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Shady Side MD Real Estate & Homes for Sale

17 Properties Found

The median home value in Shady Side, MD is $410,000. This is higher than the county median home value of $400,000. The national median home value is $308,980. The average price of homes sold in Shady Side, MD is $410,000. Approximately 78.5% of Shady Side homes are owned, compared to 11% rented, while 10.5% are vacant. Shady Side real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Shady Side real estate agent to arrange a tour today!
Learn more about Shady Side Real Estate.


1–17 of 17 properties displayed
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Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,392
Status:
NEW LISTING
MLS#:
MDAA2114752
Type:
Single Family, Single Family-Detached
Subdivision:
SHADY SIDE
Lot size:
1.92 Acres
Year built:
1999
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Charming and spacious colonial, situated on nearly 2 picturesque acres in Shady Side. Boasting 4 bedrooms and 2.5 bathrooms, this lovely home features a formal dining room, a spacious family room with a fireplace, and large sitting rooms off to the side, a finely appointed kitchen with granite counters and SS appliances, a large addition off the back of the home with vaulted ceilings and wood ceiling accents. The home also features a large 2 car garage, and a spacious yard which includes ample front back and side yards.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,176
Status:
NEW LISTING
MLS#:
MDAA2114456
Type:
Single Family, Single Family-Detached
Subdivision:
COLUMBIA BEACH
Lot size:
0.19 Acres
Year built:
2004
Courtesy: Schwartz Realty, Inc.
View additional info

Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond from the rear and views of the Chesapeake Bay from the front. Enjoy watching local waterfowl and soaking in the natural beauty from every angle. Inside, the spacious kitchen opens to the family room, perfect for gathering, along with a formal living room and a main-level office or potential 5th bedroom. Upstairs features four bedrooms, including a primary suite with views of both the Bay and Flag Pond, plus an en-suite bath, three additional bedrooms, and a full hall bath. A two-car garage includes an extra storage room. While the home could use some updating and TLC, it presents a fantastic opportunity to make it your own. Located in a vibrant waterfront community with amenities such as a boat ramp, pier, tennis courts, and more. Come experience the Chesapeake Bay lifestyle.

Beds:
2
Baths:
1 Full
Sq.Ft.:
782
Status:
NEW LISTING
MLS#:
MDAA2113478
Type:
Single Family, Single Family-Detached
Subdivision:
CEDARHURST ON THE BAY
Lot size:
0.11 Acres
Year built:
1981
Courtesy: Cummings & Co. Realtors
View additional info

Welcome to 1191 Bay View Avenue in Cedarhurst on the Bay, a lovely water privileged community just blocks from the Chesapeake Bay. With wood flooring throughout and just recently painted, this home is ready for your own personal touches!

Beds:
5
Baths:
3 Full/1 Half
Sq.Ft.:
2,179
Status:
NEW LISTING
MLS#:
MDAA2112508
Type:
Single Family, Single Family-Detached
Subdivision:
FELICITY COVE
Lot size:
0.23 Acres
Year built:
1976
Courtesy: Taylor Properties
View additional info

Ready for Viewing! Welcome to this wonderfully unique and updated home in the small community of Felicity Cove. Felicity Cove is a private, waterfront community of only 34 homes with a large community pier and outdoor areas. With part-time and full-time residences there is not a lot of turnover in the community. This home is 2 story brick and vinyl clad Cape Cod style with a Mid-century Modern vibe. Built in 1976. The home is move in ready! In about 2200 square feet there are 4/5 bedrooms, 3.5 bathrooms, bonus office or 5th bedroom and family room. The family room has vaulted ceiling and hearth for a wood or pellet stove. Living room and office/5th bedroom have fireplaces. Enjoy the bay air and view from the 3-season porch. There is oak flooring throughout both floors. Custom wood trim and slate floor in the open 2-story foyer. 3 full bathrooms were remodeled in 2024-25 with custom tile. The Primary bedroom has plenty of room for a king size bed. Be the first to utilize the new ensuite walk-in shower and dual vanities. The galley style kitchen was remodeled with granite counters. The fridge, range and water heater were replaced this year. In 2014, 2 heat pump systems were installed including ducting (recently serviced). 2016 New insulation and vapor barrier installed in the crawl space. New vinyl siding, house wrap, vinyl eaves, vinyl wrapped exterior beams and a new bay window were installed. New roof was installed with 40 year shingles in the fall of 2023, flat roof portion was replaced in 2014. New gutters system installed spring of 2024. The home sits on almost 1/4 acre with partial privacy hedges and off-street parking for 3 vehicles and/or a boat. Large shed in great condition and conveys.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,344
Status:
NEW LISTING
MLS#:
MDAA2113934
Type:
Single Family, Single Family-Detached
Subdivision:
SHADY SIDE
Lot size:
3.38 Acres
Year built:
2000
Courtesy: Century 21 Downtown
View additional info

Don't miss this wonderful opportunity to own this porch front home seated in an expansive private lot approximately 3.38 acres. Home features hardwood floors that flows from the combine living and dining rooms to the a nice sized kitchen with appliances and main level bedroom. There is a full bath in each level and three more bedrooms in the upper level. The sunroom with wide windows and lots of natural lights have a great view of the backyard and leads to the rear deck, which is a perfect spot for outdoor fun. The rear exterior includes a 3-car detached garage with large workshop and a shed. Home is located in a water-oriented community and is conveniently close to the beach, marina and Shady Side Market.

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
1,540
Status:
Active
MLS#:
MDAA2113330
Type:
Single Family, Single Family-Detached
Subdivision:
REGULARS
Lot size:
0.42 Acres
Year built:
1965
Courtesy: EXP Realty, LLC
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Water! Water everywhere! This adorable mid-century cottage faces Hopkins Cove , borders Parish Creek and looks out to the Chesapeake Bay Bridge. It is a dream come true for those who love living on the water, and could be your weekend getaway cottage. Not a fan of cottages? Then, go all in and remodel to make it your own! The possibilities are endless..... The property is being sold "as is". Please contact AACO and the Critical Area Division regarding remodeling permit requirements.

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
1,244
Status:
Active
MLS#:
MDAA2109400
Type:
Single Family, Single Family-Detached
Subdivision:
COLUMBIA BEACH
Lot size:
0.12 Acres
Year built:
1955
Courtesy: Coldwell Banker Realty
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Just in time for summer, this coastal contemporary â??cottageâ? offers you panoramic views and the soothing sounds of the Chesapeake Bay. This Bay fronting property has an open airy interior, warm and inviting, with two story vaulted ceilings, walls of windows which showcase the Bay view. The ease of main level living, enhanced with wood floors, includes the living, dining, kitchen, 2 bedrooms, a full bathroom, and laundry . Take advantage of the loft, with its natural light, perfect for a home office or studio. Plus a half bathroom and additional storage. Enjoy seamless indoor - outdoor living, expanded with a new low maintenance deck. Perfect for morning coffee and entertaining on the bay. Replaced: Deck in 2024.. Sump Pump and exterior faucet 2024.., Main level bathroom 2020.. Leaf Filter Gutter Guards , 2019,.. Split 2018.. Bedroom windows, 2016.. Roof, 2014 . Upper half bathroom added in 2009. Situated in the gated water privileged community of Columbia Beach. The community offers residents opportunities for boating, fishing, and other recreation: boat launch, short fishing pier, a long pier, waterfront park, childrens play area, regulation size basketball court, and tennis. The community walking path, along the rocks that line the cove, is marked by oval signs featuring a swan. Vacation Year Round !

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
8,143
Status:
Active
MLS#:
MDAA2111342
Type:
Single Family, Single Family-Detached
Subdivision:
NONE AVAILABLE
Lot size:
0.96 Acres
Year built:
1955
Courtesy: Real Broker, LLC - Annapolis
View additional info

Merchant Unmatched water views. Nearly 8,000 sq ft of curated living. A property that doesnt just stand out-it stands alone. Tucked away in the quiet, rural charm of Shady Side, this architecturally bold residence offers year-round views of the West River and a lifestyle that feels worlds away-yet keeps you close to everything that matters. Step inside and youre immediately immersed in nearly 8,000 square feet of living space-designed with intention, filled with original art, historical artifacts, and featured in multiple publications for its distinctive character. This, all because this home, this masterpiece, boasts design elements created by one of the worlds most renowned artists. From the banquet-sized dining room to the grand living space that opens to the water, every room delivers scale, flow, and timeless style. The chefs kitchen anchors the home with form and function, while five spacious bedrooms and 5.5 baths offer more than enough room to retreat away for moments of relaxation and peace. Outside, an acre of manicured gardens and carefully curated sculptures surrounds the home-offering a peaceful backdrop for everything from morning coffee to sunset wine. And with no HOA, this is freedom at its finest. Just off the beaten path, yet only minutes from the dockside restaurants of Deale, the historic charm of Galesville, and the energy of Annapolis-with a surprisingly easy commute to DC and Baltimore-this home offers a balance few properties can match. Offered with the ability for the new owner to keep much of the furnishing and art pieces (to be negotiated with offers), this home isnt just a place to live-its a place to belong. Live bold. Live different. Welcome home.

Beds:
5
Baths:
2 Full/1 Half
Sq.Ft.:
2,051
Status:
Active
MLS#:
MDAA2105584
Type:
Single Family, Single Family-Detached
Subdivision:
CEDARHURST ON THE BAY
Lot size:
0.11 Acres
Year built:
1965
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with Architectural shingles in 2018. It has an oversized 1 car garage with workshop for storage for those handyman/handywomen projects. Sale contingent on owner finding a home of their choice and they may need a rent back to make that work. New photos will be coming!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
3,445
Status:
Active
MLS#:
MDAA2101480
Type:
Single Family, Single Family-Detached
Subdivision:
AVALON SHORES
Lot size:
0.31 Acres
Year built:
1993
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Open Saturday, April 26 11:00 to 1:00. Post & beam architect design home with passive solar elements and lots of glass facing the water. A beautiful waterfront lot with southern exposure and wonderful view! Very well protected water on West River, stone rip rap. Pier only a few years old. Hop in your boat and be at one of 2 waterfront restaurants or West River Sailing Club in a couple of minutes. You can join Chesapeake Yacht Club at the end of Hine Drive and walk there! The Yacht Club offers slips, a pool, restaurant and other amenities. This is a unique property with 2 separate 2 story living areas, 2 exterior entrances. The two sides are easily united by just opening the living room to the other side.

Beds:
3
Baths:
3 Full
Sq.Ft.:
1,920
Status:
Active
MLS#:
MDAA2104698
Type:
Single Family, Single Family-Detached
Subdivision:
AVALON SHORES
Lot size:
0.34 Acres
Year built:
2005
Courtesy: Redfin Corp
View additional info

PRICE REDUCED! Waterfront Stunner! This home features main-level living with a large bedroom and full bath. The kitchen opens to the living area with tons of natural light. Upstairs, two additional bedrooms with private baths ensure everyone has their own space & privacy. Outside is a small finished entertainment area or walk to your private dock. Crab in the summer or take a kayak, SUP, or canoe out for a sunset paddle. New Roof in 2024. Make sure to see this house before it's gone! Flood Insurance Required- Flood Zone AE. $135 annual Civil Owners Association is included with the taxes. It covers road maintenance, the two playground parks, and the boat ramp maintenance.

Beds:
8
Baths:
8 Full/1 Half
Sq.Ft.:
8,412
Status:
Active
MLS#:
MDAA2105742
Type:
Single Family, Single Family-Detached
Subdivision:
NONE
Lot size:
2.44 Acres
Year built:
2014
Courtesy: Long & Foster Real Estate, Inc.
View additional info

MAJOR PRICE ADJUSTMENT on this incredible property! You could not build this home in this location for this amount! Located on a private 2.5-acre lot with over 300 ft of West River waterfront, 1346 E West Shady Side Road offers immediate access to the Chesapeake Bay via a private pier with lifts for jet skis and a boat. This grand home combines luxury, craftsmanship, and stunning water views. The double-story foyer, with a Schonbeck chandelier and floating staircases, opens to a fabulous great room and waterside porch. The floor plan includes two main-level primary suites with gas fireplaces, an informal dining area, great room with two-story ceiling, and a chefs kitchen with Sub-Zero and Wolf appliances, all overlooking the water. Hardwood floors and unique features, like a water view window through the stone fireplace, make the home even more special. The second floor has four bedrooms with ensuite bathrooms, a bonus room, and an elevator servicing all three levels. The third floor has two more bedrooms, a bathroom, and a casual seating area-ideal for guests or as an au pair suite. The oversized four-car garage includes space for a boat or RV. Outside, a large terrace leads to the private beach and pier. The property is equipped with geothermal heating and cooling, multiple hot water heaters, and two backup generators. Just an hour from Washington DC and 40 minutes from Annapolis, this is an unparalleled waterfront retreat.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,060
Status:
Active
MLS#:
MDAA2105330
Type:
Single Family, Single Family-Detached
Subdivision:
COLUMBIA BEACH
Lot size:
0.15 Acres
Year built:
2014
Courtesy: Chaney Homes, LLC
View additional info

OPEN Bay-front at this newly listed, Custom Coastal with private pier! Located in coveted Columbia Beach, this airy WATERFRONT is a head-turner, boasting an open floor-plan, with the finest of finishes! Direct Chesapeake Bay location, 100' private pier & 3 jet-ski lifts makes this the perfect retreat - or year round treat- With 3 spacious bedrooms, 2.5 beautiful baths, 9' ceilings & hickory flooring- throughout!- Inviting gourmet kitchen with gleaming granite countertops, large island with seating to host grandly, shiny stainless appliances & open to bright dining & living spaces w/ cozy gas fireplace & direct Bay views! Living spaces are extended by BOTH main-level AND upper-level full-length spaces- covered porch for late day cocktails and crabs after a fun day of boating, to coffee on upper deck waking up to the lap of the waves. Anderson windows, dual-zone HVAC, 'Generac' generator conveys!, Close to work & play with unbeatable open views, unmatched community amenities include boat ramp, tennis courts, playground, clubhouse, gated entry & fun events! Just minutes outside of Annapolis- and less than an hour to DC, this gorgeous retreat is sure to please! Hurry to claim today!

Beds:
3
Baths:
1 Full
Sq.Ft.:
960
Status:
Active
MLS#:
MDAA2102856
Type:
Single Family, Single Family-Detached
Subdivision:
CEDARHURST ON THE BAY
Lot size:
0.17 Acres
Year built:
1985
Courtesy: Douglas Realty, LLC
View additional info

Welcome to 1508 Cedarhurst Road in the water-privileged community of Cedarhurst on the Bay. The home features 3 bedrooms, 1 bathroom, and a spacious, fenced-in backyard. Super waterfront community featuring a pier, community house, and nearly 4 acres of waterfront property. Cedarhurst on the Bay is not a homeowners' association (HOA) and does not have monthly fees. It is a tax benefit district. The county collects taxes for Cedarhursts Special Community Benefit District (SCBD) and Shoreline Erosion Control District (SECD). Flood Insurance is NOT required for this property. Home is being SOLD AS-IS. Inspections are for informational purposes only.

Beds:
1
Baths:
1 Full
Sq.Ft.:
948
Status:
Active
MLS#:
MDAA2101548
Type:
Single Family, Single Family-Detached
Subdivision:
REGULARS
Lot size:
0.23 Acres
Year built:
1940
Courtesy: Premiere Realty LLC
View additional info

Welcome to 1419 Shady Rest Rd, it located on a quiet street not far from the water in one of Marylands Chesapeake Bay boating communities. This property has a drive way with plenty of space for parking. Being sold AS IS. Priced to sell so schedule your showing today! Please contact Torrence Hall for showings..

Beds:
2
Baths:
1 Full
Sq.Ft.:
862
Status:
Active
MLS#:
MDAA2092570
Type:
Single Family, Single Family-Detached
Subdivision:
SHADY SIDE
Lot size:
1.5 Acres
Year built:
1930
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Your Own Private Retreat, get away from the Rat Race and make this a great place for you and your family. 1337 West River Road , located in Shady Side, MD is a secluded waterfront property that sits on 1.5 acres with 592 feet of waterfront on the South Creek. This property has a home with 2 beds and 1 bath that will need remodeling and/or teardown. it's located 1/4 mile off the main road (West River Road ) follow signs to property. use GPS (once on West River Road make a left turn pass the first house on the left and follow gravel road to the end.)

Beds:
4
Baths:
1 Full/1 Half
Sq.Ft.:
2,144
Status:
Active
MLS#:
MDAA2011224
Type:
Single Family, Single Family-Detached
Subdivision:
SHADY SIDE
Lot size:
0.57 Acres
Year built:
1940
Courtesy: Schwartz Realty, Inc.
View additional info

4 beds/ 1 full bath and 1/2 bath with shower.2144 SQ FT. Home and income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MA2) marine zoned property, totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8feet, that can accommodate boats in excess of 40 feet. Total income from 7 of the 12 slips in 2021 was $11,300. POTENTIAL $20,000 PLUS RENTAL INCOME IN ADDITION TO DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. Cold box has been removed.

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