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

3,584 homes near Winter Garden

Sort by:

Relevance

No reviews yet

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

<$100k - $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

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)

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

1272 BONITA CANYON DR, KISSIMMEE, FL, 34...

Community: Solivita

Latitude Margaritaville

770 JOLLYMON WAY, DAYTONA BEACH, FL, 321..., Daytona Beach, FL 32124

$639,900

2 beds

2 baths

1,681 sq ft

House

770 JOLLYMON WAY, DAYTONA BEACH, FL, 321...

Community: Latitude Margaritaville

Kings Ridge

4202 HAMMERSMITH DR, CLERMONT, FL, 34711, Clermont, FL 34711

$439,900

2 beds

2 baths

1,968 sq ft

House

4202 HAMMERSMITH DR, CLERMONT, FL, 34711

Community: Kings Ridge

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

Questions? Call us: (689) 407-5757

Huntington at Hunter's Ridge

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

$369,900

2 beds

2 baths

1,603 sq ft

House

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

Community: Huntington at Hunter's Ridge

The Villages®

$850,000

3 beds

2 baths

2,061 sq ft

House

4406 CREIGHTON LOOP, THE VILLAGES, FL, 3...

Community: The Villages®

On Top of the World

9820 SW 99TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$234,900

2 beds

2 baths

1,344 sq ft

House

9820 SW 99TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Stonecrest

17720 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$227,000

2 beds

2 baths

1,120 sq ft

House

17720 SE 115TH CT, SUMMERFIELD, FL, 3449...

Community: Stonecrest

On Top of the World

8885 SW 90TH LN, OCALA, FL, 34481, Ocala, FL 34481

$175,000

2 beds

2 baths

1,688 sq ft

Villa

8885 SW 90TH LN, OCALA, FL, 34481

Community: On Top of the World

Spruce Creek South

17835 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$237,900

2 beds

2 baths

1,158 sq ft

House

17835 SE 95TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Latitude Margaritaville

512 BAREFOOT LIFE LN, DAYTONA BEACH, FL,..., Daytona Beach, FL 32124

$719,900

2 beds

3 baths

2,339 sq ft

House

512 BAREFOOT LIFE LN, DAYTONA BEACH, FL,...

Community: Latitude Margaritaville

Spruce Creek Preserve

13784 SW 115TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432

$234,000

3 beds

3 baths

1,692 sq ft

House

13784 SW 115TH CIR, DUNNELLON, FL, 34432

Community: Spruce Creek Preserve

On Top of the World

8420 SW 92ND ST B, OCALA, FL, 34481, Ocala, FL 34481

$174,900

2 beds

2 baths

1,688 sq ft

Villa

8420 SW 92ND ST B, OCALA, FL, 34481

Community: On Top of the World

Solivita

2340 PALM TREE DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$359,000

3 beds

3 baths

2,272 sq ft

Villa

2340 PALM TREE DR, KISSIMMEE, FL, 34759

Community: Solivita

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

Questions? Call us: (689) 407-5757

Oak Run

11475 SW 85TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$234,900

2 beds

2 baths

1,160 sq ft

House

11475 SW 85TH AVE, OCALA, FL, 34481

Community: Oak Run

On Top of the World

9805 SW 95TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$324,900

2 beds

2 baths

1,596 sq ft

House

9805 SW 95TH LOOP, OCALA, FL, 34481

Community: On Top of the World

Solivita

531 BARCELONA DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$369,900

3 beds

2 baths

1,966 sq ft

House

531 BARCELONA DR, POINCIANA, FL, 34759

Community: Solivita

Lake Ashton

4433 VENTANA LN, LAKE WALES, FL, 33859, Lake Wales, FL 33859

$489,900

3 beds

2 baths

2,512 sq ft

House

4433 VENTANA LN, LAKE WALES, FL, 33859

Community: Lake Ashton

Pennbrooke Fairways

143 WESTWOOD DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$159,000

2 beds

2 baths

1,148 sq ft

Manufactured Home

143 WESTWOOD DR, LEESBURG, FL, 34748

Community: Pennbrooke Fairways

Ocala Preserve

3862 NW 49TH CT, OCALA, FL, 34482, Ocala, FL 34482

$530,000

2 beds

3 baths

2,455 sq ft

House

3862 NW 49TH CT, OCALA, FL, 34482

Community: Ocala Preserve

Solivita

772 SAN RAPHAEL ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$589,900

3 beds

4 baths

2,616 sq ft

House

772 SAN RAPHAEL ST, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

418 TREVISO DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$615,000

3 beds

3 baths

2,427 sq ft

House

418 TREVISO DR, KISSIMMEE, FL, 34759

Community: Solivita

Solivita

105 PALAZZO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$326,000

2 beds

2 baths

1,590 sq ft

House

105 PALAZZO LN, KISSIMMEE, FL, 34759

Community: Solivita

Venetian Bay

424 LUNA BELLA LN APT 330, NEW SMYRNA BE..., New Smyrna Beach, FL 32168

$369,000

3 beds

3 baths

1,953 sq ft

Condo

424 LUNA BELLA LN APT 330, NEW SMYRNA BE...

Community: Venetian Bay

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

Questions? Call us: (689) 407-5757

Lakes of Mount Dora

2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3..., Mount Dora, FL 32757

$559,990

3 beds

2 baths

2,180 sq ft

House

2046 WALLINGFORD LOOP, MOUNT DORA, FL, 3...

Community: Lakes of Mount Dora

Lakes of Mount Dora

8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275..., Mount Dora, FL 32757

$450,000

3 beds

2 baths

1,524 sq ft

House

8592 HEMPSTEAD WAY, MOUNT DORA, FL, 3275...

Community: Lakes of Mount Dora

Oak Run

11591 SW 78TH AVE, OCALA, FL, 34476, Ocala, FL 34476

$199,000

2 beds

2 baths

1,226 sq ft

House

11591 SW 78TH AVE, OCALA, FL, 34476

Community: Oak Run

Highlands Ridge

4005 CARTER CREEK DR, AVON PARK, FL, 338..., Avon Park, FL 33825

$299,500

3 beds

2 baths

1,826 sq ft

House

4005 CARTER CREEK DR, AVON PARK, FL, 338...

Community: Highlands Ridge

Solivita

1398 DEL MAR DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$328,000

2 beds

2 baths

1,595 sq ft

House

1398 DEL MAR DR, KISSIMMEE, FL, 34759

Community: Solivita

Cherrywood

10286 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476

$159,900

2 beds

3 baths

2,019 sq ft

House

10286 SW 61ST TERRACE RD, OCALA, FL, 344...

Community: Cherrywood

On Top of the World

9859 SW 97TH ST, OCALA, FL, 34481, Ocala, FL 34481

$160,000

2 beds

2 baths

1,732 sq ft

House

9859 SW 97TH ST, OCALA, FL, 34481

Community: On Top of the World

Solivita

153 MARABELLA LOOP, POINCIANA, FL, 34759, Poinciana, FL 34759

$250,000

2 beds

2 baths

1,467 sq ft

House

153 MARABELLA LOOP, POINCIANA, FL, 34759

Community: Solivita

Sun City Center

$102,900

1 beds

2 baths

800 sq ft

Condo

302 CANTON CT 54, SUN CITY CENTER, FL, 3...

Community: Sun City Center

Spruce Creek Preserve

11298 SW 138TH LN, DUNNELLON, FL, 34432, Dunnellon, FL 34432

$249,000

2 beds

2 baths

1,408 sq ft

House

11298 SW 138TH LN, DUNNELLON, FL, 34432

House

14117 SW 115TH CIR, DUNNELLON, FL, 34432

Community: Spruce Creek Preserve

1…52 53 54 55 56 57 58 59 60 61 62 63 64…90

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?

Global - Lead Form - Buyer or Renter

First Name

Last Name

Phone/Mobile

Text

I'm looking to:

Rent

Buy

*55places does not provide or maintain community HOA information.

Yes, I want to subscribe to email updates from 55places.com, including newsletters, community announcements, and more.

I agree to receive SMS messages to connect me with a local expert.

By requesting more information, you agree that 55places may call, text, or email you about your inquiry, which may be made with automated means (including recorded voice messages, SMS, or text messages). You understand that your consent is not a prerequisite for buying, selling or renting a property. You may revoke your consent at any time by contacting [email protected]. Message/data rates may apply. You also agree to 55places.com’s Privacy Policy and Terms of Use.

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

Call us: (689) 407-5757

3,584 homes near Winter Garden

Remove Boundaries ×

Map Satellite

Call Us Call Us

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

1,255 sq ft

House

2 beds

2 baths

1,670 sq ft

House

2 beds

2 baths

1,705 sq ft

House

2 beds

2 baths

1,681 sq ft

House

2 beds

2 baths

1,968 sq ft

House

2 beds

2 baths

1,603 sq ft

House

3 beds

2 baths

2,061 sq ft

House

2 beds

2 baths

1,344 sq ft

House

2 beds

2 baths

1,120 sq ft

House

2 beds

2 baths

1,688 sq ft

Villa

2 beds

2 baths

1,158 sq ft

House

2 beds

3 baths

2,339 sq ft

House

3 beds

3 baths

1,692 sq ft

House

2 beds

2 baths

1,688 sq ft

Villa

3 beds

3 baths

2,272 sq ft

Villa

2 beds

2 baths

1,160 sq ft

House

2 beds

2 baths

1,596 sq ft

House

3 beds

2 baths

1,966 sq ft

House

3 beds

2 baths

2,512 sq ft

House

2 beds