$455,900

2 beds

2 baths

1,557 sq ft

Villa

7637 SAND PIERRE CT, KISSIMMEE, FL, 3474...

Community: Four Seasons at Orlando

SummerGlen

15842 SW 11TH TERRACE RD, OCALA, FL, 344..., Ocala, FL 34473

$339,900

2 beds

2 baths

1,750 sq ft

House

15842 SW 11TH TERRACE RD, OCALA, FL, 344...

Community: SummerGlen

Hidden Creek

$239,000

2 beds

2 baths

1,298 sq ft

Villa

2214 HIDDEN CREEK CIR, SEBRING, FL, 3387...

Community: Hidden Creek

Sun City Center

$299,900

2 beds

2 baths

1,206 sq ft

Condo

2071 SIFIELD GREENS WAY # 103, SUN CITY ...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Summer Trees

151 MAGNOLIA LOOP, PORT ORANGE, FL, 3212..., Port Orange, FL 32128

$217,500

2 beds

2 baths

1,048 sq ft

House

151 MAGNOLIA LOOP, PORT ORANGE, FL, 3212...

Community: Summer Trees

Twin Lakes

2312 DATURA LOOP, SAINT CLOUD, FL, 34772, Saint Cloud, FL 34772

$319,000

2 beds

2 baths

1,464 sq ft

Villa

2312 DATURA LOOP, SAINT CLOUD, FL, 34772

Community: Twin Lakes

On Top of the World

8782 SW 82ND COURT RD, OCALA, FL, 34481, Ocala, FL 34481

$449,000

3 beds

2 baths

2,139 sq ft

House

8782 SW 82ND COURT RD, OCALA, FL, 34481

Community: On Top of the World

Highland Fairways

3203 BEAR CREEK LN, LAKELAND, FL, 33810, Lakeland, FL 33810

$190,990

2 beds

2 baths

1,004 sq ft

House

3203 BEAR CREEK LN, LAKELAND, FL, 33810

Community: Highland Fairways

The Villages®

$419,000

3 beds

2 baths

1,559 sq ft

House

3812 NOTTINGHAM LOOP, THE VILLAGES, FL, ...

Community: The Villages®

1…85 86 87 88 89 90 91 92 93 94 95 96 97 98 99

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?

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.

3,958 homes near Winter Garden

Remove Boundaries ×

Map Satellite

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

Call us: (689) 407-5757

Call Us Call Us

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

2,074 sq ft

House

2 beds

2 baths

1,503 sq ft

Villa

3 beds

2 baths

1,467 sq ft

House

4 beds

3 baths

2,326 sq ft

House

3 beds

2 baths

1,800 sq ft

Condo

3 beds

3 baths

2,110 sq ft

House

3 beds

2 baths

1,943 sq ft

House

2 beds

2 baths

1,670 sq ft

House

3 beds

2 baths

2,198 sq ft

House

3 beds

4 baths

2,616 sq ft

House

2 beds

2 baths

1,560 sq ft

House

2 beds

2 baths

1,569 sq ft

House

3 beds

2 baths

1,714 sq ft

House

2 beds

2 baths

1,584 sq ft

Villa

2 beds

3 baths

2,158 sq ft

House

3 beds

2 baths

1,428 sq ft

House

3 beds

2 baths

1,958 sq ft

House

2 beds

3 baths

1,827 sq ft

Townhouse

4 beds

2 baths

1,827 sq ft

House

3 beds