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

2769 ATTWATER LOOP, WINTER HAVEN, FL, 33...

Community: Traditions at Lake Ruby

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

Questions? Call us: (689) 407-5757

Sun City Center

$287,500

2 beds

2 baths

1,493 sq ft

Villa

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

Community: Sun City Center

The Villages®

$354,900

3 beds

2 baths

1,477 sq ft

House

2528 BUTTONWOOD RUN, THE VILLAGES, FL, 3...

Community: The Villages®

On Top of the World

8580 SW 97TH LANE RD B, OCALA, FL, 34481, Ocala, FL 34481

$214,999

2 beds

2 baths

1,278 sq ft

Villa

8580 SW 97TH LANE RD B, OCALA, FL, 34481

Community: On Top of the World

Venetian Bay

3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$589,900

3 beds

2 baths

1,712 sq ft

House

3611 MARISOL CT, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

High Vista at Ridgewood Lakes

53 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$325,000

3 beds

2 baths

1,856 sq ft

House

53 HIGH VISTA DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Solivita

340 GRAND CANAL DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$259,000

2 beds

2 baths

1,507 sq ft

House

340 GRAND CANAL DR, POINCIANA, FL, 34759

Community: Solivita

On Top of the World

8864 SW 85TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$657,999

3 beds

3 baths

2,895 sq ft

House

8864 SW 85TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Highland Lakes

26736 CASH CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$243,000

2 beds

2 baths

1,293 sq ft

Villa

26736 CASH CT, LEESBURG, FL, 34748

Community: Highland Lakes

Sun City Center

$259,800

2 beds

2 baths

1,459 sq ft

Halfplex

2015 GARDENIA LANDINGS LN, SUN CITY CENT...

Community: Sun City Center

On Top of the World

9667 SW 94TH CT C, OCALA, FL, 34481, Ocala, FL 34481

$150,000

2 beds

2 baths

1,412 sq ft

Villa

9667 SW 94TH CT C, 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

Solivita

453 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$474,900

3 beds

4 baths

2,580 sq ft

House

453 SORRENTO RD, KISSIMMEE, FL, 34759

Community: Solivita

On Top of the World

9107 SW 102ND CIR, OCALA, FL, 34481, Ocala, FL 34481

$319,900

3 beds

2 baths

1,784 sq ft

House

9107 SW 102ND CIR, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$611,000

3 beds

3 baths

2,192 sq ft

House

1454 NEUPORT PATH, THE VILLAGES, FL, 321...

Community: The Villages®

Carillon Lakes

4048 WINDCHIME LN, LAKELAND, FL, 33811, Lakeland, FL 33811

$430,000

5 beds

3 baths

2,788 sq ft

House

4048 WINDCHIME LN, LAKELAND, FL, 33811

Community: Carillon Lakes

The Villages®

$325,000

2 beds

2 baths

1,090 sq ft

Villa

1410 CONCHAS DR, THE VILLAGES, FL, 32162

Community: The Villages®

Harbor Hills Country Club

5515 CITATION CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$479,999

3 beds

2 baths

1,967 sq ft

House

5515 CITATION CT, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

On Top of the World

9773 SW 90TH ST, OCALA, FL, 34481, Ocala, FL 34481

$212,999

2 beds

2 baths

1,504 sq ft

House

9773 SW 90TH ST, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$149,900

2 beds

2 baths

984 sq ft

Condo

401 DORCHESTER PL 55, SUN CITY CENTER, F...

Community: Sun City Center

Cresswind at Victoria Gardens

1018 HERON POINT CIR, DELAND, FL, 32724, Deland, FL 32724

$455,000

4 beds

3 baths

2,091 sq ft

House

1018 HERON POINT CIR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

The Villages®

$369,900

3 beds

2 baths

1,392 sq ft

House

17009 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

The Villages®

$369,000

3 beds

2 baths

1,561 sq ft

House

1318 GUERRA AVE, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$639,900

3 beds

2 baths

1,918 sq ft

House

907 TRIFU TER, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$234,000

2 beds

2 baths

1,139 sq ft

Manufactured Home

811 SAINT ANDREWS BLVD, THE VILLAGES, FL...

Community: The Villages®

On Top of the World

7917 SW 85TH LOOP, OCALA, FL, 34476, Ocala, FL 34476

$359,900

3 beds

2 baths

1,953 sq ft

House

7917 SW 85TH LOOP, OCALA, FL, 34476

Community: On Top of the World

Palm Cay

11118 SW 76TH AVE, OCALA, FL, 34476, Ocala, FL 34476

$182,500

2 beds

2 baths

932 sq ft

House

11118 SW 76TH AVE, OCALA, FL, 34476

Community: Palm Cay

Marco Polo Village

10884 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476

$324,999

3 beds

2 baths

2,026 sq ft

House

10884 SW 53RD CIR, OCALA, FL, 34476

Community: Marco Polo Village

Cherrywood

10016 SW 62ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$210,000

3 beds

2 baths

1,367 sq ft

House

10016 SW 62ND CIR, OCALA, FL, 34476

Community: Cherrywood

Lake Jovita Golf and Country Club

14198 THOROUGHBRED DR, DADE CITY, FL, 33..., Dade City, FL 33525

$569,900

3 beds

3 baths

2,277 sq ft

House

14198 THOROUGHBRED DR, DADE CITY, FL, 33...

Community: Lake Jovita Golf and Country Club

On Top of the World

9014 SW 96TH TER, OCALA, FL, 34481, Ocala, FL 34481

$233,700

2 beds

2 baths

1,520 sq ft

House

9014 SW 96TH TER, OCALA, FL, 34481

Community: On Top of the World

Marion Landing

8783 SW 66TH TER, OCALA, FL, 34476, Ocala, FL 34476

$216,900

2 beds

2 baths

1,008 sq ft

Manufactured Home

8783 SW 66TH TER, OCALA, FL, 34476

Community: Marion Landing

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

Questions? Call us: (689) 407-5757

Four Seasons at Orlando

1671 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$349,900

2 beds

2 baths

1,557 sq ft

House

1671 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

Plantation at Leesburg

3909 RIVER CREST CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$355,000

3 beds

2 baths

1,690 sq ft

House

3909 RIVER CREST CIR, LEESBURG, FL, 3474...

3218 WOODRIDGE DR, THE VILLAGES, FL, 321...

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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3,964 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

2 beds

2 baths

1,530 sq ft

House

3 beds

2 baths

1,774 sq ft

House

2 beds

2 baths

1,440 sq ft

Mobile Home

2 beds

2 baths

1,710 sq ft

House

2 beds

2 baths

1,385 sq ft

Villa

2 beds

2 baths

1,493 sq ft

Villa

3 beds

2 baths

1,477 sq ft

House

2 beds

2 baths

1,278 sq ft

Villa

3 beds

2 baths

1,712 sq ft

House

3 beds

2 baths

1,856 sq ft

House

2 beds

2 baths

1,507 sq ft

House

3 beds

3 baths

2,895 sq ft

House

2 beds

2 baths

1,293 sq ft

Villa

2 beds

2 baths

1,459 sq ft

Halfplex

2 beds

2 baths

1,412 sq ft

Villa

3 beds

4 baths

2,580 sq ft

House

3 beds

2 baths

1,784 sq ft

House

3 beds

3 baths

2,192 sq ft

House

5 beds

3 baths

2,788 sq ft

House

2 beds