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$775,000
3 Beds ⋅ 2 Baths
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, stainless steel appliances, a center island with seating, and a sleek range hood. Large bay windows flood the main level with natural light. Enjoy beautifully finished bathrooms, a bedroom on the main living level, and two spacious bedrooms upstairs. Want more room? There’s extra space for an office, playroom, or a bedroom in the loft. Step outside to discover 63 feet of premier waterfront along South Creek. The spacious fully-fenced backyard and private dock with electric & water offer the perfect launchpad for kayaking, paddleboarding, or simply soaking in the tranquil scenery. The primary bedroom has a private balcony to enjoy the creek views. Enjoy peace of mind with new kitchen appliances (dishwasher, fridge - 2025; range hood - 2026), new roof (2025), new HVAC (2026), and sealing work and crawl space encapsulation (2020). Complete with an attached two-car garage with a 12kW Level 2 EV charger, offering secure inside access, and the convenience of a personal air-conditioned gym (or open the doors and enjoy the view and sounds of nature!). This turnkey property is a rare opportunity to live the ultimate waterfront lifestyle. Schedule your tour today!

4950 Bonniewood Dr, Shady Side

Listing courtesy of RE/MAX Leading Edge. Contact:

$120,000
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 access, a beach, boat ramp, pier, clubhouse, and playground, providing endless opportunities for boating, fishing, kayaking, sailing, swimming, and waterfront recreation. Whether you're spending the day on the water, enjoying a sunset by the Bay, or simply embracing the slower pace of coastal living, this location offers the perfect balance of recreation and tranquility. Public sewer hookup is available, and the property is conveniently located within commuting distance of Annapolis, Baltimore, and Washington, D.C. A rare opportunity to secure an oversized homesite in an established waterfront community and create the home you've always envisioned.

1186 & 1188 Poplar Ave, Shady Side

Listing courtesy of Keller Williams Flagship. Contact:

$725,000
3 Beds ⋅ 2 Baths
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 room off the kitchen with no closed-off spaces — ideal for entertaining. Deltec home, designed with durability and efficiency in mind. Deltec homes are known for their strength, energy efficiency, and resistance to high winds and severe weather. Large windows surround the home, filling the interior with natural light and enhancing the panoramic water views. Wood floors flow throughout, adding warmth and character. Step outside to the wraparound deck, perfect for relaxing and taking in the dreamy scenery. Additional quality exterior upgrades include durable Hardi-plank siding and architectural roof shingles, both known for their superior longevity, performance, and curb appeal. Situated on a peninsula tucked between the Chesapeake Bay and 500 acres of state park, this property is currently enjoyed as a charming second-home retreat and part-time Airbnb. Come experience this one-of-a-kind home and incredible setting! Gated community offers a boat ramp, 2 private piers for fishing, crabbing, and boating, and a walking trail along the Bay.

5341 Al Jones Dr, Shady Side

Listing courtesy of Redfin Corp. Contact:

$450,000
3 Beds ⋅ 2 Baths
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 hardwood floors throughout and a spacious layout designed for both comfortable living and entertaining. The oversized 21’ x 23’ primary suite offers a true retreat with plenty of room to unwind, while the additional bedrooms are generously sized as well. The main level features a versatile gym/office space that could easily serve as a fourth bedroom, guest room, or playroom depending on your needs. The heart of the home is the large eat-in kitchen with ample space for gathering, complemented by a separate formal dining room and an expansive family room featuring a cozy wood-burning fireplace. Major updates include a new roof installed in 2020, offering peace of mind for years to come. Conveniently located in a USDA-approved area, this home also qualifies for 100% financing eligibility for qualified buyers. If you’ve been searching for spacious living paired with a sought-after water lifestyle, this Cedarhurst gem checks all the boxes.

1217 Pine Ave, Shady Side

Listing courtesy of RE/MAX One. Contact: 4105356291
$125,000
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, allowing for potential subdivision or custom builds that can yield significant returns. With the growing demand for housing and recreational spaces, this land is poised for appreciation in value. Imagine the possibilities: lush gardens, outdoor activities, or even eco-friendly initiatives that align with modern sustainability trends. The tranquil surroundings foster a sense of peace, making it an ideal canvas for your next investment. Seize this chance to invest in a promising future-where your vision can flourish and your investment can thrive. Don't miss out on this rare opportunity to own a piece of land with endless potential!

1495 Shady Rest Rd, Shady Side

Listing courtesy of Union Preferred Realty. Contact: 4436594454
$725,000
Endless potential in this versatile C1-zoned property — live in one side and run your business from the other, or use the entire building for commercial use. Originally the Shady Side Post Office, this character-filled building sits on just over half an acre with approximately 400 feet of road frontage, offering excellent visibility and easy access. Highlights: C1 commercial zoning — flexible uses Live/work configuration or full commercial conversion Multiple offices / bedrooms 3 Bath rooms 2 kitchens and 2 laundry areas Just over 0.5 acre lot with 400' road frontage Suitable for: accountant, attorney, construction office, daycare, antiques, boat sales/service, retail, studio, café, professional offices, and more Why this property: Great exposure and versatility make this an ideal opportunity for owner-operators or investors looking to attract customers and create a distinctive business presence. High frontage and flexible zoning mean almost any business concept could work here.

6285 Shady Side Rd, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$394,700
3 Beds ⋅ 3 Baths
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 kitchen, boasting sleek white cabinetry, premium quartz countertops, and matte black fixtures, all set against striking herringbone plank flooring. The spacious living area features hardwood flooring and French doors that open to your back deck—perfect for indoor-outdoor entertaining. Bathed in natural light, the home leads you upstairs to a serene primary suite and two additional bedrooms. This turn-key gem is the retreat you’ve been waiting for. Schedule your tour today and start living the Bay life!

1527 Lincoln Rd, Shady Side

Listing courtesy of Home Towne Real Estate. Contact: 8882252736
$100,000
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 convenient access to Route 2, commuting to Annapolis, Baltimore, or Washington, D.C., is effortless—yet the moment you arrive, you'll feel miles away from the urban rush. Surrounded by lush trees and natural scenery, this blank canvas is ready for you to bring your vision to life. Shady Side is known for its close-knit community and outdoor recreation, from boating and fishing on the West River and Chesapeake Bay to exploring local parks and nature trails. Nearby shopping and dining ensure you have modern conveniences without compromising the charm of country living. Don’t miss this unique opportunity—contact us today to schedule a private tour and start planning your future in Shady Side, MD!

Haile Parkway, Shady Side

Listing courtesy of Samson Properties. Contact: 3017602136
$100,000
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 the moment you arrive, you'll feel miles away from the urban rush. Surrounded by lush trees and natural scenery, this blank canvas is ready for you to bring your vision to life. Shady Side is known for its close-knit community and outdoor recreation, from boating and fishing on the West River and Chesapeake Bay to exploring local parks and nature trails. Nearby shopping and dining ensure you have modern conveniences without compromising the charm of country living. Don’t miss this unique opportunity— start planning your future in Shady Side, MD!

1445 & 1447 Haile Pkwy, Shady Side

Listing courtesy of Samson Properties. Contact: 3017602136
$25,000
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 Washington, D.C., is effortless—yet the moment you arrive, you'll feel miles away from the urban rush. Surrounded by lush trees and natural scenery, this blank canvas is ready for you to bring your vision to life. Shady Side is known for its close-knit community and outdoor recreation, from boating and fishing on the West River and Chesapeake Bay to exploring local parks and nature trails. Nearby shopping and dining ensure you have modern conveniences without compromising the charm of country living. Don’t miss this unique opportunity— and start planning your future in Shady Side, MD!

Haile Pkwy, Shady Side

Listing courtesy of Samson Properties. Contact: 3017602136
$649,990
4 Beds ⋅ 3 Baths
Home is ready for immediate occupancy. Ask about 3.99% for FHA & VA loans or $10,000 in closing assistance. 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 welcoming front porch, the exterior sets a striking first impression. Upper level offers water views and an open-concept layout that seamlessly connects the dining and family rooms, offering the perfect setting for everyday living or entertaining. At the heart of the home is an upgraded kitchen with oversized island, upgraded countertops, stainless steel appliances, and abundant cabinetry—ideal for casual meals or gatherings with friends. A private home office (or flexible choice room) on the main level adds convenience, while upstairs the serene owner’s suite boasts a large picture window with Bay views, a spacious walk-in closet, and a spa-inspired bath with a luxury shower. Walk to community pier, boat ramp, playground, tennis courts and more. Renderings and photos are for illustrative purposes only and may show optional features, upgrades, or configurations not included as standard. Actual features, finishes, and layouts may vary. Flood insurance is approximately $650.00 year.

5314 Al Jones Dr, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$650,990
4 Beds ⋅ 3 Baths
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, making it perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry for both casual meals and gatherings. A main-level home office or flexible choice room offers the ideal space for working from home or relaxing. Upstairs, the owner’s suite features a large picture window, expansive walk-in closet, and a spa-inspired bath with a luxury shower. Just a short walk to the community center and playground, residents also enjoy Cedarhurst’s rare four acres of community-owned waterfront property with panoramic bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and opportunities to watch sunrises, sailboats, waterfowl, and local watermen working the bay.

1235 Spruce Ave, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

$549,990
4 Beds ⋅ 3 Baths
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 timeless curb appeal. Inside, the open-concept layout seamlessly connects the dining area and family room, making it perfect for everyday living and entertaining. The spacious kitchen is the heart of the home, showcasing an oversized quartz island, stainless steel appliances, and abundant cabinetry. A main-level home office or flex room provides the ideal space for working from home or relaxing. Upstairs, the owner's suite features a large picture window, an expansive walk-in closet, and a spa-inspired bath with a luxury shower. Just a short walk from the community center and playground, residents enjoy Cedarhurst's rare four acres of community-owned waterfront with panoramic Chesapeake Bay views, open lawns, wetlands, picnic areas, playgrounds, ball fields, and opportunities to watch sailboats, waterfowl, and local watermen at work.

1225 Juniper St, Shady Side

Listing courtesy of RE/MAX United Real Estate. Contact:

$699,000
4 Beds ⋅ 2 Baths
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 accommodate 40ft+ boats. Total income for 2025 was $6900. with only a few slips rented. Will require a commercial lender or cash to purchase.

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$699,000
4 BEDS/1FULL BATH AND1/2 BATH WITH SHOWER. 2144SQ FT. Home income opportunity goes with this four bedroom home on .57 acres of (C1B) commercial zoned property. Additional .375 acres and .1243 acres of (MC) heavy commercial marine zoned property totaling 1.0693 acres, with 135 feet of bulk headed waterfront, 200 foot pier, and 12 boat slips. Water depth from 4 to 8 feet that can accommodate boats in excess of 40 feet. Total income from 6 of the 12 slips in 2025 was $6900!! POTENTIAL for much more PLUS Additional rental income from DRY STORAGE AVAILABLE. Many upgrades and extras. Information sheet in the document section of the listing or may be emailed to interested parties. .

1462 Snug Harbor Rd, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$699,900
3 Beds ⋅ 2 Baths
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 even within sight. The home features a relaxing screened porch, a spacious kitchen that flows into a cozy living area with a wood stove—perfect for chilly evenings. The main level includes a bedroom and full bath, plus an additional room ideal for an office or second living space, also with a wood stove. Upstairs, the primary bedroom offers breathtaking water views, accompanied by another bedroom and a full bath. A barn/stable on the property makes it ideal for horses or a home-based business with office space. This is truly a one-of-a-kind property—peaceful, picturesque, and full of potential. Come see it for yourself.

1650 Cedar Ln, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$50,000
Per the recorded Conservation Easement. No primary residence shall be constructed

4907 Quince St, Shady Side

Listing courtesy of Schwartz Realty, Inc.. Contact:

$90,000
**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. No study periods. Beautiful community. Builders in area already working on a new 3 story home. Private boat ramp to the Chesapeake Bay and community playgrounds and courts. Gate code in showing time!

5250 Al Jones Dr, Shady Side

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$249,999
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.

4846 Woods Wharf Rd, Shady Side

Listing courtesy of RE/MAX One. Contact: 4105356291