not an image

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 84

3,497 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 (56 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
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
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
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.
4.6 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 (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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
3.8 rating (6 reviews) Trilogy® Orlando
$200ks - $500ks
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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 homes
5 rating (8 reviews) Royal Highlands
$200ks - $400ks
Royal Highlands, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1999 - 2006 | 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.
5 rating (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 homes
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
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
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 (1 reviews) Sandpiper Golf & Coun...
$100ks - $300ks
Sandpiper Golf & Coun..., Lakeland, FL
New and Resale | 55+ age-restricted | Built 1985 - present | 1,193 homes
4 rating (4 reviews) Lakes of Mount Dora
$300ks - $1Ms
Lakes of Mount Dora, Mount Dora, FL
New and Resale | 55+ age-restricted | Built 2006 - present | 950 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
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
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
5 rating (1 reviews) Del Webb Sunbridge
$400ks - $800ks
Del Webb Sunbridge, St. Cloud, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 1,300 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.
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
5 rating (1 reviews) Cresswind at Victoria Gar...
$200ks - $500ks
Cresswind at Victoria Gar..., DeLand, FL
Resale Only | 55+ age-restricted | Built 2001 - 2022 | 1,070 homes
Mirada
$300ks - $500ks
Mirada, San Antonio, FL
New and Resale | 55+ age-restricted | Built 2019 - present | 858 homes
3.8 rating (5 reviews) Marion Landing
$100ks - $300ks
Marion Landing, Ocala, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 600 homes
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 homes
Quail Meadow
$200ks - $400ks
Quail Meadow, Ocala, FL
Resale Only | 55+ age-restricted | Built 1988 - 2006 | 460 homes
The Lakes at Harmony
$200ks - $400ks
The Lakes at Harmony, Harmony, FL
New and Resale | 55+ age-restricted | Built 2016 - present | 400 homes
Summer Trees
$200ks - $400ks
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? 55places can help!
Questions? Call us: (689) 407-5757
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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.
12...3
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
Sullivan Ranch 30308 CHEVAL ST, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$374,950

3 beds

|

2 baths

|

1,851 sq ft

|

House

30308 CHEVAL ST, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Venetian Bay 349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32..., New Smyrna Beach, FL 32168
$364,900

3 beds

|

2 baths

|

1,520 sq ft

|

House

349 CARYOTA CT, NEW SMYRNA BEACH, FL, 32...
Community: Venetian Bay
Ocala Preserve 4340 NW 56TH CT, OCALA, FL, 34482, Ocala, FL 34482
$399,500

2 beds

|

3 baths

|

2,054 sq ft

|

House

4340 NW 56TH CT, OCALA, FL, 34482
Community: Ocala Preserve
The Villages® 362 ARBELLA LOOP, THE VILLAGES, FL, 3216..., The Villages, FL 32162
$339,000

2 beds

|

2 baths

|

1,393 sq ft

|

House

362 ARBELLA LOOP, THE VILLAGES, FL, 3216...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Cresswind at Victoria Gardens 600 GARDEN CLUB DR, DELAND, FL, 32724, Deland, FL 32724
$549,900

4 beds

|

3 baths

|

2,569 sq ft

|

House

600 GARDEN CLUB DR, DELAND, FL, 32724
Highland Fairways 3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33..., Lakeland, FL 33810
$235,000

2 beds

|

2 baths

|

1,529 sq ft

|

House

3154 PRAIRIE DUNES CIR, LAKELAND, FL, 33...
Community: Highland Fairways
Del Webb Minneola 2759 PURPLE MEADOW CT, MINNEOLA, FL, 347..., Minneola, FL 34715
$459,000

2 beds

|

2 baths

|

1,405 sq ft

|

House

2759 PURPLE MEADOW CT, MINNEOLA, FL, 347...
Community: Del Webb Minneola
Legacy of Leesburg 27328 PINE STRAW RD, LEESBURG, FL, 34748, Leesburg, FL 34748
$349,900

3 beds

|

2 baths

|

1,894 sq ft

|

House

27328 PINE STRAW RD, LEESBURG, FL, 34748
Community: Legacy of Leesburg
Marco Polo Village 5239 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$409,990

4 beds

|

3 baths

|

2,484 sq ft

|

House

5239 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo 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.
Lake James 7770 LAKE JAMES BLVD, LAKELAND, FL, 3381..., Lakeland, FL 33810
$430,000

2 beds

|

2 baths

|

1,990 sq ft

|

House

7770 LAKE JAMES BLVD, LAKELAND, FL, 3381...
Community: Lake James
Ocala Palms 2515 NW 53 AVE, OCALA, FL, 34482, Ocala, FL 34482
$349,000

3 beds

|

2 baths

|

2,399 sq ft

|

House

2515 NW 53 AVE, OCALA, FL, 34482
Community: Ocala Palms
Lakes at Laurel Highlands 2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33..., Lakeland, FL 33811
$370,000

5 beds

|

3 baths

|

2,696 sq ft

|

House

2062 BLUE HIGHLANDS DR, LAKELAND, FL, 33...
Ocala Preserve 5235 NW 33RD PL, OCALA, FL, 34482, Ocala, FL 34482
$220,000

2 beds

|

2 baths

|

1,318 sq ft

|

House

5235 NW 33RD PL, OCALA, FL, 34482
Community: Ocala Preserve
On Top of the World 8380 SW 82ND CIR, OCALA, FL, 34481, Ocala, FL 34481
$285,000

3 beds

|

2 baths

|

1,701 sq ft

|

House

8380 SW 82ND CIR, OCALA, FL, 34481
Community: On Top of the World
Lake Ashton 4188 MUIRFIELD LOOP, LAKE WALES, FL, 338..., Lake Wales, FL 33859
$265,000

2 beds

|

2 baths

|

1,520 sq ft

|

House

4188 MUIRFIELD LOOP, LAKE WALES, FL, 338...
Community: Lake Ashton
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Stone Creek 9158 SW 65TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$579,950

3 beds

|

3 baths

|

2,534 sq ft

|

House

9158 SW 65TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Stone Creek 8989 SW 57TH PLACE RD, OCALA, FL, 34481, Ocala, FL 34481
$458,000

2 beds

|

2 baths

|

1,891 sq ft

|

House

8989 SW 57TH PLACE RD, OCALA, FL, 34481
Community: Stone Creek
On Top of the World 9587 SW 84TH TER E, OCALA, FL, 34481, Ocala, FL 34481
$185,000

2 beds

|

2 baths

|

1,748 sq ft

|

Villa

9587 SW 84TH TER E, OCALA, FL, 34481
Community: On Top of the World
Cherrywood 10121 SW 61ST TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$289,900

3 beds

|

2 baths

|

2,052 sq ft

|

House

10121 SW 61ST TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
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.
Sun City Center 301 KINGS BLVD 130, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$75,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

301 KINGS BLVD 130, SUN CITY CENTER, FL,...
Community: Sun City Center
Harbor Hills Country Club 6008 APEX WAY, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$675,000

4 beds

|

3 baths

|

3,432 sq ft

|

House

6008 APEX WAY, LADY LAKE, FL, 32159
Spruce Creek Country Club 9588 SE 124TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$319,900

2 beds

|

2 baths

|

1,979 sq ft

|

House

9588 SE 124TH LOOP, SUMMERFIELD, FL, 344...
Spruce Creek South 9499 SE 174TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$219,900

2 beds

|

2 baths

|

1,678 sq ft

|

House

9499 SE 174TH LOOP, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Sandpiper Golf & Country Club 5976 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5976 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5970 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5970 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5992 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5992 TEAL TRL, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sandpiper Golf & Country Club 5987 TEAL TRL, LAKELAND, FL, 33809, Lakeland, FL 33809
$370,000

3 beds

|

2 baths

|

1,478 sq ft

|

House

5987 TEAL TRL, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5982 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5982 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5914 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5914 CORMORANT CT, LAKELAND, FL, 33809
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.
Kings Ridge 2131 BURLEY AVE, CLERMONT, FL, 34711, Clermont, FL 34711
$264,900

2 beds

|

2 baths

|

1,394 sq ft

|

House

2131 BURLEY AVE, CLERMONT, FL, 34711
Community: Kings Ridge
Solivita 726 IRVINE RANCH RD, KISSIMMEE, FL, 3475..., Kissimmee, FL 34759
$449,900

3 beds

|

3 baths

|

2,427 sq ft

|

House

726 IRVINE RANCH RD, KISSIMMEE, FL, 3475...
Community: Solivita
Sandpiper Golf & Country Club 5920 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$375,000

3 beds

|

2 baths

|

1,582 sq ft

|

House

5920 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5927 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5927 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5926 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5926 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5933 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$350,000

2 beds

|

2 baths

|

1,321 sq ft

|

House

5933 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5921 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5921 CORMORANT CT, LAKELAND, FL, 33809
Sandpiper Golf & Country Club 5909 CORMORANT CT, LAKELAND, FL, 33809, Lakeland, FL 33809
$385,000

3 beds

|

2 baths

|

1,640 sq ft

|

House

5909 CORMORANT CT, LAKELAND, FL, 33809
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 1417 LANGLEY DR, SUN CITY CENTER, FL, 33..., Sun City Center, FL 33573
$159,900

2 beds

|

2 baths

|

1,529 sq ft

|

Condo

1417 LANGLEY DR, SUN CITY CENTER, FL, 33...
Community: Sun City Center
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
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 [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
3,497 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: May 25, 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