Shady Side, MD Homes for Sale

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  /6

  $649,900 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 3,178 Sq Ft

  4911 Lerch Dr, Shady Side, MD 20764

  Coming Soon: Expansive Colonial in Water-Oriented Avalon Shores!Get ready to discover your dream home! A welcoming and spacious Colonial is soon to hit the market, perfectly situated on a desirable corner lot within the serene, water-oriented community of Avalon Shores on the peaceful Shady Side Peninsula.This impressive 4-bedroom, 3-bath residence offers an idyllic Chesapeake Bay

  

  Kara Leddy

  Coldwell Banker Realty

  (410) 421-7593

  4911 Lerch Dr, Shady Side, MD 20764
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  /68

  $515,000

  • 4 Beds
  • 2.5 Baths
  • 1,756 Sq Ft

  4906 Lee Blvd, Shady Side, MD 20764

  **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

  

  Sandy Wing

  RE/MAX Leading Edge

  (443) 234-8208

  4906 Lee Blvd, Shady Side, MD 20764
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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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  /42

  $449,900

  • 4 Beds
  • 2.5 Baths
  • 1,904 Sq Ft

  1207 Avalon Blvd, Shady Side, MD 20764

  Welcome to this classic colonial, nestled in the desirable water-privileged community of Avalon Shores! A wide covered front porch spans the entire front of the home, creating the perfect spot to sit and unwind in the evenings and chat with neighbors, or enjoy a quiet cup of coffee. This estate sale is being sold as-is, yet the home is in solid condition, simply awaiting a few personal touches

  Mary Gatton Redfin Corp

  1207 Avalon Blvd, Shady Side, MD 20764
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  /27

  $603,000

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

  1605 Depriest Dr, Shady Side, MD 20764

  HONEY STOP THE CAR!!! 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

  Lydia Newman Fairfax Realty Premier

  1605 Depriest Dr, Shady Side, MD 20764
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  /65

  $750,000

  • 4 Beds
  • 4.5 Baths
  • 3,352 Sq Ft

  1109 Cherry Point Rd, West River, MD 20778

  First time on the market! This custom-built water view home, set on a picturesque one-acre lot, was thoughtfully designed by its original owners. Featuring a first-floor primary suite, wide hallways and doors for wheelchair accessibility, and a roll-in shower in the primary bath, every detail was carefully planned. The exquisite gourmet kitchen boasts a commercial gas stove, wall oven, spacious

  Ray Mudd Schwartz Realty, Inc.

  1109 Cherry Point Rd, West River, MD 20778
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  /26

  $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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  /35

  $789,000

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

  5235 Chalk Point Rd, West River, MD 20778

  Experience a serene lifestyle by the Chesapeake Bay—trading the fast-paced chaos for peaceful coastal living. Step into timeless elegance with this beautifully updated 5-bedroom, 3-bath Colonial, offering over 3,000 sq ft of thoughtfully designed living space on a private 1.37-acre lot. Perfectly positioned in the coveted West River community, this home delivers the ideal blend of space, style,

  Bonnie O'Donnell RE/MAX One

  5235 Chalk Point Rd, West River, MD 20778
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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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  /33

  $999,900

  • 4 Beds
  • 2.5 Baths
  • 3,445 Sq Ft

  4927 Hine Dr, Shady Side, MD 20764

  Post & beam architect design home with passive solar elements and lots of glass facing the water. A beautiful waterfront lot with southern exposure and wonderful view! 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

  William Whitman Long & Foster Real Estate, Inc.

  4927 Hine Dr, Shady Side, MD 20764
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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

  $765,000

  • 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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  /67

  $1,150,000

  • 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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  /51

  $389,000

  • 3 Beds
  • 1 Bath
  • 1,407 Sq Ft

  4977 Lerch Dr, Shady Side, MD 20764

  Discover your own slice of water-view paradise at 4977 Lerch Drive—a lovingly maintained 3-bedroom, 1-bath retreat just steps from the West River. Every corner of this home reflects the care and attention poured in by its current owner, from the bright, open-concept living spaces to the thoughtful updates throughout the interior Step inside to 1,407 sq ft of refreshed living space, where an

  Suebina Wong Douglas Realty, LLC

  4977 Lerch Dr, Shady Side, MD 20764
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  /32

  $495,500

  • 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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  /63

  $1,650,000

  • 5 Beds
  • 3 Baths
  • 4,109 Sq Ft

  1471 Nieman Rd, Shady Side, MD 20764

  Waterfront Paradise with Breathtaking Chesapeake Bay Views Welcome to your private waterfront retreat, nestled on a serene point along the West River with sweeping, panoramic views of the Chesapeake Bay. Just one hour from Washington, DC and without the hassle of crossing the Bay Bridge, this immaculate 5-bedroom, 3-bathroom home offers over 4,100 square feet of updated living space and

  Chris Craddock EXP Realty, LLC

  1471 Nieman Rd, Shady Side, MD 20764
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  /51

  $359,500

  • 2 Beds
  • 1 Bath
  • 900 Sq Ft

  1731 Columbia Beach Rd, Shady Side, MD 20764

  Welcome to this delightful coastal cottage nestled in the heart of the Columbia Beach community! Spacious wide beach, tot lot, tennis courts and basketball too. This beautifully updated home perfectly balances modern comfort with timeless charm. Offering two spacious bedrooms and a full bath, the layout is thoughtfully designed for easy living and effortless style.Step inside to find

  Amy Juras Long & Foster Real Estate, Inc.

  1731 Columbia Beach Rd, Shady Side, MD 20764
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  /34

  $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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  /100

  $1,095,000

  • 5 Beds
  • 3.5 Baths
  • 5,694 Sq Ft

  1015 S Creek View Ct, Churchton, MD 20733

  Some homes impress you with features. This one leaves you with a feeling: luxury, elegance, features, form, utility, and most of all—home.Hidden in its own oasis of a quiet cul-de-sac, this home opens to sweeping, year-round water views—sunrises casting light across its front, golden-hour sunsets melting into the trees behind. It’s the kind of place that gives you permission to slow down

  Phil Gerdes Real Broker, LLC - Annapolis

  1015 S Creek View Ct, Churchton, MD 20733
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  /34

  $469,900

  • 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, enjoy a

  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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  /32

  $305,000

  • 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

  $384,000

  • 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 the

  John Kreamer Taylor Properties

  1617 Winters Ave, Shady Side, MD 20764
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  /21

  $380,000

  • 3 Beds
  • 2.5 Baths
  • 1,100 Sq Ft

  1216 Hawthorne St, Shady Side, MD 20764

  Move-In Ready Coastal Gem in Shady Side – No HOA, Big Yard, and Modern Upgrades!Tucked away in a peaceful, water-oriented community just minutes from the Chesapeake Bay, this 3-bedroom, 2.5-bathroom home offers the perfect blend of charm and convenience. Enjoy recent updates including a new HVAC system, water heater, well pump & softener, electrical upgrades, and fresh paint — plus stylish

  TJ Alves Cummings & Co. Realtors

  1216 Hawthorne St, Shady Side, MD 20764
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  /84

  $2,450,000

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

  1100 Steamboat Rd, Shady Side, MD 20764

  Imagine: welcoming friends and guests as they approach your home by powerboat, sailboat, or stand-up paddleboard; greeting osprey as they return to their annual nesting spot to raise their young each spring; watching Wednesday night sailboat racers make their way out of the river; relishing spectacular year-round sunsets. And now imagine enjoying this incredible backdrop from the comfort of your

  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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  /30

  $566,304

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

  5211 Al Jones Dr, Shady Side, MD 20764

  Here is your chance to own and enjoy a coastal contemporary “cottage” with panoramic views and the soothing sounds of the Chesapeake Bay. 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 living, dining, kitchen, 2 bedrooms, a

  Celeste Blessin Coldwell Banker Realty

  5211 Al Jones Dr, 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

  $179,900

  • Land
  • 0.14 Acre
  • $1,285,000 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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  /61

  $1,180,000

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

  1538 Robinson Rd, Shady Side, MD 20764

  OPEN Bay-front at this STUNNING 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-

  Jennifer Chaney Chaney Homes, LLC

  1538 Robinson Rd, 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

  $42,000

  • Land
  • 1.53 Acres
  • $27,451 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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  /11

  $185,000

  • Land
  • 1.00 Acre
  • $185,000 per Acre

  6508 Shady Side Rd, Shady Side, MD 20764

  Build your dream home! few lots like this one. Dry area, very private & wooded lot surrounded by 73 acres in conservation easement. Enjoy peaceful nature. This lot has a right of way agreement along with lot at 6512 W Shady Side Rd See attached documents and maps. Located close to the west river and community Baseball diamond and basketball courts.

  George Heine Schwartz Realty, Inc.

  6508 Shady Side Rd, Shady Side, MD 20764
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  /12

  $198,000

  • Land
  • 1.44 Acres
  • $137,500 per Acre

  6512 Shady Side Rd, Shady Side, MD 20764

  This lot could .be yours, surrounded by nature, in conservation easement, Dry wooded lot! Build your dream home, surrounded by trees and by 73 acres in conservation easement. Next to 6508 lot, they share an easement for driveway. The best lot in the area!! Close to Baltimore, DC, and Annapolis. Located near the West River and community baseball diamond and basketball court.

  George Heine Schwartz Realty, Inc.

  6512 Shady Side 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

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