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

3,584 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

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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 - $600Ks

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

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)

Trilogy® Orlando

$300Ks - $600Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 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

1 2...3

The Villages®

$339,900

2 beds

2 baths

1,132 sq ft

Villa

1787 FOLIAGE LN, THE VILLAGES, FL, 32162

Community: The Villages®

Harbor Hills Country Club

5252 GROVE MNR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$388,000

3 beds

2 baths

1,844 sq ft

House

5252 GROVE MNR, LADY LAKE, FL, 32159

Community: Harbor Hills Country Club

Spruce Creek Country Club

12860 SE 92ND COURT RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$469,965

2 beds

2 baths

1,639 sq ft

House

12860 SE 92ND COURT RD, SUMMERFIELD, FL,...

Community: Spruce Creek Country Club

The Lakes at Harmony

7480 WING SPAN WAY, HARMONY, FL, 34773, Harmony, FL 34773

$540,000

5 beds

4 baths

2,717 sq ft

House

7480 WING SPAN WAY, HARMONY, FL, 34773

Community: The Lakes at Harmony

Highland Fairways

3279 PEBBLE BEND DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$259,000

2 beds

2 baths

1,456 sq ft

Manufactured Home

3279 PEBBLE BEND DR, LAKELAND, FL, 33810

Community: Highland Fairways

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

Questions? Call us: (689) 407-5757

Summer Trees

79 CYPRESS POND RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$230,000

2 beds

2 baths

1,300 sq ft

House

79 CYPRESS POND RD, PORT ORANGE, FL, 321...

Community: Summer Trees

Breakaway Trails

35 CARRIAGE CREEK WAY, ORMOND BEACH, FL,..., Ormond Beach, FL 32174

$389,900

3 beds

2 baths

1,799 sq ft

House

35 CARRIAGE CREEK WAY, ORMOND BEACH, FL,...

Community: Breakaway Trails

Venetian Bay

2915 N ASCIANO CT, NEW SMYRNA BEACH, FL,..., New Smyrna Beach, FL 32168

$750,000

3 beds

3 baths

2,181 sq ft

House

2915 N ASCIANO CT, NEW SMYRNA BEACH, FL,...

Community: Venetian Bay

Venetian Bay

3418 LEONARDO LN, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$636,900

3 beds

2 baths

1,912 sq ft

House

3418 LEONARDO LN, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Kings Ridge

3853 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711

$295,000

2 beds

2 baths

1,366 sq ft

House

3853 EVERSHOLT ST, CLERMONT, FL, 34711

Community: Kings Ridge

Kings Ridge

3817 DOUNE WAY, CLERMONT, FL, 34711, Clermont, FL 34711

$309,990

2 beds

2 baths

1,625 sq ft

House

3817 DOUNE WAY, CLERMONT, FL, 34711

Community: Kings Ridge

The Villages®

$289,000

2 beds

2 baths

1,258 sq ft

Villa

5719 SPARTINA TER, THE VILLAGES, FL, 321...

Community: The Villages®

SummerGlen

1192 SW 161ST PL, OCALA, FL, 34473, Ocala, FL 34473

$350,000

3 beds

3 baths

1,893 sq ft

House

1192 SW 161ST PL, OCALA, FL, 34473

Community: SummerGlen

SummerGlen

1443 SW 161ST ST, OCALA, FL, 34473, Ocala, FL 34473

$388,000

3 beds

2 baths

2,283 sq ft

House

1443 SW 161ST ST, OCALA, FL, 34473

Community: SummerGlen

SummerGlen

1427 SW 161ST ST, OCALA, FL, 34473, Ocala, FL 34473

$480,000

4 beds

3 baths

2,837 sq ft

House

1427 SW 161ST ST, OCALA, FL, 34473

Community: SummerGlen

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

Questions? Call us: (689) 407-5757

The Villages®

$509,700

3 beds

3 baths

1,869 sq ft

House

1285 PERKINS AVE, THE VILLAGES, FL, 3216...

Community: The Villages®

Lake Ashton

4004 SABLE LOOP DR, LAKE WALES, FL, 3385..., Lake Wales, FL 33859

$590,000

4 beds

3 baths

2,937 sq ft

House

4004 SABLE LOOP DR, LAKE WALES, FL, 3385...

Community: Lake Ashton

Alhambra Villas Condominiums

151 N HILL AVE # 100, DELAND, FL, 32724, Deland, FL 32724

$173,000

2 beds

2 baths

979 sq ft

Condo

151 N HILL AVE # 100, DELAND, FL, 32724

Community: Alhambra Villas Condominiums

Del Webb Oasis

15569 ORCHID ROSE CT, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$949,000

4 beds

4 baths

3,489 sq ft

House

15569 ORCHID ROSE CT, WINTER GARDEN, FL,...

Community: Del Webb Oasis

Del Webb Oasis

13563 PEARL BEACH ST, WINTER GARDEN, FL,..., Winter Garden, FL 34787

$430,000

2 beds

2 baths

1,579 sq ft

House

13563 PEARL BEACH ST, WINTER GARDEN, FL,...

Community: Del Webb Oasis

Stone Creek

6018 SW 86TH CIR, OCALA, FL, 34481, Ocala, FL 34481

$549,900

2 beds

3 baths

2,261 sq ft

House

6018 SW 86TH CIR, OCALA, FL, 34481

Community: Stone Creek

Solivita

2188 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$309,900

2 beds

2 baths

1,364 sq ft

House

2188 PALM TREE DR, KISSIMMEE, FL, 34759

Community: Solivita

Arlington Ridge

26917 WHITE PLAINS WAY, LEESBURG, FL, 34..., Leesburg, FL 34748

$265,000

2 beds

2 baths

1,251 sq ft

Villa

26917 WHITE PLAINS WAY, LEESBURG, FL, 34...

Community: Arlington Ridge

Stone Creek

7316 SW 94TH CT, OCALA, FL, 34481, Ocala, FL 34481

$380,000

3 beds

2 baths

2,413 sq ft

House

7316 SW 94TH CT, OCALA, FL, 34481

Community: Stone Creek

Cherrywood

10317 SW 63RD AVE, OCALA, FL, 34476, Ocala, FL 34476

$335,900

3 beds

2 baths

2,560 sq ft

House

10317 SW 63RD AVE, OCALA, FL, 34476

Community: Cherrywood

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

Questions? Call us: (689) 407-5757

The Villages®

$310,000

2 beds

2 baths

1,248 sq ft

House

704 BOLIVAR ST, THE VILLAGES, FL, 32159

Community: The Villages®

Sun City Center

$325,000

2 beds

2 baths

2,036 sq ft

House

2216 W DEL WEBB BLVD, SUN CITY CENTER, F...

Community: Sun City Center

Spruce Creek North

10983 SW 65TH AVE, OCALA, FL, 34476, Ocala, FL 34476

$189,000

2 beds

2 baths

1,008 sq ft

House

10983 SW 65TH AVE, OCALA, FL, 34476

Community: Spruce Creek North

Summit Greens

3083 PINNACLE CT, CLERMONT, FL, 34711, Clermont, FL 34711

$349,900

2 beds

2 baths

1,765 sq ft

House

3083 PINNACLE CT, CLERMONT, FL, 34711

Community: Summit Greens

Oak Run

6836 SW 112TH ST, OCALA, FL, 34476, Ocala, FL 34476

$248,777

3 beds

2 baths

1,366 sq ft

House

6836 SW 112TH ST, OCALA, FL, 34476

Community: Oak Run

Sun City Center

$339,999

2 beds

2 baths

1,528 sq ft

House

301 CALOOSA PALMS CT, SUN CITY CENTER, F...

Community: Sun City Center

Venetian Bay

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

$579,000

3 beds

2 baths

1,712 sq ft

House

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

Community: Venetian Bay

The Villages®

$565,000

3 beds

3 baths

2,057 sq ft

House

5857 MACKENZIE AVE, THE VILLAGES, FL, 32...

Community: The Villages®

Sun City Center

$297,400

2 beds

2 baths

1,803 sq ft

House

613 LA JOLLA AVE, SUN CITY CENTER, FL, 3...

Community: Sun City Center

Venetian Bay

3211 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$989,132

3 beds

3 baths

2,542 sq ft

House

3211 MODENA WAY, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

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

Questions? Call us: (689) 407-5757

The Villages®

$289,900

2 beds

2 baths

1,156 sq ft

Villa

1381 ZEST AVE, THE VILLAGES, FL, 32163

Community: The Villages®

Del Webb Oasis

15084 CANOPY COVER DR, WINTER GARDEN, FL..., Winter Garden, FL 34787

$1,019,000

3 beds

3 baths

2,270 sq ft

House

15084 CANOPY COVER DR, WINTER GARDEN, FL...

Community: Del Webb Oasis

Majestic Oaks Ocala

8761 SW 52ND CT, OCALA, FL, 34476, Ocala, FL 34476

$399,000

3 beds

2 baths

2,496 sq ft

House

8761 SW 52ND CT, OCALA, FL, 34476

Community: Majestic Oaks Ocala

On Top of the World

7942 SW 86TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$363,000

2 beds

2 baths

1,747 sq ft

House

7942 SW 86TH TERRACE RD, OCALA, FL, 3448...

Community: On Top of the World

Sullivan Ranch

30304 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757

$555,000

6 beds

4 baths

3,499 sq ft

House

30304 CHEVAL ST, MOUNT DORA, FL, 32757

Community: Sullivan Ranch

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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.

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Want to learn more about 55+ communities in Winter Garden?

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3,584 homes near Winter Garden

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

106 communities near Winter Garden

3,584 homes near Winter Garden

2 beds

2 baths

1,132 sq ft

Villa

3 beds

2 baths

1,844 sq ft

House

2 beds

2 baths

1,639 sq ft

House

5 beds

4 baths

2,717 sq ft

House

2 beds

2 baths

1,456 sq ft

Manufactured Home

2 beds

2 baths

1,300 sq ft

House

3 beds

2 baths

1,799 sq ft

House

3 beds

3 baths

2,181 sq ft

House

3 beds

2 baths

1,912 sq ft

House

2 beds

2 baths

1,366 sq ft

House

2 beds

2 baths

1,625 sq ft

House

2 beds

2 baths

1,258 sq ft

Villa

3 beds

3 baths

1,893 sq ft

House

3 beds

2 baths

2,283 sq ft

House

4 beds

3 baths

2,837 sq ft

House

3 beds

3 baths

1,869 sq ft

House

4 beds

3 baths

2,937 sq ft

House

2 beds

2 baths

979 sq ft

Condo

4 beds

4 baths

3,489 sq ft

House

2 beds