Homes for Sale in 20764

• 

  

  

  /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
• 

  

  /2

  $495,000

  Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,730 Sq Ft

  5222 Spring Ave, Shady Side, MD 20764

  

  Chris James

  Northrop Realty

  (410) 541-1258

  5222 Spring Ave, Shady Side, MD 20764
• 

  

  

  /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
• 

  

  

  /55

  $650,990

  New Construction $1K PRICE INCREASE

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

  1235 Spruce Ave, Shady Side, MD 20764

  AUGUST Delivier!!!!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

  

  Jamie Richardson

  RE/MAX United Real Estate

  (443) 363-1364

  1235 Spruce Ave, Shady Side, MD 20764
• 

  

  

  /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
• 

  

  /32

  $419,900

  • 3 Beds
  • 1 Bath
  • 1,008 Sq Ft

  4921 Olive St, Shady Side, MD 20764

  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 cozy screened-in front porch, or step out into the level,

  Eric Hovanky Redfin Corp

  4921 Olive St, Shady Side, MD 20764
• 

  

  /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
• 

  

  /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
• 

  /2

  $535,000

  Coming Soon

  • 4 Beds
  • 3 Baths
  • 1,964 Sq Ft

  1183 Cedar Ave, Shady Side, MD 20764

  Photos coming soon! Rarely available and proudly offered for the first time, this spacious split-foyer home sits on nearly a quarter-acre lot in the desirable water-privileged community of Cedarhurst. Built and lovingly maintained by the original owner, this home features 4 bedrooms, 3 full bathrooms, two separate living areas, and an updated open-concept kitchen designed for comfortable everyday

  John Tarpley Schwartz Realty, Inc.

  1183 Cedar Ave, Shady Side, MD 20764
• 

  

  /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
• 

  

  /40

  $499,900

  • 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, basketball

  Erica Baker TTR Sotheby's International Realty

  4909 Olive St, Shady Side, MD 20764
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /39

  $535,000

  • 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

  $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
• 

  

  /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
• 

  /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
• 

  

  /27

  $379,900

  $20K PRICE DROP

  • 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
• 

  

  /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
• 

  

  /17

  $349,870

  • Land
  • 6,534 Sq Ft
  • $2,332,467 per Acre

  5235 Al Jones Dr, Shady Side, MD 20764

  Unique Waterfront Lot Opportunity at Columbia Beach – Build Your Dream Home on the Chesapeake Bay. Don't miss this rare chance to own a buildable waterfront lot in the serene, gated community of Columbia Beach, offering breathtaking views of the Chesapeake Bay. This exclusive neighborhood is just 30 minutes from the I-495 Beltway and Annapolis, and only 45 minutes to Washington, D.C., and the

  Rodrigo Cruz Long & Foster Real Estate, Inc.

  5235 Al Jones Dr, Shady Side, MD 20764
• 

  /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 6/29/2026, 10:00 AM. Bidding ends 7/1/2026, 7:00 PM. The list price is the 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

  Adam Shpritz Ashland Auction Group LLC

  1205 Poplar Ave, Shady Side, MD 20764
• 

  

  /40

  $354,500

  • 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
• 

  /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
• 

  

  /9

  $560,000

  Open Sat 11AM - 1PM

  • 4 Beds
  • 2 Baths
  • 1,713 Sq Ft

  6213 Shady Side Rd, Shady Side, MD 20764

  Charming 4-bedroom, 2-bath cottage situated on 10 picturesque acres, offering the perfect blend of comfort, privacy, and country living. Enjoy endless opportunities for gardening, outdoor recreation, and creating your own private retreat. The expansive property provides plenty of space for entertaining family and friends, hosting gatherings, or simply relaxing and enjoying the peaceful

  Shate Jackson Coldwell Banker Realty

  6213 Shady Side Rd, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  

  /43

  $619,900

  Open Sun 12PM - 2PM

  • 4 Beds
  • 2.5 Baths
  • 1,915 Sq Ft

  1582 Snug Harbor Rd, Shady Side, MD 20764

  Rare 1-acre private lot located in sought after Idlewilde Acres backing up to Jack Creek Park! Upgrades include: 2023 enlarged rear decking, ADT Alarm system, generator hook up. 2023 full kitchen renovation - upgraded cabinetry, leathered granite counter-top, farmhouse sink, back splash upgraded stove top / microwave, and all new wood flooring on main level. Renovated half bath-2023. 2024 new

  Steven Songer Maryland Waterfront Properties LLC

  1582 Snug Harbor Rd, Shady Side, MD 20764
• 

  

  /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
• 

  

  /38

  $609,990

  New Construction $30K PRICE INCREASE

  • 4 Beds
  • 2.5 Baths
  • 2,068 Sq Ft

  1209 Johnson Dr, Shady Side, MD 20764

  6/15/26 HOME UNDER ROOF. EXPECTED JULY/AUGUST 2026 DELIVERY. Schaefer Homes brings to you their latest Monroe model located in water privilege community offering community beach, pier, boat ramp, playground, slips, and more. Select from 3 exterior elevations! This home will come standard with plenty of upgraded features, and there is still the opportunity to make your personal selections to suit

  Ray Mudd Schwartz Realty, Inc.

  1209 Johnson Dr, 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
• 

  

  /79

  $450,000

  • 3 Beds
  • 2 Baths
  • 2,006 Sq Ft

  1217 Pine Ave, Shady Side, MD 20764

  Welcome to this beautifully maintained Colonial perfectly positioned on a desirable corner lot in the water-oriented community of Cedarhurst—where Chesapeake Bay living is part of everyday life. Just in time for summer, enjoy the opportunity to lease a boat slip for only $400 per year with direct access to the Chesapeake Bay, making weekends on the water easier than ever. Inside, you’ll find

  Nicki Palermo RE/MAX One

  1217 Pine Ave, Shady Side, MD 20764
• 

  /2

  $475,000

  Coming Soon

  • 3 Beds
  • 2.5 Baths
  • 1,456 Sq Ft

  4951 Bonniewood Dr, Shady Side, MD 20764

  John Tarpley Schwartz Realty, Inc.

  4951 Bonniewood Dr, Shady Side, MD 20764

Showing Results 1 - 40, Page 1 of 2