Winter Garden, FL 55+ active adult communities & homes for sale - Page 24

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

10063 LAKE MIONA WAY, OXFORD, FL, 34484

Community: Lakeside Landings

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

Questions? Call us: (689) 407-5757

Summer Trees

6046 WINDING RIDGE LN, PORT ORANGE, FL, ..., Port Orange, FL 32128

$348,000

3 beds

2 baths

1,500 sq ft

House

6046 WINDING RIDGE LN, PORT ORANGE, FL, ...

Community: Summer Trees

Sun City Center

$275,000

2 beds

2 baths

1,857 sq ft

House

1709 S PEBBLE BEACH BLVD, SUN CITY CENTE...

700 MIRROR TER 404, WINTER HAVEN, FL, 33...

Community: Spring Lake Towers

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

Questions? Call us: (689) 407-5757

Del Webb Minneola

1109 CANOPY VIEW WAY, MINNEOLA, FL, 3471..., Minneola, FL 34715

$609,120

3 beds

2 baths

2,214 sq ft

House

1109 CANOPY VIEW WAY, MINNEOLA, FL, 3471...

Community: Del Webb Minneola

Stone Creek

9586 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$289,900

2 beds

2 baths

1,556 sq ft

Villa

9586 SW 70TH LOOP, OCALA, FL, 34481

Community: Stone Creek

Royal Highlands

22125 DRAW BRIDGE DR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$377,000

3 beds

2 baths

2,200 sq ft

House

22125 DRAW BRIDGE DR, LEESBURG, FL, 3474...

Community: Royal Highlands

Summer Trees

79 CYPRESS POND RD # 79, PORT ORANGE, FL..., Port Orange, FL 32128

$227,000

2 beds

2 baths

888 sq ft

Condo

79 CYPRESS POND RD # 79, PORT ORANGE, FL...

Community: Summer Trees

Valencia Lakes

15737 CRYSTAL WATERS DR, WIMAUMA, FL, 33..., Wimauma, FL 33598

$400,000

2 beds

2 baths

1,954 sq ft

House

15737 CRYSTAL WATERS DR, WIMAUMA, FL, 33...

Community: Valencia Lakes

Valencia Lakes

5016 STONE HARBOR CIR, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$520,000

3 beds

2 baths

1,882 sq ft

House

5016 STONE HARBOR CIR, WIMAUMA, FL, 3359...

Community: Valencia Lakes

Valencia Lakes

16051 GOLDEN LAKES DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$475,000

4 beds

3 baths

2,409 sq ft

House

16051 GOLDEN LAKES DR, WIMAUMA, FL, 3359...

Community: Valencia Lakes

Del Webb Sunbridge

2900 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$392,990

3 beds

3 baths

1,767 sq ft

Townhouse

2900 VOYAGER AVE, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

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

Questions? Call us: (689) 407-5757

Del Webb Sunbridge

2904 VOYAGER AVE, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$364,990

3 beds

3 baths

1,744 sq ft

Townhouse

2904 VOYAGER AVE, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

Scottish Highlands

305 BRIGADOON CIR, LEESBURG, FL, 34788, Leesburg, FL 34788

$212,000

2 beds

2 baths

1,270 sq ft

House

305 BRIGADOON CIR, LEESBURG, FL, 34788

Community: Scottish Highlands

High Vista at Ridgewood Lakes

46 HIGH VISTA DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$349,000

3 beds

2 baths

1,816 sq ft

House

46 HIGH VISTA DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

Marion Landing

8532 SW 65TH COURT RD, OCALA, FL, 34476, Ocala, FL 34476

$252,800

3 beds

2 baths

1,817 sq ft

House

8532 SW 65TH COURT RD, OCALA, FL, 34476

Community: Marion Landing

Twin Lakes

2600 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3..., Saint Cloud, FL 34772

$659,000

3 beds

3 baths

2,935 sq ft

House

2600 MEADOWEDGE LOOP, SAINT CLOUD, FL, 3...

Community: Twin Lakes

Legacy of Leesburg

5135 AURORA DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$344,900

3 beds

2 baths

2,055 sq ft

House

5135 AURORA DR, LEESBURG, FL, 34748

Community: Legacy of Leesburg

Huntington at Hunter's Ridge

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$499,700

3 beds

2 baths

2,238 sq ft

House

99 HUNTINGTON PL, ORMOND BEACH, FL, 3217...

Community: Huntington at Hunter's Ridge

Huntington at Hunter's Ridge

42 HUNTINGTON PL, ORMOND BEACH, FL, 3217..., Ormond Beach, FL 32174

$395,000

4 beds

2 baths

2,003 sq ft

House

42 HUNTINGTON PL, ORMOND BEACH, FL, 3217...

Community: Huntington at Hunter's Ridge

Oak Run

10777 SW 71ST CIR, OCALA, FL, 34476, Ocala, FL 34476

$330,000

3 beds

3 baths

2,082 sq ft

House

10777 SW 71ST CIR, OCALA, FL, 34476

Community: Oak Run

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

Questions? Call us: (689) 407-5757

Spruce Creek South

10599 SE 178TH ST, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$214,900

2 beds

2 baths

1,008 sq ft

House

10599 SE 178TH ST, SUMMERFIELD, FL, 3449...

Community: Spruce Creek South

Harbor Hills Country Club

6145 SPINNAKER LOOP, LADY LAKE, FL, 3215..., Lady Lake, FL 32159

$638,900

4 beds

3 baths

3,294 sq ft

House

6145 SPINNAKER LOOP, LADY LAKE, FL, 3215...

Community: Harbor Hills Country Club

Silver Lakes

$430,000

3 beds

3 baths

1,902 sq ft

House

6323 SILVER LAKES DR, LAKELAND, FL, 3381...

Community: Silver Lakes

Solivita

514 SAN JOAQUIN RD, POINCIANA, FL, 34759, Poinciana, FL 34759

$479,000

2 beds

3 baths

2,184 sq ft

House

514 SAN JOAQUIN RD, POINCIANA, FL, 34759

Community: Solivita

Valencia Lakes

16005 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$599,900

3 beds

4 baths

2,725 sq ft

House

16005 CAPE CORAL DR, WIMAUMA, FL, 33598

Community: Valencia Lakes

The Villages®

$305,000

2 beds

2 baths

1,452 sq ft

House

16899 SE 96TH CHAPELWOOD CIR, THE VILLAG...

Community: The Villages®

Pelican Bay Daytona Beach

100 BITTERN CT, DAYTONA BEACH, FL, 32119, Daytona Beach, FL 32119

$499,000

4 beds

3 baths

3,140 sq ft

House

100 BITTERN CT, DAYTONA BEACH, FL, 32119

Community: Pelican Bay Daytona Beach

Carlsberg Estates on Lake Suzanne

284 LAKE SUZANNE DR, LAKE WALES, FL, 338..., Lake Wales, FL 33859

$218,900

2 beds

2 baths

1,170 sq ft

House

284 LAKE SUZANNE DR, LAKE WALES, FL, 338...

Community: Carlsberg Estates on Lake Suzanne

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

Questions? Call us: (689) 407-5757

On Top of the World

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

$235,000

2 beds

2 baths

1,504 sq ft

House

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

Community: On Top of the World

Venetian Bay

2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168

$979,000

3 beds

3 baths

2,034 sq ft

House

2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...

Community: Venetian Bay

1…18 19 20 21 22 23 24 25 26 27 28 29 30…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 24

109 communities near Winter Garden

3,517 homes near Winter Garden

4 beds

2 baths

2,034 sq ft

House

3 beds

2 baths

1,850 sq ft

House

3 beds

3 baths

2,808 sq ft

House

3 beds

2 baths

2,175 sq ft

House

3 beds

2 baths

2,066 sq ft

House

3 beds

2 baths

1,500 sq ft

House

2 beds

2 baths

1,857 sq ft

House

3 beds

2 baths

1,848 sq ft

Townhouse

3 beds

2 baths

1,603 sq ft

House

2 beds

2 baths

1,569 sq ft

House

3 beds

2 baths

1,820 sq ft

House

2 beds

2 baths

1,855 sq ft

House

2 beds

2 baths

1,190 sq ft

Condo

3 beds

2 baths

2,214 sq ft

House

2 beds

2 baths

1,556 sq ft

Villa

3 beds

2 baths

2,200 sq ft

House

2 beds

2 baths

888 sq ft

Condo

2 beds

2 baths

1,954 sq ft

House

3 beds

2 baths

1,882 sq ft

House

4 beds