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

109 communities near Winter Garden

Sort by:

Relevance

Mirada

$200Ks - $500Ks

Mirada, San Antonio, FL

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

5 rating (4 reviews)

Highlands Ridge

<$100k - $400Ks

Highlands Ridge, Avon Park, FL

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

4.4 rating (9 reviews)

Spruce Creek Preserve

$100Ks - $300Ks

Spruce Creek Preserve, Dunnellon, FL

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

5 rating (1 reviews)

Palm Cay

$100Ks - $300Ks

Palm Cay, Ocala, FL

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

Want to learn more about 55+ communities in Winter Garden, FL? 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

5 rating (1 reviews)

Royal Harbor

$300Ks - $400Ks

Royal Harbor, Tavares, FL

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

Lakeside Landings

$200Ks - $500Ks

Lakeside Landings, Oxford, FL

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

2.3 rating (6 reviews)

Cherrywood

$100Ks - $300Ks

Cherrywood, Ocala, FL

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

1 rating (1 reviews)

Sullivan Ranch

$300Ks - $700Ks

Sullivan Ranch, Mount Dora, FL

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

Highland Fairways

$100Ks - $300Ks

Highland Fairways, Lakeland, FL

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

Southshore Bay

$200Ks - $600Ks

Southshore Bay, Wimauma, FL

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

Scottish Highlands

$100Ks - $200Ks

Scottish Highlands, Leesburg, FL

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

5 rating (4 reviews)

Carillon Lakes

$200Ks - $600Ks

Carillon Lakes, Lakeland, FL

Resale Only | Age-targeted | Built 2000 - 2006 | 650 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

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

Questions? Call us: (689) 407-5757

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

3.8 rating (5 reviews)

Marion Landing

$100Ks - $400Ks

Marion Landing, Ocala, FL

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

Cresswind DeLand

$300Ks - $500Ks

Cresswind DeLand, DeLand, FL

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

Majestic Oaks Ocala

$200Ks - $600Ks

Majestic Oaks Ocala, Ocala, FL

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

5 rating (2 reviews)

Palms at Serenoa

$300Ks - $400Ks

Palms at Serenoa, Clermont, FL

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

5 rating (1 reviews)

Valencia del Sol

$200Ks - $700Ks

Valencia del Sol, Wimauma, FL

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

Four Seasons at Orlando

$200Ks - $700Ks

Four Seasons at Orlando, Kissimmee, FL

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

3.8 rating (5 reviews)

Traditions at Lake Ruby

$200Ks - $400Ks

Traditions at Lake Ruby, Winter Haven, FL

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

Foxwood Lake Estates

$100Ks - $200Ks

Foxwood Lake Estates, Lakeland, FL

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

Summer Trees

$200Ks

Summer Trees, Port Orange, FL

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

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

Questions? Call us: (689) 407-5757

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

Quail Meadow

$200Ks - $300Ks

Quail Meadow, Ocala, FL

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

Royal Palm

$300Ks - $400Ks

Royal Palm, Port Orange, FL

Resale Only | 55+ age-restricted | Built 2002 - 2016 | 458 homes

5 rating (1 reviews)

Spruce Creek North

$100Ks - $200Ks

Spruce Creek North, Ocala, FL

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

The Lakes at Harmony

$200Ks - $500Ks

The Lakes at Harmony, Harmony, FL

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

Valencia Ridge

$500Ks - $900Ks

Valencia Ridge, Wesley Chapel, FL

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

Colonnades

$100Ks - $300Ks

Colonnades, Lakeland, FL

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

JB Ranch

$200Ks - $400Ks

JB Ranch, Ocala, FL

New and Resale | 55+ age-restricted | Built 2017 - present | 346 homes

Huntington at Hunter's Ri...

$300Ks - $400Ks

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

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

Lake Henry Estates

$200Ks

Lake Henry Estates, Haines City, FL

Resale Only | 55+ age-restricted | Built 1992 - 2004 | 280 homes

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

Questions? Call us: (689) 407-5757

Ormond Renaissance

$300Ks - $400Ks

Ormond Renaissance, Ormond Beach, FL

New Construction | 55+ age-restricted | Built 2016 - present | 280 homes

Marco Polo Village

$200Ks - $500Ks

Marco Polo Village, Ocala, FL

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

Tohoqua Reserve

$300Ks - $400Ks

Tohoqua Reserve, Kissimmee, FL

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

Encore at Fishhawk Ranch

$300Ks - $600Ks

Encore at Fishhawk Ranch, Lithia, FL

New and Resale | 55+ age-restricted | Built 2016 - present | 240 homes

Baytree

$200Ks

Baytree, Tavares, FL

Resale Only | 55+ age-restricted | Built 1990 - 2003 | 221 homes

1 2...3

Spruce Creek South

9645 SE 173RD PL, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$319,000

3 beds

2 baths

1,450 sq ft

House

9645 SE 173RD PL, SUMMERFIELD, FL, 34491

Community: Spruce Creek South

On Top of the World

9686 SW 92ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$272,000

2 beds

2 baths

1,515 sq ft

House

9686 SW 92ND PLACE RD, OCALA, FL, 34481

Community: On Top of the World

Pine Run Estates

10040 SW 98TH AVE, OCALA, FL, 34481, Ocala, FL 34481

$168,000

2 beds

2 baths

1,144 sq ft

House

10040 SW 98TH AVE, OCALA, FL, 34481

Community: Pine Run Estates

Valencia Ridge

32608 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543

$669,900

3 beds

3 baths

2,209 sq ft

House

32608 NEROLI ST, WESLEY CHAPEL, FL, 3354...

Community: Valencia Ridge

Del Webb Sunbridge

6501 CYRILS DR, SAINT CLOUD, FL, 34771, Saint Cloud, FL 34771

$450,000

3 beds

3 baths

1,738 sq ft

Townhouse

6501 CYRILS DR, SAINT CLOUD, FL, 34771

Community: Del Webb Sunbridge

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

Questions? Call us: (689) 407-5757

Ocala Preserve

5333 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482

$275,000

2 beds

2 baths

1,368 sq ft

Halfplex

5333 NW 33RD PL, OCALA, FL, 34482

Community: Ocala Preserve

Pelican Bay Daytona Beach

149 BLUE HERON DR C, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32119

$190,000

2 beds

2 baths

1,192 sq ft

Condo

149 BLUE HERON DR C, DAYTONA BEACH, FL, ...

Community: Pelican Bay Daytona Beach

On Top of the World

9662 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481

$174,500

2 beds

2 baths

1,412 sq ft

Villa

9662 SW 95TH CT A, OCALA, FL, 34481

Community: On Top of the World

Stone Creek

9009 SW 52ND PLACE RD, OCALA, FL, 34481, Ocala, FL 34481

$392,810

2 beds

3 baths

2,080 sq ft

House

9009 SW 52ND PLACE RD, OCALA, FL, 34481

Community: Stone Creek

New Sandpiper Golf & Country Club

6119 SANDPIPERS DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$245,000

2 beds

2 baths

1,148 sq ft

House

6119 SANDPIPERS DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

Stonecrest

12135 SE 172ND LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$450,000

3 beds

2 baths

2,031 sq ft

House

12135 SE 172ND LN, SUMMERFIELD, FL, 3449...

Community: Stonecrest

Sun City Center

$295,000

3 beds

2 baths

1,568 sq ft

Villa

802 CHIPPER DR, SUN CITY CENTER, FL, 335...

Community: Sun City Center

Palms at Serenoa

17581 SUMMERSWEET WAY, CLERMONT, FL, 347..., Clermont, FL 34714

$325,000

2 beds

2 baths

1,627 sq ft

Villa

17581 SUMMERSWEET WAY, CLERMONT, FL, 347...

Community: Palms at Serenoa

The Villages®

$499,000

3 beds

2 baths

1,696 sq ft

House

5617 STRICKLIN ST, THE VILLAGES, FL, 321...

Community: The Villages®

Plantation at Leesburg

25129 RIVERWALK DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$289,900

2 beds

2 baths

2,063 sq ft

House

25129 RIVERWALK DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

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

Questions? Call us: (689) 407-5757

Cresswind at Victoria Gardens

1128 HERON POINT WAY, DELAND, FL, 32724, Deland, FL 32724

$577,500

2 beds

3 baths

2,670 sq ft

House

1128 HERON POINT WAY, DELAND, FL, 32724

Community: Cresswind at Victoria Gardens

Cherrywood

10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476

$190,000

3 beds

2 baths

1,667 sq ft

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...

Community: Cherrywood

Solivita

274 MARABELLA LOOP, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$325,000

3 beds

2 baths

1,786 sq ft

House

274 MARABELLA LOOP, KISSIMMEE, FL, 34759

Community: Solivita

The Villages®

$320,000

2 beds

2 baths

1,174 sq ft

Villa

1428 ALMANZA DR, THE VILLAGES, FL, 32159

Community: The Villages®

New Plantation at Leesburg

25205 CRANES ROOST CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$255,000

2 beds

2 baths

1,328 sq ft

House

25205 CRANES ROOST CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

New Ocala Preserve

3399 NW 56TH AVE, OCALA, FL, 34482, Ocala, FL 34482

$650,000

3 beds

3 baths

2,763 sq ft

House

3399 NW 56TH AVE, OCALA, FL, 34482

Community: Ocala Preserve

The Villages®

$459,000

3 beds

2 baths

1,924 sq ft

House

17602 SE 82ND WOODLAWN AVE, THE VILLAGES...

Community: The Villages®

The Villages®

$725,000

3 beds

2 baths

1,630 sq ft

House

2737 AVA ST, THE VILLAGES, FL, 32163

Community: The Villages®

New The Villages®

13651 COUNTY ROAD 109H, LADY LAKE, FL, 3..., Lady Lake, FL 32159

$199,000

3 beds

2 baths

1,456 sq ft

Manufactured Home

13651 COUNTY ROAD 109H, LADY LAKE, FL, 3...

Community: The Villages®

The Villages®

$349,000

2 beds

2 baths

1,471 sq ft

House

802 MIRANDA WAY, THE VILLAGES, FL, 32159

House

5457 SW 82ND TER, OCALA, FL, 34481

House

5230 SW 88TH CIR, OCALA, FL, 34481

Community: Stone Creek

1 2 3 4 5 6 7 8 9 10 11 12 13 14…89

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

109 communities 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: Dec 16, 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 - Page 2

109 communities near Winter Garden

3,551 homes near Winter Garden

3 beds

2 baths

1,450 sq ft

House

2 beds

2 baths

1,515 sq ft

House

2 beds

2 baths

1,144 sq ft

House

3 beds

3 baths

2,209 sq ft

House

3 beds

3 baths

1,738 sq ft

Townhouse

2 beds

2 baths

1,368 sq ft

Halfplex

2 beds

2 baths

1,192 sq ft

Condo

2 beds

2 baths

1,412 sq ft

Villa

2 beds

3 baths

2,080 sq ft

House

2 beds

2 baths

1,148 sq ft

House

3 beds

2 baths

2,031 sq ft

House

3 beds

2 baths

1,568 sq ft

Villa

2 beds

2 baths

1,627 sq ft

Villa

3 beds

2 baths

1,696 sq ft

House

2 beds

2 baths

2,063 sq ft

House

2 beds

3 baths

2,670 sq ft

House

3 beds

2 baths

1,667 sq ft

House

3 beds

2 baths

1,786 sq ft

House

2 beds

2 baths

1,174 sq ft

Villa

2 beds