Shady Side, MD Homes

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  /2

  $265,000 Pending

  • 1 Bed
  • 1 Bath
  • 948 Sq Ft

  1419 Shady Rest Rd, Shady Side, MD 20764

  Cindy Martin Samson Properties

  1419 Shady Rest Rd, Shady Side, MD 20764
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  /41

  $2,100,000 Sold Jul 25, 2025

  • 8,412 Sq Ft
  • $250/SF
  • 96 Days On Market

  • 8 Beds
  • 8.5 Baths
  • Built 2014

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

  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

  Reid Buckley Long & Foster Real Estate, Inc.

  1346 E West Shady Side Rd, Shady Side, MD 20764
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  /30

  Est $455,008 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,006 Sq Ft

  1217 Pine Ave, Shady Side, MD 20764

  1217 Pine Ave, Shady Side, MD 20764
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  /41

  $399,000 Sold Jul 17, 2025

  • 1,027 Sq Ft
  • $389/SF
  • 40 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1940

  1215 Pine Ave, Shady Side, MD 20764

  Location, location, location! Just blocks from the sparkling Chesapeake Bay, this Shady Side gem is cute as can be and full of charm. This 2-bedroom, 2-bath home is flooded with natural light and features cathedral & vaulted ceilings, exposed beams, two brick fireplaces, and luxury vinyl plank flooring throughout. The kitchen opens up to a spacious, versatile room that can serve as a dining room

  Joan Stansfield Samson Properties

  1215 Pine Ave, Shady Side, MD 20764
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  /56

  Est $587,358 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,160 Sq Ft

  1631 Snug Harbor Rd, Shady Side, MD 20764

  1631 Snug Harbor Rd, Shady Side, MD 20764
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  /12

  $185,000 Sold Jul 11, 2025

  • Land
  • 2.86 Acres
  • $64,685 per Acre

  • 91 Days On Market

  1344 E West Shady Side Rd, Shady Side, MD 20764

  Great price for this beautiful 2.86 acre wooded lot with deeded access to the West River! Public sewer access nearby. Short walk to Shady Side Park with ball fields / tennis court / pickleball court / basketball courts / tot lot & more! Easements and plat layout uploaded in documents / disclosures. Call listing agent for details to walk the lot and if you have any questions!

  Bill Beam Beam Realty Group, Inc.

  1344 E West Shady Side Rd, Shady Side, MD 20764
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  /28

  Est $338,694 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 956 Sq Ft

  4912 Dogwood St, Shady Side, MD 20764

  4912 Dogwood St, Shady Side, MD 20764
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  /66

  $515,000 Sold Jul 08, 2025

  • 2,179 Sq Ft
  • $236/SF
  • 34 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 1976

  4726 Poplar Rd, Shady Side, MD 20764

  Great Price Improvement! Beautiful, well maintained, and updated home in the small Private community of Felicity Cove. This is a small community of 34 homes with a large community pier and outdoor areas. The home is 2 story brick and vinyl clad Cape Cod style. The home is move in ready. There are 4/5 bedrooms, 3.5 bathrooms, bonus office or 5th bedroom and family room. There is a lot of extra

  Suzanne Kerill Taylor Properties

  4726 Poplar Rd, Shady Side, MD 20764
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  /29

  Est $346,564 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  6322 Shady Side Rd, Shady Side, MD 20764

  6322 Shady Side Rd, Shady Side, MD 20764
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  /47

  $305,000 Sold Jun 30, 2025

  • 960 Sq Ft
  • $318/SF
  • 98 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1985

  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
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  /7

  Est $303,539 Not Listed For Sale

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  1603 Depriest Dr, Shady Side, MD 20764

  1603 Depriest Dr, Shady Side, MD 20764
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  /50

  $1,495,000 Sold Jun 30, 2025

  • 2,402 Sq Ft
  • $622/SF
  • 21 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1996

  4929 W Chalk Point Rd, West River, MD 20778

  OPEN HOUSE CANCELED; PROPERTY UNDER CONTRACT Welcome to 4929 West Chalk Point Road, a boaters paradise! This whole home underwent a stunning renovation down to the studs in 2022. Updates include a gourmet kitchen, incredible owner's suite and beautiful finishes throughout. This is that turn key home on the water you have been searching for. Just pack your things and move right in, there is no

  Michele Deckman TTR Sotheby's International Realty

  4929 W Chalk Point Rd, West River, MD 20778
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  /35

  Est $379,884 Not Listed For Sale

  • 3 Beds
  • 1.5 Baths
  • 1,240 Sq Ft

  1304 Juniper St, Shady Side, MD 20764

  1304 Juniper St, Shady Side, MD 20764
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  /26

  $405,000 Sold Jun 27, 2025

  • 1,215 Sq Ft
  • $333/SF
  • 11 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 1991

  4904 Beech St, Shady Side, MD 20764

  Welcome to 4904 Beech Street, a beautiful Cape Cod located in the sought-after waterfront community of Avalon Shores. The inside of this home has plenty of rooms and feels larger than you may think from the outside. This home is ideal for enjoying life near the water.The main level features a living room, an open kitchen, a full bath with a main level bedroom, and a second half bath with

  Emily McGann Compass

  4904 Beech St, Shady Side, MD 20764
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  /67

  Est $611,723 Not Listed For Sale

  • 5 Beds
  • 2.5 Baths
  • 2,086 Sq Ft

  5149 Cedarlea Dr, West River, MD 20778

  5149 Cedarlea Dr, West River, MD 20778
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  /36

  $195,000 Sold Jun 26, 2025

  • 682 Sq Ft
  • $286/SF
  • 5 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  5914 Shady Side Rd, Shady Side, MD 20764

  **Offer Deadline Monday June 9th 5:00 PM** Welcome to 5914 Shady Side Road in Shady Side, Maryland! This 1 acre lot offers plenty of room to expand your new homestead. Currently set up as a single story Bungalow home with a very large Detached Barn all on an existing well and public sewer. Live in the home as it sits and enjoy the expansive outdoor space OR raze & easily build your dream

  Jeff Lipkin EXP Realty, LLC

  5914 Shady Side Rd, Shady Side, MD 20764
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  /50

  Est $591,440 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,600 Sq Ft

  1556 Dennis Rd, Shady Side, MD 20764

  1556 Dennis Rd, Shady Side, MD 20764
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  /18

  $414,900 Sold Jun 24, 2025

  • 1,269 Sq Ft
  • $327/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1940

  5227 Al Jones Dr, Shady Side, MD 20764

  Incredible opportunity to make it your own beach house haven! A true diamond in the rough. Enjoy some of the most beautiful bay views you'll ever experience from the comfort of your own backyard. This home has significance to Columbia Beach. This is the original home of Al Jones. Home is in need of major restoration. This 1940 Cape Cod features 3 Bedrooms and 2 Full Baths, fireplace, built in

  Lydia Newman Fairfax Realty Premier

  5227 Al Jones Dr, Shady Side, MD 20764
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  /33

  Est $382,351 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,248 Sq Ft

  4929 Chestnut St, Shady Side, MD 20764

  4929 Chestnut St, Shady Side, MD 20764
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  /3

  $33,500 Sold Jun 17, 2025

  • Land
  • 3.04 Acres
  • $11,020 per Acre

  • 24 Days On Market

  5347 Offer Ln, Churchton, MD 20733

  ONLINE REAL ESTATE AUCTION TO THE HIGHEST BIDDER OVER 20,000!! Bidding Opens - Tuesday, June 3, 2025. Bidding Closes - Thursday, June 5, 2025 at 11:00 AM. List price is opening bid only. 5347 Offer Lane is located in the Churchton area of southern Anne Arundel County. Churchton sits between Shady Side and Deale, approximately 15 miles south of Annapolis. Washington, D.C. is 34 miles to the west,

  Luis Arrazola A.J. Billig & Company

  5347 Offer Ln, Churchton, MD 20733
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  /50

  Est $777,010 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,520 Sq Ft

  4937 Thomas Dr, Shady Side, MD 20764

  4937 Thomas Dr, Shady Side, MD 20764
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  /42

  $270,000 Sold Jun 13, 2025

  • 782 Sq Ft
  • $345/SF
  • 8 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1981

  1191 Bay View Ave, Shady Side, MD 20764

  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! Multiple offers have been received and the Seller has requested submitting your highest, best and final by 7PM Wednesday May 14.

  Steven Miller Cummings & Co. Realtors

  1191 Bay View Ave, Shady Side, MD 20764
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  /26

  Est $291,286 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  1508 Baker Rd, Shady Side, MD 20764

  1508 Baker Rd, Shady Side, MD 20764
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  /62

  $900,000 Sold Jun 13, 2025

  • 4,808 Sq Ft
  • $187/SF
  • 0 Days On Market

  • 5 Beds
  • 3.5 Baths
  • Built 2003

  605 Lavender Ct, West River, MD 20778

  Welcome to 605 Lavender Court—a beautifully updated brick-front colonial set on a peaceful wooded lot in the heart of West River Estates, one of Southern Anne Arundel County’s most sought-after waterfront communities. Offering over 7,000 square feet of finished living space, this stately residence blends timeless design with modern upgrades and an abundance of flexible living areas. Within the

  Carol Snyder Monument Sotheby's International Realty

  605 Lavender Ct, West River, MD 20778
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  /59

  Est $445,458 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,600 Sq Ft

  1304 Holly St, Shady Side, MD 20764

  1304 Holly St, Shady Side, MD 20764
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  /2

  $50,000 Sold Jun 10, 2025

  • Land
  • 1 Acre
  • $50,000 per Acre

  • 135 Days On Market

  1428 Snug Harbor Rd, Shady Side, MD 20764

  Escape the hustle and bustle of city life and immerse yourself in the serene beauty of Shady Side, MD. Nestled within a picturesque landscape, this one-acre parcel of land offers a rare opportunity to create your own sanctuary surrounded by nature's bounty. Situated in the charming community of Shady Side, this property enjoys the best of both worlds – tranquility and convenience. With easy

  Joan Stansfield Samson Properties

  1428 Snug Harbor Rd, Shady Side, MD 20764
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  /39

  Est $508,820 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,838 Sq Ft

  1175 Maple Ave, Shady Side, MD 20764

  1175 Maple Ave, Shady Side, MD 20764
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  /14

  $320,000 Sold Jun 10, 2025

  • 1,240 Sq Ft
  • $258/SF
  • 10 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1987

  1299 Steamboat Rd, Shady Side, MD 20764

  *****MULTIPLE OFFERS RECEIVED ON THIS PROPERTY. THE SELLER HAS REQUESTED HIGHEST AND BEST OFFERS BY COB WEDNESDAY*******UPDATE 5/2/25 - SELLER HAS SELECTED AN OFFER, AWAITING SIGNED DOCUMENTS*****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

  Michael Patrick RE/MAX United Real Estate

  1299 Steamboat Rd, Shady Side, MD 20764
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  /70

  Est $427,639 Not Listed For Sale

  • 2 Beds
  • 2 Baths
  • 1,301 Sq Ft

  4913 Lerch Dr, Shady Side, MD 20764

  4913 Lerch Dr, Shady Side, MD 20764
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  /20

  $310,000 Sold May 30, 2025

  • 836 Sq Ft
  • $371/SF
  • 4 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1940

  4871 Avery Rd, Shady Side, MD 20764

  What an opportunity to own almost 2 acres on public sewer in Shady Side Maryland. This super cute 1940's cottage offering 2 bedrooms and 1 bath with a detached garage has so many options for a buyer. Keep it the way it is and live the tiny house lifestyle or tear it down and build a new home for your family! Zoned R1 this will allow residential This District is generally intended for

  Melanie Montague EXP Realty, LLC

  4871 Avery Rd, Shady Side, MD 20764
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  /59

  Est $771,652 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 2,868 Sq Ft

  5320 Sweetwater Dr, West River, MD 20778

  5320 Sweetwater Dr, West River, MD 20778
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  /17

  $335,000 Sold May 30, 2025

  • 840 Sq Ft
  • $399/SF
  • 5 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1944

  1248 Hawthorne St, Shady Side, MD 20764

  This home shows pride of ownership, many recent upgrades, Enjoy the local beaches. marinas and dining. recently replaced roof, HVAC unit and duct work, newly installed carpet, Gravel driveway large enough for two cars and a boat. Shed with electric and multiple outlets New LG stainless steel 33 in. 26 cu. refrigerator,Beautiful level fenced yard with patio and shed.

  Terry Catalano RE/MAX Leading Edge

  1248 Hawthorne St, Shady Side, MD 20764
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  /48

  Est $578,557 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,629 Sq Ft

  1233 Steamboat Rd, Shady Side, MD 20764

  1233 Steamboat Rd, Shady Side, MD 20764
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  /54

  $460,000 Sold May 29, 2025

  • 1,931 Sq Ft
  • $238/SF
  • 7 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1990

  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
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  /46

  Est $443,059 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 1,312 Sq Ft

  1176 Bayview Ave, Shady Side, MD 20764

  1176 Bayview Ave, Shady Side, MD 20764
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  /4

  $11,500 Sold May 29, 2025

  • Land
  • 0.33 Acre
  • $34,848 per Acre

  • 126 Days On Market

  1209 Poplar Ave, Shady Side, MD 20764

  Located in the Cedarhurst Subdivision in Anne Arundel County just blocks away from the Chesapeake Bay. Three lots being sold together. Fantastic opportunity for a new owner. Road has yet to be built for this parcel. Buyer is responsible for conducting all due diligence on property including location, use, restrictions, and taxes. This property is now active in an online auction. All offers must

  Samuel Kim Jason Mitchell Group

  1209 Poplar Ave, Shady Side, MD 20764
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  /18

  Est $567,397 Not Listed For Sale

  • 4 Beds
  • 2.5 Baths
  • 2,255 Sq Ft

  1207 Hawthorne St, Shady Side, MD 20764

  1207 Hawthorne St, Shady Side, MD 20764
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  /30

  $306,000 Sold May 23, 2025

  • 704 Sq Ft
  • $435/SF
  • 2 Days On Market

  • 2 Beds
  • 1 Bath
  • Built 1930

  4854 Avery Rd, Shady Side, MD 20764

  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

  4854 Avery Rd, Shady Side, MD 20764
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  /54

  Est $765,912 Not Listed For Sale

  • 3 Beds
  • 3.5 Baths
  • 2,850 Sq Ft

  1721 Columbia Beach Rd, Shady Side, MD 20764

  1721 Columbia Beach Rd, Shady Side, MD 20764
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  /37

  $420,000 Sold May 20, 2025

  • 1,272 Sq Ft
  • $330/SF
  • 60 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1950

  5228 Chesapeake Ave, Shady Side, MD 20764

  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.

  5228 Chesapeake Ave, Shady Side, MD 20764

Showing Results 161 - 200, Page 5 of 18