Winter Garden, FL 55+ active adult communities & homes for sale - Page 3

113 communities near Winter Garden

Sort by:

Relevance

Valencia Ridge

$400ks - $800ks

Valencia Ridge, Wesley Chapel, FL

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

Heritage - The Cottages o...

$300ks

Heritage - The Cottages o..., Okahumpka, FL

New Construction | 55+ age-restricted | Built 2022 - present | 179 homes

3.9 rating (7 reviews)

Summit Greens

$300ks - $400ks

Summit Greens, Clermont, FL

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

2 rating (1 reviews)

Heritage Landings

$200ks - $300ks

Heritage Landings, Lakeland, FL

New Construction | 55+ age-restricted | Built 2017 - 2020 | 65 homes

Cresswind at Lake Harris

$300ks - $500ks

Cresswind at Lake Harris, Tavares, FL

New Construction | 55+ age-restricted | Built 2025 - present | 625 homes

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

Questions? Call us: (689) 407-5757

5 rating (4 reviews)

Carillon Lakes

$200ks - $400ks

Carillon Lakes, Lakeland, FL

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

Cresswind DeLand

$300ks - $500ks

Cresswind DeLand, DeLand, FL

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

Fountain View

$300ks - $400ks

Fountain View, Ormond Beach, FL

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

Tarawood

$200ks

Tarawood, Floral City, FL

New and Resale | 55+ age-restricted | Built 1990 - present | 150 homes

El Dorado

$400ks - $600ks

El Dorado, Ocala, FL

Resale Only | Age-targeted | Built 1978 - 2003 | 56 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.

Summit Chase Villas

$100ks

Summit Chase Villas, Tavares, FL

Resale Only | 55+ age-restricted | Built 1982 - 1989 | 60 homes

Encore at Fishhawk Ranch

$200ks - $500ks

Encore at Fishhawk Ranch, Lithia, FL

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

Carlsberg Estates on Lake...

$200ks

Carlsberg Estates on Lake..., Lake Wales, FL

Resale Only | 55+ age-restricted | Built 1998 - 2006 | 162 homes

Baytree

$100ks - $300ks

Baytree, Tavares, FL

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

Alhambra Villas Condomini...

$100ks - $200ks

Alhambra Villas Condomini..., DeLand, FL

Resale Only | 55+ age-restricted | Built 1970 - 1972 | 60 homes

Enclave at VillageWalk

$700ks - $1Ms

Enclave at VillageWalk, Orlando, FL

Resale Only | Age-targeted | Built 2015 - 2021 | 144 homes

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

Questions? Call us: (689) 407-5757

Cresswind at Hammock Oaks

$300ks - $500ks

Cresswind at Hammock Oaks, Lady Lake, FL

New and Resale | 55+ age-restricted | Built 2024 - 2025 | 141 homes

Hidden Creek

$100ks - $200ks

Hidden Creek, Sebring, FL

Resale Only | 55+ age-restricted | Built 1986 - 2007 | 55 homes

Royal Palm

$200ks - $300ks

Royal Palm, Port Orange, FL

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

Archers Mill

$300ks - $500ks

Archers Mill, Ormond Beach, FL

New Construction | Age-targeted | 94 homes

Bridgewater Landing

$200ks - $300ks

Bridgewater Landing, Riverview, FL

Resale Only | 55+ age-restricted | Built 2017 - 2024 | 64 homes

Spring Lake Towers

$100ks

Spring Lake Towers, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1970 - 1970 | 79 homes

The Wellington

$100ks - $200ks

The Wellington, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1969 - 1981 | 77 homes

Villas On The Green

$200ks - $300ks

Villas On The Green, Riverview, FL

Resale Only | 55+ age-restricted | Built 1989 - 1992 | 105 homes

Serenity Reserve

$400ks

Serenity Reserve, St. Cloud, FL

Resale Only | 55+ age-restricted | Built 2016 - 2020 | 85 homes

5 rating (1 reviews)

Cypress Lakes

$100ks

Cypress Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1987 - 2016 | 1,604 homes

Oakview

$100ks - $200ks

Oakview, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1988 - 1999 | 48 homes

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

Questions? Call us: (689) 407-5757

Preserve at Lakeside Land...

$200ks - $300ks

Preserve at Lakeside Land..., Winter Haven, FL

Resale Only | 55+ age-restricted | Built 2016 - 2019 | 44 homes

5 rating (1 reviews)

Silver Lakes

$100ks - $300ks

Silver Lakes, Lakeland, FL

Resale Only | 55+ age-restricted | Built 1996 - 2001 | 148 homes

Poinsettia Heights

$100ks - $200ks

Poinsettia Heights, Winter Haven, FL

Resale Only | 55+ age-restricted | Built 1978 - 2000 | 49 homes

Anand Nilay

$500ks - $700ks

Anand Nilay, Tampa, FL

New Construction | Age-targeted | Built 2025 - present | 105 homes

Lennar at Sanctuary at We...

$300ks - $500ks

Lennar at Sanctuary at We..., Clermont, FL

New Construction | 55+ age-restricted | Built 2025 - 2026 | 203 homes

Ormond Renaissance

$300ks - $400ks

Ormond Renaissance, Ormond Beach, FL

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

1 2 3

New Windermere

800 BALMORAL CT, INVERNESS, FL, 34453, Inverness, FL 34453

$298,000

3 beds

2 baths

1,591 sq ft

House

800 BALMORAL CT, INVERNESS, FL, 34453

Community: Windermere

New High Vista at Ridgewood Lakes

201 PRATHER DR, DAVENPORT, FL, 33837, Davenport, FL 33837

$321,900

2 beds

2 baths

1,910 sq ft

House

201 PRATHER DR, DAVENPORT, FL, 33837

Community: High Vista at Ridgewood Lakes

New Spruce Creek Country Club

9235 SE 128TH ST, SUMMERFIELD, FL, 34491, Summerfield, FL 34491

$339,900

2 beds

2 baths

1,716 sq ft

House

9235 SE 128TH ST, SUMMERFIELD, FL, 34491

Community: Spruce Creek Country Club

New Plantation at Leesburg

24814 PINE HL, LEESBURG, FL, 34748, Leesburg, FL 34748

$215,000

2 beds

2 baths

1,358 sq ft

Manufactured Home

24814 PINE HL, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New The Villages®

1033 OAK FOREST DR, THE VILLAGES, FL, 32..., The Villages, FL 32162

$359,000

3 beds

2 baths

1,840 sq ft

House

1033 OAK FOREST DR, THE VILLAGES, FL, 32...

Community: The Villages®

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

Questions? Call us: (689) 407-5757

New Marion Landing

6623 SW 84TH ST, OCALA, FL, 34476, Ocala, FL 34476

$199,999

3 beds

2 baths

1,404 sq ft

Manufactured Home

6623 SW 84TH ST, OCALA, FL, 34476

Community: Marion Landing

New Solivita

513 HEARTWELL DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$285,000

2 beds

2 baths

1,488 sq ft

House

513 HEARTWELL DR, KISSIMMEE, FL, 34759

Community: Solivita

New The Villages®

3431 SIPSEY ST, THE VILLAGES, FL, 32162, The Villages, FL 32162

$320,000

3 beds

2 baths

1,392 sq ft

House

3431 SIPSEY ST, THE VILLAGES, FL, 32162

Community: The Villages®

New On Top of the World

8459 SW 84TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$389,000

3 beds

2 baths

2,438 sq ft

House

8459 SW 84TH LOOP, OCALA, FL, 34481

Community: On Top of the World

New Arlington Ridge

4240 JAMES RIVER CIR, LEESBURG, FL, 3474..., Leesburg, FL 34748

$457,900

3 beds

2 baths

1,948 sq ft

House

4240 JAMES RIVER CIR, LEESBURG, FL, 3474...

Community: Arlington Ridge

New The Villages®

1426 HONEA PATH, THE VILLAGES, FL, 32162, The Villages, FL 32162

$575,000

3 beds

2 baths

2,236 sq ft

House

1426 HONEA PATH, THE VILLAGES, FL, 32162

Community: The Villages®

New Sandpiper Golf & Country Club

5832 SWALLOW DR, LAKELAND, FL, 33809, Lakeland, FL 33809

$350,000

3 beds

2 baths

1,814 sq ft

House

5832 SWALLOW DR, LAKELAND, FL, 33809

Community: Sandpiper Golf & Country Club

New The Villages®

1461 EMMA PL, THE VILLAGES, FL, 32163, The Villages, FL 32163

$375,000

2 beds

2 baths

1,295 sq ft

House

1461 EMMA PL, THE VILLAGES, FL, 32163

Community: The Villages®

New The Villages®

1202 CHAPARRAL DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$329,000

3 beds

2 baths

1,527 sq ft

House

1202 CHAPARRAL DR, THE VILLAGES, FL, 321...

Community: The Villages®

New The Villages®

2767 DUNHAM DR, THE VILLAGES, FL, 32163, The Villages, FL 32163

$1,295,000

4 beds

3 baths

2,378 sq ft

House

2767 DUNHAM DR, THE VILLAGES, FL, 32163

Community: The Villages®

New Sun City Center

2304 GLENMORE CIR 327, SUN CITY CENTER, ..., Sun City Center, FL 33573

$135,000

2 beds

2 baths

984 sq ft

Condo

2304 GLENMORE CIR 327, SUN CITY CENTER, ...

Community: Sun City Center

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

Questions? Call us: (689) 407-5757

New Stonecrest

17920 SE 115TH CT, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491

$265,000

3 beds

2 baths

1,544 sq ft

House

17920 SE 115TH CT, SUMMERFIELD, FL, 3449...

Community: Stonecrest

New Oak Run

7279 SW 115 PL, OCALA, FL, 34476, Ocala, FL 34476

$240,000

2 beds

2 baths

1,533 sq ft

House

7279 SW 115 PL, OCALA, FL, 34476

Community: Oak Run

New Traditions at Lake Ruby

4130 BEDFORD AVE, WINTER HAVEN, FL, 3388..., Winter Haven, FL 33884

$309,900

2 beds

2 baths

1,819 sq ft

House

4130 BEDFORD AVE, WINTER HAVEN, FL, 3388...

Community: Traditions at Lake Ruby

New The Villages®

2047 DUNSTER CT, THE VILLAGES, FL, 32162, The Villages, FL 32162

$434,999

3 beds

2 baths

1,851 sq ft

House

2047 DUNSTER CT, THE VILLAGES, FL, 32162

Community: The Villages®

New The Villages®

1577 BLYTHEWOOD LOOP, THE VILLAGES, FL, ..., The Villages, FL 32162

$398,000

3 beds

2 baths

1,513 sq ft

House

1577 BLYTHEWOOD LOOP, THE VILLAGES, FL, ...

Community: The Villages®

New Kings Ridge

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711

$328,900

2 beds

2 baths

1,548 sq ft

House

3525 ROLLINGBROOK ST, CLERMONT, FL, 3471...

Community: Kings Ridge

New Plantation at Leesburg

5000 SAWGRASS LAKE CIR, LEESBURG, FL, 34..., Leesburg, FL 34748

$284,900

2 beds

2 baths

1,775 sq ft

House

5000 SAWGRASS LAKE CIR, LEESBURG, FL, 34...

Community: Plantation at Leesburg

New Ocala Palms

2040 NW 55TH AVE RD, OCALA, FL, 34482, Ocala, FL 34482

$349,900

3 beds

2 baths

1,909 sq ft

House

2040 NW 55TH AVE RD, OCALA, FL, 34482

Community: Ocala Palms

New Sun City Center

319 KNOTTWOOD CT 2, SUN CITY CENTER, FL,..., Sun City Center, FL 33573

$119,900

2 beds

2 baths

1,073 sq ft

Condo

319 KNOTTWOOD CT 2, SUN CITY CENTER, FL,...

Community: Sun City Center

New Royal Harbor

2880 MEDITERRANEAN LOOP, TAVARES, FL, 32..., Tavares, FL 32778

$347,500

3 beds

2 baths

2,189 sq ft

House

2880 MEDITERRANEAN LOOP, TAVARES, FL, 32...

Community: Royal Harbor

New Ocala Preserve

3506 NW 55TH CIR, OCALA, FL, 34482, Ocala, FL 34482

$600,000

3 beds

3 baths

2,755 sq ft

House

3506 NW 55TH CIR, OCALA, FL, 34482

Community: Ocala Preserve

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

Questions? Call us: (689) 407-5757

New Royal Harbor

3257 BALTIC SEA BLVD, TAVARES, FL, 32778, Tavares, FL 32778

$392,000

3 beds

3 baths

2,012 sq ft

House

3257 BALTIC SEA BLVD, TAVARES, FL, 32778

Community: Royal Harbor

New The Villages®

418 FLOSSMOOR CT, THE VILLAGES, FL, 3216..., The Villages, FL 32162

$420,000

3 beds

2 baths

1,685 sq ft

Villa

418 FLOSSMOOR CT, THE VILLAGES, FL, 3216...

Community: The Villages®

New Plantation at Leesburg

5030 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$233,000

2 beds

2 baths

1,308 sq ft

House

5030 EL DESTINO DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Latitude Margaritaville

317 POP TOP LN, DAYTONA BEACH, FL, 32124, Daytona Beach, FL 32124

$358,900

2 beds

2 baths

1,160 sq ft

House

317 POP TOP LN, DAYTONA BEACH, FL, 32124

Community: Latitude Margaritaville

New Ocala Palms

4709 NW 51ST CT, OCALA, FL, 34482, Ocala, FL 34482

$625,000

4 beds

4 baths

2,843 sq ft

House

4709 NW 51ST CT, OCALA, FL, 34482

Community: Ocala Palms

New Solivita

478 BALBOA DR, KISSIMMEE, FL, 34759, Kissimmee, FL 34759

$359,000

2 beds

2 baths

2,038 sq ft

House

478 BALBOA DR, KISSIMMEE, FL, 34759

Community: Solivita

New Pelican Bay Daytona Beach

766 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119

$589,999

4 beds

4 baths

3,769 sq ft

House

766 PELICAN BAY DR, DAYTONA BEACH, FL, 3...

Community: Pelican Bay Daytona Beach

New The Villages®

1344 AUGUSTINE DR, THE VILLAGES, FL, 321..., The Villages, FL 32159

$482,000

3 beds

2 baths

1,954 sq ft

House

1344 AUGUSTINE DR, THE VILLAGES, FL, 321...

Community: The Villages®

New Plantation at Leesburg

26234 GLEN EAGLE DR, LEESBURG, FL, 34748, Leesburg, FL 34748

$238,000

3 beds

2 baths

1,761 sq ft

House

26234 GLEN EAGLE DR, LEESBURG, FL, 34748

Community: Plantation at Leesburg

New Marco Polo Village

11132 SW 53RD CIR, OCALA, FL, 34476, Ocala, FL 34476

$429,900

3 beds

2 baths

2,537 sq ft

House

11132 SW 53RD CIR, OCALA, FL, 34476

Community: Marco Polo Village

New Highland Lakes

26912 BECKER CT, LEESBURG, FL, 34748, Leesburg, FL 34748

$360,000

3 beds

2 baths

2,498 sq ft

House

26912 BECKER CT, LEESBURG, FL, 34748

Community: Highland Lakes

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

Questions? Call us: (689) 407-5757

New On Top of the World

10378 SW 96TH LOOP, OCALA, FL, 34481, Ocala, FL 34481

$387,000

2 beds

2 baths

1,983 sq ft

House

10378 SW 96TH LOOP, OCALA, FL, 34481

Community: On Top of the World

New Valencia Lakes

16010 GOLDEN LAKES DR, WIMAUMA, FL, 3359..., Wimauma, FL 33598

$395,000

3 beds

2 baths

2,058 sq ft

House

16010 GOLDEN LAKES DR, WIMAUMA, FL, 3359...

Community: Valencia Lakes

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.

How long do listings in 55+ communities in Winter Garden typically stay on the market, and what is the average price of homes for sale?

On average, listings in 55+ communities in Winter Garden stay on the market for around 399 days. The average price of homes for sale in these communities is approximately $476,615, though prices can range widely based on the size, location, and amenities of the communities. For example, homes in Del Webb Oasis average around $476,615.

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

113 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: May 25, 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 3

113 communities near Winter Garden

3,497 homes near Winter Garden

3 beds

2 baths

1,591 sq ft

House

2 beds

2 baths

1,910 sq ft

House

2 beds

2 baths

1,716 sq ft

House

2 beds

2 baths

1,358 sq ft

Manufactured Home

3 beds

2 baths

1,840 sq ft

House

3 beds

2 baths

1,404 sq ft

Manufactured Home

2 beds

2 baths

1,488 sq ft

House

3 beds

2 baths

1,392 sq ft

House

3 beds

2 baths

2,438 sq ft

House

3 beds

2 baths

1,948 sq ft

House

3 beds

2 baths

2,236 sq ft

House

3 beds

2 baths

1,814 sq ft

House

2 beds

2 baths

1,295 sq ft

House

3 beds

2 baths

1,527 sq ft

House

4 beds

3 baths

2,378 sq ft

House

2 beds

2 baths

984 sq ft

Condo

3 beds

2 baths

1,544 sq ft

House

2 beds

2 baths

1,533 sq ft

House

2 beds

2 baths

1,819 sq ft

House

3 beds