PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
---|---|---|---|
4900 THOMAS DriveShady Side, MDJust two doors from the water and steps from a children's park and boat ramp, this 3-bedro... |
3 beds | 2 baths | 1,408 sq.ft. |
$375,000 |
Airbnb cash on cash: 6.74%
|
1462 SNUG HARBOR RoadShady Side, MD4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes ... |
4 beds | 2 baths | 2,144 sq.ft. |
$735,000 |
Airbnb cash on cash: 4.74%
|
4922 LERCH DriveShady Side, MDYou can't beat the price for the WATERFRONT lifestyle in the Chesapeake Bay area! This stu... |
3 beds | 3 baths | 1,920 sq.ft. |
$699,000 |
Airbnb cash on cash: 2.78%
|
4738 IDLEWILDE RoadShady Side, MDAmazing opportunity to own a beautifully remodeled home in the waterfront community of Idl... |
4 beds | 2 baths | 1,300 sq.ft. |
$449,000 |
Airbnb cash on cash: 8.43%
|
4908 ASPEN StreetShady Side, MDWelcome to this 2-story home nestled in the serene Avalon Shores community. This home feat... |
3 beds | 3 baths | 1,500 sq.ft. |
$304,000 |
Airbnb cash on cash: 8.4%
|
5211 AL JONES DriveShady Side, MDCoastal Living in a Gated Waterfront Community a Short Distance from Annapolis and Washing... |
2 beds | 2 baths | 1,244 sq.ft. |
$554,500 |
Airbnb cash on cash: 2.14%
|
1711 COLUMBIA BEACH RoadShady Side, MDNestled between serene waters, this home offers stunning, unobstructed views of Flag Pond ... |
4 beds | 3 baths | 2,176 sq.ft. |
$499,900 |
Airbnb cash on cash: 7.04%
|
4725 IDLEWILDE RoadShady Side, MDCalling all investors, second-home seekers, and visionaries-this is the project you've bee... |
2 beds | 1 baths | 1,000 sq.ft. |
$275,000 |
Airbnb cash on cash: 6.23%
|
1731 COLUMBIA BEACH RDShady Side, MDJust Reduced, seller says sell! Welcome to this delightful coastal cottage nestled in the ... |
2 beds | 1 baths | N/A |
$336,900 |
Airbnb cash on cash: 4.63%
|
4738 WASHINGTON AvenueShady Side, MDEasy Living by the Bay - Perfect for Downsizing! Looking to simplify without sacrificing c... |
3 beds | 1 baths | 1,000 sq.ft. |
$360,000 |
Airbnb cash on cash: 7.11%
|
1617 WINTERS AvenueShady Side, MDWelcome to 1617 Winters Ave - Coastal Charm with Modern Updates in Idlewild on the Bay Bea... |
2 beds | 2 baths | 1,000 sq.ft. |
$368,000 |
Airbnb cash on cash: 4.19%
|
1330 JORDAN DriveShady Side, MDWelcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highl... |
3 beds | 3 baths | 1,440 sq.ft. |
$429,000 |
Airbnb cash on cash: 5.75%
|
4949 IDLEWILDE RoadShady Side, MDThis spacious and well-maintained home offers the ease of one-level living at it's best. T... |
3 beds | 2 baths | 2,024 sq.ft. |
$535,000 |
Airbnb cash on cash: 4.21%
|
5235-A Al Jones DrShady Side, MD5235-A Al Jones Dr, Shady Side, MD 20764 | Single Family Residential |
4 beds | 3 baths | 3,727 sq.ft. |
$1,524,000 |
Airbnb cash on cash: 0.89%
|
4180 Shoreham Beach RdShady Side, MD4180 Shoreham Beach Rd, Shady Side, MD 21037 | Single Family Residential |
N/A beds | N/A baths | 1,064 sq.ft. |
$449,000 |
Airbnb cash on cash: 1.38%
|
1219 Rogers RdShady Side, MD1219 Rogers Rd, Shady Side, MD 21037 | Single Family Residential |
N/A beds | N/A baths | 792 sq.ft. |
$2,200,000 |
Airbnb cash on cash: -1.37%
|
6118 Shady Side RdShady Side, MD6118 Shady Side Rd, Shady Side, MD 20764 | Other |
N/A beds | N/A baths | N/A |
$239,500 |
Airbnb cash on cash: 4.35%
|
Shady Side RdShady Side, MDShady Side Rd, Shady Side, MD 20764 | Other |
N/A beds | N/A baths | N/A |
$150,000 |
Airbnb cash on cash: 8.07%
|
Mayo RdShady Side, MD
|
N/A beds | N/A baths | N/A |
$250,000 |
Airbnb cash on cash: 4.09%
|
5250 Al Jones DrShady Side, MD5250 Al Jones Dr, Shady Side, MD 20764 | Other |
N/A beds | N/A baths | N/A |
$175,000 |
Airbnb cash on cash: 6.49%
|
4846 Woods Wharf RdShady Side, MD
|
N/A beds | N/A baths | N/A |
$259,999 |
Airbnb cash on cash: 3.85%
|
1520 LINCOLN RoadShady Side, MDGreat Cape Cod on 4 lots with nice upgrades in beautiful gated beach community. Photos com... |
4 beds | 2 baths | 1,248 sq.ft. |
$441,000 |
Airbnb cash on cash: 8.55%
|
1323 JORDAN DRShady Side, MD**OFFER DEADLINE SUNDAY SEPTEMBER 14th AT 6:00PM**OPEN HOUSES THIS WEEKEND ONLY, SATURDAY ... |
5 beds | 3 baths | N/A |
$1,050,000 |
Airbnb cash on cash: 3.65%
|
1261 Mayo Ridge RdShady Side, MD1261 Mayo Ridge Rd, Shady Side, MD 21037 | Single Family Residential |
6 beds | 6 baths | 4,371 sq.ft. |
$949,800 |
Airbnb cash on cash: 3.94%
|
1250 Juniper StShady Side, MD1250 Juniper St, Shady Side, MD 20764 | Single Family Residential |
3 beds | 2 baths | 1,332 sq.ft. |
$449,950 |
Airbnb cash on cash: 5.12%
|
6440 W Shady Side RdShady Side, MD6440 W Shady Side Rd, Shady Side, MD 20764 | Single Family Residential |
4 beds | 2 baths | 2,000 sq.ft. |
$619,900 |
Airbnb cash on cash: 5.26%
|
1302 SPRUCE StreetShady Side, MD10/10/25 Update: Home is under roof. Estimated completion is projected for January/Februar... |
4 beds | 3 baths | 2,424 sq.ft. |
$609,990 |
Airbnb cash on cash: 6.45%
|
4721 GIRTON AvenueShady Side, MDPerfect time to buy this updated home with a detached garage in the beautiful Chesapeake B... |
3 beds | 2 baths | 1,456 sq.ft. |
$435,000 |
Airbnb cash on cash: 5.7%
|
5314 Al Jones DrShady Side, MD5314 Al Jones Dr, Shady Side, MD 20764 | Other |
N/A beds | N/A baths | N/A |
$145,000 |
Airbnb cash on cash: 8.4%
|
6512 Shady Side RdShady Side, MD6512 Shady Side Rd, Shady Side, MD 20764 | Single Family Residential |
4 beds | 2 baths | 2,485 sq.ft. |
$815,000 |
Airbnb cash on cash: 3.51%
|
1650 CEDAR LaneShady Side, MDExperience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home... |
3 beds | 2 baths | 1,866 sq.ft. |
$729,900 |
Airbnb cash on cash: 2.87%
|
There are 32 properties for sale in the city of Shady Side . The median list price in Shady Side is $375,000 and the average price per square foot is $218. In October 2025, the average monthly cash on cash return in Shady Side is 4.00%. The average monthly rental income in Shady Side is $2,156.