3,269

Shady Side, MD Homes

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  • /3

    $225,000 Sold Mar 21, 2025

    • 1,010 Sq Ft
    • $223/SF
    • 33 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1983

    4738 Idlewilde Rd, Shady Side, MD 20764

    This inviting 3-bedroom, 2-bathroom home presents a fantastic opportunity for buyers with a vision. Nestled in Idlewilde on the Bay neighborhood, this property is being sold as-is, offering the chance to customize and renovate to your taste.With a spacious layout, this home is ready for your personal touch. The bright living area is perfect for gatherings, while the bedrooms offer plenty

    Monique Willard Coldwell Banker Realty

    4738 Idlewilde Rd, Shady Side, MD 20764
    • /76

      Est $393,632 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,062 Sq Ft

      1208 Oak Ave, Shady Side, MD 20764

      1208 Oak Ave, Shady Side, MD 20764
  • /49

    $2,200,000

    • 9 Beds
    • 6.5 Baths
    • 8,425 Sq Ft

    4701 Girton Ave, Shady Side, MD 20764

    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

    4701 Girton Ave, Shady Side, MD 20764
  • /70

    $950,000 Sold Mar 14, 2025

    • 2,604 Sq Ft
    • $365/SF
    • 2 Days On Market
    • 4 Beds
    • 2 Baths
    • Built 1944

    5064 Lerch Dr, Shady Side, MD 20764

    Welcome to your Chesapeake Bay retreat in the heart of Shady Side, MD! Nestled along the serene shores of the West River, with direct access to the Bay, this fabulous 4-bedroom, 2-bath home offers over 100 feet of shoreline, a covered dock with boat lifts, a slip and breathtaking natural beauty. As you step inside, you'll be captivated by the natural light, walls of windows, and

    Joan Stansfield Samson Properties

    5064 Lerch Dr, Shady Side, MD 20764
    • /48

      Est $454,855 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,500 Sq Ft

      4957 Elm St, Shady Side, MD 20764

      4957 Elm St, Shady Side, MD 20764
  • /54

    $439,990

    • 3 Beds
    • 2.5 Baths
    • 1,931 Sq Ft

    1485 Cedarhurst Rd, Shady Side, MD 20764

    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 and casual dining.Enjoy your

    Nicki Palermo RE/MAX One

    1485 Cedarhurst Rd, Shady Side, MD 20764
  • /38

    $625,000 Sold Mar 12, 2025

    • 3,613 Sq Ft
    • $173/SF
    • 81 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2008

    4933 Aspen St, Shady Side, MD 20764

    This 3600+ sq. ft. provides water views in a water privileged community to go along with this spacious home. This is one of the few houses of this size in the area. The main floor starts with a grand entrance that leads to the den, eat in kitchen, dining room and living room providing plenty of space for hosting and spending time with family. The half bathroom is in the middle of the action to

    Pedro Paz Samson Properties

    4933 Aspen St, Shady Side, MD 20764
    • /45

      Est $351,451 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,000 Sq Ft

      1617 Winters Ave, Shady Side, MD 20764

      1617 Winters Ave, Shady Side, MD 20764
  • /28

    $1,399,900

    • 3 Beds
    • 2 Baths
    • 1,792 Sq Ft

    1114 Cherry Point Rd, West River, MD 20778

    Attention all savvy buyers/investors! This is a truly great opportunity hitting the market! A combination of two parcels totaling 2.18 acres with private access to the wonderful South Creek. 1114 Cherry Point Road is 1.01 acres with a single family home , 3 bedrooms and 2 full bathrooms and a 2 car attached garage. Home will need a complete remodel or tear it down and build your dream home. The

    E. Gabriela Vasco Realty Advantage of Maryland LLC

    1114 Cherry Point Rd, West River, MD 20778
  • /27

    $330,000 Sold Mar 10, 2025

    • 1,020 Sq Ft
    • $324/SF
    • 10 Days On Market
    • 3 Beds
    • 1.5 Baths
    • Built 1940

    1219 Holly Ave, Shady Side, MD 20764

    Adorable cottage just a couple blocks from the Chesapeake Bay. Major Reno done in 2020. Roof, HVAC indoor and outdoor, water heater, washer dryer, added square footage on main floor as well as added finished upper level bonus room, Large but cozy covered porch, paver/hardscape walkway, landscaping boxes, carpet, flooring, appliances, water filter. Huge yard, partially fenced. Room for 2-3 cars

    Sandy Fullerton RE/MAX United Real Estate

    1219 Holly Ave, Shady Side, MD 20764
    • /35

      Est $325,814 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 840 Sq Ft

      1311 Holly St, Shady Side, MD 20764

      1311 Holly St, Shady Side, MD 20764
  • /42

    $515,620

    • 5 Beds
    • 2.5 Baths
    • 2,051 Sq Ft

    1216 Grove Ave, Shady Side, MD 20764

    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.

    1216 Grove Ave, Shady Side, MD 20764
  • /30

    $440,000 Sold Mar 05, 2025

    • 1,564 Sq Ft
    • $281/SF
    • 37 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2019

    1222 Hawthorne St, Shady Side, MD 20764

    Welcome to this stunning 3-bedroom, 2.5-bath home in Shady Side!Built in just 2019 and meticulously maintained, the front door opens to a spacious main floor, featuring a cozy living room with grey-wash vinyl flooring and large windows that fill the space with an abundance of natural light. The main floor also boasts a half bath, a coat closet, and an open-concept eat-in kitchen with TWO

    Kaleigh cook Keller Williams Flagship

    1222 Hawthorne St, Shady Side, MD 20764
    • /67

      Est $769,418 Not Listed For Sale

      • 6 Beds
      • 3.5 Baths
      • 2,918 Sq Ft

      629 Plantation Blvd, West River, MD 20778

      629 Plantation Blvd, West River, MD 20778
  • /2

    $100,000

    • Land
    • 0.68 Acre
    • $147,059 per Acre

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764

    Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility.With convenient access to Route 2, commuting to Annapolis, Baltimore, or Washington, D.C., is

    Joan Stansfield Samson Properties

    1445 & 1447 Haile Pkwy, Shady Side, MD 20764
  • /50

    $318,000 Sold Feb 28, 2025

    • 680 Sq Ft
    • $468/SF
    • 31 Days On Market
    • 2 Beds
    • 1 Bath
    • Built 1965

    1501 Garst Rd, Shady Side, MD 20764

    Welcome to this charming coastal cottage in the Columbia Beach neighborhood! This home offers a perfect blend of modern luxury and inviting warmth. With 2 spacious bedrooms and a full bath, this home is designed for comfort and style. Featuring elegant hardwood flooring, updated kitchen with new appliances and ample storage. Nestled on a delightful corner lot, the property boasts a level yard

    David Orso Berkshire Hathaway HomeServices PenFed Realty

    1501 Garst Rd, Shady Side, MD 20764
    • /53

      Est $495,505 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,956 Sq Ft

      1211 Oak Ave, Shady Side, MD 20764

      1211 Oak Ave, Shady Side, MD 20764
  • /2

    $65,000

    • Land
    • 0.30 Acre
    • $216,667 per Acre

    1408 & 1410 Haile Pkwy, Shady Side, MD 20764

    Discover the perfect retreat from city life in the serene setting of Shady Side, MD. This parcel of land offers a rare opportunity to build your dream home amidst nature’s beauty. Tucked away in a peaceful community, the property provides the ideal balance of tranquility and accessibility.With convenient access to Route 2 & Route 4, commuting to Annapolis, Baltimore, or Washington, D.C.,

    Joan Stansfield Samson Properties

    1408 & 1410 Haile Pkwy, Shady Side, MD 20764
  • /84

    $1,475,000 Sold Feb 28, 2025

    • 4,720 Sq Ft
    • $312/SF
    • 80 Days On Market
    • 4 Beds
    • 4.5 Baths
    • Built 2010

    4923 Thomas Dr, Shady Side, MD 20764

    Located just an hour from Washington, D.C., this custom-built waterfront estate on Chesapeake Bay offers a rare blend of modern luxury, serene views, and premier water access, making it the perfect retreat or high-potential vacation rental. At nearly 5,000 square feet, this thoughtfully designed home captures the essence of relaxation and recreation along over 100 feet of pristine

    Kara Chaffin Donofrio Long & Foster Real Estate, Inc.

    4923 Thomas Dr, Shady Side, MD 20764
    • /77

      Est $477,191 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,064 Sq Ft

      1207 Juniper St, Shady Side, MD 20764

      1207 Juniper St, Shady Side, MD 20764
  • /41

    $2,875,000

    • 8 Beds
    • 8.5 Baths
    • 8,412 Sq Ft

    1346 E West Shady Side Rd, Shady Side, MD 20764

    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.

    1346 E West Shady Side Rd, Shady Side, MD 20764
  • /23

    $480,000 Sold Feb 17, 2025

    • 1,326 Sq Ft
    • $362/SF
    • 60 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1993

    1241 Avalon Blvd, Shady Side, MD 20764

    Check with your lender as this home qualifies for 100% financing through USDA Rural loan. Welcome to this Fully Remodeled home in the Avalon Shores neighborhood! This home offers a perfect blend of modern luxury and inviting warmth. Boasting 3 bedrooms and 2.5 bathrooms, this home is designed for comfort and style. All new open floor plan, custom kitchen and all-new bathrooms exude elegance and

    DAVID LUCKE Turnock Real Est. Services, Inc.

    1241 Avalon Blvd, Shady Side, MD 20764
    • /77

      Est $803,479 Not Listed For Sale

      • 5 Beds
      • 3.5 Baths
      • 4,166 Sq Ft

      619 Plantation Blvd, West River, MD 20778

      619 Plantation Blvd, West River, MD 20778
  • /11

    $183,200

    • Land
    • 0.14 Acre
    • $1,308,571 per Acre

    5250 Al Jones Dr, Shady Side, MD 20764

    LAND LAND in a gated private community! The lot is 3 small lots in total all adjacent to each other. The county has approved building on the lots as ONE dwelling. The home will need to adhere to the building envelope but can be as high as needed (county approved height change)...building a car garage on bottom and build up in SF from there!! A well is needed and there is public septic. I

    Jennifer Koenig Long & Foster Real Estate, Inc.

    5250 Al Jones Dr, Shady Side, MD 20764
  • /14

    $100,000 Sold Feb 14, 2025

    • Land
    • 0.23 Acre
    • $434,783 per Acre
    • 25 Days On Market

    4748 Chestnut Rd, Shady Side, MD 20764

    Beautiful large 100x100 Water-view Corner Lot in the QUAINT Community of Felicity Cove!! Come build your dream home in this private community tucked away in a "Cove". This amenity rich Community offers a Community Pier with breathtaking views of the Chesapeake Bay, a Boat ramp and Playground. This one will not last long!!

    Katherine Grimley RE/MAX Leading Edge

    4748 Chestnut Rd, Shady Side, MD 20764
    • /42

      Est $373,094 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 800 Sq Ft

      4737 Chesapeake Ave, Shady Side, MD 20764

      4737 Chesapeake Ave, Shady Side, MD 20764
  • /61

    $1,300,000

    • 3 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    1538 Robinson Rd, Shady Side, MD 20764

    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

    1538 Robinson Rd, Shady Side, MD 20764
  • /35

    $400,000 Sold Feb 13, 2025

    • 1,196 Sq Ft
    • $334/SF
    • 17 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1944

    6320 Shady Side Rd, Shady Side, MD 20764

    Experience modern elegance in this beautifully updated home situated on a .23-acre corner lot in the highly desirable Avalon Shores community. Offering three spacious bedrooms with new flooring and carpeting, along with 2.5 renovated bathrooms, this property balances comfort and contemporary style. The kitchen stands out with brand-new granite countertops, a sleek island, upgraded storage, a

    Thomas Gavin Coldwell Banker Realty

    6320 Shady Side Rd, Shady Side, MD 20764
    • /41

      Est $637,691 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,560 Sq Ft

      4930 Lerch Dr, Shady Side, MD 20764

      4930 Lerch Dr, Shady Side, MD 20764
  • /2

    $74,999

    • Land
    • 2.50 Acres
    • $30,000 per Acre

    5347 Offer Ln, Churchton, MD 20733

    2.5 Acres, Offer ln leads directly to this. See survey. As is sale, bring offers. public sewer is very close.

    Kyle Squires Lazar Real Estate

    5347 Offer Ln, Churchton, MD 20733
  • /150

    $1,350,000 Sold Feb 12, 2025

    • 3,142 Sq Ft
    • $430/SF
    • 214 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 1977

    4754 Chestnut Rd, Shady Side, MD 20764

    Gorgeous 2.76 acre waterfront estate with a beautiful Victorian style home on the Chesapeake Bay. Unique 3 bedroom 3 bath open flowing floor plan exudes casual elegance with quality design and workmanship, perfect for coastal living. This lovely home provides great entertaining spaces inside and out. Equipped with Anderson windows and french doors, multiple Trex decks and porches, hardwood and

    Martin Welsh Monument Sotheby's International Realty

    4754 Chestnut Rd, Shady Side, MD 20764
    • /38

      Est $455,137 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,824 Sq Ft

      1195 Bayview Ave, Shady Side, MD 20764

      1195 Bayview Ave, Shady Side, MD 20764
  • /6

    $259,999

    • Land
    • 0.77 Acre
    • $337,661 per Acre

    4846 Woods Wharf Rd, Shady Side, MD 20764

    Vacant Lot Ideal for Expansion or New Venture. Perfect for Boat Storage or New Building. Leverage its proximity to high-demand recreational areas for profitable boat and trailer storage, or business vehicles, or develop the lot into a commercial building for your business, or to lease the space to a business who is looking to serve the local community.

    Scott Cleary RE/MAX One

    4846 Woods Wharf Rd, Shady Side, MD 20764
  • /30

    $595,000 Sold Feb 11, 2025

    • 2,237 Sq Ft
    • $266/SF
    • 59 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1989

    920 Judge Ct E, West River, MD 20778

    This Beautiful 4-Bedroom Home has Water-Privilege in the wonderful Cedarlea CommunityWelcome to 920 Judge Ct E, a move-in-ready gem located in the sought-after Cedarlea community of West River, MD in wonderful Anne Arundel County. This charming 4-bedroom, 2.5-bathroom home is tucked away on a quiet cul-de-sac, offering privacy and tranquil living in a well-established, water-privileged

    Bryan Stubblefield Town & Country Real Estate

    920 Judge Ct E, West River, MD 20778
    • /45

      Est $405,415 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,296 Sq Ft

      1183 Oak Ave, Shady Side, MD 20764

      1183 Oak Ave, Shady Side, MD 20764
  • /2

    $48,900

    • Land
    • 0.08 Acre
    • $611,250 per Acre

    1639 Columbia Beach Rd, Shady Side, MD 20764

    Nice, level lot ready for your dream home! Located right by Flag Pond, this property has a sewer hookup available, and the suggested building footprint is 30 ft x 40 ft. Bring your own builder and make it your own.

    Rob Schou EXP Realty, LLC

    1639 Columbia Beach Rd, Shady Side, MD 20764
  • /15

    $127,000 Sold Feb 07, 2025

    • 936 Sq Ft
    • $136/SF
    • 4 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1940

    5218 Nick Rd, Shady Side, MD 20764

    INVESTOR ALERT: Property priced under tax assessed land value only. Rehab or teardown located on large lot. Existing Well and Municipal Sewer. Existing home is 3 bedroom and 1 bathroom rancher. Selling AS IS!!

    Candice Bothun CENTURY 21 New Millennium

    5218 Nick Rd, Shady Side, MD 20764
    • /41

      Est $337,718 Not Listed For Sale

      • 2 Beds
      • 1.5 Baths
      • 1,095 Sq Ft

      1613 Winters Ave, Shady Side, MD 20764

      1613 Winters Ave, Shady Side, MD 20764
  • /47

    $295,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    1508 Cedarhurst Rd, Shady Side, MD 20764

    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

    1508 Cedarhurst Rd, Shady Side, MD 20764
  • /51

    $422,500 Sold Jan 31, 2025

    • 1,476 Sq Ft
    • $286/SF
    • 101 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1949

    1552 Dennis Rd, Shady Side, MD 20764

    Welcome to 1552 Dennis Rd, a beautiful home constructed from the foundation up in 2002 and fully renovated in 2024. This 3-bedroom, 2-bathroom property offers one-level living with a versatile upstairs space that can be used as an additional bedroom, rec room, or office. The home features new flooring, a stunning modern kitchen with stainless steel appliances, quartz countertops, and new

    Adam Murphy RE/MAX Realty Centre, Inc.

    1552 Dennis Rd, Shady Side, MD 20764

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