Homes for Sale near Shady Side Elementary School

• 

  

  

  /40

  $465,000

  Open Sat 1PM - 3PM $10K PRICE DROP

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

  1220 Grove Ave, Shady Side, MD 20764

  Welcome to the Waterfront Community of Cedarhurst by the Bay tucked away on the quiet Shady Side Penninsula. This Spacious 5 Bedroom, 2 Full Bath home sits just steps away from the amazing community waterfront offering stunning views of the Chesapeake Bay from the Upper Balcony and a multitude of community ammenities. Wake up to breathtaking sunrises and end your evenings watching colorful

  

  Kara Leddy

  Coldwell Banker Realty

  1220 Grove Ave, Shady Side, MD 20764
• 

  Explore Shady Side Elementary School

• 

  

  

  /55

  $619,990

  New Construction

  • 4 Beds
  • 2.5 Baths

  1237 Spruce Ave, Shady Side, MD 20764

  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.Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for

  

  Jamie Richardson

  RE/MAX United Real Estate

  1237 Spruce Ave, Shady Side, MD 20764
• 

  

  

  /55

  $650,990

  New Construction $1K PRICE INCREASE

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

  1235 Spruce Ave, Shady Side, MD 20764

  November Delivery!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.Inside, the open-concept layout seamlessly connects the dining area and family room,

  

  Jamie Richardson

  RE/MAX United Real Estate

  1235 Spruce Ave, Shady Side, MD 20764
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  /36

  $549,990

  New Construction $30K PRICE DROP

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

  1225 Juniper St, Shady Side, MD 20764

  Move-in Ready!!! Builder offering $,5,000 in closing with preferred Lender and Title Company-speak with sales for details!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

  

  Jamie Richardson

  RE/MAX United Real Estate

  1225 Juniper St, Shady Side, MD 20764
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  /48

  $725,000

  $20K PRICE DROP

  • 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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  /47

  $799,000

  • 3 Beds
  • 3 Baths
  • 3,192 Sq Ft

  1211 Linton Ln, Shady Side, MD 20764

  Welcome to 1211 Linton Lane, where space, comfort, and water-access living come together in the heart of Shady Side. Located near the Chesapeake Bay, local marinas, boat ramps, parks, and fishing spots, this home offers the ideal opportunity to enjoy Southern Anne Arundel County’s relaxed coastal lifestyle. Set on a generous lot, the property provides plenty of outdoor space for entertaining,

  Marlena McWilliams Keller Williams Capital Properties

  1211 Linton Ln, Shady Side, MD 20764
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  /32

  $349,900

  $70K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  4921 Olive St, Shady Side, MD 20764

  *** OPEN HOUSE - 2-4:00PM, SUNDAY, SEPT 13, 2026! ***Coastal charm meets modern comfort in Avalon Shores! This sun-drenched, corner-lot 1940s cottage boasts beautiful water views from both floors. The inviting interior features a spacious kitchen with stainless steel appliances, while wrap-around windows flood the entire main living area with bright, natural light. Relax or entertain on the

  Eric Hovanky Redfin Corp

  4921 Olive St, Shady Side, MD 20764
• 

  

  /46

  $449,900

  • 3 Beds
  • 1.5 Baths
  • 1,680 Sq Ft

  5604 Dover St, Churchton, MD 20733

  Welcome to this beautifully updated Colonial in the water-oriented Franklin Manor Beach community, just steps from the Chesapeake Bay. Offering the perfect blend of comfort, style, and coastal living, this move-in ready home is ready for its next owner. The home features an updated kitchen with granite countertops, stainless steel appliances, attractive cabinetry, and durable flooring throughout

  Rick Gloekler RE/MAX Executive

  5604 Dover St, Churchton, MD 20733
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  /2

  $20,000

  • Land
  • 4,791 Sq Ft
  • $181,818 per Acre

  1168 Holly Ave, Shady Side, MD 20764

  Prime Wooded Lot for Sale 1168 Holly Ave, Shady Side, MDExplore the possibilities with this beautiful wooded lot located at 1168 Holly Ave in Shady Side, MD 20764. Nestled in a serene and desirable community, this 4750 SF lot offers the perfect setting for your dream home or a smart investment. Enjoy the tranquility of nature while being just minutes away from local amenities, the Chesapeake

  Andrew Ye Insight Real Estate LLC

  1168 Holly Ave, Shady Side, MD 20764
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  /30

  $380,000

  $45K PRICE DROP

  • 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
• 

  /2

  $30,000

  • Land
  • 1.32 Acres
  • $22,727 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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  /6

  $249,999

  • Land
  • 33,541 Sq Ft
  • $324,674 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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  /40

  $480,000

  $20K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  4909 Olive St, Shady Side, MD 20764

  Welcome to 4909 Olive Street, a newer construction three bedroom, two and a half bath home in the waterfront community of Avalon Shores. Offering a functional layout, contemporary finishes, open living spaces, a fully fenced in backyard, and a private driveway.Avalon Shores residents enjoy access to a community beach, fishing pier, boat ramp, kayak launch, waterfront park, playground,

  Erica Baker TTR Sotheby's International Realty

  4909 Olive St, Shady Side, MD 20764
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  /36

  $430,000

  • Land
  • 8.5 Acres
  • $50,588 per Acre

  1495 Cedarhurst Rd, Shady Side, MD 20764

  Large lot ready for you to build your private compound! 8.5 acres contains wetland areas. Located in a water-privileged community and two blocks to the Chesapeake Bay. Cedarhurst on the Bay has a private marina, pier, beachfront and community house for owners use only. Located on a peninsula, Cedarhurst on the Bay has easy access to the water and amazing views of the Bay! Nearby Annapolis,

  Lisa Irving Taylor Properties

  1495 Cedarhurst Rd, Shady Side, MD 20764
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  /63

  $1,100,000

  Open Sat 11AM - 1PM

  • 3 Beds
  • 4.5 Baths
  • 2,642 Sq Ft

  5060 Lerch Dr, Shady Side, MD 20764

  Waterfront living at its finest in Avalon Shores on South Creek! This 3-bedroom, 4.5-bath home features a versatile study/bonus room, beautiful wood floors, updated kitchen and baths, and modern fixtures throughout. Enjoy water views from the expansive screened-in back porch or multiple decks spanning the second and third levels. The waterfront setup is ideal for boating enthusiasts with a

  Tracy Vasquez Redfin Corp

  5060 Lerch Dr, Shady Side, MD 20764
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  /43

  $499,000

  • 5 Beds
  • 4 Baths
  • 2,680 Sq Ft

  1194 Oak Ave, Shady Side, MD 20764

  Tastefully updated, magnificent and charming Home for Sale in the water-oriented community of Cedarhurst on the Bay. This Beautiful 5 bedroom 4 bathroom house will deliver on all your needs. Main floor greets you with a bright and spacious open floor plan. Large living room, updated kitchen with quartz countertops, oversized island for 3-4 people and stainless steel appliances, walk-in pantry and

  Selim Demirkan Maryland Realty Company

  1194 Oak Ave, Shady Side, MD 20764
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  /61

  $699,000

  $140K PRICE DROP

  • 5 Beds
  • 3 Baths
  • 3,100 Sq Ft

  6066 Shady Side Rd, Shady Side, MD 20764

  MAJOR PRICE IMPROVEMENT AND $5,000 SELLER CONTTRIBUTION TOWARDS BUYER'S CLOSING WITH ACCEPTABLE CONTRACT.Rare Opportunity with 2 detached homes on 4 Flat, Usable Acres in Shady Side!Welcome to 6066 Shady Side Rd, an incredible property offering endless versatility, income potential, and space to grow. Situated on 4 expansive, flat acres, this unique listing features two standalone

  Pete Costello Century 21 Downtown

  6066 Shady Side Rd, Shady Side, MD 20764
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  /73

  $775,000

  $20K PRICE DROP

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

  4950 Bonniewood Dr, Shady Side, MD 20764

  Waterfront living with a private dock—all for only $775,000!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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  /25

  $149,900

  • Land
  • 4,356 Sq Ft
  • $1,499,000 per Acre

  5209 Al Jones Dr, Shady Side, MD 20764

  WATERFRONT OPPORTUNITY!! Discover the perfect setting to build your dream home or weekend retreat on this waterfront lot offering breathtaking views of the Chesapeake Bay. Nestled in the quiet, secluded community of Columbia Beach, this approximately 4,450-square-foot homesite is already serviced by public sewer, making it an exceptional opportunity to bring your vision to life. Wake up to

  Mark Frisco CENTURY 21 New Millennium

  5209 Al Jones Dr, Shady Side, MD 20764
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  /42

  $600,000

  $25K PRICE DROP

  • 3 Beds
  • 4 Baths
  • 2,677 Sq Ft

  1410 Dent Rd, Churchton, MD 20733

  One level living on one acre of total privacy in Churchton, facing Deep Creek and buffered by protected vegetation, positioned between Deep Creek and Franklin Point State Park. Three bedrooms, a bonus room, an office, four bathrooms, and three separate decks built for watching wildlife instead of neighbors. The property is tucked away off the main road, surrounded by nature on every side.

  Samantha Zarnes Serhant

  1410 Dent Rd, Churchton, MD 20733
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  /11

  $90,000

  • Land
  • 6,098 Sq Ft
  • $642,857 per Acre

  5250 Al Jones Dr, Shady Side, MD 20764

  **REDUCED** 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. County allowed neighbor to put well on this parcel by mistake many years ago. The county will allow for setback forgiveness for their mistake. Back corner @ 10ft is where the well for neighbor is. So it percs! Sold As Is.

  Jennifer Koenig Long & Foster Real Estate, Inc.

  5250 Al Jones Dr, Shady Side, MD 20764
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  /34

  $380,000

  • 3 Beds
  • 3 Baths
  • 2,450 Sq Ft

  6372 Shady Side Rd, Shady Side, MD 20764

  Opportunity awaits at this charming farmhouse nestled in the waterfront community of Shady Side. Situated on a spacious lot, this home offers a peaceful setting with convenient access to local marinas, parks, dining, and commuter routes. The interior presents a functional layout with generous living spaces, abundant natural light, and endless potential for customization. Enjoy the privacy of the

  Brenda Sarver Maryland Realty Connection

  6372 Shady Side Rd, Shady Side, MD 20764
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  /49

  $625,000

  • 4 Beds
  • 2.5 Baths
  • 2,511 Sq Ft

  4734 Oak Rd, Shady Side, MD 20764

  Enjoy breathtaking views of the Chesapeake Bay from this charming home in the quaint waterfront community of Felicity Cove. The ground level features two bedrooms (one without a closet), a full bathroom, and a second kitchen, making it an ideal space for guests, extended family, or multi-generational living. The main living area is located on the second floor to take full advantage of the

  Ray Mudd Schwartz Realty, Inc.

  4734 Oak Rd, Shady Side, MD 20764
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  /45

  $415,000

  $10K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 1,296 Sq Ft

  1193 Oak Ave, Shady Side, MD 20764

  Welcome to the Chesapeake Bay lifestyle in the waterfront community of Cedarhurst! Just one block from the Bay, this picture-perfect Colonial combines classic curb appeal, comfortable living spaces, and the kind of community amenities that make everyday life feel a little more like vacation.Start your mornings on the welcoming front porch and spend summer evenings entertaining on the rear

  Nicki Palermo RE/MAX One

  1193 Oak Ave, 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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  /41

  $998,000

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

  4721 Oak Rd, Shady Side, MD 20764

  Waterfront living at its finest! This custom-built Chesapeake Bay home offers breathtaking panoramic views stretching all the way to the Bay Bridge. Meticulously maintained and truly move-in ready, this exceptional property combines luxury, comfort, and the best of coastal living. The main level features beautiful hardwood floors, a spacious gourmet kitchen with granite countertops, stainless

  Ray Mudd Schwartz Realty, Inc.

  4721 Oak Rd, Shady Side, MD 20764
• 

  /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
• 

  

  /19

  $344,900

  $5K PRICE DROP

  • 4 Beds
  • 2 Baths
  • 1,930 Sq Ft

  1704 Maryland Ave, Shady Side, MD 20764

  Welcome to this charming 4-bedroom, 2-bath home in the desirable Snug Harbor community of Shady Side. Offering approximately 1,930 square feet of living space, this property features a spacious layout, detached garage, and generous yard with plenty of room to enjoy outdoor living. Conveniently located near marinas, parks, local dining, and Chesapeake Bay recreation, this home presents a wonderful

  Daniel Demers Sell Your Home Services

  1704 Maryland Ave, Shady Side, MD 20764
• 

  

  /44

  $1,600,000

  Pre-Foreclosure

  • 8 Beds
  • 6.5 Baths
  • 6,873 Sq Ft

  4701 Girton Ave, Shady Side, MD 20764

  BY APPOINTMENT ONLY Saturday September 12th 12-3. Rich in history, timeless in character, and unmatched in location, this extraordinary waterfront estate traces its origins to the early 1900s as the historic Girton House Hotel. Perfectly positioned at the tip of Curtis Point, where the West River meets the Chesapeake Bay, the property later became the beloved Danes on the Bay restaurant, a

  Amber Krause TTR Sotheby's International Realty

  4701 Girton Ave, Shady Side, MD 20764
• 

  /2

  $54,900

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

  6152 Shady Side Rd, Shady Side, MD 20764

  SELLER FINANCING AVAILABLE! 1.53-acre residential tract in Shady Side, Maryland is an unmatched deal! Located at 6152 Shady Side Rd, this spacious property is tax-assessed at $100,300, but we are offering it to you for just $54,900. Finding premium, cheap land for sale priced at nearly 50% below tax assessment value is extremely rare in Anne Arundel County—making this an investor’s or future

  Anjie Deonauth Rise Real Estate, LLC

  6152 Shady Side Rd, Shady Side, MD 20764
• 

  

  /46

  $419,000

  • 3 Beds
  • 2 Baths
  • 1,248 Sq Ft

  1437 Cedarhurst Rd, Shady Side, MD 20764

  Welcome to 1437 Cedarhurst Road in Shady Side, MD! This beautifully updated 3-bedroom, 2-full-bath rancher was completely remodeled in 2023 and offers comfortable one-level living with fresh, modern finishes throughout. Major updates include a newer HVAC system, newer roof and gutters, and a new water filtration system.Additional highlights include a one-car garage, abundant parking, and

  Bob Chew Samson Properties

  1437 Cedarhurst Rd, 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
• 

  

  /45

  $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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  /9

  $149,500

  • Land
  • 7,405 Sq Ft
  • $879,412 per Acre

  1198 Oak Ave, Shady Side, MD 20764

  Beautiful corner lot located just one block from the Chesapeake Bay and the community amenities, including a marina, clubhouse, pier, beach, playground, and more. The lot is level and cleared, making it ready for your plans. Public sewer is available at the road. Boat, RV, and car currently on the property will be removed prior to settlement.

  Ray Mudd Schwartz Realty, Inc.

  1198 Oak Ave, Shady Side, MD 20764
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  /37

  $429,900

  $10K PRICE DROP

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

  1161 Steamboat Rd, Shady Side, MD 20764

  Welcome to this charming home located in a sought-after water-privileged community, just a short walk to the beach, boat slips, playground, boat ramp, and other neighborhood amenities. The main level features a spacious primary suite with a private full bath, offering convenient one-level living. The beautifully appointed kitchen boasts a center island with a gas cooktop, wall oven, abundant

  Ray Mudd Schwartz Realty, Inc.

  1161 Steamboat Rd, Shady Side, MD 20764
• 

  

  /4

  $429,950

  • 3 Beds
  • 2.5 Baths
  • 1,171 Sq Ft

  4922 Dogwood St, Shady Side, MD 20764

  Katie Neighoff RE/MAX United Real Estate

  4922 Dogwood St, Shady Side, MD 20764
• 

  /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
• 

  /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
• 

  

  /46

  $625,000

  • 4 Beds
  • 2 Baths
  • 2,089 Sq Ft

  1221 Bast Ln, Shady Side, MD 20764

  There is something special about life near the Chesapeake Bay—and 1221 Bast Lane captures it beautifully. Completely remodeled from top to bottom, this charming one-level Coastal Craftsman combines fresh, sophisticated interiors with incredible outdoor space and one of the most impressive detached garages you will find. Set on a beautiful lot just shy of an acre in Shady Side, the home offers

  Wendy Oliver Coldwell Banker Realty

  1221 Bast Ln, Shady Side, MD 20764
• 

  

  /119

  $799,000

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

  5331 Sweetwater Dr, West River, MD 20778

  Welcome to this stately brick-front Colonial located in the highly sought-after, water-privileged community of West River Estates. Situated on approximately half an acre, this impressive home offers 5 bedrooms, 3.5 bathrooms, a finished walkout basement, 9-foot ceilings, and exceptional indoor and outdoor living space.Step inside to a spacious and inviting main level featuring 9-foot ceilings

  Jose Salvador Rivera Jr RE/MAX Excellence Realty

  5331 Sweetwater Dr, West River, MD 20778

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