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

3,648 homes near Winter Garden

Sort by:

Relevance

5 rating (1 reviews)

Del Webb Oasis

$400Ks - $900Ks

Del Webb Oasis, Winter Garden, FL

New Construction | 55+ age-restricted | Built 2020 - present | 422 homes

4 rating (17 reviews)

The Villages®

<$100k - $1Ms

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 - $500Ks

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 (48 reviews)

Latitude Margaritaville

$300Ks - $900Ks

Latitude Margaritaville, Daytona Beach, FL

Resale Only | 55+ age-restricted | Built 2017 - 2025 | 3,900 homes

4.2 rating (10 reviews)

Stone Creek

$200Ks - $700Ks

Stone Creek, Ocala, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 3,800 homes

4.1 rating (29 reviews)

Oak Run

$100Ks - $300Ks

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 - $500Ks

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

<$100k - $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 - $600Ks

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

$100Ks - $200Ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

5 rating (3 reviews)

Lake Ashton

$200Ks - $800Ks

Lake Ashton, Lake Wales, FL

Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes

No reviews yet

Venetian Bay

$300Ks - $2Ms

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 - $500Ks

Trilogy® Orlando, Groveland, FL

Resale Only | 55+ age-restricted | Built 2005 - 2022 | 1,500 homes

5 rating (8 reviews)

Royal Highlands

$200Ks - $500Ks

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 - $1Ms

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

<$100k - $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 - $500Ks

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 - $500Ks

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

$400Ks - $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

4.4 rating (16 reviews)

Del Webb Orlando

$300Ks - $400Ks

Del Webb Orlando, Davenport, FL

Resale Only | 55+ age-restricted | Built 2007 - 2021 | 937 homes

No reviews yet

Pine Run Estates

<$100k - $300Ks

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

Venetian Bay

2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$315,000

4 beds

3 baths

2,070 sq ft

House

2937 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

SummerGlen

1707 SW 155TH PLACE RD, OCALA, FL, 34473, Ocala, FL 34473

$275,987

3 beds

2 baths

1,676 sq ft

House

1707 SW 155TH PLACE RD, OCALA, FL, 34473

Community: SummerGlen

On Top of the World

10427 SW 98TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$312,750

2 beds

2 baths

1,467 sq ft

House

10427 SW 98TH PLACE RD, OCALA, FL, 34481

Community: On Top of the World

Venetian Bay

3088 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168

$440,000

2 beds

2 baths

1,003 sq ft

Townhouse

3088 ISLES WAY, NEW SMYRNA BEACH, FL, 32...

Community: Venetian Bay

Southshore Bay

17231 HOLLY WELL AVE, WIMAUMA, FL, 33598, Wimauma, FL 33598

$347,500

2 beds

3 baths

1,744 sq ft

Villa

17231 HOLLY WELL AVE, WIMAUMA, FL, 33598

Community: Southshore Bay

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

Questions? Call us: (689) 407-5757

The Villages®

$711,900

2 beds

2 baths

2,439 sq ft

House

1276 BENNETT PL, THE VILLAGES, FL, 32162

Community: The Villages®

Valencia Lakes

4817 SANDY GLEN WAY, WIMAUMA, FL, 33598, Wimauma, FL 33598

$399,900

3 beds

2 baths

2,087 sq ft

House

4817 SANDY GLEN WAY, WIMAUMA, FL, 33598

Community: Valencia Lakes

On Top of the World

9706 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$258,888

2 beds

2 baths

1,504 sq ft

House

9706 SW 92ND PLACE RD, OCALA, FL, 34481

Community: On Top of the World

Solivita

670 CARMEL LN, POINCIANA, FL, 34759, Poinciana, FL 34759

$435,000

2 beds

3 baths

2,343 sq ft

House

670 CARMEL LN, POINCIANA, FL, 34759

Community: Solivita

Oak Run

11745 SW 72ND CIR, OCALA, FL, 34476, Ocala, FL 34476

$269,999

2 beds

2 baths

1,163 sq ft

House

11745 SW 72ND CIR, OCALA, FL, 34476

Community: Oak Run

Sun City Center

$295,000

2 beds

2 baths

1,516 sq ft

Villa

1002 STRAWPOCKET PL, SUN CITY CENTER, FL...

Community: Sun City Center

The Villages®

$791,000

3 beds

2 baths

1,491 sq ft

House

1225 EDGEWATER LN, THE VILLAGES, FL, 321...

Community: The Villages®

Stone Creek

7066 SW 91ST CT, OCALA, FL, 34481, Ocala, FL 34481

$254,500

2 beds

2 baths

1,756 sq ft

Villa

7066 SW 91ST CT, OCALA, FL, 34481

Community: Stone Creek

The Villages®

5092 NE 81ST BLVD, WILDWOOD, FL, 34785, Wildwood, FL 34785

$1,177,000

3 beds

3 baths

3,407 sq ft

House

5092 NE 81ST BLVD, WILDWOOD, FL, 34785

Community: The Villages®

Mirada

31565 CANNON RUSH DR, SAN ANTONIO, FL, 3..., San Antonio, FL 33576

$392,500

2 beds

2 baths

1,968 sq ft

House

31565 CANNON RUSH DR, SAN ANTONIO, FL, 3...

Community: Mirada

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

Questions? Call us: (689) 407-5757

Scottish Highlands

803 DUNDEE CIR, LEESBURG, FL, 34788, Leesburg, FL 34788

$259,000

2 beds

2 baths

1,436 sq ft

House

803 DUNDEE CIR, LEESBURG, FL, 34788

Community: Scottish Highlands

Spruce Creek South

17738 SE 95TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$188,000

3 beds

2 baths

1,466 sq ft

House

17738 SE 95TH CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Sun City Center

$259,900

2 beds

2 baths

1,444 sq ft

Condo

721 MASTERPIECE DR # 141, SUN CITY CENTE...

Community: Sun City Center

Del Webb Sunbridge

2476 PINE PRESERVE CT, SAINT CLOUD, FL, ..., Saint Cloud, FL 34771

$599,000

4 beds

3 baths

2,249 sq ft

House

2476 PINE PRESERVE CT, SAINT CLOUD, FL, ...

Community: Del Webb Sunbridge

Esplanade at Wiregrass Ranch

4399 ROSATTI RD, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$498,000

2 beds

2 baths

1,694 sq ft

House

4399 ROSATTI RD, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

Highlands Ridge

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

$279,500

3 beds

2 baths

1,826 sq ft

House

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

Community: Highlands Ridge

Ocala Palms

2199 NW 50TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$325,000

3 beds

2 baths

1,822 sq ft

House

2199 NW 50TH CIR, OCALA, FL, 34482

Community: Ocala Palms

Sun City Center

$215,000

2 beds

2 baths

1,506 sq ft

House

1608 COMFY CT, SUN CITY CENTER, FL, 3357...

Community: Sun City Center

Ocala Palms

5939 NW 26TH ST, OCALA, FL, 34482, Ocala, FL 34482

$340,000

2 beds

3 baths

1,835 sq ft

House

5939 NW 26TH ST, OCALA, FL, 34482

Community: Ocala Palms

On Top of the World

8705 SW 95TH ST C, OCALA, FL, 34481, Ocala, FL 34481

$154,900

2 beds

2 baths

1,748 sq ft

Villa

8705 SW 95TH ST C, OCALA, FL, 34481

House

Community: Sun City Center

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

4044 NW 44TH CIR, OCALA, FL, 34482

Community: Ocala Preserve

1…48 49 50 51 52 53 54 55 56 57 58 59 60…92

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

3,648 homes near Winter Garden

Remove Boundaries ×

Map Satellite

The listings data displayed on this medium comes in part from the Real Estate Information Network Inc. (REIN) and has been authorized by participating listing Broker Members of REIN for display. REIN's listings are based upon Data submitted by its Broker Members, and REIN therefore makes no representation or warranty regarding the accuracy of the Data. All users of REIN's listings database should confirm the accuracy of the listing information directly with the listing agent.
© 2025 REIN. REIN's listings Data and information is protected under federal copyright laws. Federal law prohibits, among other acts, the unauthorized copying or alteration of, or preparation of derivative works from, all or any part of copyrighted materials, including certain compilations of Data and information. COPYRIGHT VIOLATORS MAY BE SUBJECT TO SEVERE FINES AND PENALTIES UNDER FEDERAL LAW.
REIN updates its listings on a daily basis. Data last updated: Nov 04, 2025.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us

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

108 communities near Winter Garden

3,648 homes near Winter Garden

4 beds

3 baths

2,070 sq ft

House

3 beds

2 baths

1,676 sq ft

House

2 beds

2 baths

1,467 sq ft

House

2 beds

2 baths

1,003 sq ft

Townhouse

2 beds

3 baths

1,744 sq ft

Villa

2 beds

2 baths

2,439 sq ft

House

3 beds

2 baths

2,087 sq ft

House

2 beds

2 baths

1,504 sq ft

House

2 beds

3 baths

2,343 sq ft

House

2 beds

2 baths

1,163 sq ft

House

2 beds

2 baths

1,516 sq ft

Villa

3 beds

2 baths

1,491 sq ft

House

2 beds

2 baths

1,756 sq ft

Villa

3 beds

3 baths

3,407 sq ft

House

2 beds

2 baths

1,968 sq ft

House

2 beds

2 baths

1,436 sq ft

House

3 beds

2 baths

1,466 sq ft

House

2 beds

2 baths

1,444 sq ft

Condo

4 beds

3 baths

2,249 sq ft

House

2 beds