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Shady Side, MD Homes for Sale

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  • /4

    $52,500

    • Land
    • 0.33 Acre
    • $159,091 per Acre

    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

    Agent Photo

    Samuel Kim

    Jason Mitchell Group

    (410) 936-7840

    1209 Poplar Ave, Shady Side, MD 20764
  • /3

    $850,000

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

    5235 Chalk Point Rd, West River, MD 20778

    Updated Colonial Retreat in Prime West River Location!Welcome to 5235 Chalk Point Road – a beautifully updated 5-bedroom, 3.5-bath Colonial offering 3,052 sq ft of refined living space on a serene 1.37-acre lot. Built in 1990 and thoughtfully enhanced throughout, this spacious home features two primary suites, including one conveniently located on the main floor—perfect for flexible living.Recent

    Bonnie O'Donnell RE/MAX One

    5235 Chalk Point Rd, West River, MD 20778
  • /89

    $1,180,000

    • 5 Beds
    • 5.5 Baths
    • 8,143 Sq Ft

    6561 Shady Side Rd, Shady Side, MD 20764

    Merchant Unmatched water views. Nearly 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
  • /66

    $879,900

    • 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
  • /33

    $1,150,000 Open Sat 11AM - 1PM

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

    4927 Hine Dr, Shady Side, MD 20764

    Open Saturday, April 26 11:00 to 1:00. 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

    William Whitman Long & Foster Real Estate, Inc.

    4927 Hine Dr, Shady Side, MD 20764
  • /32

    $769,900 Open Sun 1PM - 3PM

    • 3 Beds
    • 3 Baths
    • 1,920 Sq Ft

    4922 Lerch Dr, Shady Side, MD 20764

    PRICE REDUCED! Waterfront Stunner! This home features main-level living with a large bedroom and full bath. The kitchen opens to the living area with tons of natural light. Upstairs, two additional bedrooms with private baths ensure everyone has their own space & privacy. Outside is a small finished entertainment area or walk to your private dock. Crab in the summer or take a kayak, SUP, or canoe

    Dorothy Bistransin Redfin Corp

    4922 Lerch Dr, Shady Side, MD 20764
  • /61

    $1,300,000 Open Sun 12PM - 2PM

    • 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
  • /32

    $729,000

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

    4801 Avery Rd, Shady Side, MD 20764

    An adorable cottage with almost 200' of waterfront facing Hopkins Cove with views of the Chesapeake Bay Bridge. This could be your weekend getaway cottage, or go all in and remodel to make it your own! The possibilities are endless..... The property is being sold "as is". Please contact AACO and the Critical Area Division regarding remodeling permit requirements.

    Theresa Kurtz EXP Realty, LLC

    4801 Avery Rd, Shady Side, MD 20764
  • /10

    $700,000

    • 2 Beds
    • 1 Bath
    • 862 Sq Ft

    1337 W River Rd, Shady Side, MD 20764

    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

    Bruce Thompson Long & Foster Real Estate, Inc.

    1337 W River Rd, Shady Side, MD 20764
  • /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
  • /48

    $2,500,000 Open Sat 1PM - 3PM

    • 9 Beds
    • 6.5 Baths
    • 9,325 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
  • /42

    $530,620

    • 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
  • /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
  • /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
  • /41

    $2,875,000 Open Sun 12PM - 2PM

    • 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
  • /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
  • /37

    $475,000

    • 3 Beds
    • 2 Baths
    • 1,272 Sq Ft

    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
  • /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
  • /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
  • /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
  • /34

    $2,000,000

    • 9 Beds
    • 6.5 Baths
    • 7,898 Sq Ft

    4701 Girton Ave, Shady Side, MD 20764

    This waterfront property at 4701 Girton Ave truly is a luxurious retreat, offering the perfect balance of space, privacy, and stunning views of the Chesapeake Bay and West River. This expansive home is in a very private setting and has 260 feet of pristine waterfront, coupled with a large 250' pier with boat and jet ski lifts offering unparalleled access to water activities. The pier also has

    Dee Dee McCracken Coldwell Banker Realty

    4701 Girton 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
  • /15

    $265,000

    • 1 Bed
    • 1 Bath
    • 948 Sq Ft

    1419 Shady Rest Rd, Shady Side, MD 20764

    Welcome to 1419 Shady Rest Rd, it located on a quiet street not far from the water in one of Maryland’s Chesapeake Bay boating communities. This property has a drive way with plenty of space for parking. Being sold AS IS. Priced to sell so schedule your showing today! Please contact Torrence Hall for showings..

    Cindy Tao Premiere Realty LLC

    1419 Shady Rest Rd, Shady Side, MD 20764
  • /2

    $51,900

    • Land
    • 1.53 Acres
    • $33,922 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
  • /3

    $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
  • /4

    $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
  • /2

    $125,000

    • Land
    • 0.10 Acre
    • $1,250,000 per Acre

    1626 Columbia Beach Rd, Shady Side, MD 20764

    Variance approved! Floor plans being drafted for a 4 bedroom, 2.5 bath home with a 1 car garage. Awesome neighborhood with many amenities and water access.

    Kyle Squires Lazar Real Estate

    1626 Columbia Beach Rd, 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
  • /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

    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,

    Joan Stansfield Samson Properties

    0 Haile Pkwy Unit MDAA2109444, Shady Side, MD 20764
  • /2

    $30,000

    • Land
    • 0.52 Acre
    • $57,692 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
  • /32

    $2,200,000 New Construction

    • 5 Beds
    • 5 Baths
    • 3,600 Sq Ft

    1133 Steamboat Rd, Shady Side, MD 20764

    Welcome to this incredible home to-be-built on 1.6 waterfront acres just south of Annapolis. This waterfront lot offers breathtaking West River Views, a deep-water pier, two docks and two boat lifts that convey. Located in shady Side, this property offers the best of both worlds; quiet, small-town charm with easy access to Annapolis and DC.Proposed home is by Whitehall Building, a

    Lynn Peaper Next Step Realty

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

    $439,990 Open Thu 5PM - 7PM

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

    1485 Cedarhurst Rd, Shady Side, MD 20764

    Professional Photos Coming Soon!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

    Nicki Palermo RE/MAX One

    1485 Cedarhurst Rd, Shady Side, MD 20764
  • /30

    $299,900 Coming Soon

    • 2 Beds
    • 1 Bath
    • 704 Sq Ft

    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
  • /8

    $589,900 Open Sun 1PM - 3PM

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

    5211 Al Jones Dr, Shady Side, MD 20764

    Open House , Sunday, 4/27, 1PM - 3PM....Just in time for summer, this coastal contemporary “cottage” offers you 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

    Celeste Blessin Coldwell Banker Realty

    5211 Al Jones Dr, Shady Side, MD 20764
  • /14

    $520,000 Coming Soon

    • 4 Beds
    • 2.5 Baths
    • 2,198 Sq Ft

    4755 Idlewilde Rd, Shady Side, MD 20764

    Wonderful 4Br/2.5Ba in the waterfront community of Felicity Cove! Come take a look at the open floorplan from kitchen to family room to deck with tons of entertaining potential! Granite counters, stainless steel appliances, and a huge island for meals or homework are featured in this updated kitchen! Engineered hardwood flooring throughout main level! Freshly painted large deck for enjoying the

    Angie Carr Riverscape Realty

    4755 Idlewilde Rd, Shady Side, MD 20764
  • /2

    $2,395,000 Coming Soon

    • 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 over one hundred fifty 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
  • /14

    $329,900

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

    1299 Steamboat Rd, Shady Side, MD 20764

    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 property is located close to the Chesapeake Bay with easy commute to AAFB, DC & Annapolis. Sold in AS IS condition, seller will make no repairs.

    Michael Patrick RE/MAX United Real Estate

    1299 Steamboat Rd, Shady Side, MD 20764
  • /3

    $80,000

    • Land
    • 1.05 Acres
    • $76,190 per Acre

    1130 Oak Ave, Shady Side, MD 20764

    POST AUCTION: MAKE AN OFFER! Lot of Land located in Shady Side, Maryland within Anne Arundel County. Property is in close proximity to the Jack Creek Park and all of the attractions located in Shady Side, Maryland. Easy Access to Major Traffic Artery Shady Side Road. Deposit: $7,500.

    Adam Shpritz Ashland Auction Group LLC

    1130 Oak Ave, Shady Side, MD 20764
  • /2

    $16,000

    • Land
    • 1.00 Acre
    • $16,000 per Acre

    5350 Browns Way, Churchton, MD 20733

    POST AUCTION: MAKE AN OFFER! ATTENTION INVESTORS! +/- 1.00 Acre Lot in the Churchton area of Anne Arundel County. Prime Location- Moments to Deep Creek Cover Waterfront- Close Proximity to schools, parks, shopping, restaurants & so much more! Convenient Access to Major Traffic Artery, MD-468

    Adam Shpritz Ashland Auction Group LLC

    5350 Browns Way, Churchton, MD 20733

Showing Results 1 - 40, Page 1 of 2

Frequently Asked Questions

What are the most popular zip codes in Shady Side, MD?
The most popular zip codes in Shady Side, MD include 20774, 20772, 21401, 21666 and 21403.
What are the most popular neighborhoods near Shady Side, MD?
The most popular neighborhoods near Shady Side, MD are Selby-on-the-Bay, Harwood, Davidsonville, Victor Haven and Tyler Heights-Primrose Acres.
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