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

1 2...3

Oak Run

8321 SW 108TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$220,000

2 beds

2 baths

1,428 sq ft

House

8321 SW 108TH PLACE RD, OCALA, FL, 34481

10534 COLLAR DR, SAN ANTONIO, FL, 33576

Community: Tampa Bay Golf and Country Club

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

Questions? Call us: (689) 407-5757

The Country Club of Mount Dora

1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ..., Mount Dora, FL 32757

$389,000

2 beds

2 baths

1,515 sq ft

House

1812 STAFFORD SPRINGS BLVD, MOUNT DORA, ...

Community: The Country Club of Mount Dora

Breakaway Trails

9 FOREST VIEW WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$1,095,000

5 beds

5 baths

4,840 sq ft

House

9 FOREST VIEW WAY, ORMOND BEACH, FL, 321...

Community: Breakaway Trails

Summer Trees

127 CYPRESS POND RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$267,900

3 beds

2 baths

1,426 sq ft

House

127 CYPRESS POND RD, PORT ORANGE, FL, 32...

Community: Summer Trees

Latitude Margaritaville

557 HIGH TIDE LN, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$409,900

2 beds

2 baths

1,321 sq ft

House

557 HIGH TIDE LN, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Stonecrest

11019 SE 170TH LANE RD, SUMMERFIELD, FL,..., Summerfield, FL 34491

$304,000

3 beds

2 baths

1,324 sq ft

House

11019 SE 170TH LANE RD, SUMMERFIELD, FL,...

Community: Stonecrest

Royal Highlands

21125 BRAVEHEART DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$320,000

3 beds

2 baths

1,868 sq ft

House

21125 BRAVEHEART DR, LEESBURG, FL, 34748

Community: Royal Highlands

Stonecrest

11961 SE 176TH PLACE RD, SUMMERFIELD, FL..., Summerfield, FL 34491

$375,000

3 beds

2 baths

1,723 sq ft

House

11961 SE 176TH PLACE RD, SUMMERFIELD, FL...

Community: Stonecrest

The Villages®

$400,000

3 beds

2 baths

1,665 sq ft

House

3198 ABANA PATH, THE VILLAGES, FL, 32163

Community: The Villages®

The Villages®

$375,000

2 beds

2 baths

1,220 sq ft

Villa

1751 BRANDENBURG CT, THE VILLAGES, FL, 3...

Community: The Villages®

The Villages®

$498,500

3 beds

2 baths

2,242 sq ft

House

2002 ENRIQUE DR, THE VILLAGES, FL, 32159

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Lake Jovita Golf and Country Club

13342 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525

$689,000

3 beds

3 baths

2,312 sq ft

House

13342 TRAILING MOSS DR, DADE CITY, FL, 3...

Community: Lake Jovita Golf and Country Club

The Villages®

12046 NE 51ST CIR, OXFORD, FL, 34484, Oxford, FL 34484

$310,000

3 beds

2 baths

1,572 sq ft

House

12046 NE 51ST CIR, OXFORD, FL, 34484

Community: The Villages®

Palms at Serenoa

17571 BLAZING STAR CIR, CLERMONT, FL, 34..., Clermont, FL 34714

$425,000

3 beds

2 baths

1,822 sq ft

House

17571 BLAZING STAR CIR, CLERMONT, FL, 34...

Community: Palms at Serenoa

On Top of the World

7682 SW 89TH CT, OCALA, FL, 34481, Ocala, FL 34481

$354,900

3 beds

2 baths

1,959 sq ft

House

7682 SW 89TH CT, OCALA, FL, 34481

Community: On Top of the World

Foxwood Lake Estates

4886 DEERWOOD DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$199,000

2 beds

2 baths

1,680 sq ft

Manufactured Home

4886 DEERWOOD DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

The Villages®

$449,999

3 beds

2 baths

1,927 sq ft

House

611 ALLENWOOD LOOP, THE VILLAGES, FL, 32...

Community: The Villages®

The Villages®

$487,500

3 beds

2 baths

1,630 sq ft

Villa

1818 TRIMARCHE TER, THE VILLAGES, FL, 32...

Community: The Villages®

Pelican Bay Daytona Beach

176 PALM SPARROW CT, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$325,000

2 beds

2 baths

1,335 sq ft

House

176 PALM SPARROW CT, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

Summer Trees

111 GREY BRANCH RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$278,401

3 beds

2 baths

1,950 sq ft

House

111 GREY BRANCH RD, PORT ORANGE, FL, 321...

Community: Summer Trees

Latitude Margaritaville

429 LOST SHAKER WAY, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124

$550,000

3 beds

2 baths

1,848 sq ft

House

429 LOST SHAKER WAY, DAYTONA BEACH, FL, ...

Community: Latitude Margaritaville

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

Questions? Call us: (689) 407-5757

Summer Trees

39 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128

$280,000

2 beds

2 baths

1,406 sq ft

House

39 CROOKED PINE RD, PORT ORANGE, FL, 321...

Community: Summer Trees

Summer Trees

109 CROOKED PINE RD, PORT ORANGE, FL, 32..., Port Orange, FL 32128

$273,827

2 beds

2 baths

1,106 sq ft

House

109 CROOKED PINE RD, PORT ORANGE, FL, 32...

Community: Summer Trees

New JB Ranch

6138 SW 89TH LANE RD, OCALA, FL, 34476, Ocala, FL 34476

$307,000

3 beds

2 baths

1,857 sq ft

House

6138 SW 89TH LANE RD, OCALA, FL, 34476

Community: JB Ranch

On Top of the World

9790 SW 99TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$234,500

2 beds

2 baths

1,569 sq ft

House

9790 SW 99TH AVE, OCALA, FL, 34481

Community: On Top of the World

Esplanade at Highland Ranch

1282 ZEEK RIDGE ST, CLERMONT, FL, 34715, Clermont, FL 34715

$459,000

2 beds

2 baths

1,710 sq ft

House

1282 ZEEK RIDGE ST, CLERMONT, FL, 34715

Community: Esplanade at Highland Ranch

Venetian Bay

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3..., New Smyrna Beach, FL 32168

$625,000

3 beds

2 baths

1,916 sq ft

House

3322 MODENA WAY, NEW SMYRNA BEACH, FL, 3...

Community: Venetian Bay

Sun City Center

$375,000

2 beds

2 baths

1,854 sq ft

Condo

2419 RICHMOND GREENS CT, SUN CITY CENTER...

Community: Sun City Center

VillageWalk at Lake Nona

12185 OBELIA LN, ORLANDO, FL, 32827, Orlando, FL 32827

$645,000

3 beds

3 baths

2,022 sq ft

House

12185 OBELIA LN, ORLANDO, FL, 32827

Community: VillageWalk at Lake Nona

The Villages®

$230,000

1 beds

1 baths

804 sq ft

Villa

1405 ESPINOZA LN, THE VILLAGES, FL, 3215...

Community: The Villages®

Latitude Margaritaville

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

$439,900

2 beds

2 baths

1,563 sq ft

House

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

House

537 MONTAGE LN, KISSIMMEE, FL, 34759

Community: Solivita

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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

2 beds

2 baths

1,428 sq ft

House

2 beds

3 baths

2,339 sq ft

House

4 beds

3 baths

1,684 sq ft

House

4 beds

2 baths

1,833 sq ft

House

3 beds

2 baths

1,729 sq ft

House

2 beds

2 baths

1,515 sq ft

House

5 beds

5 baths

4,840 sq ft

House

3 beds

2 baths

1,426 sq ft

House

2 beds

2 baths

1,321 sq ft

House

3 beds

2 baths

1,324 sq ft

House

3 beds

2 baths

1,868 sq ft

House

3 beds

2 baths

1,723 sq ft

House

3 beds

2 baths

1,665 sq ft

House

2 beds

2 baths

1,220 sq ft

Villa

3 beds

2 baths

2,242 sq ft

House

3 beds

3 baths

2,312 sq ft

House

3 beds

2 baths

1,572 sq ft

House

3 beds

2 baths

1,822 sq ft

House

3 beds

2 baths

1,959 sq ft

House

2 beds