Shady Side MD Real Estate & Homes for Sale

Rare Find on half acre lot in idyllic location! This beautifully updated 3 bedroom/2 full bath "super" rancher, surrounded by natural beauty and mature trees, offers space, style, and an unbeatable location! Vaulted ceilings in the kitchen and living room create a bright, open feel, while fresh paint and brand-new flooring add a modern touch throughout. The extra-large primary suite features a full bath and walk-in closet, providing a private retreat. Located across from Shady Side Park and Playground and just minutes from multiple marinas, this home is perfect for those who love the outdoors. With its spacious layout and serene setting, this is a must-see!

Location, location, location! Bring your vision and creativity.! "As-Is/FixerUpper/TearDown" single family home in Shady Side, MD! -- just steps to Renos, the Corner Grill & the most amazing soft-serve ice-cream shop for miles! This 2-bedroom, 1-bathroom home, located in the desirable Shady Side community, presents an incredible opportunity for those looking to invest, renovate, or rebuild! With its prime location just 25 minutes from Annapolis and 40 minutes from Washington, D.C., this location offers both convenience and potential. Shady Side is known for its charming, peaceful surroundings and proximity to the Chesapeake Bay, West River, and so many other tributaries surrounding the Bay! -- making this an ideal spot for anyone seeking a tranquil lifestyle with easy access to the vibrant city life of Annapolis and D.C. Don't miss out on this unique opportunity to bring this home back to life! Please note the buyer is responsible for conducting all due diligence on property including location, use, restrictions, and taxes.

A beautiful waterfront lot with southern exposure and wonderful view! House is a post & beam architect design with passive solar elements and lots of glass facing the water. 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. It should be practical to unite the two sides with a 2nd floor hallway overlooking the living room.

This home will make you feel like you are living on a permanent vacation! This home features main-level living with a large bedroom and full bath. The kitchen is stunning & 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.

**Move-in ready home in the private, water-privileged Westelee community of Avalon Shores **Access to beach, boat ramp, boat slips with electric, kayak rack, new waterfront playground and gazebo **Owner Suite on main level with walk in closet and private bath **Open cathedral ceilings in family room with cozy gas Fireplace and 8' double windows for abundant natural light **Hardwood floors throughout main level **Newly rebuilt deck (2025) **Updated kitchen with granite countertops, glass cabinetry, SS appliances, and propane gas stove/cooktop ** Reverse Osmosis under kitchen sink **4th bedroom/Den upstairs does not have window makes great gaming room **Carrier 3-ton HVAC (2016) ** Hot water heater (2023) **Water softener with chlorine injection **Mud room with Samsung washer/dryer (2024) **3 TV's convey **Large driveway for boat/RV parking and **12x8 shed for gear storage **Oversized 2 car garage! **Large spacious yard backs to open lot. Efficient Solar Energy!

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.

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 premier waterfront builder in the Annapolis area. While the design is already thoughtfully planned, you have the unique opportunity to personalize selections and make modifications, ensuring your home fits your vision. Surrounded by estate homes, the drive-in is picturesque, setting the tone for this exceptional property. If you're looking for stunning waterfront and privacy without the hustle of city life, this is it. Ready to build your dream home?

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!

Beautifully maintained 4-bedroom, 2.5-bath home in the coveted Westelee neighborhood. This residence has everything you desire and more, including a spacious eat-in kitchen with a separate dining room, a main-level office, spa-inspired bathrooms, fresh paint, and new carpet. The upper level features a huge bonus room over the garage that can serve as a playroom or a potential 5th bedroom. Primary suite has a private balcony with gorgeous WATER VIEWS! Outside, enjoy a large private deck and a fenced-in yard, perfect for entertaining. Additionally, the oversized attached garage offers ample space for both parking and projects. Take advantage of the voluntary community association, providing access to a private beach, playground, pavilion, and pier for only $65 a year! Boat slips and kayak racks can also be rented out thru the Association.

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 very private setting, an expansive home, has 260 feet of pristine waterfront, coupled with the boat lift, jet ski lifts, and large pier, offers unparalleled access to water activities. The pier also has deep water that can hold above average watercraft and gear for all the fun on the Chesapeake Bay. The in-law suite is a great touch for visitors or extended family, offering complete privacy with its own living space and entrance. Its clear that the home is designed for both functionality and luxury, from the chefs kitchen with its top-tier appliances and water views to the primary suite. Primary suite is located on the first floor and is expansive both on size and views. The vast living space includes an in-law suite with two bedrooms, there are five additional bedrooms on second floor with two bedrooms with private baths, total of eight bedrooms and six baths. There are two laundry rooms located on each level, special Geothermal heat and air system, three car garage, stucco siding, Anderson windows and heated driveway. Home will need up-dates to your personal liking. Possible AB&B no HOA buyer would need to research, Anne Arundel County requirements for AB&B and any local ordinances for restrictions and requirements. With its proximity to cities like Annapolis, DC, and Baltimore, this property offers the perfect combination of a tranquil waterfront retreat and access to urban conveniences. The ultimate game changer for this property is not only the space it provides, but the location and privacy. Seller is offering up to $700,000.00 in seller financing. Possible Airbnb no HOA buyer would need to research, Anne Arundel County requirements for Airbnb and any local ordinances prior to purchase and offer if plan is for Airbnb.

Welcome to 1508 Cedarhurst Road in the water-privileged community of Cedarhurst on the Bay. The home consists of 3 bedrooms, 1 bathroom, and a large fenced-in backyard. Super waterfront community with a pier, community house and almost 4 acres on the water. Cedarhurst on the Bay is not an 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).

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.

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..

New Construction (To-Be-Built). Meet the Monroe: this stunning home design comes with three distinct elevations to choose from, ensuring your home reflects your unique style and preferences: Traditional, Modern, or Craftsman. The spacious layout encompasses four bedrooms, Owner's suite with ensuite bathroom, and 2nd Floor laundry. Work from home effortlessly in the dedicated office space, providing a quiet sanctuary for productivity and focus. The two-car garage ensures ample parking and storage space for vehicles, outdoor gear, and more. Still time to choose your interior options...hurry this one will sell quickly!! Disclaimer: All renderings/photos provided herein are for illustrative purposes only and are intended to showcase design options.  Actual products, features, finishes, and layouts may vary.  The images may depict optional features, upgrades, or configurations that are not included as standard or available in all homes.

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.)

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.