Shady Side, MD Houses for Sale

Updated Colonial Retreat in Prime West River Location!Welcome to 5235 Chalk Point Road – a beautifully updated 5-bedroom, 3.5-bath Colonial offering 3,052 sq ft of refined living space on a serene 1.37-acre lot. Built in 1990 and thoughtfully enhanced throughout, this spacious home features two primary suites, including one conveniently located on the main floor—perfect for flexible living.Recent

Bonnie O'Donnell RE/MAX One

Merchant Unmatched water views. Nearly 8,000 sq ft of curated living. A property that doesn’t 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 you’re immediately immersed in

Phil Gerdes Real Broker, LLC - Annapolis

First time on the market! This custom-built water view home, set on a picturesque one-acre lot, was thoughtfully designed by its original owners. Featuring a first-floor primary suite, wide hallways and doors for wheelchair accessibility, and a roll-in shower in the primary bath, every detail was carefully planned. The exquisite gourmet kitchen boasts a commercial gas stove, wall oven, spacious

Ray Mudd Schwartz Realty, Inc.

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

William Whitman Long & Foster Real Estate, Inc.

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

Dorothy Bistransin Redfin Corp

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

Jennifer Chaney Chaney Homes, LLC

An adorable cottage with almost 200' of waterfront facing Hopkins Cove with views of the Chesapeake Bay Bridge. This could be your weekend getaway cottage, or 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.

Theresa Kurtz EXP Realty, LLC

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, MDis 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

Bruce Thompson Long & Foster Real Estate, Inc.

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

George Heine Schwartz Realty, Inc.

Very rare to find an adorable little cottage located on approximately 2 acres. Newer roof, windows & doors. This one has 2 beds, 1 bath, a bright open sunroom thats perfect for a family / living room, a cute little kitchen & dining room. Full size stackable washer/dryer. Newer two zone ductless mini-split. This beauty sits on almost two acres of flat & open land backing to woods. There is a

Vincent Damico RE/MAX Advantage Realty

Welcome to an extraordinary waterfront estate offering the perfect balance of luxury, function, and efficiency on Maryland’s treasured Western Shore. This 9-bedroom, 6.5-bath residence spans 8,400+ square feet and is built to withstand the elements while embracing the serene lifestyle of the Chesapeake Bay.Set on over 2/3 of an acre with 260 feet of water frontage, this solid brick & block home

Dawn Riley RE/MAX One

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

Paul Lee Long & Foster Real Estate, Inc.

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

Reid Buckley Long & Foster Real Estate, Inc.

Charming Chesapeake Bay cottage with breathtaking water views from nearly every room! Start your mornings with a stunning sunrise from the all-season front porch. This well-maintained home features beautiful hardwood floors, new windows (2013), fresh paint (2015), and a fully encapsulated crawl space (2022). A detached garage provides extra storage. Just steps from the community beach, marina,

Ray Mudd Schwartz Realty, Inc.

This waterfront property at 4701 Girton Ave truly is a luxurious retreat, offering the perfect balance of space, privacy, and stunning views of the Chesapeake Bay and West River. This expansive home is in a very private setting and has 260 feet of pristine waterfront, coupled with a large 250' pier with boat and jet ski lifts offering unparalleled access to water activities. The pier also has

Dee Dee McCracken Coldwell Banker Realty

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.

Heather Mullinix Douglas Realty, LLC

Welcome to 1419 Shady Rest Rd, it located on a quiet street not far from the water in one of Maryland’s 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..

Cindy Tao Premiere Realty LLC

Welcome to this incredible home to-be-built on 1.6 waterfront acres just south of Annapolis. This waterfront lot offers breathtaking West River Views, a deep-water pier, two docks and two boat lifts that convey. Located in shady Side, this property offers the best of both worlds; quiet, small-town charm with easy access to Annapolis and DC.Proposed home is by Whitehall Building, a

Lynn Peaper Next Step Realty

Professional Photos Coming Soon!Welcome to this beautifully maintained Colonial nestled on a spacious corner lot in a peaceful cul-de-sac. Freshly painted in neutral tones, this home offers a light and airy feel throughout. The heart of the home is the stunning kitchen—featuring granite countertops, light cabinetry, and a large center island topped with butcher block, perfect for both meal prep

Nicki Palermo RE/MAX One

Open House , Sunday, 4/27, 1PM - 3PM....Just in time for summer, this coastal contemporary “cottage” 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

Celeste Blessin Coldwell Banker Realty

Wonderful 4Br/2.5Ba in the waterfront community of Felicity Cove! Come take a look at the open floorplan from kitchen to family room to deck with tons of entertaining potential! Granite counters, stainless steel appliances, and a huge island for meals or homework are featured in this updated kitchen! Engineered hardwood flooring throughout main level! Freshly painted large deck for enjoying the

Angie Carr Riverscape Realty

Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering over one hundred fifty feet of private shoreline and breathtaking views. Designed for refined living and effortless entertaining, this home delivers an exceptional lifestyle both inside and out. The exterior is a private resort, featuring a heated in-ground pool, outdoor grilling area, fire

Adam Light Monument Sotheby's International Realty

Two story Colonial style home on Steamboat Road. The exterior has a front porch, fenced rear yard and large deck. There is an open floorplan on the first level, 3 bedrooms are located upstairs. This property is located close to the Chesapeake Bay with easy commute to AAFB, DC & Annapolis. Sold in AS IS condition, seller will make no repairs.

Michael Patrick RE/MAX United Real Estate

Major price drop owners want sold this week!!!!!!! RA zoning landscaping company or tree guys or just keep as a farm this is a great location it has a newer well and the house does need a full rehab do not go in house this is a full rehab cash ,hard money or bank loan this will not be able to get regular mtg. Also 5336 will be included in sale which is 1.8 AC CASH OR HARD MONEY THIS IS A FULL

Christopher Wroten RE/MAX United Real Estate

Major price drop owners want it sold this week !!!!!!!!RA zoning landscaping company or tree guys or just keep as a farm this is a great location it has a newer well and the house does need a full rehab do not go in house this is a full rehab CASH ,Hard Money only this will not be able to get regular mtg. Also 5336 will be included in sale which is 1.8 AC . THIS IS A FULL REHAB

Christopher Wroten RE/MAX United Real Estate