Winter Garden, FL 55+ active adult communities & homes for sale - Page 50

3,654 homes near Winter Garden

Sort by:

Relevance

4 rating (17 reviews)

The Villages®

$100ks - $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

$100ks - $800ks

Sun City Center, Sun City Center, FL

Resale Only | 55+ age-restricted | Built 1961 - 2018 | 9,500 homes

4.2 rating (10 reviews)

Stone Creek

$200ks - $500ks

Stone Creek, Ocala, FL

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

4.7 rating (18 reviews)

Solivita

$300ks - $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

4.5 rating (11 reviews)

Spruce Creek Country Club

$100ks - $400ks

Spruce Creek Country Club, Summerfield, FL

Resale Only | 55+ age-restricted | Built 1996 - 2007 | 3,250 homes

Venetian Bay

$300ks - $1Ms

Venetian Bay, New Smyrna Beach, FL

New and Resale | Age-targeted | Built 2004 - present | 1,561 homes

5 rating (2 reviews)

Plantation at Leesburg

$100ks - $300ks

Plantation at Leesburg, Leesburg, FL

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

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.

3.6 rating (48 reviews)

Latitude Margaritaville

$300ks - $800ks

Latitude Margaritaville, Daytona Beach, FL

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

5 rating (3 reviews)

Stonecrest

$200ks - $500ks

Stonecrest, Summerfield, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 2,200 homes

4.6 rating (5 reviews)

Ocala Preserve

$100ks - $500ks

Ocala Preserve, Ocala, FL

New and Resale | 55+ age-restricted | Built 2014 - present | 1,800 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

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

Questions? Call us: (689) 407-5757

5 rating (1 reviews)

Ocala Palms

$200ks - $300ks

Ocala Palms, Ocala, FL

Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes

3.8 rating (4 reviews)

Spruce Creek South

$100ks - $200ks

Spruce Creek South, Summerfield, FL

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

5 rating (5 reviews)

SummerGlen

$200ks - $400ks

SummerGlen, Ocala, FL

Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes

Southshore Bay

$200ks - $500ks

Southshore Bay, Wimauma, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes

4.7 rating (11 reviews)

Valencia Lakes

$200ks - $700ks

Valencia Lakes, Wimauma, FL

Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes

5 rating (8 reviews)

Royal Highlands

$200ks - $400ks

Royal Highlands, Leesburg, FL

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

5 rating (1 reviews)

Del Webb Sunbridge

$400ks - $800ks

Del Webb Sunbridge, St. Cloud, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 homes

5 rating (7 reviews)

Kings Ridge

$200ks - $400ks

Kings Ridge, Clermont, FL

Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes

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

Questions? Call us: (689) 407-5757

4 rating (7 reviews)

Tampa Bay Golf and Countr...

$200ks - $500ks

Tampa Bay Golf and Countr..., San Antonio, FL

Resale Only | 55+ age-restricted | Built 1994 - 2015 | 1,336 homes

3.8 rating (6 reviews)

Trilogy® Orlando

$200ks - $500ks

Trilogy® Orlando, Groveland, FL

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

5 rating (1 reviews)

Sandpiper Golf & Coun...

$100ks - $300ks

Sandpiper Golf & Coun..., Lakeland, FL

New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes

2.8 rating (6 reviews)

Arlington Ridge

$200ks - $500ks

Arlington Ridge, Leesburg, FL

New and Resale | 55+ age-restricted | Built 2005 - present | 629 homes

Pelican Bay Daytona Beach

$100ks - $600ks

Pelican Bay Daytona Beach, Daytona Beach, FL

Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes

4 rating (4 reviews)

Lakes of Mount Dora

$300ks - $900ks

Lakes of Mount Dora, Mount Dora, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 950 homes

2.3 rating (6 reviews)

Cherrywood

$100ks - $800ks

Cherrywood, Ocala, FL

Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes

4 rating (2 reviews)

Harbor Hills Country Club

$300ks - $900ks

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

1 rating (1 reviews)

Sullivan Ranch

$200ks - $500ks

Sullivan Ranch, Mount Dora, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 692 homes

3.6 rating (5 reviews)

Heritage Hills

$200ks - $400ks

Heritage Hills, Clermont, FL

New and Resale | 55+ age-restricted | Built 2006 - present | 1,154 homes

Pine Run Estates

$100ks - $200ks

Pine Run Estates, Ocala, FL

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

Mirada

$300ks - $500ks

Mirada, San Antonio, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes

5 rating (1 reviews)

Palm Cay

$100ks - $200ks

Palm Cay, Ocala, FL

Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes

Lake Jovita Golf and Coun...

$400ks - $1Ms

Lake Jovita Golf and Coun..., Dade City, FL

New and Resale | Age-targeted | Built 1999 - present | 875 homes

4.8 rating (6 reviews)

Highland Lakes

$100ks - $200ks

Highland Lakes, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1990 - 1999 | 938 homes

5 rating (8 reviews)

Pennbrooke Fairways

<$100k - $300ks

Pennbrooke Fairways, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes

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

Questions? Call us: (689) 407-5757

5 rating (1 reviews)

Royal Harbor

$200ks - $800ks

Royal Harbor, Tavares, FL

Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2017 - present | 557 homes

1 2...3

Venetian Bay

2912 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$360,000

3 beds

3 baths

1,779 sq ft

House

2912 MELETO BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

The Villages®

$254,000

2 beds

2 baths

1,143 sq ft

Villa

3245 RIVERTON RD, THE VILLAGES, FL, 3216...

Community: The Villages®

Solivita

684 SAN AUGUSTO DR, POINCIANA, FL, 34759, Poinciana, FL 34759

$519,000

3 beds

3 baths

2,363 sq ft

House

684 SAN AUGUSTO DR, POINCIANA, FL, 34759

Community: Solivita

On Top of the World

9077 SW 81ST LOOP, OCALA, FL, 34481, Ocala, FL 34481

$469,000

2 beds

2 baths

2,076 sq ft

House

9077 SW 81ST LOOP, OCALA, FL, 34481

Community: On Top of the World

Esplanade at Wiregrass Ranch

4618 ISONZO WAY, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$585,000

2 beds

3 baths

2,100 sq ft

House

4618 ISONZO WAY, WESLEY CHAPEL, FL, 3354...

Community: Esplanade at Wiregrass Ranch

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

Questions? Call us: (689) 407-5757

Stone Creek

9601 SW 65TH PL, OCALA, FL, 34481, Ocala, FL 34481

$399,999

2 beds

2 baths

2,164 sq ft

House

9601 SW 65TH PL, OCALA, FL, 34481

13160 SE 93RD CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

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

Questions? Call us: (689) 407-5757

On Top of the World

9698 SW 103RD TER, OCALA, FL, 34481, Ocala, FL 34481

$265,000

2 beds

2 baths

1,342 sq ft

House

9698 SW 103RD TER, OCALA, FL, 34481

Community: On Top of the World

Sun City Center

$129,000

2 beds

2 baths

984 sq ft

Condo

401 FARADAY TRL A, SUN CITY CENTER, FL, ...

Community: Sun City Center

Lake Jovita Golf and Country Club

13302 TRAILING MOSS DR, DADE CITY, FL, 3..., Dade City, FL 33525

$750,000

4 beds

3 baths

2,632 sq ft

House

13302 TRAILING MOSS DR, DADE CITY, FL, 3...

Community: Lake Jovita Golf and Country Club

On Top of the World

10691 SW 99TH PL, OCALA, FL, 34481, Ocala, FL 34481

$465,000

2 beds

2 baths

2,019 sq ft

House

10691 SW 99TH PL, OCALA, FL, 34481

Community: On Top of the World

The Villages®

$299,000

2 beds

2 baths

1,161 sq ft

Villa

2346 ARBORDALE AVE, THE VILLAGES, FL, 32...

Community: The Villages®

Stone Creek

9498 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$450,000

3 beds

3 baths

2,536 sq ft

House

9498 SW 70TH LOOP, OCALA, FL, 34481

Community: Stone Creek

The Villages®

$354,900

3 beds

2 baths

1,527 sq ft

House

3001 EGERTON PL, THE VILLAGES, FL, 32162

Community: The Villages®

Marion Landing

8459 SW 60TH CT, OCALA, FL, 34476, Ocala, FL 34476

$279,900

3 beds

3 baths

1,778 sq ft

House

8459 SW 60TH CT, OCALA, FL, 34476

Community: Marion Landing

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

Questions? Call us: (689) 407-5757

Kings Ridge

4246 NEWLAND ST, CLERMONT, FL, 34711, Clermont, FL 34711

$369,900

3 beds

2 baths

1,755 sq ft

House

4246 NEWLAND ST, CLERMONT, FL, 34711

Community: Kings Ridge

Sun City Center

$327,000

2 beds

2 baths

1,503 sq ft

House

1908 STERLING GLEN CT, SUN CITY CENTER, ...

Community: Sun City Center

Venetian Bay

428 N AIRPORT RD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$318,000

3 beds

3 baths

1,794 sq ft

Townhouse

428 N AIRPORT RD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

The Villages®

$315,000

2 beds

2 baths

1,248 sq ft

House

1289 ADDISON AVE, THE VILLAGES, FL, 3216...

Community: The Villages®

Ocala Palms

5016 NW 18TH ST, OCALA, FL, 34482, Ocala, FL 34482

$377,000

3 beds

2 baths

1,788 sq ft

House

5016 NW 18TH ST, OCALA, FL, 34482

952 TALAPIA LOOP, THE VILLAGES, FL, 3216...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

Sun City Center

$289,950

2 beds

2 baths

1,732 sq ft

Villa

325 GREEN MANOR DR, SUN CITY CENTER, FL,...

Community: Sun City Center

Venetian Bay

3371 MEDICI BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168

$369,900

3 beds

2 baths

1,466 sq ft

House

3371 MEDICI BLVD, NEW SMYRNA BEACH, FL, ...

Community: Venetian Bay

Kings Ridge

3914 ALLAMANDA CT, CLERMONT, FL, 34711, Clermont, FL 34711

$375,000

3 beds

2 baths

1,893 sq ft

House

3914 ALLAMANDA CT, CLERMONT, FL, 34711

Community: Kings Ridge

The Villages®

717 ROYAL PALM AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$240,000

2 beds

2 baths

1,248 sq ft

Modular

717 ROYAL PALM AVE, LADY LAKE, FL, 32159

Community: The Villages®

Lake Jovita Golf and Country Club

13235 PALMILLA CIR, DADE CITY, FL, 33525, Dade City, FL 33525

$354,900

3 beds

2 baths

1,683 sq ft

House

13235 PALMILLA CIR, DADE CITY, FL, 33525

Community: Lake Jovita Golf and Country Club

Spruce Creek Country Club

11703 SE 91ST CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$399,500

3 beds

2 baths

1,958 sq ft

House

11703 SE 91ST CIR, SUMMERFIELD, FL, 3449...

Community: Spruce Creek Country Club

Pine Run Estates

10182 SW 87TH TER, OCALA, FL, 34481, Ocala, FL 34481

$160,000

2 beds

2 baths

1,144 sq ft

House

10182 SW 87TH TER, OCALA, FL, 34481

Community: Pine Run Estates

Cresswind DeLand

1274 BRUSH CREEK DR, DELAND, FL, 32724, Deland, FL 32724

$789,990

3 beds

4 baths

2,776 sq ft

House

1274 BRUSH CREEK DR, DELAND, FL, 32724

Community: Cresswind DeLand

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

Questions? Call us: (689) 407-5757

Cresswind DeLand

1292 JACKSON HOLE CT, DELAND, FL, 32724, Deland, FL 32724

$449,990

3 beds

2 baths

1,724 sq ft

House

1292 JACKSON HOLE CT, DELAND, FL, 32724

Community: Cresswind DeLand

On Top of the World

9289 SW 92ND LANE LN, OCALA, FL, 34481, Ocala, FL 34481

$209,000

2 beds

2 baths

1,362 sq ft

House

9289 SW 92ND LANE LN, OCALA, FL, 34481

Community: On Top of the World

1…44 45 46 47 48 49 50 51 52 53 54 55 56…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

3,654 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: Apr 10, 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 50

110 communities near Winter Garden

3,654 homes near Winter Garden

3 beds

3 baths

1,779 sq ft

House

2 beds

2 baths

1,143 sq ft

Villa

3 beds

3 baths

2,363 sq ft

House

2 beds

2 baths

2,076 sq ft

House

2 beds

3 baths

2,100 sq ft

House

2 beds

2 baths

2,164 sq ft

House

2 beds

2 baths

1,408 sq ft

House

3 beds

2 baths

1,726 sq ft

House

2 beds

2 baths

1,869 sq ft

House

2 beds

2 baths

1,464 sq ft

House

3 beds

2 baths

2,416 sq ft

House

3 beds

2 baths

1,840 sq ft

House

2 beds

2 baths

1,875 sq ft

House

2 beds

2 baths

1,342 sq ft

House

2 beds

2 baths

984 sq ft

Condo

4 beds

3 baths

2,632 sq ft

House

2 beds

2 baths

2,019 sq ft

House

2 beds

2 baths

1,161 sq ft

Villa

3 beds

3 baths

2,536 sq ft

House

3 beds