3,275

Shady Side, MD Homes

Section Image
  • /2

    $100,000

    • Land
    • 1 Acre
    • $100,000 per Acre

    1436 Haile Pkwy, Shady Side, MD 20764

    Sub-division potential for this undeveloped, 1 acre lot! May be able to reconfigure to 2 separate lots. 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

    Joan Stansfield Samson Properties

    1436 Haile Pkwy, Shady Side, MD 20764
  • /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
    • /49

      Est $537,331 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,964 Sq Ft

      6132 Shady Side Rd, Shady Side, MD 20764

      6132 Shady Side Rd, Shady Side, MD 20764
  • /2

    $150,000

    • Land
    • 4.03 Acres
    • $37,221 per Acre

    0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764

    This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

    Sam Tanner Keller Williams Flagship

    0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764
  • /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
    • /79

      Est $1,009,900 Not Listed For Sale

      • 3 Beds
      • 4.5 Baths
      • 1,888 Sq Ft

      5060 Lerch Dr, Shady Side, MD 20764

      5060 Lerch Dr, Shady Side, MD 20764
  • /2

    $54,000

    • Land
    • 1.32 Acres
    • $40,909 per Acre

    1461 Cedarhurst Rd, Shady Side, MD 20764

    Escape the hustle and bustle of city life with this exceptional land opportunity in Shady Side, MD. Nestled in a tranquil community, this parcel offers the perfect setting to build your dream home surrounded by nature’s beauty. Enjoy the best of both worlds—peaceful seclusion with easy access to Route 2 and Route 4, making travel to Annapolis, Baltimore, and Washington, D.C., a breeze. Immerse

    Joan Stansfield Samson Properties

    1461 Cedarhurst Rd, Shady Side, MD 20764
  • /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
    • /26

      Est $427,604 Not Listed For Sale

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

      1210 Oak Ave, Shady Side, MD 20764

      1210 Oak Ave, Shady Side, MD 20764
  • /2

    $25,000

    • Land
    • 0.57 Acre
    • $43,860 per Acre

    0 Haile Pkwy Unit MDAA2109444, Shady Side, MD 20764

    No address assigned for Lots 6 & 7. 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,

    Joan Stansfield Samson Properties

    0 Haile Pkwy Unit MDAA2109444, Shady Side, MD 20764
  • /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
    • /16

      Est $316,872 Not Listed For Sale

      • 2 Beds
      • 1 Bath
      • 880 Sq Ft

      5312 Al Jones Dr, Shady Side, MD 20764

      5312 Al Jones Dr, Shady Side, MD 20764
  • /29

    $815,000 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,485 Sq Ft

    6512 Shady Side Rd, Shady Side, MD 20764

    For buyers desiring a quicker move-in, this same model is under construction less than a mile away and will be completed in approximately 60 days — a perfect opportunity to preview the craftsmanship and finishes in person. This to-be-built custom Arts & Crafts residence by local builder Laine Street Homes blends timeless design with modern luxury. Set on a premium 1.5-acre homesite, the property

    Joshua Mast HomeSource Pro Real Estate

    6512 Shady Side Rd, Shady Side, MD 20764
  • /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
    • /62

      Est $476,585 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,540 Sq Ft

      1345 Jordan Dr, Shady Side, MD 20764

      1345 Jordan Dr, Shady Side, MD 20764
  • /44

    $609,990 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    1302 Spruce St, Shady Side, MD 20764

    10/10/25 Update: Home is under roof. Estimated completion is projected for January/February 2026. Introducing the Adams model — a beautifully designed home featuring an open-concept floor plan that blends comfort, style, and functionality. At the center of the home, the gourmet kitchen boasts a large island, stainless steel appliances, a walk-in pantry, and premium finishes—perfect for everyday

    Ray Mudd Schwartz Realty, Inc.

    1302 Spruce St, Shady Side, MD 20764
  • /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
    • /44

      Est $477,557 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,544 Sq Ft

      1229 Holly Ave, Shady Side, MD 20764

      1229 Holly Ave, Shady Side, MD 20764
  • /51

    $619,900 New Construction

    • 4 Beds
    • 2.5 Baths
    • 2,000 Sq Ft

    6440 W Shady Side Rd, Shady Side, MD 20764

    Another quality built New Construction Home by Jim Robinson/Real Estate General, LLC in the highly desired Shady Side Community. Ready to Move In! 4 bedrooms, 2.5 bathrooms, with a side entry 2 car garage on a large private .45 acre level lot. This beautiful home is filled with natural light and features an open floor plan on the main level with wide-plank LVP flooring, 9 foot ceilings, detailed

    John Rogers J. J. Rogers Real Estate

    6440 W Shady Side Rd, Shady Side, MD 20764
  • /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
    • /50

      Est $543,064 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 2,012 Sq Ft

      4940 W End Ave, Shady Side, MD 20764

      4940 W End Ave, Shady Side, MD 20764
  • /24

    $1,524,000 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,727 Sq Ft

    5235 Al Jones Dr, Shady Side, MD 20764

    To be built by Whitehall Building & Co., Annapolis’ largest luxury waterfront builder. Located in the desirable Columbia Beach neighborhood, this coastal-style home will offer 3,700 sqft of living space and the rare combination of panoramic Chesapeake Bay views with the protection of a cove-front setting. Designed for modern waterfront living, the open-concept layout features soaring 10' ceilings

    Lynn Peaper Hubble Bisbee Christie's International Real Estate

    5235 Al Jones Dr, Shady Side, MD 20764
  • /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
    • /55

      Est $525,719 Not Listed For Sale

      • 5 Beds
      • 3 Baths
      • 2,220 Sq Ft

      4727 Frederick Ave, Shady Side, MD 20764

      4727 Frederick Ave, Shady Side, MD 20764
  • /44

    $1,999,900 Pending

    • 5 Beds
    • 4.5 Baths
    • 5,151 Sq Ft

    4819 Avery Rd, Shady Side, MD 20764

    Welcome to a truly remarkable waterfront retreat where timeless design meets resort-style living. Set along the shores of Hopkins Cove with sweeping views of the West River, this residence offers over 150 feet of water frontage and a private pier stretching nearly 270 feet, complete with boat lift and covered pavilion—everything you need to embrace life on the water.This five-bedroom,

    Brad Kappel TTR Sotheby's International Realty

    4819 Avery Rd, Shady Side, MD 20764
  • /29

    $667,000 Sold Jun 24, 2025

    • 2,200 Sq Ft
    • $303/SF
    • 6 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2022

    4938 Rullman Rd, Shady Side, MD 20764

    Westelee Welcome's You Home! This 2 year old "Pottery Barn" Colonial home is set perfectly on a corner lot with views of the West River. This home has 4 bedrooms and 2.5 baths. Patio was just put in and a 6 foot privacy fence around the backyard in 2024. GREAT FOR HAVING A CRAB FEAST IN THE SUMMER OR BONFIRES IN THE FALL. THIS YARD IS GREAT FOR ENTERTAINING BRING YOUR FAMILY AND FRIENDS. There

    Carey Laycock RE/MAX Leading Edge

    4938 Rullman Rd, Shady Side, MD 20764
    • /49

      Est $470,336 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,728 Sq Ft

      1213 Grove Ave, Shady Side, MD 20764

      1213 Grove Ave, Shady Side, MD 20764
  • /61

    $1,500,000 Pending

    • 5 Beds
    • 4 Baths
    • 3,064 Sq Ft

    1457 Nieman Rd, Shady Side, MD 20764

    Stunning waterfront retreat nestled along the serene shores of the Chesapeake Bay, located in the charming community of Shady Side, Maryland. Perfectly situated on Parish Creek, this spacious, move-in ready home offers a unique combination of comfort, privacy, and coastal living. The open-concept floor plan on the main level features a gourmet kitchen with sleek quartz countertops and island, a

    Doc Keane Washington Fine Properties, LLC

    1457 Nieman Rd, Shady Side, MD 20764
  • /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
    • /31

      Est $548,523 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 1,900 Sq Ft

      1006 Allen Ave, West River, MD 20778

      1006 Allen Ave, West River, MD 20778
  • /2

    $25,000 Pending

    • Land
    • 0.52 Acre
    • $48,077 per Acre

    5349 A Offer Ln, Shady Side, MD 20733

    Property address is 5349A Offer ln Buyer to confirm all information

    Keith French Blue Star Real Estate, LLC

    5349 A Offer Ln, Shady Side, MD 20733
  • /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
    • /40

      Est $1,698,179 Not Listed For Sale

      • 5 Beds
      • 5 Baths
      • 4,179 Sq Ft

      1243 Bast Ln, Shady Side, MD 20764

      1243 Bast Ln, Shady Side, MD 20764
  • /2

    $69,000 Pending

    • Land
    • 0.17 Acre
    • $405,882 per Acre

    1185 Holly Ave, Shady Side, MD 20764

    Lot available in Shady side Water oriented community. Buyer must confirm all information and perform their own Due diligence. Seller makes no representations for use etc

    Keith French Blue Star Real Estate, LLC

    1185 Holly Ave, Shady Side, MD 20764
  • /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
    • /27

      Est $496,024 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,788 Sq Ft

      4722 Girton Ave, Shady Side, MD 20764

      4722 Girton Ave, Shady Side, MD 20764
  • /2

    $39,000 Pending

    • Land
    • 0.21 Acre
    • $185,714 per Acre

    1428 Haile Pkwy, Shady Side, MD 20764

    Stacey Gembicki Berkshire Hathaway HomeServices PenFed Realty

    1428 Haile Pkwy, Shady Side, MD 20764
  • /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
    • /41

      Est $583,566 Not Listed For Sale

      • 3 Beds
      • 3.5 Baths
      • 2,081 Sq Ft

      1240 W River Rd, Shady Side, MD 20764

      1240 W River Rd, Shady Side, MD 20764
  • /8

    $349,900 Coming Soon

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    4913 Chestnut St, Shady Side, MD 20764

    Coming Soon. Roof, facia, windows, sliding rear door, HVAC, deck, vinyl fence, carpet all replaced within last 2 years. Appliances are less than 3 years old.

    Ray Mudd Schwartz Realty, Inc.

    4913 Chestnut St, Shady Side, MD 20764

Showing Results 121 - 160, Page 4 of 18

How to Buy a Home How to Finance a Home How to Sell a Home