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 94

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
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
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
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
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
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.
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
Venetian Bay 2948 BELLA FLORE TER, NEW SMYRNA BEACH, ..., New Smyrna Beach, FL 32168
$855,900

3 beds

|

3 baths

|

2,034 sq ft

|

House

2948 BELLA FLORE TER, NEW SMYRNA BEACH, ...
Community: Venetian Bay
Oak Run 8137 SW 117TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$194,999

2 beds

|

2 baths

|

1,148 sq ft

|

House

8137 SW 117TH LOOP, OCALA, FL, 34481
Community: Oak Run
Cindy Certified
159 WATERSTONE LOOP, TAVARES, FL, 32778, Tavares, FL 32778
$397,999

4 beds

|

3 baths

|

2,051 sq ft

|

House

159 WATERSTONE LOOP, TAVARES, FL, 32778
Sun City Center 420 S BROCKFIELD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$335,000

2 beds

|

2 baths

|

1,656 sq ft

|

House

420 S BROCKFIELD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Venetian Bay 2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$320,000

3 beds

|

3 baths

|

1,754 sq ft

|

House

2916 MELETO BLVD, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Valencia Ridge 32523 NEROLI ST, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$811,900

3 beds

|

3 baths

|

2,450 sq ft

|

House

32523 NEROLI ST, WESLEY CHAPEL, FL, 3354...
Community: Valencia Ridge
Solivita 619 TAPATIO LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$523,000

5 beds

|

5 baths

|

2,881 sq ft

|

House

619 TAPATIO LN, KISSIMMEE, FL, 34759
Community: Solivita
Solivita 537 MONTAGE LN, KISSIMMEE, FL, 34759, Kissimmee, FL 34759
$514,900

3 beds

|

3 baths

|

2,441 sq ft

|

House

537 MONTAGE LN, KISSIMMEE, FL, 34759
Community: Solivita
Plantation at Leesburg 25800 BELLE HELENE, LEESBURG, FL, 34748, Leesburg, FL 34748
$228,000

3 beds

|

2 baths

|

1,653 sq ft

|

House

25800 BELLE HELENE, LEESBURG, FL, 34748
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.
Ocala Preserve 5610 NW 37TH LANE RD, OCALA, FL, 34482, Ocala, FL 34482
$249,000

2 beds

|

2 baths

|

1,454 sq ft

|

House

5610 NW 37TH LANE RD, OCALA, FL, 34482
Community: Ocala Preserve
Lake Jovita Golf and Country Club 13805 CARRYBACK DR, DADE CITY, FL, 33525, Dade City, FL 33525
$1,150,000

3 beds

|

4 baths

|

3,201 sq ft

|

House

13805 CARRYBACK DR, DADE CITY, FL, 33525
Plantation at Leesburg 25339 CRESTWATER DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$284,900

3 beds

|

2 baths

|

1,765 sq ft

|

House

25339 CRESTWATER DR, LEESBURG, FL, 34748
Sun City Center 1809 HAVERFORD AVE, SUN CITY CENTER, FL,..., Sun City Center, FL 33573
$249,900

2 beds

|

2 baths

|

1,402 sq ft

|

House

1809 HAVERFORD AVE, SUN CITY CENTER, FL,...
Community: Sun City Center
Vienna Square 1224 VIENNA SQUARE DR, WINTER HAVEN, FL,..., Winter Haven, FL 33884
$205,000

2 beds

|

2 baths

|

1,118 sq ft

|

Villa

1224 VIENNA SQUARE DR, WINTER HAVEN, FL,...
Community: Vienna Square
Royal Highlands 20631 PRINCE RANIER PL, LEESBURG, FL, 34..., Leesburg, FL 34748
$347,900

3 beds

|

2 baths

|

2,070 sq ft

|

House

20631 PRINCE RANIER PL, LEESBURG, FL, 34...
Community: Royal Highlands
Kings Ridge 3684 EVERSHOLT ST, CLERMONT, FL, 34711, Clermont, FL 34711
$309,900

3 beds

|

2 baths

|

1,552 sq ft

|

House

3684 EVERSHOLT ST, CLERMONT, FL, 34711
Community: Kings Ridge
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek Country Club 9290 SE 120TH LOOP, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$379,900

3 beds

|

2 baths

|

2,126 sq ft

|

House

9290 SE 120TH LOOP, SUMMERFIELD, FL, 344...
Sun City Center 2202 CLUBHOUSE DR 174, SUN CITY CENTER, ..., Sun City Center, FL 33573
$89,000

1 beds

|

2 baths

|

800 sq ft

|

Condo

2202 CLUBHOUSE DR 174, SUN CITY CENTER, ...
Community: Sun City Center
Spruce Creek Country Club 13729 SE 89TH AVE, SUMMERFIELD, FL, 3449..., Summerfield, FL 34491
$245,900

3 beds

|

2 baths

|

1,760 sq ft

|

House

13729 SE 89TH AVE, SUMMERFIELD, FL, 3449...
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 Wellington 689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,..., Winter Haven, FL 33880
$124,000

2 beds

|

2 baths

|

1,050 sq ft

|

Condo

689 LAKE HOWARD DR 1E, WINTER HAVEN, FL,...
Community: The Wellington
Royal Highlands 20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ..., Leesburg, FL 34748
$364,900

3 beds

|

3 baths

|

2,224 sq ft

|

House

20751 QUEEN ALEXANDRA DR, LEESBURG, FL, ...
Community: Royal Highlands
Cindy Certified
17014 OVAL RUM DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$275,000

3 beds

|

2 baths

|

1,516 sq ft

|

House

17014 OVAL RUM DR, WIMAUMA, FL, 33598
Vienna Square 1703 LINZ CT, WINTER HAVEN, FL, 33884, Winter Haven, FL 33884
$248,000

2 beds

|

2 baths

|

1,164 sq ft

|

Villa

1703 LINZ CT, WINTER HAVEN, FL, 33884
Community: Vienna Square
Majestic Oaks Ocala 4961 SW 88TH PL, OCALA, FL, 34476, Ocala, FL 34476
$335,000

4 beds

|

2 baths

|

1,827 sq ft

|

House

4961 SW 88TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Kings Ridge 3667 KINGSWOOD CT, CLERMONT, FL, 34711, Clermont, FL 34711
$339,900

2 beds

|

2 baths

|

1,552 sq ft

|

House

3667 KINGSWOOD CT, CLERMONT, FL, 34711
Community: Kings Ridge
On Top of the World 9662 SW 95TH CT A, OCALA, FL, 34481, Ocala, FL 34481
$160,000

2 beds

|

2 baths

|

1,412 sq ft

|

Villa

9662 SW 95TH CT A, OCALA, FL, 34481
Community: On Top of the World
Spruce Creek Country Club 12592 SE 97TH TERRACE RD, SUMMERFIELD, F..., Summerfield, FL 34491
$445,000

3 beds

|

2 baths

|

2,413 sq ft

|

House

12592 SE 97TH TERRACE RD, SUMMERFIELD, F...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Sun City Center 2315 NEW ORCHARD CT 40, SUN CITY CENTER,..., Sun City Center, FL 33573
$149,900

2 beds

|

2 baths

|

1,125 sq ft

|

Condo

2315 NEW ORCHARD CT 40, SUN CITY CENTER,...
Community: Sun City Center
On Top of the World 10406 SW 96 LOOP, OCALA, FL, 34481, Ocala, FL 34481
$235,000

2 beds

|

2 baths

|

1,432 sq ft

|

House

10406 SW 96 LOOP, OCALA, FL, 34481
Community: On Top of the World
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