Call us at (689) 407-5757 to learn more about active adult communities in Winter Garden

Winter Garden, FL 55+ active adult communities & homes for sale - Page 82

3,776 homes near Winter Garden

Sort by:

Relevance

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
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 rating (57 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
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
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
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.
5 rating (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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) Twin Lakes
$200ks - $600ks
Twin Lakes, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 2,000 homes
Pelican Bay Daytona Beach
$100ks - $600ks
Pelican Bay Daytona Beach, Daytona Beach, FL
Resale Only | Age-targeted | Built 1980 - 2006 | 1,806 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 1,500 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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
5 rating (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
5 rating (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
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.
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
5 rating (8 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
5 rating (1 reviews) Cresswind at Victoria Gar...
$300ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 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
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
Pine Run Estates
$100ks - $200ks
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
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2017 - 2024 | 655 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 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.
The Country Club of Mount...
$200ks - $1Ms
The Country Club of Mount..., Mount Dora, FL
Resale Only | Age-targeted | Built 1991 - 2005 | 827 homes
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 homes
5 rating (1 reviews) Legacy of Leesburg
$200ks - $400ks
Legacy of Leesburg, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2017 | 1,000 homes
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 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
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
4.4 rating (9 reviews) Spruce Creek Preserve
$100ks - $200ks
Spruce Creek Preserve, Dunnellon, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 810 homes
Scottish Highlands
$100ks - $200ks
Scottish Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1983 - 1992 | 653 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 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.
123...4
Valencia Lakes 5056 RUBY FLATS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$599,000

3 beds

|

3 baths

|

2,795 sq ft

|

House

5056 RUBY FLATS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Summit Chase Villas 12449 ORANGEWOOD CIR 17, TAVARES, FL, 32..., Tavares, FL 32778
$174,900

2 beds

|

2 baths

|

918 sq ft

|

Condo

12449 ORANGEWOOD CIR 17, TAVARES, FL, 32...
Community: Summit Chase Villas
Summit Greens 2197 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$332,500

3 beds

|

2 baths

|

1,703 sq ft

|

House

2197 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Pine Run Estates 9881 SW 101ST PL, OCALA, FL, 34481, Ocala, FL 34481
$161,900

2 beds

|

2 baths

|

1,424 sq ft

|

House

9881 SW 101ST PL, OCALA, FL, 34481
Community: Pine Run Estates
Sun City Center 1010 N PEBBLE BEACH BLVD, SUN CITY CENTE..., Sun City Center, FL 33573
$129,890

2 beds

|

1 baths

|

899 sq ft

|

Townhouse

1010 N PEBBLE BEACH BLVD, SUN CITY CENTE...
Community: Sun City Center
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Lake Henry Estates 558 PINNACLE DR, HAINES CITY, FL, 33844, Haines City, FL 33844
$249,500

2 beds

|

2 baths

|

1,273 sq ft

|

House

558 PINNACLE DR, HAINES CITY, FL, 33844
Community: Lake Henry Estates
Arlington Ridge 27118 ROANOKE DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$364,900

3 beds

|

2 baths

|

1,713 sq ft

|

House

27118 ROANOKE DR, LEESBURG, FL, 34748
Community: Arlington Ridge
Spruce Creek Country Club 14160 SE 85TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$200,000

2 beds

|

2 baths

|

1,238 sq ft

|

Villa

14160 SE 85TH AVE, SUMMERFIELD, FL, 3449...
Encore at Fishhawk Ranch 13892 KINGFISHER GLEN DR, LITHIA, FL, 33..., Lithia, FL 33547
$319,000

2 beds

|

2 baths

|

1,612 sq ft

|

Villa

13892 KINGFISHER GLEN DR, LITHIA, FL, 33...
Liberty Village 7369 SW 77TH AVE, OCALA, FL, 34481, Ocala, FL 34481
$345,000

4 beds

|

2 baths

|

2,292 sq ft

|

House

7369 SW 77TH AVE, OCALA, FL, 34481
Community: Liberty Village
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.
Stone Creek 9491 SW 52ND LOOP, OCALA, FL, 34481, Ocala, FL 34481
$354,900

3 beds

|

2 baths

|

1,662 sq ft

|

House

9491 SW 52ND LOOP, OCALA, FL, 34481
Community: Stone Creek
Sun City Center 202 BEDFORD ST 68, SUN CITY CENTER, FL, ..., Sun City Center, FL 33573
$90,000

2 beds

|

2 baths

|

960 sq ft

|

Condo

202 BEDFORD ST 68, SUN CITY CENTER, FL, ...
Community: Sun City Center
Cindy Certified
469 MARION OAKS LN, OCALA, FL, 34473, Ocala, FL 34473
$337,900

4 beds

|

3 baths

|

1,784 sq ft

|

House

469 MARION OAKS LN, OCALA, FL, 34473
Stone Creek 6816 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$445,000

3 beds

|

2 baths

|

2,099 sq ft

|

House

6816 SW 95TH CIR, OCALA, FL, 34481
Community: Stone Creek
Spruce Creek Country Club 13811 SE 85TH CIR, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$389,900

3 beds

|

2 baths

|

1,823 sq ft

|

House

13811 SE 85TH CIR, SUMMERFIELD, FL, 3449...
The Villages® 110 CHULA VISTA AVE, LADY LAKE, FL, 3215..., Lady Lake, FL 32159
$400,000

3 beds

|

2 baths

|

2,038 sq ft

|

House

110 CHULA VISTA AVE, LADY LAKE, FL, 3215...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia Lakes 16015 CAPE CORAL DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$850,500

3 beds

|

3 baths

|

3,302 sq ft

|

House

16015 CAPE CORAL DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
Highland Lakes 26627 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$219,000

2 beds

|

2 baths

|

1,120 sq ft

|

Villa

26627 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
The Country Club of Mount Dora 2040 PARK FOREST BLVD, MOUNT DORA, FL, 3..., Mount Dora, FL 32757
$700,000

3 beds

|

3 baths

|

3,174 sq ft

|

House

2040 PARK FOREST BLVD, MOUNT DORA, FL, 3...
Del Webb Orlando 112 CASTELLON CT, DAVENPORT, FL, 33837, Davenport, FL 33837
$419,900

2 beds

|

2 baths

|

1,961 sq ft

|

House

112 CASTELLON CT, DAVENPORT, FL, 33837
Community: Del Webb Orlando
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.
Cindy Certified
5256 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762
$375,000

4 beds

|

2 baths

|

1,928 sq ft

|

House

5256 MEADOW SONG DR, OKAHUMPKA, FL, 3476...
Sun City Center 1801 BEDFORD LN 27, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$78,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

1801 BEDFORD LN 27, SUN CITY CENTER, FL,...
Community: Sun City Center
Venetian Bay 3058 ISLES WAY, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$388,500

2 beds

|

2 baths

|

1,003 sq ft

|

Townhouse

3058 ISLES WAY, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Summer Trees 47 CROOKED PINE RD, PORT ORANGE, FL, 321..., Port Orange, FL 32128
$259,000

2 beds

|

2 baths

|

1,502 sq ft

|

House

47 CROOKED PINE RD, PORT ORANGE, FL, 321...
Community: Summer Trees
Pelican Bay Daytona Beach 576 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$499,900

4 beds

|

4 baths

|

3,734 sq ft

|

House

576 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
On Top of the World 8566 SW 79TH AVE, OCALA, FL, 34476, Ocala, FL 34476
$334,900

4 beds

|

2 baths

|

1,874 sq ft

|

House

8566 SW 79TH AVE, OCALA, FL, 34476
Community: On Top of the World
Highlands Ridge 3234 E PEBBLE CREEK DR, AVON PARK, FL, 3..., Avon Park, FL 33825
$259,995

3 beds

|

2 baths

|

1,800 sq ft

|

House

3234 E PEBBLE CREEK DR, AVON PARK, FL, 3...
Community: Highlands Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cindy Certified
19313 LOCHSIDE LN, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$530,469

4 beds

|

2 baths

|

2,115 sq ft

|

House

19313 LOCHSIDE LN, MOUNT DORA, FL, 32757
Cresswind at Victoria Gardens 261 OLD MOSS CIR, DELAND, FL, 32724, Deland, FL 32724
$559,000

3 beds

|

3 baths

|

2,804 sq ft

|

House

261 OLD MOSS CIR, DELAND, FL, 32724
Trilogy® Orlando 184 CREPE MYRTLE DR, GROVELAND, FL, 3473..., Groveland, FL 34736
$519,000

4 beds

|

3 baths

|

3,044 sq ft

|

House

184 CREPE MYRTLE DR, GROVELAND, FL, 3473...
Community: Trilogy® Orlando
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.
Arlington Ridge 26645 MANASSAS DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$450,000

3 beds

|

2 baths

|

2,236 sq ft

|

House

26645 MANASSAS DR, LEESBURG, FL, 34748
Community: Arlington Ridge
Stone Creek 5702 SW 90TH COURT RD, OCALA, FL, 34481, Ocala, FL 34481
$618,999

2 beds

|

3 baths

|

2,110 sq ft

|

House

5702 SW 90TH COURT RD, OCALA, FL, 34481
Community: Stone Creek
Ocala Preserve 4007 NW 44TH CIR, OCALA, FL, 34482, Ocala, FL 34482
$219,990

3 beds

|

2 baths

|

1,504 sq ft

|

House

4007 NW 44TH CIR, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 17403 SE 77TH SYCAMORE AVE, THE VILLAGES..., The Villages, FL 32162
$270,000

2 beds

|

2 baths

|

1,160 sq ft

|

Villa

17403 SE 77TH SYCAMORE AVE, THE VILLAGES...
Community: The Villages®
The Villages® 108 N TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$119,900

2 beds

|

2 baths

|

1,232 sq ft

|

Manufactured Home

108 N TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
Cindy Certified
1727 SECOND ST, WINTER HAVEN, FL, 33881, Winter Haven, FL 33881
$260,000

3 beds

|

2 baths

|

1,470 sq ft

|

House

1727 SECOND ST, WINTER HAVEN, FL, 33881
Oak Run 11510 SW 85TH CT, OCALA, FL, 34481, Ocala, FL 34481
$231,900

3 beds

|

2 baths

|

1,800 sq ft

|

House

11510 SW 85TH CT, OCALA, FL, 34481
Community: Oak Run
The Villages® 415 S TIMBER TRL, WILDWOOD, FL, 34785, Wildwood, FL 34785
$79,900

2 beds

|

2 baths

|

1,144 sq ft

|

Manufactured Home

415 S TIMBER TRL, WILDWOOD, FL, 34785
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stonecrest 10948 SE 167TH PL, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$405,000

3 beds

|

2 baths

|

1,891 sq ft

|

House

10948 SE 167TH PL, SUMMERFIELD, FL, 3449...
Community: Stonecrest
Stonecrest 11217 SE 170TH LN, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$285,000

3 beds

|

2 baths

|

1,472 sq ft

|

House

11217 SE 170TH LN, SUMMERFIELD, FL, 3449...
Community: Stonecrest
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.

Frequently Asked Questions


Want more information about active adult communities around Winter Garden?

Global - Lead Form - Buyer or Renter
*55places does not provide or maintain community HOA information.
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 optout@55places.com. 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
3,776 homes
Remove Boundaries ×
Map Satellite

Reinmlsx

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: Oct 10, 2026.
This application does not include information on all of the properties available for sale at this time.

Call Us Call Us
Scroll to Top