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

3,573 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 - $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

1823 ATRIUM DR, SUN CITY CENTER, FL, 335...

House

27103 CAMERONS RUN, LEESBURG, FL, 34748

Community: Arlington Ridge

Latitude Margaritaville

192 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$388,500

2 beds

2 baths

1,321 sq ft

House

192 GYPSY PALACE LN, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

Lakeside Landings

5368 COMPASS PT # 202, OXFORD, FL, 34484, Oxford, FL 34484

$239,900

2 beds

2 baths

1,402 sq ft

Condo

5368 COMPASS PT # 202, OXFORD, FL, 34484

Community: Lakeside Landings

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

Questions? Call us: (689) 407-5757

Marco Polo Village

11060 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476

$409,999

3 beds

2 baths

2,087 sq ft

House

11060 SW 53RD CIR, OCALA, FL, 34476

Community: Marco Polo Village

Harbor Hills Country Club

38633 LAKEVIEW WALK, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$424,900

4 beds

2 baths

2,322 sq ft

House

38633 LAKEVIEW WALK, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

Lakeside Landings

10010 LAKE MIONA WAY, OXFORD, FL, 34484, Oxford, FL 34484

$319,900

3 beds

2 baths

1,856 sq ft

House

10010 LAKE MIONA WAY, OXFORD, FL, 34484

Community: Lakeside Landings

Sun City Center

$180,000

2 beds

2 baths

1,008 sq ft

Condo

123 GLENDOWER CIR # 123, SUN CITY CENTER...

Community: Sun City Center

Solivita

501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34..., Kissimmee, FL 34759

$320,000

2 beds

2 baths

1,574 sq ft

House

501 HERITAGE TRAIL ST, KISSIMMEE, FL, 34...

Community: Solivita

Pelican Bay Daytona Beach

289 GULL DR, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$399,000

3 beds

4 baths

2,196 sq ft

House

289 GULL DR, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

Huntington at Hunter's Ridge

51 WRENDALE LOOP, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$369,000

2 beds

2 baths

1,603 sq ft

House

51 WRENDALE LOOP, ORMOND BEACH, FL, 3217...

Community: Huntington at Hunter's Ridge

Sun City Center

$235,000

2 beds

2 baths

1,475 sq ft

House

2015 W DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

Spruce Creek Country Club

13982 SE 86TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$229,995

2 beds

1 baths

943 sq ft

House

13982 SE 86TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Highland Fairways

3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810

$224,900

2 beds

2 baths

1,210 sq ft

House

3130 PRAIRIE DUNES CIR, LAKELAND, FL, 33...

Community: Highland Fairways

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

Questions? Call us: (689) 407-5757

Southshore Bay

17578 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$289,900

2 beds

2 baths

1,406 sq ft

Townhouse

17578 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

On Top of the World

8471 SW 84TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$328,000

3 beds

2 baths

1,721 sq ft

House

8471 SW 84TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Tampa Bay Golf and Country Club

29533 FADE CT, SAN ANTONIO, FL, 33576, San Antonio, FL 33576

$350,000

2 beds

2 baths

1,265 sq ft

Villa

29533 FADE CT, SAN ANTONIO, FL, 33576

Community: Tampa Bay Golf and Country Club

Pennbrooke Fairways

32752 TIMBERWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$329,900

3 beds

2 baths

1,940 sq ft

House

32752 TIMBERWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

New Latitude Margaritaville

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

$540,000

2 beds

2 baths

1,684 sq ft

House

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

Community: Latitude Margaritaville

On Top of the World

8669 SW 88TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$256,400

2 beds

2 baths

1,711 sq ft

House

8669 SW 88TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$203,000

2 beds

2 baths

1,444 sq ft

Condo

607 MANCHESTER WOODS DR # 84, SUN CITY C...

Community: Sun City Center

Venetian Bay

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$529,000

3 beds

3 baths

2,203 sq ft

Townhouse

2820 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

SummerGlen

16405 SW 14TH AVENUE RD, OCALA, FL, 3447..., Ocala, FL 34473

$279,870

3 beds

2 baths

1,676 sq ft

House

16405 SW 14TH AVENUE RD, OCALA, FL, 3447...

Community: SummerGlen

Valencia Lakes

4943 SANDY BROOK CIR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$420,000

2 beds

2 baths

2,061 sq ft

House

4943 SANDY BROOK CIR, WIMAUMA, FL, 33598

Condo

7573 LAUREATE BLVD UNIT 1301, ORLANDO, F...

Community: Gatherings of Lake Nona

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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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3,573 homes near Winter Garden

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

106 communities near Winter Garden

3,573 homes near Winter Garden

3 beds

2 baths

1,450 sq ft

House

3 beds

2 baths

2,413 sq ft

House

2 beds

2 baths

1,948 sq ft

House

4 beds

2 baths

1,774 sq ft

House

2 beds

2 baths

1,194 sq ft

House

3 beds

2 baths

1,728 sq ft

House

2 beds

2 baths

1,848 sq ft

House

3 beds

2 baths

1,652 sq ft

House

3 beds

3 baths

2,427 sq ft

House

3 beds

2 baths

1,644 sq ft

House

3 beds

2 baths

1,986 sq ft

House

3 beds

2 baths

1,655 sq ft

Villa

3 beds

2 baths

2,236 sq ft

House

2 beds

2 baths

1,321 sq ft

House

2 beds

2 baths

1,402 sq ft

Condo

3 beds

2 baths

2,087 sq ft

House

4 beds

2 baths

2,322 sq ft

House

3 beds

2 baths

1,856 sq ft

House

2 beds

2 baths

1,008 sq ft

Condo

2 beds