Winter Garden, FL 55+ active adult communities & homes for sale - Page 60

3,517 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 - $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 - $700Ks

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 - $600Ks

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 - $900Ks

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

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 (2 reviews)

Plantation at Leesburg

$100Ks - $500Ks

Plantation at Leesburg, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1987 - 2008 | 2,820 homes

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 - $600Ks

Twin Lakes, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes

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

Questions? Call us: (689) 407-5757

Pelican Bay Daytona Beach

$100Ks - $400Ks

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

4.7 rating (3 reviews)

Spruce Creek South

$100Ks - $400Ks

Spruce Creek South, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1989 - 1995 | 1,650 homes

4.7 rating (11 reviews)

Valencia Lakes

$200Ks - $600Ks

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

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

$200Ks - $600Ks

Trilogy® Orlando, Groveland, FL

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

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

Questions? Call us: (689) 407-5757

5 rating (8 reviews)

Royal Highlands

$200Ks - $400Ks

Royal Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 homes

4 rating (7 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

$300Ks - $1Ms

VillageWalk at Lake Nona, Orlando, FL

Resale Only | Age-targeted | Built 2006 - 2016 | 1,300 homes

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 - $400Ks

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

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

Questions? Call us: (689) 407-5757

5 rating (5 reviews)

SummerGlen

$100Ks - $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

Breakaway Trails

$400Ks - $800Ks

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

4.8 rating (6 reviews)

Highland Lakes

$100Ks - $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

Pine Run Estates

<$100k - $300Ks

Pine Run Estates, Ocala, FL

Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 homes

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

Questions? Call us: (689) 407-5757

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

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

Stone Creek

6032 SW 86TH TERRACE RD, OCALA, FL, 3448..., Ocala, FL 34481

$544,800

2 beds

3 baths

2,295 sq ft

House

6032 SW 86TH TERRACE RD, OCALA, FL, 3448...

Community: Stone Creek

Sun City Center

$134,900

2 beds

2 baths

984 sq ft

Condo

2345 GLENMORE CIR, SUN CITY CENTER, FL, ...

Community: Sun City Center

Harbor Hills Country Club

39320 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159

$484,000

3 beds

2 baths

2,120 sq ft

House

39320 HARBOR HILLS BLVD, LADY LAKE, FL, ...

Community: Harbor Hills Country Club

Sun City Center

$285,000

2 beds

2 baths

1,750 sq ft

House

703 OJAI AVE, SUN CITY CENTER, FL, 33573

Community: Sun City Center

Royal Harbor

5740 BOUNTY CIR, TAVARES, FL, 32778, Tavares, FL 32778

$460,000

4 beds

3 baths

3,136 sq ft

House

5740 BOUNTY CIR, TAVARES, FL, 32778

House

9385 SE 125TH ST, SUMMERFIELD, FL, 34491

6338 FLAXMAYER RD, THE VILLAGES, FL, 321...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Breakaway Trails

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321..., Ormond Beach, FL 32174

$499,900

4 beds

3 baths

2,544 sq ft

House

24 LAKE VISTA WAY, ORMOND BEACH, FL, 321...

Community: Breakaway Trails

The Villages®

$689,000

3 beds

3 baths

2,478 sq ft

House

8690 SE 173RD WISTERIA ST, THE VILLAGES,...

Community: The Villages®

On Top of the World

9662 SW 97TH LN, OCALA, FL, 34481, Ocala, FL 34481

$229,000

3 beds

2 baths

1,742 sq ft

House

9662 SW 97TH LN, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$170,000

2 beds

2 baths

1,227 sq ft

House

1760 ATRIUM DR, SUN CITY CENTER, FL, 335...

Community: Sun City Center

Solivita

487 MONTEREY ST, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$329,000

2 beds

2 baths

1,655 sq ft

House

487 MONTEREY ST, KISSIMMEE, FL, 34759

Community: Solivita

Highland Fairways

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

$245,000

2 beds

2 baths

1,456 sq ft

Manufactured Home

3279 PEBBLE BEND DR, LAKELAND, FL, 33810

Community: Highland Fairways

Solivita

142 OLYMPUS WAY, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$420,000

3 beds

3 baths

2,070 sq ft

House

142 OLYMPUS WAY, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$675,000

3 beds

2 baths

1,914 sq ft

House

506 DEAUVILLE CT, THE VILLAGES, FL, 3216...

House

Community: Royal Harbor

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

Questions? Call us: (689) 407-5757

Ocala Preserve

5403 NW 48TH PL, OCALA, FL, 34482, Ocala, FL 34482

$299,500

2 beds

2 baths

1,552 sq ft

Villa

5403 NW 48TH PL, OCALA, FL, 34482

Community: Ocala Preserve

The Villages®

5453 WILLIAMSBURG LN, WILDWOOD, FL, 3478..., Wildwood, FL 34785

$185,000

2 beds

2 baths

1,581 sq ft

Manufactured Home

5453 WILLIAMSBURG LN, WILDWOOD, FL, 3478...

Community: The Villages®

Huntington at Hunter's Ridge

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

$359,900

2 beds

2 baths

1,603 sq ft

House

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

Community: Huntington at Hunter's Ridge

Ormond Renaissance

799 STERTHAUS DR 207, ORMOND BEACH, FL, ..., Ormond Beach, FL 32174

$375,000

3 beds

2 baths

1,523 sq ft

Condo

799 STERTHAUS DR 207, ORMOND BEACH, FL, ...

Community: Ormond Renaissance

Palm Cay

11179 SW 78TH CT, OCALA, FL, 34476, Ocala, FL 34476

$169,000

2 beds

2 baths

1,086 sq ft

House

11179 SW 78TH CT, OCALA, FL, 34476

Community: Palm Cay

Palm Cay

11170 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476

$124,700

2 beds

2 baths

864 sq ft

House

11170 SW 79TH AVE, OCALA, FL, 34476

Community: Palm Cay

Solivita

461 TREVISO DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$448,000

3 beds

3 baths

2,266 sq ft

House

461 TREVISO DR, POINCIANA, FL, 34759

Community: Solivita

Scottish Highlands

16 EASTER ROSS CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$215,000

2 beds

2 baths

1,418 sq ft

House

16 EASTER ROSS CT, LEESBURG, FL, 34788

Community: Scottish Highlands

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

Questions? Call us: (689) 407-5757

Sun City Center

$85,000

1 beds

2 baths

800 sq ft

Condo

1826 FOXHUNT DR B, SUN CITY CENTER, FL, ...

Community: Sun City Center

Highlands Ridge

3003 OAKHILL DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$314,900

3 beds

2 baths

1,836 sq ft

House

3003 OAKHILL DR, AVON PARK, FL, 33825

Community: Highlands Ridge

1…54 55 56 57 58 59 60 61 62 63 64 65 66…88

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

3,517 homes

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.
© 2026 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: Jan 11, 2026.
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 - Page 60

109 communities near Winter Garden

3,517 homes near Winter Garden

2 beds

3 baths

2,295 sq ft

House

2 beds

2 baths

984 sq ft

Condo

3 beds

2 baths

2,120 sq ft

House

2 beds

2 baths

1,750 sq ft

House

4 beds

3 baths

3,136 sq ft

House

2 beds

2 baths

1,351 sq ft

Halfplex

3 beds

2 baths

2,311 sq ft

House

2 beds

2 baths

1,160 sq ft

Villa

2 beds

2 baths

1,677 sq ft

House

2 beds

2 baths

1,870 sq ft

House

2 beds

2 baths

1,321 sq ft

House

4 beds

3 baths

2,127 sq ft

House

3 beds

2 baths

1,361 sq ft

House

4 beds

3 baths

2,544 sq ft

House

3 beds

3 baths

2,478 sq ft

House

3 beds

2 baths

1,742 sq ft

House

2 beds

2 baths

1,227 sq ft

House

2 beds

2 baths

1,655 sq ft

House

2 beds

2 baths

1,456 sq ft

Manufactured Home

3 beds