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

106 communities 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 - $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)

VillageWalk at Lake Nona

$400Ks - $900Ks

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? 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

3136 PORTOFINO BLVD, NEW SMYRNA BEACH, F...

Community: Venetian Bay

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

Questions? Call us: (689) 407-5757

New The Villages®

491 HARLOW LN, THE VILLAGES, FL, 32163, The Villages, FL 32163

$549,000

3 beds

2 baths

1,958 sq ft

House

491 HARLOW LN, THE VILLAGES, FL, 32163

Community: The Villages®

New Foxwood Lake Estates

1797 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$159,900

2 beds

2 baths

1,120 sq ft

Manufactured Home

1797 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

Cherrywood

10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476

$205,000

2 beds

2 baths

1,667 sq ft

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...

Community: Cherrywood

The Villages®

$439,900

3 beds

3 baths

2,394 sq ft

House

702 MELENDEZ WAY, THE VILLAGES, FL, 3215...

Community: The Villages®

The Villages®

$339,900

3 beds

2 baths

1,392 sq ft

House

289 ZINGALE LN, THE VILLAGES, FL, 32163

Community: The Villages®

New The Villages®

522 WADE HAMPTON PL, THE VILLAGES, FL, 3..., The Villages, FL 32162

$425,000

3 beds

2 baths

1,807 sq ft

House

522 WADE HAMPTON PL, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$349,900

3 beds

2 baths

1,509 sq ft

House

9345 SE 171ST LE FLORE LN, THE VILLAGES,...

Community: The Villages®

The Villages®

$359,900

3 beds

2 baths

1,882 sq ft

House

1910 ANTONIA PL, THE VILLAGES, FL, 32159

Community: The Villages®

The Villages®

$539,000

2 beds

2 baths

1,734 sq ft

House

1032 VENTURA DR, THE VILLAGES, FL, 32159

Community: The Villages®

Sun City Center

$229,900

2 beds

2 baths

992 sq ft

Condo

1349 NEW BEDFORD DR # 6, SUN CITY CENTER...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

Legacy of Leesburg

26908 HONEYMOON AVE, LEESBURG, FL, 34748, Leesburg, FL 34748

$317,500

3 beds

2 baths

1,858 sq ft

House

26908 HONEYMOON AVE, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Spruce Creek Country Club

13320 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491

$474,900

2 beds

3 baths

2,346 sq ft

House

13320 SE 97TH TERRACE RD, SUMMERFIELD, F...

Community: Spruce Creek Country Club

Palm Cay

8449 SW 106TH PL, OCALA, FL, 34481, Ocala, FL 34481

$174,900

2 beds

2 baths

1,114 sq ft

House

8449 SW 106TH PL, OCALA, FL, 34481

Community: Palm Cay

New Pelican Bay Daytona Beach

150 BLUE HERON DR B, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$239,700

3 beds

2 baths

1,365 sq ft

Condo

150 BLUE HERON DR B, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

The Villages®

$205,000

1 beds

1 baths

833 sq ft

Villa

9321 SE 172ND AUGUSTA LN, THE VILLAGES, ...

Community: The Villages®

Palm Cay

10881 SW 79TH TER, OCALA, FL, 34476, Ocala, FL 34476

$183,000

2 beds

2 baths

1,112 sq ft

House

10881 SW 79TH TER, OCALA, FL, 34476

Community: Palm Cay

Esplanade at Wiregrass Ranch

4639 GAROFALO RD, WESLEY CHAPEL, FL, 335..., Wesley Chapel, FL 33543

$395,000

2 beds

2 baths

1,689 sq ft

House

4639 GAROFALO RD, WESLEY CHAPEL, FL, 335...

Community: Esplanade at Wiregrass Ranch

The Villages®

916 CANCUN CT, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$265,000

2 beds

2 baths

1,223 sq ft

Villa

916 CANCUN CT, LADY LAKE, FL, 32159

Community: The Villages®

New Oak Run

7710 SW 114TH LOOP, OCALA, FL, 34476, Ocala, FL 34476

$249,620

3 beds

2 baths

1,733 sq ft

House

7710 SW 114TH LOOP, OCALA, FL, 34476

Community: Oak Run

New The Villages®

3440 GALESBURG CT, THE VILLAGES, FL, 321..., The Villages, FL 32162

$344,918

3 beds

2 baths

1,920 sq ft

House

3440 GALESBURG CT, 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

Cresswind at Victoria Gardens

1373 HAZELDENE MNR, DELAND, FL, 32724, Deland, FL 32724

$429,900

2 beds

2 baths

1,966 sq ft

House

1373 HAZELDENE MNR, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

New The Villages®

3457 CARRABELLE CT, THE VILLAGES, FL, 32..., The Villages, FL 32163

$323,900

2 beds

2 baths

1,156 sq ft

Villa

3457 CARRABELLE CT, THE VILLAGES, FL, 32...

Community: The Villages®

Solivita

217 SORRENTO RD, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$463,000

3 beds

3 baths

2,319 sq ft

House

217 SORRENTO RD, KISSIMMEE, FL, 34759

Community: Solivita

New Oak Run

8045 SW 108TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$189,900

2 beds

2 baths

1,148 sq ft

House

8045 SW 108TH LOOP, OCALA, FL, 34481

Community: Oak Run

New Oak Run

8748 SW 109TH LN, OCALA, FL, 34481, Ocala, FL 34481

$195,888

2 beds

2 baths

1,224 sq ft

House

8748 SW 109TH LN, OCALA, FL, 34481

Community: Oak Run

Royal Palm

5415 SWORDFERN CT, PORT ORANGE, FL, 3212..., Port Orange, FL 32128

$409,900

3 beds

2 baths

3,293 sq ft

House

5415 SWORDFERN CT, PORT ORANGE, FL, 3212...

Community: Royal Palm

New Oak Run

8012 SW 109TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$240,000

2 beds

2 baths

1,224 sq ft

House

8012 SW 109TH PLACE RD, OCALA, FL, 34481

Community: Oak Run

Del Webb Oasis

13536 AUTUMN HARVEST AVE, WINTER GARDEN,..., Winter Garden, FL 34787

$470,000

3 beds

3 baths

1,785 sq ft

Townhouse

13536 AUTUMN HARVEST AVE, WINTER GARDEN,...

Community: Del Webb Oasis

New Pennbrooke Fairways

32716 WESTWOOD LOOP, LEESBURG, FL, 34748, Leesburg, FL 34748

$244,900

2 beds

2 baths

1,370 sq ft

House

32716 WESTWOOD LOOP, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New The Villages®

2495 DUNDEE TER, THE VILLAGES, FL, 32162, The Villages, FL 32162

$339,000

2 beds

2 baths

1,258 sq ft

House

2495 DUNDEE TER, THE VILLAGES, FL, 32162

House

4315 ASHTON CLUB DR, LAKE WALES, FL, 338...

Community: Lake Ashton

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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?

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106 communities near Winter Garden

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

106 communities near Winter Garden

3,564 homes near Winter Garden

3 beds

2 baths

1,848 sq ft

House

3 beds

2 baths

1,917 sq ft

House

2 beds

2 baths

1,800 sq ft

House

2 beds

2 baths

2,108 sq ft

House

3 beds

3 baths

1,916 sq ft

House

3 beds

2 baths

1,958 sq ft

House

2 beds

2 baths

1,120 sq ft

Manufactured Home

2 beds

2 baths

1,667 sq ft

House

3 beds

3 baths

2,394 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

1,807 sq ft

House

3 beds

2 baths

1,509 sq ft

House

3 beds

2 baths

1,882 sq ft

House

2 beds

2 baths

1,734 sq ft

House

2 beds

2 baths

992 sq ft

Condo

3 beds

2 baths

1,858 sq ft

House

2 beds

3 baths

2,346 sq ft

House

2 beds

2 baths

1,114 sq ft

House

3 beds

2 baths

1,365 sq ft

Condo

1 beds