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 51

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
Kings Ridge 3673 ROLLINGBROOK ST, CLERMONT, FL, 3471..., Clermont, FL 34711
$299,000

2 beds

|

2 baths

|

1,334 sq ft

|

House

3673 ROLLINGBROOK ST, CLERMONT, FL, 3471...
Community: Kings Ridge
SummerGlen 1338 SW 161ST PL, OCALA, FL, 34473, Ocala, FL 34473
$315,000

3 beds

|

2 baths

|

2,287 sq ft

|

House

1338 SW 161ST PL, OCALA, FL, 34473
Community: SummerGlen
Palm Cay 10838 SW 78TH CT, OCALA, FL, 34476, Ocala, FL 34476
$165,000

2 beds

|

2 baths

|

1,102 sq ft

|

House

10838 SW 78TH CT, OCALA, FL, 34476
Community: Palm Cay
Stone Creek 9123 SW 70TH LOOP, OCALA, FL, 34481, Ocala, FL 34481
$264,025

2 beds

|

2 baths

|

1,700 sq ft

|

Villa

9123 SW 70TH LOOP, OCALA, FL, 34481
Community: Stone Creek
Summit Greens 2390 CALEDONIAN ST, CLERMONT, FL, 34711, Clermont, FL 34711
$440,000

3 beds

|

2 baths

|

1,961 sq ft

|

House

2390 CALEDONIAN ST, CLERMONT, FL, 34711
Community: Summit Greens
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Marco Polo Village 5123 SW 114TH STREET RD, OCALA, FL, 3447..., Ocala, FL 34476
$409,990

4 beds

|

3 baths

|

2,491 sq ft

|

House

5123 SW 114TH STREET RD, OCALA, FL, 3447...
Community: Marco Polo Village
The Villages® 8761 SE 168TH KITTREDGE LOOP, THE VILLAG..., The Villages, FL 32162
$430,000

3 beds

|

2 baths

|

1,916 sq ft

|

House

8761 SE 168TH KITTREDGE LOOP, THE VILLAG...
Community: The Villages®
Royal Harbor 5732 FREEPORT DR, TAVARES, FL, 32778, Tavares, FL 32778
$354,000

3 beds

|

2 baths

|

1,756 sq ft

|

House

5732 FREEPORT DR, TAVARES, FL, 32778
Community: Royal Harbor
On Top of the World 7890 SW 87TH LOOP, OCALA, FL, 34476, Ocala, FL 34476
$289,000

2 beds

|

2 baths

|

1,338 sq ft

|

House

7890 SW 87TH LOOP, OCALA, FL, 34476
Community: On Top of the World
Stone Creek 6868 SW 95TH CIR, OCALA, FL, 34481, Ocala, FL 34481
$477,800

3 beds

|

3 baths

|

2,659 sq ft

|

House

6868 SW 95TH CIR, OCALA, FL, 34481
Community: Stone Creek
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.
Spruce Creek Preserve 13824 SW 114TH CIR, DUNNELLON, FL, 34432, Dunnellon, FL 34432
$209,000

3 beds

|

2 baths

|

1,726 sq ft

|

House

13824 SW 114TH CIR, DUNNELLON, FL, 34432
Cresswind at Lake Harris 1599 BELLAGIO LOOP, TAVARES, FL, 32778, Tavares, FL 32778
$517,000

2 beds

|

2 baths

|

1,968 sq ft

|

House

1599 BELLAGIO LOOP, TAVARES, FL, 32778
Plantation at Leesburg 5062 EL DESTINO DR, LEESBURG, FL, 34748, Leesburg, FL 34748
$239,999

3 beds

|

2 baths

|

1,021 sq ft

|

House

5062 EL DESTINO DR, LEESBURG, FL, 34748
Scottish Highlands 1625 NEW ABBEY AVE, LEESBURG, FL, 34788, Leesburg, FL 34788
$225,000

2 beds

|

2 baths

|

1,040 sq ft

|

House

1625 NEW ABBEY AVE, LEESBURG, FL, 34788
Community: Scottish Highlands
Palm Cay 7858 SW 112TH LN, OCALA, FL, 34476, Ocala, FL 34476
$214,000

2 beds

|

2 baths

|

1,292 sq ft

|

House

7858 SW 112TH LN, OCALA, FL, 34476
Community: Palm Cay
The Villages® 2569 ERROL TER, THE VILLAGES, FL, 32162, The Villages, FL 32162
$284,900

2 beds

|

2 baths

|

1,156 sq ft

|

Villa

2569 ERROL TER, THE VILLAGES, FL, 32162
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Thunderbird Hill 3700 THUNDERBIRD HILL CIR, SEBRING, FL, ..., Sebring, FL 33872
$180,000

2 beds

|

2 baths

|

1,318 sq ft

|

Villa

3700 THUNDERBIRD HILL CIR, SEBRING, FL, ...
Community: Thunderbird Hill
Lakeside Landings 5427 COMPASS PT 1, OXFORD, FL, 34484, Oxford, FL 34484
$214,900

2 beds

|

2 baths

|

1,281 sq ft

|

Condo

5427 COMPASS PT 1, OXFORD, FL, 34484
Community: Lakeside Landings
The Villages® 1003 MATTHEW AVE, LADY LAKE, FL, 32159, Lady Lake, FL 32159
$224,000

2 beds

|

2 baths

|

1,191 sq ft

|

Manufactured Home

1003 MATTHEW AVE, LADY LAKE, FL, 32159
Community: The Villages®
Tampa Bay Golf and Country Club 10824 COLLAR DR, SAN ANTONIO, FL, 33576, San Antonio, FL 33576
$377,000

3 beds

|

2 baths

|

1,777 sq ft

|

House

10824 COLLAR DR, SAN ANTONIO, FL, 33576
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.
Sullivan Ranch 20913 SULLIVAN RANCH BLVD, MOUNT DORA, F..., Mount Dora, FL 32757
$389,900

3 beds

|

2 baths

|

1,990 sq ft

|

House

20913 SULLIVAN RANCH BLVD, MOUNT DORA, F...
Community: Sullivan Ranch
Venetian Bay 3004 BORASSUS DR, NEW SMYRNA BEACH, FL, ..., New Smyrna Beach, FL 32168
$579,000

4 beds

|

3 baths

|

2,115 sq ft

|

House

3004 BORASSUS DR, NEW SMYRNA BEACH, FL, ...
Community: Venetian Bay
The Villages® 8338 SE 178TH DEVEAUX LN, THE VILLAGES, ..., The Villages, FL 32162
$339,900

3 beds

|

2 baths

|

1,392 sq ft

|

House

8338 SE 178TH DEVEAUX LN, THE VILLAGES, ...
Community: The Villages®
Majestic Oaks Ocala 5870 SW 80TH PL, OCALA, FL, 34476, Ocala, FL 34476
$399,750

4 beds

|

3 baths

|

2,553 sq ft

|

House

5870 SW 80TH PL, OCALA, FL, 34476
Community: Majestic Oaks Ocala
Cherrywood 10350 SW 62ND TERRACE RD, OCALA, FL, 344..., Ocala, FL 34476
$174,000

3 beds

|

2 baths

|

1,749 sq ft

|

House

10350 SW 62ND TERRACE RD, OCALA, FL, 344...
Community: Cherrywood
Ocala Palms 5226 NW 21ST LOOP, OCALA, FL, 34482, Ocala, FL 34482
$258,500

2 beds

|

2 baths

|

1,221 sq ft

|

House

5226 NW 21ST LOOP, OCALA, FL, 34482
Community: Ocala Palms
Lake Jovita Golf and Country Club 12518 LAKE JOVITA BLVD, DADE CITY, FL, 3..., Dade City, FL 33525
$825,000

3 beds

|

3 baths

|

2,569 sq ft

|

House

12518 LAKE JOVITA BLVD, DADE CITY, FL, 3...
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
Harbor Hills Country Club 39644 HARBOR HILLS BLVD, LADY LAKE, FL, ..., Lady Lake, FL 32159
$419,000

3 beds

|

2 baths

|

2,009 sq ft

|

House

39644 HARBOR HILLS BLVD, LADY LAKE, FL, ...
The Villages® 210 PALERMO PL, THE VILLAGES, FL, 32159, The Villages, FL 32159
$439,900

3 beds

|

3 baths

|

2,118 sq ft

|

House

210 PALERMO PL, THE VILLAGES, FL, 32159
Community: The Villages®
Solivita 812 SAN RAPHAEL ST, POINCIANA, FL, 34759, Poinciana, FL 34759
$579,900

4 beds

|

3 baths

|

2,430 sq ft

|

House

812 SAN RAPHAEL ST, POINCIANA, FL, 34759
Community: Solivita
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® 840 FOLSUM PL, THE VILLAGES, FL, 32162, The Villages, FL 32162
$450,000

3 beds

|

2 baths

|

1,927 sq ft

|

House

840 FOLSUM PL, THE VILLAGES, FL, 32162
Community: The Villages®
The Villages® 8645 SE 177TH GRASSMERE ST, THE VILLAGES..., The Villages, FL 32162
$1,250,000

3 beds

|

2 baths

|

3,085 sq ft

|

House

8645 SE 177TH GRASSMERE ST, THE VILLAGES...
Community: The Villages®
Gatherings of Lake Nona 7545 LAUREATE BLVD 7301, ORLANDO, FL, 32..., Orlando, FL 32827
$427,990

2 beds

|

2 baths

|

1,445 sq ft

|

Condo

7545 LAUREATE BLVD 7301, ORLANDO, FL, 32...
Gatherings of Lake Nona 7557 LAUREATE BLVD 6401, ORLANDO, FL, 32..., Orlando, FL 32827
$379,990

2 beds

|

2 baths

|

1,368 sq ft

|

Condo

7557 LAUREATE BLVD 6401, ORLANDO, FL, 32...
Sandpiper Golf & Country Club 6260 CRANE DR, LAKELAND, FL, 33809, Lakeland, FL 33809
$349,900

3 beds

|

2 baths

|

1,830 sq ft

|

House

6260 CRANE DR, LAKELAND, FL, 33809
Valencia Lakes 4822 GRAND BANKS DR, WIMAUMA, FL, 33598, Wimauma, FL 33598
$460,000

3 beds

|

3 baths

|

2,271 sq ft

|

House

4822 GRAND BANKS DR, WIMAUMA, FL, 33598
Community: Valencia Lakes
The Country Club of Mount Dora 1500 EDGEWATER DR, MOUNT DORA, FL, 32757, Mount Dora, FL 32757
$665,000

4 beds

|

3 baths

|

2,544 sq ft

|

House

1500 EDGEWATER DR, MOUNT DORA, FL, 32757
The Villages® 1462 PELICAN PATH, THE VILLAGES, FL, 321..., The Villages, FL 32162
$429,900

3 beds

|

2 baths

|

1,715 sq ft

|

House

1462 PELICAN PATH, THE VILLAGES, FL, 321...
Community: The Villages®
Want to learn more about 55+ communities in Winter Garden? 55places can help!
Questions? Call us: (689) 407-5757
The Villages® 242 JUAREZ WAY, THE VILLAGES, FL, 32159, The Villages, FL 32159
$210,000

2 beds

|

2 baths

|

1,066 sq ft

|

House

242 JUAREZ WAY, THE VILLAGES, FL, 32159
Community: The Villages®
Windermere 819 LANARK DR, INVERNESS, FL, 34453, Inverness, FL 34453
$219,000

2 beds

|

2 baths

|

1,197 sq ft

|

House

819 LANARK DR, INVERNESS, FL, 34453
Community: Windermere
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