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

3,964 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

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? 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

4577 BACK NINE DR, WINTER HAVEN, FL, 338...

Community: Lake Ashton

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

Questions? Call us: (689) 407-5757

Ocala Preserve

3396 NW 55TH CT, OCALA, FL, 34482, Ocala, FL 34482

$500,000

2 beds

3 baths

2,535 sq ft

House

3396 NW 55TH CT, OCALA, FL, 34482

Community: Ocala Preserve

Highlands Ridge

3195 E PEBBLE CREEK DR, AVON PARK, FL, 3..., Avon Park, FL 33825

$315,000

3 beds

2 baths

2,107 sq ft

House

3195 E PEBBLE CREEK DR, AVON PARK, FL, 3...

Community: Highlands Ridge

Ocala Preserve

3554 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$330,000

2 beds

2 baths

1,666 sq ft

House

3554 NW 55TH CIR, OCALA, FL, 34482

Community: Ocala Preserve

SummerGlen

15268 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$325,000

3 beds

2 baths

2,093 sq ft

House

15268 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

On Top of the World

8681 SW 93RD PL B, OCALA, FL, 34481, Ocala, FL 34481

$210,000

2 beds

2 baths

1,409 sq ft

Villa

8681 SW 93RD PL B, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$355,000

2 beds

2 baths

1,299 sq ft

House

5238 DALESSANDRO RD, THE VILLAGES, FL, 3...

Community: The Villages®

Spruce Creek Country Club

13195 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$479,500

3 beds

3 baths

2,266 sq ft

House

13195 SE 93RD CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Plantation at Leesburg

5505 TANGELO ST, LEESBURG, FL, 34748, Leesburg, FL 34748

$255,000

2 beds

2 baths

1,673 sq ft

House

5505 TANGELO ST, LEESBURG, FL, 34748

Community: Plantation at Leesburg

The Villages®

$400,000

2 beds

2 baths

1,139 sq ft

Villa

632 DELGADO AVE, THE VILLAGES, FL, 32159

Community: The Villages®

Pine Run Estates

8973 SW 103RD LN, OCALA, FL, 34481, Ocala, FL 34481

$149,500

2 beds

1 baths

1,176 sq ft

House

8973 SW 103RD LN, OCALA, FL, 34481

Community: Pine Run Estates

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

Questions? Call us: (689) 407-5757

Sun City Center

$149,900

2 beds

2 baths

1,128 sq ft

Condo

1828 FOXHUNT DR A, SUN CITY CENTER, FL, ...

Community: Sun City Center

Spruce Creek Country Club

13015 SE 93RD CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$479,999

3 beds

3 baths

2,429 sq ft

House

13015 SE 93RD CIR, SUMMERFIELD, FL, 3449...

1713 JADESTONE TER, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Solivita

142 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$510,000

3 beds

3 baths

2,598 sq ft

House

142 OLYMPUS WAY, KISSIMMEE, FL, 34759

Community: Solivita

Stone Creek

5728 SW 90TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481

$554,900

2 beds

3 baths

2,110 sq ft

House

5728 SW 90TH COURT RD, OCALA, FL, 34481

Community: Stone Creek

JB Ranch

9354 SW 60TH TERRACE RD, OCALA, FL, 3447..., Ocala, FL 34476

$331,045

3 beds

2 baths

1,816 sq ft

House

9354 SW 60TH TERRACE RD, OCALA, FL, 3447...

Community: JB Ranch

The Villages®

$286,000

3 beds

2 baths

1,392 sq ft

House

9514 SE 168TH MAPLESONG LN, THE VILLAGES...

Community: The Villages®

Traditions at Lake Ruby

2919 WOODWARD LN, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$350,000

3 beds

2 baths

1,649 sq ft

House

2919 WOODWARD LN, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

Sun City Center

$349,000

2 beds

2 baths

1,989 sq ft

House

2128 WORTHINGTON GREENS DR, SUN CITY CEN...

Community: Sun City Center

Sun City Center

$115,000

1 beds

2 baths

800 sq ft

Condo

102 CAMBRIDGE TRL APT 230, SUN CITY CENT...

Community: Sun City Center

On Top of the World

10553 SW 98TH PL, OCALA, FL, 34481, Ocala, FL 34481

$511,000

3 beds

3 baths

2,907 sq ft

House

10553 SW 98TH PL, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

8447 SW 82ND LOOP, OCALA, FL, 34481, Ocala, FL 34481

$399,900

3 beds

2 baths

2,059 sq ft

House

8447 SW 82ND LOOP, OCALA, FL, 34481

Community: On Top of the World

Solivita

636 GRAND CANAL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$235,000

2 beds

2 baths

1,258 sq ft

House

636 GRAND CANAL DR, KISSIMMEE, FL, 34759

House

5430 SIR CHURCHILL DR, LEESBURG, FL, 347...

Community: Royal Highlands

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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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3,964 homes near Winter Garden

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

106 communities near Winter Garden

3,964 homes near Winter Garden

3 beds

2 baths

1,484 sq ft

Villa

3 beds

2 baths

2,635 sq ft

House

2 beds

2 baths

1,152 sq ft

Manufactured Home

3 beds

2 baths

2,237 sq ft

House

3 beds

2 baths

1,918 sq ft

House

2 beds

3 baths

2,535 sq ft

House

3 beds

2 baths

2,107 sq ft

House

2 beds

2 baths

1,666 sq ft

House

3 beds

2 baths

2,093 sq ft

House

2 beds

2 baths

1,409 sq ft

Villa

2 beds

2 baths

1,299 sq ft

House

3 beds

3 baths

2,266 sq ft

House

2 beds

2 baths

1,673 sq ft

House

2 beds

2 baths

1,139 sq ft

Villa

2 beds

1 baths

1,176 sq ft

House

2 beds

2 baths

1,128 sq ft

Condo

3 beds

3 baths

2,429 sq ft

House

2 beds

2 baths

1,146 sq ft

House

2 beds

2 baths

1,687 sq ft

House

2 beds