Shady Side, MD Homes for Sale

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  /38

  $699,500 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,710 Sq Ft

  1195 Cedar Ave, Shady Side, MD 20764

  This beautifully crafted home blends timeless coastal charm with modern luxury. Featuring classic board and batten siding and a welcoming front porch, the exterior makes a striking first impression. Step inside to an open-concept layout that seamlessly connects the dining and family room, ideal for both everyday living and entertaining.At the heart of the home is a spacious kitchen

  

  Jamie Richardson

  Coldwell Banker Realty

  (410) 724-1563

  1195 Cedar Ave, Shady Side, MD 20764
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  /52

  $550,000

  • 3 Beds
  • 2.5 Baths
  • 2,550 Sq Ft

  5122 Marx Dr, West River, MD 20778

  Welcome to 5122 Marx Drive, nestled in the highly sought-after, water-privileged community of Cedarlea. Situated on nearly half an acre, this home features bright, open spaces with large windows and vaulted ceilings in the living room, primary bedroom, and sunroom. Arrive home to the spacious two-car garage with plenty of room for vehicles, tools, or a jet ski trailer! The main level offers a

  Tom Atwood Keller Williams Legacy

  5122 Marx Dr, West River, MD 20778
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  /27

  $593,100

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

  1605 Depriest Dr, Shady Side, MD 20764

  Price Adjustment. It's better at the Beach! Incredible peninsula location with 180 degree views of the Chesapeake Bay in the gated community of Columbia Beach in Shady Side , Maryland. This 2 level 3B/1.5 BA home with an inverted floor plan is the perfect weekend retreat or full time main residence. Vacation every day! You can see the Chesapeake Bay Bridge on clear days right from your upper

  Lydia Newman Fairfax Realty Premier

  1605 Depriest Dr, Shady Side, MD 20764
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  /25

  $650,000

  • 2 Beds
  • 1.5 Baths
  • 1,540 Sq Ft

  4801 Avery Rd, Shady Side, MD 20764

  Water! Water everywhere! This adorable mid-century cottage faces Hopkins Cove , borders Parish Creek and looks out to the Chesapeake Bay Bridge. It is a dream come true for those who love living on the water, and could be your weekend getaway cottage. Not a fan of cottages? Then, go all in and remodel to make it your own! The possibilities are endless..... The property is being sold "as is".

  Theresa Kurtz EXP Realty, LLC

  4801 Avery Rd, Shady Side, MD 20764
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  /29

  $554,500

  • 2 Beds
  • 1.5 Baths
  • 1,244 Sq Ft

  5211 Al Jones Dr, Shady Side, MD 20764

  Great New Price ... here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay year round. 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

  5211 Al Jones Dr, Shady Side, MD 20764
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  /35

  $789,000

  • 5 Beds
  • 3 Baths
  • 3,052 Sq Ft

  5235 Chalk Point Rd, West River, MD 20778

  Coastal Living Meets Timeless Elegance on the Chesapeake BayEscape the hustle and embrace the peaceful rhythm of coastal life in this beautifully updated 5-bedroom, 3-bath Colonial, perfectly situated on a private 1.37-acre lot in the sought-after West River community. With over 3,000 sq ft of thoughtfully designed living space, this home offers the ideal blend of comfort, flexibility,

  Bonnie O'Donnell RE/MAX One

  5235 Chalk Point Rd, West River, MD 20778
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  /10

  $600,000

  • 2 Beds
  • 1 Bath
  • 862 Sq Ft

  1337 W River Rd, Shady Side, MD 20764

  Price Reduction!!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 main

  Bruce Thompson Long & Foster Real Estate, Inc.

  1337 W River Rd, Shady Side, MD 20764
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  /41

  $735,000

  • 4 Beds
  • 1.5 Baths
  • 2,144 Sq Ft

  1462 Snug Harbor Rd, Shady Side, MD 20764

  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.

  1462 Snug Harbor Rd, Shady Side, MD 20764
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  /35

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 1,784 Sq Ft

  1037 Biltmore Ave, West River, MD 20778

  Welcome to 1037 Biltmore Ave — A Waterfront Dream in West River!Nestled in the peaceful and picturesque community of West River, this beautifully maintained home offers the perfect blend of comfort, style, and coastal living. Just steps from the water and minutes to the Chesapeake Bay, this property is ideal for those who crave serenity without sacrificing convenience.This

  Matt Kalogeras Houwzer, LLC

  1037 Biltmore Ave, West River, MD 20778
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  /42

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,464 Sq Ft

  1347 W River Rd, Shady Side, MD 20764

  Welcome to 1347 W River Rd. – A Private Retreat on 2.02 Acres in Shady Side, MD. This two-story colonial offers privacy, space, and the perfect blend of classic charm and a few modern updates. With approx. 2,464 sq ft of living space, this 4-bedroom, 2.5-bath home provides ample room for everyday living and entertaining. Step into the spacious foyer and take in the warmth of the shaker-style

  Elizabeth DuLaney EXP Realty, LLC

  1347 W River Rd, Shady Side, MD 20764
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  /18

  $375,000

  • 2 Beds
  • 1.5 Baths
  • 852 Sq Ft

  1700 Bayview Rd, Shady Side, MD 20764

  Don't miss this charming and well-maintained home! The main level features stylish LVP flooring and a bright, sunny eat-in kitchen with granite countertops. A convenient powder room includes a new pedestal sink. Sliding door from the kitchen open to a deck that overlooks a fully fenced backyard—perfect for relaxing or entertaining. Upstairs, you’ll find two spacious bedrooms and a full bath. This

  Ray Mudd Schwartz Realty, Inc.

  1700 Bayview Rd, Shady Side, MD 20764
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  /39

  $469,900

  • 3 Beds
  • 2.5 Baths
  • 1,440 Sq Ft

  1330 Jordan Dr, Shady Side, MD 20764

  Welcome to 1330 Jordan Drive, a charming 3-bedroom, 2.5-bathroom home nestled in the highly desirable Avalon Shores community in Shady Side, Maryland.This well-maintained home strikes the perfect balance between comfort and character. The covered front porch invites you to unwind and enjoy seasonal water views, setting the tone for peaceful, waterfront living. Inside, you’ll find a

  Emily Motto Investors Management, Inc.

  1330 Jordan Dr, Shady Side, MD 20764
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  /97

  $399,500

  • 4 Beds
  • 1.5 Baths
  • 1,399 Sq Ft

  1199 Oak Ave, Shady Side, MD 20764

  Welcome to Cedarhurst On The Bay — Your Bayside Retreat Awaits!Nestled in the serene, historic enclave of Cedarhurst On The Bay in Shady Side, Maryland, this beautiful single‐level home is the perfect blend of comfort, convenience, and coastal charm. Set on a generous double lot and built on a durable slab foundation, this residence offers 4 bedrooms, 1.5 bathrooms, and a thoughtfully

  Vilas Wright Wright Real Estate, LLC

  1199 Oak Ave, Shady Side, MD 20764
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  /10

  $625,000

  • Land
  • 11 Acres
  • $58,140 per Acre

  5860 Shady Side Rd, Churchton, MD 20733

  WATERFRONT: Own your own park! 10+ Acres and 650+ Feet of water frontage along the South Creek in Churchton! *Do not walk the property without an appointment*

  Julie Knott Lofgren-Sargent Real Estate

  5860 Shady Side Rd, Churchton, MD 20733
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  /42

  $475,120

  • 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
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  /25

  $375,000

  • 3 Beds
  • 1 Bath
  • 1,000 Sq Ft

  4738 Washington Ave, Shady Side, MD 20764

  Charming Rancher Just Steps from the Bay Front!Nestled on a peaceful corner lot and surrounded by the serenity of a protected nature reserve, this inviting 3-bedroom, 1-bath single-level rancher offers the perfect blend of privacy, charm, and location. Just a short walk to the scenic bay front, you’ll enjoy the coastal lifestyle with morning strolls, sunsets, and water views just minutes

  Nicole Hatch Samson Properties

  4738 Washington Ave, Shady Side, MD 20764
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  /65

  $1,950,000

  • 9 Beds
  • 6.5 Baths
  • 9,045 Sq Ft

  4701 Girton Ave, Shady Side, MD 20764

  HUGE PRICE REDUCTION !Welcome to 4701 Girton, waterfront estate boasting over 9,000 square feet sitting on an incredible point offering panoramic views to the Chesapeake Bay and West River. Views to take your breath away with over 250 ft of water frontage including rip rap, and bulkhead. There is plenty of room for your water toys with a deep-water pier, two boat lifts,12,000 lb, two jet ski

  Tammy Studebaker EXP Realty, LLC

  4701 Girton Ave, Shady Side, MD 20764
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  /67

  $1,100,000

  • 4 Beds
  • 2.5 Baths
  • 3,244 Sq Ft

  4715 Oak Rd, Shady Side, MD 20764

  Welcome to the Chesapeake Bay! Relax while sipping your morning coffee or unwinding with a glass of wine. This waterfront cottage offers over 3000 sf of living space with panoramic views from every room! Unique features include wood beams on the first and second levels; two staircases access the second level; authentic cedar doors, closets, and drawers take you back to the 1930s; while the

  Angie Carr Riverscape Realty

  4715 Oak Rd, Shady Side, MD 20764
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  /32

  $485,500

  • 5 Beds
  • 2 Baths
  • 1,812 Sq Ft

  1220 Grove Ave, Shady Side, MD 20764

  This spacious 5 bedroom, 2 full bath split foyer is located in the highly desirable Community; Cedarhurst on the Bay. This remarkable property showcases the epitome of every day, vacation living with stunning views of The Chesapeake Bay. You will quickly be captivated by the grandeur that awaits you. The open layout seamlessly connects the living, dining and kitchen area, creating an ideal

  Jessica Gosman-Bowen Curtis Real Estate Company

  1220 Grove Ave, Shady Side, MD 20764
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  /33

  $1,575,000

  • 3 Beds
  • 3 Baths
  • 2,985 Sq Ft

  1045 Back Bay Beach Rd, West River, MD 20778

  You said it HAD to be perfect. That you were NOT going to compromise. Good news! THIS is the one you've been waiting for, and it’s not every day that a home like this comes along. Perfectly positioned on a peaceful peninsula where the West River meets South Creek, this elegant retreat offers panoramic water views from every single room. No, really! EVERY. SINGLE. ROOM. From the moment you step

  Theresa Kurtz EXP Realty, LLC

  1045 Back Bay Beach Rd, West River, MD 20778
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  /34

  $449,999

  • 4 Beds
  • 2 Baths
  • 2,440 Sq Ft

  1440 Cedarhurst Rd, Shady Side, MD 20764

  Welcome to 1440 Cedarhurst Road! This beautifully maintained home offers over 2,400 square feet of comfortable living space, featuring 4 bedrooms and 2 bathrooms on a spacious, flat lot.Step inside to discover gleaming hardwood and tile flooring throughout. The heart of the home is a spacious kitchen with a center island, seamlessly connected to an open dining area. Just off the kitchen,

  Terry McAllister RE/MAX One

  1440 Cedarhurst Rd, Shady Side, MD 20764
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  /42

  $499,620

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

  1216 Grove Ave, Shady Side, MD 20764

  Recent Price reduction! 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

  Paul Lee Long & Foster Real Estate, Inc.

  1216 Grove Ave, Shady Side, MD 20764
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  /28

  $275,000

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft

  4725 Idlewilde Rd, Shady Side, MD 20764

  Calling all investors, second-home seekers, and visionaries—this is the project you’ve been waiting for! AND it just got better with a price improvement!! Located just steps from the water in the charming community of Idlewilde, this 2-bedroom cottage-style home sits on a rare double lot with Chesapeake Bay views from the backyard and access to fantastic community amenities.While the

  Clinton Auman EXP Realty, LLC

  4725 Idlewilde Rd, Shady Side, MD 20764
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  /18

  $378,000

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

  1617 Winters Ave, Shady Side, MD 20764

  Welcome to 1617 Winters Ave – Coastal Charm with Modern Updates in Idlewild on the BayBeautifully updated and move-in ready, this 3-bedroom, 2-bath gem is nestled in the water-access community of Idlewild on the Bay. Situated just one block from the Chesapeake Bay, this home boasts fresh interior updates, a fully fenced yard, and two spacious decks ideal for entertaining or relaxing by

  John Kreamer Taylor Properties

  1617 Winters Ave, Shady Side, MD 20764
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  /83

  $2,250,000

  • 4 Beds
  • 2.5 Baths
  • 3,745 Sq Ft

  1100 Steamboat Rd, Shady Side, MD 20764

  Spectacular West River waterfront! A serene lot with stunning, panoramic water views, an elegant, custom-built home that exudes coastal style, a private dock with two boat slips, a detached 3-car garage with a storage loft, a spacious yard for playing and entertaining, an exquisite vantage point for enjoying the area’s natural beauty, from waterfowl to sunsets: welcome to 1100 Steamboat Road,

  Kirsten Rowan Compass

  1100 Steamboat Rd, Shady Side, MD 20764
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  /69

  $2,295,000

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

  4819 Avery Rd, Shady Side, MD 20764

  Discover unparalleled luxury in this stunning Five bedroom, four and half bath waterfront home, offering two hundred and seventy 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

  4819 Avery Rd, Shady Side, MD 20764
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  /27

  $499,900

  • 4 Beds
  • 2.5 Baths
  • 2,176 Sq Ft

  1711 Columbia Beach Rd, Shady Side, MD 20764

  Nestled between serene waters, this home offers stunning, unobstructed views of Flag Pond from the rear and views of the Chesapeake Bay from the front. Enjoy watching local waterfowl and soaking in the natural beauty from every angle. Inside, the spacious kitchen opens to the family room, perfect for gathering, along with a formal living room and a main-level office or potential 5th bedroom.

  Ray Mudd Schwartz Realty, Inc.

  1711 Columbia Beach Rd, Shady Side, MD 20764
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  /89

  $998,850

  • 5 Beds
  • 5.5 Baths
  • 9,040 Sq Ft

  6561 Shady Side Rd, Shady Side, MD 20764

  Merchant Unmatched water views. Over 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

  6561 Shady Side Rd, Shady Side, MD 20764
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  /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 effortless—yet

  Joan Stansfield Samson Properties

  1445 & 1447 Haile Pkwy, Shady Side, MD 20764
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  /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., is

  Joan Stansfield Samson Properties

  1408 & 1410 Haile Pkwy, Shady Side, MD 20764
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  /11

  $177,900

  • Land
  • 0.14 Acre
  • $1,270,714 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
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  /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
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  /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
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  /2

  $54,900

  • Land
  • 1.53 Acres
  • $35,882 per Acre

  6152 Shady Side Rd, Shady Side, MD 20764

  DISCOVER THIS 1.53 ACRE LOT AVAILABLE IN SHADY SIDE , MD WITHIN ANNE ARUNDEL COUNTY. ZONING R1. DRIVE BY TODAY TO DETERMINE FOR YOURSELF HOW IT CAN WORK FOR YOUR NEEDS!

  Jennifer Drennan Taylor Properties

  6152 Shady Side Rd, Shady Side, MD 20764
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  /15

  $997,000

  • Land
  • 1.60 Acres
  • $623,125 per Acre

  1133 Steamboat Rd, Shady Side, MD 20764

  BRING ON THE RIVER BOATS... Unparalleled access to the Chesapeake Bay, ideal for boating, sailing, fishing and crabbing enthusiasts!!! Discover the perfect canvas for your waterfront dream home on this stunning undeveloped lot in the prestigious Shady Side community offering ample space for building a custom waterfront estate. With 80 feet of prime waterfront frontage on the Chesapeake Bay,

  John Halpin RE/MAX Premiere Selections

  1133 Steamboat Rd, Shady Side, MD 20764
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  /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
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  /2

  $100,000

  • Land
  • 1.00 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 accessibility.With

  Joan Stansfield Samson Properties

  1436 Haile Pkwy, 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, Baltimore, or

  Joan Stansfield Samson Properties

  0 Haile Pkwy Unit MDAA2109444, 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

  Sam Tanner Keller Williams Flagship

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

  /2

  $150,000

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

  0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764

  Sam Tanner Keller Williams Flagship

  0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764

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