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 34

3,769 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
Venetian Bay
$300ks - $1Ms
Venetian Bay, New Smyrna Beach, FL
New and Resale | Age-targeted | Built 2004 - present | 1,561 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
4.1 rating (29 reviews) Oak Run
$100ks - $300ks
Oak Run, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 2007 | 3,509 homes
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
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
4.7 rating (18 reviews) Solivita
$300ks - $700ks
Solivita, Kissimmee, FL
New and Resale | 55+ age-restricted | Built 2000 - present | 5,900 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 (3 reviews) Stonecrest
$200ks - $500ks
Stonecrest, Summerfield, FL
Resale Only | 55+ age-restricted | Built 1990 - 2024 | 2,224 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 (5 reviews) SummerGlen
$200ks - $400ks
SummerGlen, Ocala, FL
Resale Only | 55+ age-restricted | Built 2004 - 2014 | 1,024 homes
5 rating (1 reviews) Ocala Palms
$200ks - $300ks
Ocala Palms, Ocala, FL
Resale Only | 55+ age-restricted | Built 1994 - 1997 | 1,076 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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 (7 reviews) Kings Ridge
$200ks - $400ks
Kings Ridge, Clermont, FL
Resale Only | 55+ age-restricted | Built 1995 - 2000 | 2,088 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
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 (3 reviews) Lake Ashton
$200ks - $500ks
Lake Ashton, Lake Wales, FL
Resale Only | 55+ age-restricted | Built 2002 - present | 1,600 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
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
Pine Run Estates
$100ks - $200ks
Pine Run Estates, Ocala, FL
Resale Only | 55+ age-restricted | Built 1981 - 1989 | 880 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
Southshore Bay
$200ks - $500ks
Southshore Bay, Wimauma, FL
New and Resale | 55+ age-restricted | Built 2017 - present | 655 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? 55places can help!
Questions? Call us: (689) 407-5757
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
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
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
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.
2.3 rating (6 reviews) Cherrywood
$100ks - $800ks
Cherrywood, Ocala, FL
Resale Only | 55+ age-restricted | Built 1996 - 2003 | 700 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
Breakaway Trails
$400ks - $800ks
Breakaway Trails, Ormond Beach, FL
New and Resale | Age-targeted | Built 1985 - present | 976 homes
Highland Fairways
$100ks - $300ks
Highland Fairways, Lakeland, FL
Resale Only | 55+ age-restricted | Built 1983 - 1998 | 660 homes
Cresswind Lakewood Ranch
$400ks - $700ks
Cresswind Lakewood Ranch, Lakewood Ranch, FL
New and Resale | 55+ age-restricted | Built 2018 - present | 648 homes
5 rating (1 reviews) Royal Harbor
$200ks - $800ks
Royal Harbor, Tavares, FL
Resale Only | 55+ age-restricted | Built 1999 - 2008 | 755 homes
5 rating (8 reviews) Pennbrooke Fairways
<$100k - $300ks
Pennbrooke Fairways, Leesburg, FL
Resale Only | 55+ age-restricted | Built 1980 - 2004 | 1,200 homes
5 rating (1 reviews) Palm Cay
$100ks - $200ks
Palm Cay, Ocala, FL
Resale Only | 55+ age-restricted | Built 1985 - 1992 | 795 homes
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
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
4.7 rating (11 reviews) Valencia Lakes
$200ks - $700ks
Valencia Lakes, Wimauma, FL
Resale Only | 55+ age-restricted | Built 2005 - 2019 | 1,631 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
Cindy Certified
4372 MERCEDES ST, SEBRING, FL, 33872, Sebring, FL 33872
$279,900

3 beds

|

2 baths

|

1,468 sq ft

|

House

4372 MERCEDES ST, SEBRING, FL, 33872
The Villages® 4686 HILES PL, THE VILLAGES, FL, 32163, The Villages, FL 32163
$475,000

3 beds

|

2 baths

|

1,633 sq ft

|

House

4686 HILES PL, THE VILLAGES, FL, 32163
Community: The Villages®
Tampa Bay Golf and Country Club 29312 MARKER LOOP, SAN ANTONIO, FL, 3357..., San Antonio, FL 33576
$314,999

3 beds

|

2 baths

|

1,596 sq ft

|

Villa

29312 MARKER LOOP, SAN ANTONIO, FL, 3357...
Stone Creek 9530 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$385,000

2 beds

|

2 baths

|

1,708 sq ft

|

House

9530 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Colonnades 4860 GOLDENVIEW LN, LAKELAND, FL, 33811, Lakeland, FL 33811
$215,900

2 beds

|

2 baths

|

1,350 sq ft

|

House

4860 GOLDENVIEW LN, LAKELAND, FL, 33811
Community: Colonnades
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Spruce Creek South 17929 SE 105TH AVE, SUMMERFIELD, FL, 344..., Summerfield, FL 34491
$185,000

2 beds

|

2 baths

|

990 sq ft

|

House

17929 SE 105TH AVE, SUMMERFIELD, FL, 344...
Community: Spruce Creek South
Del Webb Sunbridge 2505 CLIFF WAY, ST CLOUD, FL, 34771, St Cloud, FL 34771
$394,900

2 beds

|

2 baths

|

1,401 sq ft

|

House

2505 CLIFF WAY, ST CLOUD, FL, 34771
Community: Del Webb Sunbridge
Cindy Certified
3129 ROCKWOOD WAY, MINNEOLA, FL, 34715, Minneola, FL 34715
$505,490

4 beds

|

3 baths

|

2,175 sq ft

|

House

3129 ROCKWOOD WAY, MINNEOLA, FL, 34715
Highland Lakes 27305 RACQUET CIR, LEESBURG, FL, 34748, Leesburg, FL 34748
$325,000

3 beds

|

2 baths

|

2,886 sq ft

|

House

27305 RACQUET CIR, LEESBURG, FL, 34748
Community: Highland Lakes
Cindy Certified
4666 ACKEE RD, KISSIMMEE, FL, 34758, Kissimmee, FL 34758
$489,000

4 beds

|

3 baths

|

2,404 sq ft

|

House

4666 ACKEE RD, KISSIMMEE, FL, 34758
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 1501 NEW BEDFORD DR, SUN CITY CENTER, FL..., Sun City Center, FL 33573
$320,000

3 beds

|

2 baths

|

2,304 sq ft

|

House

1501 NEW BEDFORD DR, SUN CITY CENTER, FL...
Community: Sun City Center
Spruce Creek Preserve 11588 SW 139TH PL, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$214,000

2 beds

|

2 baths

|

1,296 sq ft

|

House

11588 SW 139TH PL, DUNNELLON, FL, 34432
Plantation at Leesburg 25206 ORMOND CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$299,800

2 beds

|

2 baths

|

1,723 sq ft

|

House

25206 ORMOND CT, LEESBURG, FL, 34748
Cindy Certified
5229 MEADOW SONG DR, OKAHUMPKA, FL, 3476..., Okahumpka, FL 34762
$375,000

4 beds

|

3 baths

|

2,075 sq ft

|

House

5229 MEADOW SONG DR, OKAHUMPKA, FL, 3476...
The Country Club of Mount Dora 8059 LAUREL RIDGE DR, MOUNT DORA, FL, 32..., Mount Dora, FL 32757
$570,000

3 beds

|

3 baths

|

2,777 sq ft

|

House

8059 LAUREL RIDGE DR, MOUNT DORA, FL, 32...
Sullivan Ranch 21315 SORRAIA CV, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$425,000

4 beds

|

2 baths

|

2,164 sq ft

|

House

21315 SORRAIA CV, MOUNT DORA, FL, 32757
Community: Sullivan Ranch
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Esplanade at Wiregrass Ranch 4248 CAIROLI CT, WESLEY CHAPEL, FL, 3354..., Wesley Chapel, FL 33543
$469,900

3 beds

|

2 baths

|

1,934 sq ft

|

House

4248 CAIROLI CT, WESLEY CHAPEL, FL, 3354...
Latitude Margaritaville 225 GYPSY PALACE LN, DAYTONA BEACH, FL, ..., Daytona Beach, FL 32124
$514,900

2 beds

|

2 baths

|

1,778 sq ft

|

House

225 GYPSY PALACE LN, DAYTONA BEACH, FL, ...
Cindy Certified
35100 VALLEY RIDGE RD, DADE CITY, FL, 33..., Dade City, FL 33525
$330,000

4 beds

|

2 baths

|

1,828 sq ft

|

House

35100 VALLEY RIDGE RD, DADE CITY, FL, 33...
Tohoqua Reserve 1833 SPRING SHOWER CIR, KISSIMMEE, FL, 3..., Kissimmee, FL 34744
$320,000

3 beds

|

2 baths

|

1,559 sq ft

|

Villa

1833 SPRING SHOWER CIR, KISSIMMEE, FL, 3...
Community: Tohoqua Reserve
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 Villages® 1230 DESILVA ST, THE VILLAGES, FL, 32159, The Villages, FL 32159
$492,000

3 beds

|

2 baths

|

1,842 sq ft

|

House

1230 DESILVA ST, THE VILLAGES, FL, 32159
Community: The Villages®
The Villages® 2581 ERROL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$294,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2581 ERROL TER, THE VILLAGES, FL, 32162
Community: The Villages®
Lake Jovita Golf and Country Club 34653 HEAVENLY LN, DADE CITY, FL, 33525, Dade City, FL 33525
$785,000

4 beds

|

3 baths

|

2,565 sq ft

|

House

34653 HEAVENLY LN, DADE CITY, FL, 33525
Lakes of Mount Dora 8113 BRIDGEPORT BAY CIR, MOUNT DORA, FL,..., Mount Dora, FL 32757
$425,000

3 beds

|

2 baths

|

1,806 sq ft

|

House

8113 BRIDGEPORT BAY CIR, MOUNT DORA, FL,...
Community: Lakes of Mount Dora
Plantation at Leesburg 3851 MANOR OAKS CT, LEESBURG, FL, 34748, Leesburg, FL 34748
$350,000

3 beds

|

3 baths

|

2,555 sq ft

|

House

3851 MANOR OAKS CT, LEESBURG, FL, 34748
Pelican Bay Daytona Beach 537 PELICAN BAY DR, DAYTONA BEACH, FL, 3..., Daytona Beach, FL 32119
$875,000

5 beds

|

5 baths

|

3,523 sq ft

|

House

537 PELICAN BAY DR, DAYTONA BEACH, FL, 3...
On Top of the World 8508 SW 84TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$398,500

3 beds

|

2 baths

|

2,278 sq ft

|

House

8508 SW 84TH LOOP, OCALA, FL, 34481
Community: On Top of the World
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Scottish Highlands 32 GORDON CT, LEESBURG, FL, 34788, Leesburg, FL 34788
$259,000

2 beds

|

2 baths

|

1,528 sq ft

|

House

32 GORDON CT, LEESBURG, FL, 34788
Community: Scottish Highlands
Cindy Certified
17733 CANOPY PL, BRADENTON, FL, 34211, Bradenton, FL 34211
$444,900

4 beds

|

2 baths

|

1,828 sq ft

|

House

17733 CANOPY PL, BRADENTON, FL, 34211
Cindy Certified
5148 BRICKWOOD RISE DR, WIMAUMA, FL, 335..., Wimauma, FL 33598
$284,900

2 beds

|

2 baths

|

1,468 sq ft

|

House

5148 BRICKWOOD RISE DR, WIMAUMA, FL, 335...
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.
Twin Lakes 2789 SOUTHLAND ST, ST CLOUD, FL, 34772, St Cloud, FL 34772
$499,900

3 beds

|

3 baths

|

2,365 sq ft

|

House

2789 SOUTHLAND ST, ST CLOUD, FL, 34772
Community: Twin Lakes
Foxwood Lake Estates 1794 FOX HILL DR, LAKELAND, FL, 33810, Lakeland, FL 33810
$127,900

2 beds

|

2 baths

|

900 sq ft

|

Manufactured Home

1794 FOX HILL DR, LAKELAND, FL, 33810
Cresswind at Lake Harris 1615 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778
$739,990

3 beds

|

4 baths

|

2,776 sq ft

|

House

1615 BELLAGIO LOOP, TAVARES, FL, 32778
Cresswind at Lake Harris 1457 SANTORINI WAY, TAVARES, FL, 32778, Tavares, FL 32778
$449,990

3 beds

|

2 baths

|

1,724 sq ft

|

House

1457 SANTORINI WAY, TAVARES, FL, 32778
Cindy Certified
14535 SW 68TH TER, OCALA, FL, 34473, Ocala, FL 34473
$279,000

3 beds

|

2 baths

|

1,543 sq ft

|

House

14535 SW 68TH TER, OCALA, FL, 34473
Cresswind Lakewood Ranch 17731 SAVORY MIST CIR, BRADENTON, FL, 34..., Bradenton, FL 34211
$975,000

4 beds

|

4 baths

|

3,651 sq ft

|

House

17731 SAVORY MIST CIR, BRADENTON, FL, 34...
Cresswind DeLand 1214 CRESSWIND BLVD, DELAND, FL, 32724, Deland, FL 32724
$599,990

3 beds

|

3 baths

|

2,129 sq ft

|

House

1214 CRESSWIND BLVD, DELAND, FL, 32724
Community: Cresswind DeLand
Cindy Certified
10959 COTTON VALE PL, SAN ANTONIO, FL, 3..., San Antonio, FL 33576
$400,000

3 beds

|

2 baths

|

1,844 sq ft

|

House

10959 COTTON VALE PL, SAN ANTONIO, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Majestic Oaks Ocala 5580 SW 81ST PL, OCALA, FL, 34476, Ocala, FL 34476
$419,900

4 beds

|

3 baths

|

2,344 sq ft

|

House

5580 SW 81ST PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Cresswind Lakewood Ranch 16942 SAVORY MIST CIR, BRADENTON, FL, 34..., Bradenton, FL 34211
$740,000

4 beds

|

3 baths

|

2,559 sq ft

|

House

16942 SAVORY MIST CIR, BRADENTON, FL, 34...
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
3,769 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: Aug 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