Homes for Sale near Shady Side Elementary School

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  /32

  $399,900

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

  1199 Oak Ave, Shady Side, MD 20764

  Coastal Comfort, Steps to the Beach - Tucked in the water privileged community of Cedarhurst on the Bay and just a short stroll to the beach and neighborhood amenities, this charming cottage offers relaxed coastal living with a layout full of character. The home features three bedrooms, two with beautiful coffered ceilings that add height and architectural interest. The full bath includes a tub

  

  Bill Franklin

  Long & Foster Real Estate, Inc.

  (410) 835-7611

  1199 Oak Ave, Shady Side, MD 20764
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  Explore Shady Side Elementary School

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  /33

  $595,990

  New Construction $16K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 2,091 Sq Ft

  1225 Juniper St, Shady Side, MD 20764

  THIS IS A TO BE BUILT HOME

  

  Jamie Richardson

  RE/MAX United Real Estate

  (410) 724-1190

  1225 Juniper St, Shady Side, MD 20764
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  /53

  $674,990

  New Construction $25K PRICE INCREASE

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

  1235 Spruce Ave, Shady Side, MD 20764

  THIS IS A TO BE BUILT HOME. Act soon while you are able to still personalize this home with interior selections!Enjoy water views of the community harbor with 60 boat slips and direct access to the Chesapeake Bay—a dream setting for boating and coastal living. This beautifully crafted home features classic board-and-batten siding and a welcoming front porch that creates timeless curb appeal.

  

  Jamie Richardson

  RE/MAX United Real Estate

  (443) 363-1364

  1235 Spruce Ave, Shady Side, MD 20764
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  /48

  $745,000

  • 3 Beds
  • 2 Baths
  • 1,962 Sq Ft

  5341 Al Jones Dr, Shady Side, MD 20764

  Fantastic opportunity to own your own land lighthouse-inspired round house with water views! Perfect serene retreat for the commuter and/or investment opportunity. Quiet neighborhood, blue heron sightings, and all the advantages of coastal living without the summer beach traffic. Freshly painted! This unique home features 3 bedrooms, 2 full bathrooms, an open-concept layout, and a spacious family

  Melissa Wilson Redfin Corp

  5341 Al Jones Dr, Shady Side, MD 20764
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  /31

  $465,000

  $14K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 912 Sq Ft

  4725 Frederick Ave, Shady Side, MD 20764

  Adorable and fully renovated rancher situated on a rare double lot in the water-oriented Idlewild community of Shady Side! This cozy yet spacious home has been thoughtfully updated from top to bottom and offers easy one-level living with modern finishes throughout. Open concept living and kitchen area overlooks the expansive rear yard, creating the perfect space for entertaining or everyday

  Colleen Kerrigan Redfin Corp

  4725 Frederick Ave, Shady Side, MD 20764
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  /37

  $550,000

  $25K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 1,905 Sq Ft

  1411 Haile Pkwy, Shady Side, MD 20764

  Price reduction! This thoughtfully designed and 2022-built home blends modern finishes with a tranquil setting set against a backdrop of mature woods, creating a bright, open, and inviting space for both everyday living and entertaining. An open two-story foyer welcomes you inside to the main living area with vaulted ceilings, while 9' ceilings throughout the rest of the home enhance the airy,

  Mary Gatton Redfin Corp

  1411 Haile Pkwy, Shady Side, MD 20764
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  /30

  $424,700

  • 3 Beds
  • 2.5 Baths
  • 1,200 Sq Ft

  1527 Lincoln Rd, Shady Side, MD 20764

  Experience the best of the Chesapeake Bay in this 3-bedroom, 2.5-bathroom Colonial, in the sought-after Columbia Beach neighborhood! Nestled in a quiet, gated, water-privileged community, this home offers more than just a place to live—it offers a lifestyle complete with a private pier, boat ramp, tennis/basketball courts, and a playground. The heart of the home is the beautifully curated

  Mike Benton Home Towne Real Estate

  1527 Lincoln Rd, Shady Side, MD 20764
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  /41

  $569,900

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 1,949 Sq Ft

  1316 Juniper St, Shady Side, MD 20764

  This Stylish New home is move in ready and just in time to enjoy the summer breezes at the community Beach areas and play grounds! It is ready for your personal touch to make it your own! Main level features include Luxury Vinyl Plank flooring, 9' ceilings, Luxury kitchen with granite countertops, stainless steel appliances accented with sleek white cabinets with soft close drawers and a center

  Paul Lee Long & Foster Real Estate, Inc.

  1316 Juniper St, Shady Side, MD 20764
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  /2

  $575,000

  Coming Soon

  • 4 Beds
  • 3 Baths
  • 2,537 Sq Ft

  1261 Cove Dr, Churchton, MD 20733

  Beautiful corner lot home in the Franklin Manor Community in Churchton, MD, on a spacious 0.43-acre lot in a water-privileged community with bayfront piers, playground, ballfield, volleyball courts, marina, and half a mile of Bayfront access. A wonderful, quiet family oriented neighborhood. This unique home with a new 2026 roof features a 1955 original section with 1 bedroom (currently office), 1

  Manny Branco Douglas Realty, LLC

  1261 Cove Dr, Churchton, MD 20733
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  /68

  $599,000

  • 3 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  1221 Cove Dr, Churchton, MD 20733

  1221 Cove Drive is a rare non-riparian waterfront property on Deep Cove Creek — the publicly-owned buffer between the property line and the water gives you open creek views, shoreline access, and a pier along the waterfront, without the full tax burden of direct waterfront ownership.Set on a 3⁄4-acre, privately wooded lot in Franklin Manor, the property offers the kind of seclusion that’s

  Ben Garner Cummings & Co. Realtors

  1221 Cove Dr, Churchton, MD 20733
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  /73

  $795,000

  • 3 Beds
  • 2 Baths
  • 2,304 Sq Ft

  4950 Bonniewood Dr, Shady Side, MD 20764

  Waterfront living with a private dock—all for under $800,000! Nestled in the charming Avalon Shores community, this beautifully updated coastal home perfectly blends classic elegance with modern comfort. The open-concept layout features two distinct living areas, ideal for both entertaining and daily relaxation. At the heart of the home is a premium kitchen equipped with granite countertops,

  Jamie Angichiodo RE/MAX Leading Edge

  4950 Bonniewood Dr, Shady Side, MD 20764
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  /30

  $444,000

  $35K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,235 Sq Ft

  1161 Steamboat Rd, Shady Side, MD 20764

  Welcome to this inviting single-family home in the heart of Shady Side! This lovely residence features 3 bedrooms, 2.5 bathrooms, and approximately 2,235 sq ft of versatile living space — thoughtfully laid out to balance comfort and function.Step inside to a warm, open floor plan where natural light enhances every room, and an efficient layout makes everyday living easy. A well-appointed

  Christine Saunders Compass

  1161 Steamboat Rd, Shady Side, MD 20764
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  /39

  $445,000

  • 3 Beds
  • 1.5 Baths
  • 1,104 Sq Ft

  5533 Franklin Blvd, Churchton, MD 20733

  You Will Want to Call This Home Your Own!! Beautifully Updated Franklin Beach - 3 Bedroom 1.5 Bath This house is move in ready and waiting for you. This open concept property with recent updates including fresh paint, new LVP and the roof is 3 years old, windows and doors in 2020/2021, both bathrooms updated in 2026. The kitchen offers granite counters, Stainless Steel appliances and a farm sink.

  Adele Whitaker Douglas Realty, LLC

  5533 Franklin Blvd, Churchton, MD 20733
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  /59

  $1,160,000

  • 4 Beds
  • 3 Baths
  • 1,868 Sq Ft

  4721 Oak Rd, Shady Side, MD 20764

  Welcome to 4721 Oak Road, your waterfront paradise on the Chesapeake Bay! Nestled in the sought-after Felicity Cove community of Shady Side, this custom-built 2014 coastal home seamlessly blends modern luxury with effortless waterfront living. Boasting 4 spacious bedrooms, 3 full bathrooms, and 1,868 square feet of pristine living space, this residence shows like new. Step inside to an

  Angie Carr Riverscape Realty

  4721 Oak Rd, Shady Side, MD 20764
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  /11

  $149,999

  • Land
  • 6,098 Sq Ft
  • $1,071,421 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 can

  Jennifer Koenig Long & Foster Real Estate, Inc.

  5250 Al Jones Dr, Shady Side, MD 20764
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  /4

  $50,000

  • Land
  • 7,405 Sq Ft
  • $294,118 per Acre

  4907 Quince St, Shady Side, MD 20764

  Per the recorded Conservation Easement. No primary residence shall be constructed

  Ray Mudd Schwartz Realty, Inc.

  4907 Quince St, Shady Side, MD 20764
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  /2

  $40,000

  • Land
  • 14,810 Sq Ft
  • $117,647 per Acre

  5771 Shady Side Rd, Churchton, MD 20733

  Residential building lot awaits new owner. Sold as is .

  Joseph Butcher Long & Foster Real Estate, Inc.

  5771 Shady Side Rd, Churchton, MD 20733
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  /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 accessibility. With

  Joan Stansfield Samson Properties

  1436 Haile Pkwy, Shady Side, MD 20764
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  /51

  $500,000

  • 4 Beds
  • 4.5 Baths
  • 2,629 Sq Ft

  5629 Gunner Run Rd, Churchton, MD 20733

  Auction Property. In Collaboration with Alex Cooper Auctioneers. List price is Opening Bid at The Online Only Auction Sale to Be Held on The Auctioneers Website – Bidding begins Thursday June 4th @ 1:00PM and ends Tuesday, June 9, 2026, at 1:00PM. Absolutely Gorgeous waterfront residence in the desirable Spyglass community of Churchton, Maryland. Situated on approximately 0.46± acres, this

  Alex Fox Allfirst Realty, Inc.

  5629 Gunner Run Rd, Churchton, MD 20733
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  /2

  $25,000

  • Land
  • 4,791 Sq Ft
  • $227,273 per Acre

  0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764

  ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform. Bidding begins 6/2/2026 @ 10:00 AM. Bidding ends 6/4/2026 @ 12:50 PM. List Price is Suggested Opening Bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in located in Shady Side, MD within Anne Arundel County. Its location is just a few minutes away to Herring Bay. It also offers easy

  Adam Shpritz Ashland Auction Group LLC

  0 Pine Ave Unit MDAA2139458, Shady Side, MD 20764
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  /76

  $3,500,000

  • 5 Beds
  • 5.5 Baths
  • 4,620 Sq Ft

  4750 Frederick Ave, Shady Side, MD 20764

  Silver Water is a rare west-facing waterfront home designed in direct response to the Chesapeake—offering broad water views, remarkable sunsets, and a level of architectural clarity seldom found in the area. Set behind a private gate on a beautifully landscaped one-acre lot along the West River, the property combines seclusion with convenient access to Annapolis and Washington, DC. Spanning over

  David Orso Berkshire Hathaway HomeServices PenFed Realty

  4750 Frederick Ave, Shady Side, MD 20764
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  /2

  $25,000

  • Land
  • 24,829 Sq Ft
  • $43,860 per Acre

  0 Haile Pkwy Unit MDAA2141624, 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 MDAA2141624, Shady Side, MD 20764
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  /27

  $399,900

  • 3 Beds
  • 2 Baths
  • 1,223 Sq Ft

  4738 Washington Ave, Shady Side, MD 20764

  Perfect little rancher in a water access community. 3 bedrooms, 2 full baths, and a full fenced yard. Heated family/sun room out back and setup for a stackable washer/dryer inside.

  Kyle Squires Lazar Real Estate

  4738 Washington Ave, Shady Side, MD 20764
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  /52

  $575,000

  $10K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 1,840 Sq Ft

  5608 Bimini Ct, Churchton, MD 20733

  Perched above the Bay with sweeping water views and a private wooded setting! This is the one you've been waiting for! Major system upgrades and seamless indoor-outdoor living make it as functional as it is stunning.This 4-bedroom, 3-bath home offers a sleek, move-in-ready feel. Inside, hardwood floors run through the main living areas, and cathedral ceilings with large windows bring in

  Chris Craddock EXP Realty, LLC

  5608 Bimini Ct, Churchton, MD 20733
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  /42

  $325,000

  • 3 Beds
  • 1 Bath
  • 864 Sq Ft

  1172 Cedar Ave, Shady Side, MD 20764

  Welcome to Cedarhurst on the Bay, a charming waterfront community on the Shady Side Peninsula, conveniently located between Annapolis and Deale Maryland. This cute, updated rancher style home offers a rare affordable opportunity to enjoy Chesapeake Bay living, just one hour from the City. So much potential! Make it your weekend retreat, an Air B&B, or perhaps a tranquil place to retire, without

  James Basuel Weichert, REALTORS

  1172 Cedar Ave, Shady Side, MD 20764
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  /2

  $25,000

  • Land
  • 4,791 Sq Ft
  • $227,273 per Acre

  1205 Poplar Ave, Shady Side, MD 20764

  ONLINE AUCTION: This auction takes place on the Ashland Auction Group Website Bidding Platform. Bidding begins 6/9/2026 @ 10:00 AM. Bidding ends 6/11/2026 @ 12:05 PM. List Price is Suggested Opening Bid. Deposit: $5,000. This +/- 4,750 ft2 parcel of land is located in Shady Side, MD within Anne Arundel County. It is just minutes away to Herring Bay and offers easy access to major traffic arteries

  Adam Shpritz Ashland Auction Group LLC

  1205 Poplar Ave, Shady Side, MD 20764
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  /37

  $354,500

  Open Sun 11AM - 1PM

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

  1617 Winters Ave, Shady Side, MD 20764

  Discover your waterfront retreat with Chesapeake Bay views, community water access, and an ideal location for both everyday living and weekend escapes. The stunning upper-level living area features vaulted ceiling, a classic wood-burning fireplace, and beautiful hardwood flooring that creates a warm and inviting atmosphere. Large, upgraded windows fill the home with natural light while showcasing

  Jeffrey Lewis Berkshire Hathaway HomeServices PenFed Realty

  1617 Winters Ave, Shady Side, MD 20764
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  /2

  $100,000

  • Land
  • 29,620 Sq Ft
  • $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

  $125,000

  • Land
  • 4 Acres
  • $31,250 per Acre

  1495 Shady Rest Rd, Shady Side, MD 20764

  Discover a unique investment opportunity with this expansive 4-acre parcel of land, perfect for those looking to capitalize on future development potential. Nestled in a serene setting, this property offers ample space for creative vision-whether you envision a private retreat, agricultural venture, or a residential community. The generous lot size provides flexibility for various projects,

  Shawn Kerr Union Preferred Realty

  1495 Shady Rest Rd, Shady Side, MD 20764
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  /72

  $540,000

  $10K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 1,812 Sq Ft

  1005 Hawk Channel Ct, West River, MD 20778

  BUYERS GOT COLD FEET! No inspections were completed. Welcome to the rarely available water- privileged Cedarlea community in West River—Tucked away at the end of a quiet, family-friendly cul-de-sac, this beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of comfort, space, and privacy and is ready for its new owners. From the moment you arrive, the inviting front porch sets

  Stephanie Smith Douglas Realty, LLC

  1005 Hawk Channel Ct, West River, MD 20778
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  /2

  $120,000

  • Land
  • 19,166 Sq Ft
  • $272,727 per Acre

  1186 & 1188 Poplar Ave, Shady Side, MD 20764

  Sale includes both 1186 & 1188 Poplar Ave. Lots: 10,11,12,13 Rare opportunity to purchase two adjoining parcels totaling approximately 19,000 square feet or nearly 1/2 acre in the water-privileged community of Cedarhurst on the Bay. Build your dream home and enjoy the relaxed Chesapeake Bay lifestyle that makes Shady Side one of Anne Arundel County's hidden gems. Community amenities include Bay

  Adam Carpenter Keller Williams Flagship

  1186 & 1188 Poplar Ave, Shady Side, MD 20764
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  /61

  $850,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,204 Sq Ft

  5331 Sweetwater Dr, West River, MD 20778

  Stately brick-front Colonial located in the highly sought-after water-privileged community of West River Estates. This absolutely gorgeous home offers exceptional space, charm, and amenities throughout. The beautifully appointed kitchen features granite countertops, double wall ovens, a large center island with built-in cooktop, and ample cabinetry. French doors open to a bright all-season

  Ray Mudd Schwartz Realty, Inc.

  5331 Sweetwater Dr, West River, MD 20778
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  /5

  $839,000

  Coming Soon

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

  5523 Ilchester St, Churchton, MD 20733

  Discover the ultimate Chesapeake Bay waterfront lifestyle in this beautifully appointed 4-bedroom, 3-bath residence, where breathtaking water views and thoughtful design create an exceptional coastal retreat. Perfectly positioned to capture panoramic bay vistas, this home offers an elegant blend of comfort, sophistication, and year-round waterfront living. The kitchen serves as the centerpiece of

  Lori Rogers Keller Williams Realty Centre

  5523 Ilchester St, Churchton, MD 20733
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  /35

  $729,900

  • 3 Beds
  • 2 Baths
  • 1,866 Sq Ft

  1650 Cedar Ln, Shady Side, MD 20764

  Experience Unmatched Privacy and Tranquility from this unique non-riparian waterfront home set on over 3+ scenic acres. Fall in love with sweeping water views and the serene presence of native wildlife—waterfowl, deer, eagles, and more—all just outside your door. Enjoy panoramic vistas of a natural pond, with the stunning Chesapeake Bay visible in the distance. On clear days, the Bay Bridge is

  Ray Mudd Schwartz Realty, Inc.

  1650 Cedar Ln, Shady Side, MD 20764
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  /40

  $365,000

  • 2 Beds
  • 2 Baths
  • 864 Sq Ft

  4912 Beech St, Shady Side, MD 20764

  Welcome to this charming 2-bedroom, 2-bath home in the water-oriented community of Avalon Shores. Perfect for those looking to start out, scale down, or a second home! Freshly updated with new flooring, a new roof, and fresh paint- this home is truly move-in ready! Enjoy a fully renovated bathroom, a spacious deck, and a fully fenced backyard—perfect for pets, gatherings, or quiet relaxation.Step

  Juliet Patterson Samson Properties

  4912 Beech St, Shady Side, MD 20764
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  /61

  $659,990

  New Construction

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

  5314 Al Jones Dr, Shady Side, MD 20764

  4/6/26. Just broke ground. Late summer delivery. Coastal Living Just Steps from the Chesapeake Bay! Schaefer Homes invites you to make this beautifully designed coastal-style residence your own located across the street from the bay offering nice water views. Offering over 3 stories of wide open living with time to personalize your selections so you can create a home that perfectly reflects your

  Ray Mudd Schwartz Realty, Inc.

  5314 Al Jones Dr, Shady Side, MD 20764
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  /39

  $550,000

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

  5211 Al Jones Dr, Shady Side, MD 20764

  Non-riparian waterfront home offering sweeping, unobstructed views of the Chesapeake Bay. Wake each morning to breathtaking sunrises over the water, best enjoyed from your expansive deck with a cup of coffee in hand—an experience that never gets old. Inside, the home is filled with natural light and features an open-concept layout designed to maximize those stunning bay views. The main level

  Ray Mudd Schwartz Realty, Inc.

  5211 Al Jones Dr, Shady Side, MD 20764
• 

  /2

  $460,000

  Open House 8/01 Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,344 Sq Ft

  1221 Fairfax Ave, Churchton, MD 20733

  Professional Photos coming soon! One of the larger lots in the neighborhood. Wait until you see the backyard oasis! Recent updates include the roof, windows, doors, & water heater. Primary suite with a vaulted ceiling. Garage is insulated and has a split unit for additional comfort. Shows well & turn key ready!This one is worth the wait!

  Nicki Palermo RE/MAX One

  1221 Fairfax Ave, Churchton, MD 20733
• 

  

  /23

  $750,000

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

  1462 Snug Harbor Rd, Shady Side, MD 20764

  4 Bedrooms/ 1 full bath and 1 half bath with shower. 2144 SQ Ft home and income opportunity goes with this home on .57 acres of C1B commercial zoned property. Additional .375 acres and .1243 acres of MC heavy commercial zoned property for a totaling 1.0693 Acres, with 135 feet of bulkheaded waterfront, 200-foot pier, with approximately 12 boat slips. Water depth from 4 to 8 feet that can

  George Heine Schwartz Realty, Inc.

  1462 Snug Harbor Rd, Shady Side, MD 20764
• 

  

  /33

  $650,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,100 Sq Ft

  1430 Haile Pkwy, Shady Side, MD 20764

  There aren't many opportunities left to build brand new in Anne Arundel County at this price point, and 1430 Haile Parkway is one of them. Haile Parkway is quiet, wooded, and tucked into the laid-back charm of Shady Side, close enough to everything you need, far enough away to actually exhale. New construction at this level of quality and finish from one of the area's most respected builders is a

  Lynn Peaper Hubble Bisbee Christie's International Real Estate

  1430 Haile Pkwy, Shady Side, MD 20764

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