Winter Garden, FL 55+ active adult communities & homes for sale - Page 2

110 communities near Winter Garden

Sort by:

Relevance

3.8 rating (5 reviews)

Marion Landing

$100ks - $300ks

Marion Landing, Ocala, FL

Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes

Four Seasons at Orlando

$300ks - $600ks

Four Seasons at Orlando, Kissimmee, FL

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

Scottish Highlands

$100ks - $200ks

Scottish Highlands, Leesburg, FL

Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes

4.4 rating (16 reviews)

Del Webb Orlando

$200ks - $500ks

Del Webb Orlando, Davenport, FL

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

Tohoqua Reserve

$300ks - $600ks

Tohoqua Reserve, Kissimmee, FL

New Construction | 55+ age-restricted | Built 2021 - present | 258 homes

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

Questions? Call us: (689) 407-5757

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

Questions? Call us: (689) 407-5757

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200ks - $300ks

Traditions at Lake Ruby, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2005 - 2020 | 552 homes

The Lakes at Harmony

$200ks - $400ks

The Lakes at Harmony, Harmony, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes

4.4 rating (9 reviews)

Spruce Creek Preserve

$100ks - $200ks

Spruce Creek Preserve, Dunnellon, FL

Resale Only | 55+ age-restricted | Built 1996 - 2003 | 810 homes

JB Ranch

$300ks

JB Ranch, Ocala, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 346 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 (4 reviews)

Highlands Ridge

<$100k - $300ks

Highlands Ridge, Avon Park, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 850 homes

Read the Ultimate 55+ Rental Guide Thinking about renting in a 55+ active adult community? Our free guide has all the must-know info and practical tips to help you navigate 55+ renting and find your ideal next home in a 55+ community.

Summer Trees

$200ks - $400ks

Summer Trees, Port Orange, FL

Resale Only | 55+ age-restricted | Built 1976 - 2005 | 500 homes

5 rating (1 reviews)

Valencia del Sol

$300ks - $700ks

Valencia del Sol, Wimauma, FL

New Construction | 55+ age-restricted | Built 2017 - present | 565 homes

Foxwood Lake Estates

$100ks - $200ks

Foxwood Lake Estates, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1982 - 1987 | 545 homes

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

Questions? Call us: (689) 407-5757

Quail Meadow

$200ks - $400ks

Quail Meadow, Ocala, FL

Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes

Breakaway Trails

$400ks - $800ks

Breakaway Trails, Ormond Beach, FL

New and Resale | Age-targeted | Built 1985 - present | 976 homes

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

Questions? Call us: (689) 407-5757

Majestic Oaks Ocala

$200ks - $300ks

Majestic Oaks Ocala, Ocala, FL

New and Resale | Age-targeted | Built 1990 - present | 599 homes

The Country Club of Mount...

$200ks - $1Ms

The Country Club of Mount..., Mount Dora, FL

Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes

Gatherings of Lake Nona

$300ks - $400ks

Gatherings of Lake Nona, Orlando, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 216 homes

5 rating (1 reviews)

VillageWalk at Lake Nona

$300ks - $700ks

VillageWalk at Lake Nona, Orlando, FL

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

Lakeside Landings

$100ks - $300ks

Lakeside Landings, Oxford, FL

New and Resale | Age-targeted | Built 2005 - present | 700 homes

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

Questions? Call us: (689) 407-5757

Lakes at Laurel Highlands

$200ks - $300ks

Lakes at Laurel Highlands, Lakeland, FL

New Construction | Age-targeted | Built 2017 - present | 65 homes

5 rating (1 reviews)

Spruce Creek North

$100ks - $300ks

Spruce Creek North, Ocala, FL

Resale Only | 55+ age-restricted | Built 1987 - 1998 | 400 homes

4 rating (4 reviews)

High Vista at Ridgewood L...

$200ks - $300ks

High Vista at Ridgewood L..., Davenport, FL

Resale Only | 55+ age-restricted | Built 1995 - 2005 | 623 homes

5 rating (1 reviews)

Esplanade at Highland Ran...

$300ks - $600ks

Esplanade at Highland Ran..., Clermont, FL

Resale Only | 55+ age-restricted | Built 2014 - 2022 | 475 homes

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

Questions? Call us: (689) 407-5757

Colonnades

$100ks - $200ks

Colonnades, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1985 - 1994 | 360 homes

Esplanade at Wiregrass Ra...

$400ks - $500ks

Esplanade at Wiregrass Ra..., Wesley Chapel, FL

New and Resale | 55+ age-restricted | Built 2019 - present | 868 homes

Del Webb Minneola

$400ks - $700ks

Del Webb Minneola, Minneola, FL

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

Ridgehaven

$300ks - $600ks

Ridgehaven, Ormond Beach, FL

New Construction | 55+ age-restricted

Cresswind DeLand

$300ks - $500ks

Cresswind DeLand, DeLand, FL

New Construction | 55+ age-restricted | Built 2023 - present | 600 homes

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

Questions? Call us: (689) 407-5757

Lake James

$300ks

Lake James, Lakeland, FL

New and Resale | 55+ age-restricted | Built 2004 - present | 216 homes

5 rating (2 reviews)

Palms at Serenoa

$200ks - $400ks

Palms at Serenoa, Clermont, FL

New Construction | 55+ age-restricted | Built 2018 - present | 570 homes

Highland Fairways

$100ks - $300ks

Highland Fairways, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes

Thunderbird Hill

$100ks - $200ks

Thunderbird Hill, Sebring, FL

Resale Only | 55+ age-restricted | Built 1984 - 2000 | 103 homes

Huntington at Hunter's Ri...

$300ks

Huntington at Hunter's Ri..., Ormond Beach, FL

New Construction | 55+ age-restricted | Built 2015 - present | 326 homes

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

Questions? Call us: (689) 407-5757

Vienna Square

$100ks - $200ks

Vienna Square, Winter Haven, FL

New and Resale | 55+ age-restricted | Built 2007 - present | 181 homes

Liberty Village

$300ks - $400ks

Liberty Village, Ocala, FL

New and Resale | 55+ age-restricted | Built 2023 - present | 100 homes

Marco Polo Village

$200ks - $300ks

Marco Polo Village, Ocala, FL

New and Resale | 55+ age-restricted | Built 1998 - present | 261 homes

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

Questions? Call us: (689) 407-5757

3.9 rating (7 reviews)

Summit Greens

$300ks - $400ks

Summit Greens, Clermont, FL

Resale Only | 55+ age-restricted | Built 2001 - 2019 | 769 homes

Valencia Ridge

$400ks - $800ks

Valencia Ridge, Wesley Chapel, FL

New Construction | 55+ age-restricted | Built 2023 - present | 395 homes

8667 SW 97TH ST C, OCALA, FL, 34481

Community: On Top of the World

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

Villa

3461 FALLBROOK 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

New Sun City Center

1804 PACIFIC DUNES DR, SUN CITY CENTER, ..., Sun City Center, FL 33573

$379,900

2 beds

3 baths

2,053 sq ft

House

1804 PACIFIC DUNES DR, SUN CITY CENTER, ...

Community: Sun City Center

New Scottish Highlands

27 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788

$215,000

2 beds

2 baths

1,252 sq ft

House

27 GORDON CT, LEESBURG, FL, 34788

Community: Scottish Highlands

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

Questions? Call us: (689) 407-5757

New Sun City Center

608 LA JOLLA AVE, SUN CITY CENTER, FL, 3..., Sun City Center, FL 33573

$249,900

2 beds

2 baths

1,852 sq ft

House

608 LA JOLLA AVE, SUN CITY CENTER, FL, 3...

Community: Sun City Center

New Plantation at Leesburg

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474..., Leesburg, FL 34748

$299,999

3 beds

2 baths

1,868 sq ft

House

3447 MOUNT HOPE LOOP, LEESBURG, FL, 3474...

Community: Plantation at Leesburg

New Gatherings of Lake Nona

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32..., Orlando, FL 32827

$329,000

2 beds

2 baths

1,549 sq ft

Condo

7517 LAUREATE BLVD 4403, ORLANDO, FL, 32...

Community: Gatherings of Lake Nona

New Southshore Bay

5336 WINDY GROVE DR, WIMAUMA, FL, 33598, Wimauma, FL 33598

$565,000

3 beds

3 baths

2,651 sq ft

House

5336 WINDY GROVE DR, WIMAUMA, FL, 33598

Community: Southshore Bay

New The Villages®

2088 VISION CT, THE VILLAGES, FL, 32163, The Villages, FL 32163

$689,000

3 beds

2 baths

2,013 sq ft

House

2088 VISION CT, THE VILLAGES, FL, 32163

Community: The Villages®

New Foxwood Lake Estates

1704 QUAIL HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$140,000

2 beds

2 baths

1,372 sq ft

Manufactured Home

1704 QUAIL HILL DR, LAKELAND, FL, 33810

House

4902 W FOUNTAINWOOD DR, ST CLOUD, FL, 34...

Community: Twin Lakes

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

Questions? Call us: (689) 407-5757

New The Villages®

1738 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$775,000

4 beds

3 baths

2,959 sq ft

House

1738 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Foxwood Lake Estates

1798 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810

$164,900

3 beds

2 baths

1,176 sq ft

Manufactured Home

1798 FOX HILL DR, LAKELAND, FL, 33810

Community: Foxwood Lake Estates

New Spruce Creek Preserve

11876 SW 137TH LOOP, DUNNELLON, FL, 3443..., Dunnellon, FL 34432

$249,900

3 beds

2 baths

1,760 sq ft

House

11876 SW 137TH LOOP, DUNNELLON, FL, 3443...

Community: Spruce Creek Preserve

New Highlands Ridge

5004 BIRKDALE DR, AVON PARK, FL, 33825, Avon Park, FL 33825

$299,000

2 beds

2 baths

1,648 sq ft

Villa

5004 BIRKDALE DR, AVON PARK, FL, 33825

Community: Highlands Ridge

New Four Seasons at Orlando

1999 KEY BAY TRL, KISSIMMEE, FL, 34747, Kissimmee, FL 34747

$429,980

2 beds

2 baths

1,557 sq ft

Villa

1999 KEY BAY TRL, KISSIMMEE, FL, 34747

Community: Four Seasons at Orlando

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

Questions? Call us: (689) 407-5757

New Lakes at Laurel Highlands

2933 IVY LAKE CT, LAKELAND, FL, 33811, Lakeland, FL 33811

$389,500

5 beds

3 baths

2,674 sq ft

House

2933 IVY LAKE CT, LAKELAND, FL, 33811

Community: Lakes at Laurel Highlands

New The Villages®

5511 HEAD WAY, THE VILLAGES, FL, 32163, The Villages, FL 32163

$394,900

3 beds

2 baths

1,708 sq ft

House

5511 HEAD WAY, THE VILLAGES, FL, 32163

Community: The Villages®

New High Vista at Ridgewood Lakes

116 FLEMING LN, DAVENPORT, FL, 33837, Davenport, FL 33837

$309,000

2 beds

2 baths

1,776 sq ft

House

116 FLEMING LN, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

New The Villages®

603 ROBIN LANE AVE, WILDWOOD, FL, 34785, Wildwood, FL 34785

$159,900

2 beds

2 baths

1,352 sq ft

Manufactured Home

603 ROBIN LANE AVE, WILDWOOD, FL, 34785

Community: The Villages®

New The Villages®

1714 EL NINO ST, THE VILLAGES, FL, 32162, The Villages, FL 32162

$289,000

2 beds

2 baths

1,121 sq ft

Villa

1714 EL NINO ST, THE VILLAGES, FL, 32162

House

6541 SW 111TH LOOP, 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

New The Villages®

3284 THEODORE TER, THE VILLAGES, FL, 321..., The Villages, FL 32163

$674,900

3 beds

3 baths

2,033 sq ft

House

3284 THEODORE TER, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

717 TANGERINE DR, LADY LAKE, FL, 32159, Lady Lake, FL 32159

$220,000

2 beds

2 baths

1,332 sq ft

Manufactured Home

717 TANGERINE DR, LADY LAKE, FL, 32159

Community: The Villages®

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

110 communities

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 2

110 communities near Winter Garden

3,654 homes near Winter Garden

3 beds

2 baths

1,733 sq ft

Villa

3 beds

2 baths

1,862 sq ft

House

3 beds

2 baths

1,505 sq ft

House

4 beds

2 baths

2,069 sq ft

House

2 beds

2 baths

1,541 sq ft

Villa

2 beds

2 baths

1,148 sq ft

House

2 beds

2 baths

1,343 sq ft

House

2 beds

2 baths

1,437 sq ft

House

2 beds

2 baths

1,158 sq ft

House

2 beds

2 baths

1,008 sq ft

House

3 beds

2 baths

2,213 sq ft

House

2 beds

2 baths

960 sq ft

Condo

2 beds

2 baths

1,499 sq ft

Villa

2 beds

3 baths

2,053 sq ft

House

2 beds

2 baths

1,252 sq ft

House

2 beds

2 baths

1,852 sq ft

House

3 beds

2 baths

1,868 sq ft

House

2 beds

2 baths

1,549 sq ft

Condo

3 beds

3 baths

2,651 sq ft

House

3 beds