Homes for Sale in 20764

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  /40

  $465,000

  $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
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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
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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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  /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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  /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

  • 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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  /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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  /11

  $89,999

  • Land
  • 6,098 Sq Ft
  • $642,850 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
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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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  /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
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  /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
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  /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
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  /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
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  /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
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  /33

  $429,950

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

  4922 Dogwood St, Shady Side, MD 20764

  Sleek Completely rebuilt and reimagined, this 3-bedroom, 2.5-bath cottage with a palette that feels equal parts cabin and studio. Every system, surface, and finish is new: Set on the West River/Chesapeake Bay peninsula in Avalon Shores of Shady Side — 25 miles south of Annapolis known for boating, crabbing, beaches and . This address puts you minutes from marinas, Franklin Point State Park, and

  Katie Neighoff RE/MAX United Real Estate

  4922 Dogwood St, 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
• 

  /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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  /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
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  /30

  $525,000

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

  1411 Haile Pkwy, Shady Side, MD 20764

  Now is the time to take a fresh look at this beautifully designed 2022-built home, where modern style, thoughtful details, and a peaceful wooded setting come together. Move-in ready and filled with natural light, this home offers the space and flexibility buyers are looking for—without the wait or expense of new construction.Step inside to an open two-story foyer and into the inviting main

  Debbie McQuaid TTR Sotheby's International Realty

  1411 Haile Pkwy, Shady Side, MD 20764
• 

  /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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  /30

  $399,000

  • 2 Beds
  • 1 Bath
  • 808 Sq Ft

  4924 Kellam Rd, Shady Side, MD 20764

  This delightful 1930s ranch-style cottage offers a perfect blend of vintage charm and modern comfort. Set on a generous 1.25-acre lot, the property boasts ample outdoor space, ideal for gardening, entertaining, or simply enjoying the tranquility of nature. An inviting outbuilding adds versatility, whether you envision a workshop, studio, or extra storage space. The expansive driveway ensures

  Abubakar Audu District Pro Realty

  4924 Kellam Rd, Shady Side, MD 20764
• 

  

  /43

  $499,900

  • 3 Beds
  • 2.5 Baths
  • 1,632 Sq Ft

  1240 Hawthorne St, Shady Side, MD 20764

  Nestled in the charming Avalon Shores community, this delightful Colonial home offers a perfect blend of comfort and modern living. This 3 bedroom and 2.5 bath has a thoughtfully designed space, ideal for both relaxation and entertaining. Step inside to discover an inviting open floor plan adorned with beautiful LVT floors. The huge eat-in kitchen with under cabinet lighting and stainless

  Katherine Grimley RE/MAX Leading Edge

  1240 Hawthorne St, Shady Side, MD 20764
• 

  

  /35

  $699,900

  $30K PRICE DROP

  • 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
• 

  

  /30

  $249,900

  $15K PRICE DROP

  • 1 Bed
  • 1 Bath
  • 672 Sq Ft

  1737 Cedar Ave, Shady Side, MD 20764

  This is an estate sale. Buyer to verify all information. Cute 1 BR 1BA cottage located a few hundred yard from the bay. Needs some TLC but livable. Roof is less than 7 years old. Solar panels are owned and not leased. Includes boat slip number 7. Would make a great getaway home or investment property. Sold strictly "as is". Seller will make no repairs.

  Raymond Miller RE/MAX Realty Plus

  1737 Cedar Ave, Shady Side, MD 20764
• 

  

  /54

  $619,990

  New Construction $40K PRICE DROP

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

  5314 Al Jones Dr, Shady Side, MD 20764

  Home is ready for immediate occupancy. 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 LVP flooring through out (Carpet in 2 bedrooms). From the classic board-and-batten siding to the

  Ray Mudd Schwartz Realty, Inc.

  5314 Al Jones Dr, Shady Side, MD 20764
• 

  

  /41

  $650,990

  New Construction

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

  1235 Spruce Ave, Shady Side, MD 20764

  December Delivery — the life you've been dreaming of is almost here!Welcome to Cedarhurst on the Bay, where every day feels like a coastal escape. This beautifully crafted home is the perfect blend of timeless charm and modern living, set against a backdrop of stunning Chesapeake Bay views that simply never get old.From the moment you arrive, the classic board-and-batten siding

  Tanya Trapani Blackwell Real Estate, LLC

  1235 Spruce Ave, Shady Side, MD 20764

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