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)

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

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

1 2...3

Sun City Center

$450,000

3 beds

2 baths

1,684 sq ft

House

2249 NEW BEDFORD DR, SUN CITY CENTER, FL...

Community: Sun City Center

On Top of the World

9480 SW 94TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$375,000

3 beds

3 baths

1,855 sq ft

House

9480 SW 94TH LOOP, OCALA, FL, 34481

Community: On Top of the World

On Top of the World

9886 SW 104TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$464,900

2 beds

2 baths

2,104 sq ft

House

9886 SW 104TH AVE, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$204,900

2 beds

2 baths

1,357 sq ft

Condo

2469 NANTUCKET HARBOR LOOP 123, SUN CITY...

Community: Sun City Center

New The Villages®

21204 SANDALWOOD DR # 21-204, WILDWOOD, ..., Wildwood, FL 34785

$145,000

2 beds

2 baths

1,110 sq ft

Condo

21204 SANDALWOOD DR # 21-204, WILDWOOD, ...

House

3978 NOTTINGHAM LOOP, THE VILLAGES, FL, ...

Community: The Villages®

Latitude Margaritaville

568 LANDSHARK BLVD, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32124

$398,000

2 beds

2 baths

1,482 sq ft

House

568 LANDSHARK BLVD, DAYTONA BEACH, FL, 3...

Community: Latitude Margaritaville

New The Villages®

2450 SOUTHERN OAK ST, THE VILLAGES, FL, ..., The Villages, FL 32162

$309,900

2 beds

2 baths

1,156 sq ft

Villa

2450 SOUTHERN OAK ST, THE VILLAGES, FL, ...

Community: The Villages®

New Sun City Center

2468 KENSINGTON GREENS DR, SUN CITY CENT..., Sun City Center, FL 33573

$250,000

2 beds

2 baths

1,630 sq ft

Condo

2468 KENSINGTON GREENS DR, SUN CITY CENT...

Community: Sun City Center

New The Villages®

639 BERMUDEZ CT, THE VILLAGES, FL, 32162, The Villages, FL 32162

$530,000

3 beds

2 baths

1,587 sq ft

Villa

639 BERMUDEZ CT, THE VILLAGES, FL, 32162

Community: The Villages®

Venetian Bay

2870 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$509,999

4 beds

4 baths

2,203 sq ft

Townhouse

2870 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

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

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

Questions? Call us: (689) 407-5757

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®

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®

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 Palm Cay

10648 SW 83RD AVE, OCALA, FL, 34481, Ocala, FL 34481

$215,900

2 beds

2 baths

1,340 sq ft

House

10648 SW 83RD AVE, OCALA, FL, 34481

Community: Palm Cay

New On Top of the World

8635 SW 95TH ST F, OCALA, FL, 34481, Ocala, FL 34481

$176,500

2 beds

2 baths

1,445 sq ft

Villa

8635 SW 95TH ST F, OCALA, FL, 34481

Community: On Top of the World

New Ocala Preserve

5297 NW 34TH ST, OCALA, FL, 34482, Ocala, FL 34482

$275,000

2 beds

2 baths

1,318 sq ft

Villa

5297 NW 34TH ST, OCALA, FL, 34482

Community: Ocala Preserve

New Sun City Center

2035 HAMPSTEAD CIR # 275, SUN CITY CENTE..., Sun City Center, FL 33573

$225,000

2 beds

2 baths

1,378 sq ft

Condo

2035 HAMPSTEAD CIR # 275, SUN CITY CENTE...

Community: Sun City Center

New Spruce Creek Country Club

8789 SE 136TH LN, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$349,900

3 beds

2 baths

2,029 sq ft

House

8789 SE 136TH LN, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

New Spruce Creek Preserve

11536 SW 140TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432

$267,500

2 beds

2 baths

1,830 sq ft

House

11536 SW 140TH LOOP, DUNNELLON, FL, 3443...

Community: Spruce Creek Preserve

New The Villages®

1120 AVENIDA DE LAS CASAS, LADY LAKE, FL..., Lady Lake, FL 32159

$439,500

2 beds

3 baths

1,575 sq ft

Villa

1120 AVENIDA DE LAS CASAS, LADY LAKE, FL...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

New Sun City Center

657 MASTERPIECE DR # 154, SUN CITY CENTE..., Sun City Center, FL 33573

$234,000

2 beds

2 baths

1,543 sq ft

Condo

657 MASTERPIECE DR # 154, SUN CITY CENTE...

Community: Sun City Center

New Sun City Center

1527 FORT DUQUESNA DR, SUN CITY CENTER, ..., Sun City Center, FL 33573

$425,000

2 beds

2 baths

2,325 sq ft

House

1527 FORT DUQUESNA DR, SUN CITY CENTER, ...

Community: Sun City Center

New Valencia Lakes

16308 GARNET GLEN PL, WIMAUMA, FL, 33598, Wimauma, FL 33598

$675,000

3 beds

4 baths

2,741 sq ft

House

16308 GARNET GLEN PL, WIMAUMA, FL, 33598

Community: Valencia Lakes

New The Villages®

707 LISBON LN, THE VILLAGES, FL, 32159, The Villages, FL 32159

$265,000

2 beds

2 baths

1,248 sq ft

House

707 LISBON LN, THE VILLAGES, FL, 32159

Community: The Villages®

New The Villages®

309 CHULA VISTA AVE, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$255,000

2 beds

2 baths

1,550 sq ft

House

309 CHULA VISTA AVE, LADY LAKE, FL, 3215...

Community: The Villages®

New Ocala Preserve

3637 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482

$470,000

3 beds

4 baths

2,341 sq ft

House

3637 NW 56TH AVE, OCALA, FL, 34482

Community: Ocala Preserve

The Villages®

1114 PARADISE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$260,000

2 beds

2 baths

1,248 sq ft

House

1114 PARADISE DR, LADY LAKE, FL, 32159

Community: The Villages®

On Top of the World

9065 SW 82ND TER D, OCALA, FL, 34481, Ocala, FL 34481

$149,800

2 beds

2 baths

1,369 sq ft

Villa

9065 SW 82ND TER D, OCALA, FL, 34481

Community: On Top of the World

VillageWalk at Lake Nona

11754 BARLETTA DR, ORLANDO, FL, 32827, Orlando, FL 32827

$589,900

3 beds

2 baths

2,211 sq ft

House

11754 BARLETTA DR, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

The Villages®

$295,000

2 beds

2 baths

1,268 sq ft

House

811 ALVARADO PL, THE VILLAGES, FL, 32159

House

26908 HONEYMOON AVE, LEESBURG, FL, 34748

Community: Legacy of Leesburg

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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

1,684 sq ft

House

3 beds

3 baths

1,855 sq ft

House

2 beds

2 baths

2,104 sq ft

House

2 beds

2 baths

1,357 sq ft

Condo

2 beds

2 baths

1,110 sq ft

Condo

2 beds

2 baths

1,483 sq ft

House

2 beds

2 baths

1,274 sq ft

Villa

3 beds

2 baths

1,611 sq ft

House

3 beds

2 baths

1,854 sq ft

House

2 beds

2 baths

1,482 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,630 sq ft

Condo

3 beds

2 baths

1,587 sq ft

Villa

4 beds

4 baths

2,203 sq ft

Townhouse

2 beds

2 baths

1,120 sq ft

Manufactured Home

3 beds

2 baths

1,733 sq ft

House

2 beds

2 baths

1,156 sq ft

Villa

2 beds

2 baths

1,370 sq ft

House

2 beds

2 baths

1,340 sq ft

House

2 beds