Shady Side, MD Homes

/7
$1,800,000 Sold Oct 17, 2025
- 5,757 Sq Ft
- $313/SF
- 0 Days On Market
- 4 Beds
- 4.5 Baths
- Built 2026
1114 Cherry Point Rd, West River, MD 20778

Waterfront Living - Enjoy Boating From Your Back Yard to the Chesapeake BayDon't miss this exclusive opportunity to own a premium waterfront property in the quaint town of West River, MD. With close proximity to Annapolis, Galesville, Edgewater, Shady Side and Deale, this brand-new, custom-built luxury home will be constructed to the highest standards of design and

Michael Reible Realty Advantage of Maryland LLC

1114 Cherry Point Rd, West River, MD 20778

/11
Est $332,470 Not Listed For Sale
- 3 Beds
- 1 Bath
- 864 Sq Ft
5806 Shady Side Rd, Churchton, MD 20733

5806 Shady Side Rd, Churchton, MD 20733

/27
$375,000
- 3 Beds
- 2.5 Baths
- 1,512 Sq Ft
1512 Lincoln Rd, Shady Side, MD 20764

Home Sweet Home! Come tour this 2 level, 3 bedroom, 2 full bath just a couple blocks to the water. Situated in Columbia Beach, feel like you're vacationing year round! Whether your taking a walk in the gated community, or entertaining in the spacious home, you'll enjoy living here! No HOA. Please read agent remarks.

Cheryl Bare CENTURY 21 New Millennium

1512 Lincoln Rd, Shady Side, MD 20764
/28
$340,000 Sold Oct 17, 2025
- 1,088 Sq Ft
- $312/SF
- 4 Days On Market
- 3 Beds
- 1 Bath
- Built 1965
1197 Poplar Ave, Shady Side, MD 20764

Charming one-level home tucked away in the waterfront community of Cedarhurst! This property is loaded with curb appeal, featuring newer navy-blue siding, a spacious driveway that easily fits 5+ cars, a welcoming front porch, and a fully fenced backyard that’s both flat and expansive & complete with a large storage shed. Inside, you’ll find 3 comfortable bedrooms and an updated full bathroom with

Delaney Burgess RE/MAX United Real Estate

1197 Poplar Ave, Shady Side, MD 20764

/14
Est $421,230 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
1437 Cedarhurst Rd, Shady Side, MD 20764

1437 Cedarhurst Rd, Shady Side, MD 20764

/32
$289,000
- 2 Beds
- 1 Bath
- 714 Sq Ft
4717 Frederick Ave, Shady Side, MD 20764

Welcome to 4717 Frederick Avenue — a charming and updated cottage just two blocks from the West River in the Idlewilde on the Bay community. This 2-bedroom, 1-bath ranch-style home offers comfortable one-level living with thoughtful improvements throughout. Step inside to a bright, open living area featuring neutral finishes and a cozy fireplace, ideal for everyday relaxation. The renovated

James Weiskerger Next Step Realty

4717 Frederick Ave, Shady Side, MD 20764
/27
$449,950 Sold Oct 16, 2025
- 1,224 Sq Ft
- $368/SF
- 8 Days On Market
- 3 Beds
- 2 Baths
- Built 1988
1192 Oak Ave, Shady Side, MD 20764

Come live the Chesapeake lifestyle!!! This amazing house features 3 bedrooms, 2 full baths, first and second floor bay windows, hardwood floors, remodeled kitchen with quality cabinetry, stainless appliances, space for a large table in the kitchen,1 car garage, front porch, rear wrap around deck, fire pit, newer shed, fenced XL yard (1.5 lots), a generous main driveway plus an additional driveway

Ronald Watson Flag Real Estate Inc.

1192 Oak Ave, Shady Side, MD 20764

/53
Est $329,521 Not Listed For Sale
- 3 Beds
- 1 Bath
- 1,182 Sq Ft
1728 Maryland Ave, Shady Side, MD 20764

1728 Maryland Ave, Shady Side, MD 20764

/41
$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 and pain- 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 outside and

Juliet Patterson Samson Properties

4912 Beech St, Shady Side, MD 20764
/81
$1,950,000 Sold Oct 16, 2025
- 3,745 Sq Ft
- $521/SF
- 108 Days On Market
- 4 Beds
- 2.5 Baths
- Built 2005
1100 Steamboat Rd, Shady Side, MD 20764

Spectacular West River waterfront! A serene lot with panoramic water views, a custom-built home that exudes coastal style, a private dock with two boat slips, a detached 3-car garage with a storage loft, a spacious yard for playing and entertaining, an exquisite vantage point for enjoying the area’s natural beauty, from waterfowl to sunsets. Welcome to 1100 Steamboat Road, offering the best of

Kirsten Rowan Compass

1100 Steamboat Rd, Shady Side, MD 20764

/34
Est $783,183 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 3,143 Sq Ft
5268 Chalk Point Rd, West River, MD 20778

5268 Chalk Point Rd, West River, MD 20778

/31
$385,000
- 3 Beds
- 2 Baths
- 1,062 Sq Ft
1208 Oak Ave, Shady Side, MD 20764

This beautiful home is steps from the Chesapeake Bay and the community marina, beach, playground, and more—making it the perfect blend of comfort and location. Step inside to discover an open floor plan featuring a spacious kitchen with quartz countertops, stainless steel appliances, and a clear view of the living room—ideal for entertaining or everyday living. Stylish LVP flooring runs

Ray Mudd Schwartz Realty, Inc.

1208 Oak Ave, Shady Side, MD 20764
/90
$1,100,000 Sold Oct 15, 2025
- 2,671 Sq Ft
- $412/SF
- 2 Days On Market
- 5 Beds
- 3 Baths
- Built 1940
1323 Jordan Dr, Shady Side, MD 20764

**OFFER DEADLINE SUNDAY SEPTEMBER 14th AT 6:00PM**OPEN HOUSES THIS WEEKEND ONLY, SATURDAY & SUNDAY 12pm to 5pm, Sept 13th & 14th** Wonderful waterfront on West River. Five bedrooms and three full baths in this modern open floor plan home with 9-foot ceilings and tranquil water views from nearly every room. The large, fenced yard keeps people and pets safe while beckoning you to the water's edge.

Karlton Morris Long & Foster Real Estate, Inc.

1323 Jordan Dr, Shady Side, MD 20764

/52
Est $530,147 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,160 Sq Ft
4907 Magnolia St, Shady Side, MD 20764

4907 Magnolia St, Shady Side, MD 20764

/35
$799,900
- 3 Beds
- 2.5 Baths
- 2,225 Sq Ft
6508 Shady Side Rd, Shady Side, MD 20764

For buyers seeking a quicker move-in, the same model is currently under construction less than a mile away and will be completed in approximately 30 days, offering the perfect opportunity to preview the craftsmanship and finishes in person or purchase if a faster timeline is preferred.This to-be-built Modern Farmhouse by local builder Laine Street Homes blends timeless architecture with

Joshua Mast HomeSource Pro Real Estate

6508 Shady Side Rd, Shady Side, MD 20764
/4
$420,000 Sold Oct 10, 2025
- 934 Sq Ft
- $450/SF
- 0 Days On Market
- 2 Beds
- 2 Baths
- Built 1986
5196 Chesapeake Ave, Shady Side, MD 20764

Stunning home situated with a direct, unobstructed waterview of the gorgeous Chesapeake Bay. Featuring 2 bedrooms and 2 full bathrooms, this one-level home offers a serene vacation getaway or full-time residence. Cedarhurst on the Bay is a wonderful community offering boat slips, a community hall, playgrounds and a pier!

Joshua Shapiro Douglas Realty, LLC

5196 Chesapeake Ave, Shady Side, MD 20764

/45
Est $371,226 Not Listed For Sale
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
1617 Winters Ave, Shady Side, MD 20764

1617 Winters 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
/67
$1,000,000 Sold Oct 10, 2025
- 3,244 Sq Ft
- $308/SF
- 67 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1936
4715 Oak Rd, Shady Side, MD 20764

Welcome to the Chesapeake Bay! Relax while sipping your morning coffee or unwinding with a glass of wine. This waterfront cottage offers over 3000 sf of living space with panoramic views from every room! Unique features include wood beams on the first and second levels; two staircases access the second level; authentic cedar doors, closets, and drawers take you back to the 1930s; while the

Angie Carr Riverscape Realty

4715 Oak Rd, Shady Side, MD 20764

/35
Est $346,866 Not Listed For Sale
- 2 Beds
- 1 Bath
- 840 Sq Ft
1311 Holly St, Shady Side, MD 20764

1311 Holly St, Shady Side, MD 20764

/31
$355,000
- 3 Beds
- 1 Bath
- 1,000 Sq Ft
4738 Washington Ave, Shady Side, MD 20764

Peaceful Living by the Bay – Perfect for Downsizing! Looking to simplify without sacrificing charm or location? This move-in ready 3-bedroom, 1-bath rancher is the ideal retreat for anyone craving a slower pace, less maintenance, and more time to enjoy the good life. Tucked on a quiet corner lot next to a protected nature reserve, this single-level home offers peace, privacy, and natural

Nicole Hatch Samson Properties

4738 Washington Ave, Shady Side, MD 20764
/26
$525,000 Sold Sep 30, 2025
- 1,806 Sq Ft
- $291/SF
- 35 Days On Market
- 3 Beds
- 2 Baths
- Built 1928
4727 Oak Rd, Shady Side, MD 20764

Rare Chesapeake Bay waterfront property with panoramic views and endless potential! This 3-bedroom, 2-bath home sits on a prime waterfront lot with a private pier, spacious yard, and mature landscaping. Enjoy sweeping Bay views from the sunroom, living room, and multiple bedrooms, along with the soothing sounds of the water just steps away.The home features charming wood ceilings, exposed

Frank Gamez REMAX Platinum Realty

4727 Oak Rd, Shady Side, MD 20764

/67
Est $788,773 Not Listed For Sale
- 6 Beds
- 3.5 Baths
- 2,918 Sq Ft
629 Plantation Blvd, West River, MD 20778

629 Plantation Blvd, West River, MD 20778

/2
$100,000
- Land
- 0.68 Acre
- $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

Joan Stansfield Samson Properties

1445 & 1447 Haile Pkwy, Shady Side, MD 20764
/33
$1,325,000 Sold Sep 30, 2025
- 2,985 Sq Ft
- $444/SF
- 82 Days On Market
- 3 Beds
- 3 Baths
- Built 1926
1045 Back Bay Beach Rd, West River, MD 20778

You said it HAD to be perfect. That you were NOT going to compromise. Good news! THIS is the one you've been waiting for, and it’s not every day that a home like this comes along. Perfectly positioned on a peaceful peninsula where the West River meets South Creek, this elegant retreat offers panoramic water views from every single room. No, really! EVERY. SINGLE. ROOM. From the moment you step

Theresa Kurtz EXP Realty, LLC

1045 Back Bay Beach Rd, West River, MD 20778

/77
Est $483,936 Not Listed For Sale
- 4 Beds
- 2.5 Baths
- 2,064 Sq Ft
1207 Juniper St, Shady Side, MD 20764

1207 Juniper St, Shady Side, MD 20764

/2
$65,000
- Land
- 0.3 Acre
- $216,667 per Acre
1408 & 1410 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 & Route 4, commuting to Annapolis, Baltimore, or Washington, D.C.,

Joan Stansfield Samson Properties

1408 & 1410 Haile Pkwy, Shady Side, MD 20764
/34
$439,000 Sold Sep 29, 2025
- 2,440 Sq Ft
- $180/SF
- 59 Days On Market
- 4 Beds
- 2 Baths
- Built 1978
1440 Cedarhurst Rd, Shady Side, MD 20764

Welcome to 1440 Cedarhurst Road! This beautifully maintained home offers over 2,400 square feet of comfortable living space, featuring 4 bedrooms and 2 bathrooms on a spacious, flat lot.Step inside to discover gleaming hardwood and tile flooring throughout. The heart of the home is a spacious kitchen with a center island, seamlessly connected to an open dining area. Just off the kitchen,

Terry McAllister RE/MAX One

1440 Cedarhurst Rd, Shady Side, MD 20764

/18
Est $328,750 Not Listed For Sale
- 2 Beds
- 1 Bath
- 960 Sq Ft
1505 Baker Rd, Shady Side, MD 20764

1505 Baker Rd, Shady Side, MD 20764

/9
$90,000
- Land
- 1.02 Acres
- $88,235 per Acre
5277 Cedar St, West River, MD 20778

Beautiful 1 acre property in the heart of Shady Side! This is an amazing opportunity for anyone looking to build their dream home in a nice secluded area with views of trees! The land is located down a gravel driveway way off the main road for maximum privacy. This is a one of a kind opportunity to build the home you've always wanted!

Michael Frank EXP Realty, LLC

5277 Cedar St, West River, MD 20778
/42
$465,000 Sold Sep 26, 2025
- 2,051 Sq Ft
- $227/SF
- 37 Days On Market
- 5 Beds
- 2.5 Baths
- Built 1965
1216 Grove Ave, Shady Side, MD 20764

Chesapeake Bay views and close to the community dock and harbor! Feels like you are on vacation all year round! This home has 4 bedrooms 2.5 baths and a 3rd floor bonus room with balcony and Chesapeake Bay views! It can be used as a family room or a 5th bedroom! Owners suite also has a balcony with Bay views! Home has many new windows and the roof was replaced with Architectural shingles in

Paul Lee Long & Foster Real Estate, Inc.

1216 Grove Ave, Shady Side, MD 20764

/13
Est $318,684 Not Listed For Sale
- 2 Beds
- 1 Bath
- 576 Sq Ft
5326 Al Jones Dr, Shady Side, MD 20764

5326 Al Jones Dr, Shady Side, MD 20764

/8
$239,500
- Land
- 8.19 Acres
- $29,243 per Acre
6118 Shady Side Rd, Shady Side, MD 20764

Only 31k per acre! This wonderful 8.19 acre wooded level lot conveniently located to the Chesapeake & West River is loaded with potential & ready to build your dream home! Off a hard surface road this terrific property is just minutes to multiple marinas, yacht clubs & harbors, shopping, dining and just 25 minutes to Annapolis & 45 minutes to DC. Public water and sewer available

Tem Popoola Real Broker, LLC

6118 Shady Side Rd, Shady Side, MD 20764
/42
$450,000 Sold Sep 19, 2025
- 2,464 Sq Ft
- $183/SF
- 16 Days On Market
- 4 Beds
- 2.5 Baths
- Built 1968
1347 W River Rd, Shady Side, MD 20764

Welcome to 1347 W River Rd. – A Private Retreat on 2.02 Acres in Shady Side, MD. This two-story colonial offers privacy, space, and the perfect blend of classic charm and a few modern updates. With approx. 2,464 sq ft of living space, this 4-bedroom, 2.5-bath home provides ample room for everyday living and entertaining. Step into the spacious foyer and take in the warmth of the shaker-style

Elizabeth DuLaney EXP Realty, LLC

1347 W River Rd, Shady Side, MD 20764

/58
Est $620,451 Not Listed For Sale
- 3 Beds
- 2 Baths
- 1,534 Sq Ft
4931 Idlewilde Rd, Shady Side, MD 20764

4931 Idlewilde Rd, Shady Side, MD 20764

/4
$50,000
- Land
- 0.17 Acre
- $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
/10
$450,000 Sold Sep 19, 2025
- 862 Sq Ft
- $522/SF
- 351 Days On Market
- 2 Beds
- 1 Bath
- Built 1930
1337 W River Rd, Shady Side, MD 20764

Price Reduction!!Your Own Private Retreat, get away from the Rat Race and make this a great place for you and your family.1337 West River Road , located in Shady Side, MDis a secluded waterfront property that sits on 1.5 acres with 592 feet of waterfront on the South Creek.This property has a home with 2 beds and 1 bath that will need remodeling and/or teardown.it's

Bruce Thompson Long & Foster Real Estate, Inc.

1337 W River Rd, Shady Side, MD 20764

/42
Est $364,480 Not Listed For Sale
- 2 Beds
- 1 Bath
- 800 Sq Ft
4737 Chesapeake Ave, Shady Side, MD 20764

4737 Chesapeake Ave, Shady Side, MD 20764

/10
$625,000
- Land
- 10.75 Acres
- $58,140 per Acre
5860 Shady Side Rd, Churchton, MD 20733

WATERFRONT: Own your own park! 10+ Acres and 650+ Feet of water frontage along the South Creek in Churchton! *Do not walk the property without an appointment*

Julie Knott Lofgren-Sargent Real Estate

5860 Shady Side Rd, Churchton, MD 20733
/84
$335,000 Sold Sep 19, 2025
- 1,160 Sq Ft
- $289/SF
- 13 Days On Market
- 3 Beds
- 1 Bath
- Built 1930
5031 Chalk Point Rd, West River, MD 20778

Escape to this charming coastal cottage, a tranquil retreat just steps from South Creek and the West River and directly across from the West River Center. Enjoy peaceful mornings and memory-making evenings in this delightful riverside haven. Let the easy coastal setting inspire your imagination. With a “perfect 10” location and plenty of square footage, this is the ideal canvas for your

Jeanette Silor Homesource United

5031 Chalk Point Rd, West River, MD 20778

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