Shady Side, MD Homes

/12
$99,000 Pending
1451 Shady Rest Rd, Shady Side, MD 20764

Rare opportunity in Shady Side on 1.58 acres, just minutes from the Chesapeake Bay.1451 Shady Rest Rd features a partially built home.. The groundwork is in place, and the next owner can bring their own vision to life. The property includes a permitted 3-bedroom septic system and a working well, giving you a strong starting point for a new build. This desirable South County area is seeing

Teal Clise EXP Realty, LLC

1451 Shady Rest Rd, Shady Side, MD 20764
/71
$1,190,000 Sold Aug 18, 2025

1538 Robinson Rd, Shady Side, MD 20764
- 3 Beds
- 2.5 Baths
- 2,060 Sq Ft
- Built 2014
Last Sold Summary
- $578/SF
- 142 Days On Market
Current Estimated Value $1,188,943

Last Listing Agent Jennifer Chaney Chaney Homes, LLC

1538 Robinson Rd, Shady Side, MD 20764

/58
Est $621,301 Not Listed For Sale

4931 Idlewilde Rd, Shady Side, MD 20764
- 3 Beds
- 2 Baths
- 1,534 Sq Ft
- Built 1993
4931 Idlewilde Rd, Shady Side, MD 20764

Last Sold Summary
- $404/SF
- 2 Days On Market
Last Sold Price $620,000

Last Listing Agent Joshua Shapiro Douglas Realty, LLC

/15
$270,750
- 3 Beds
- 1 Bath
- 1,022 Sq Ft
1419 Shady Rest Rd, Shady Side, MD 20764

SHORT SALE APPROVED AT LIST PRICE! This charming three-bedroom, one-bathroom house presents an exceptional investor opportunity in peaceful Shady Side. The property offers excellent renovation potential, allowing you to customize and add value while creating possible rental income streams. Enjoy convenient parking and generous outdoor space perfect for relaxation or entertainment. The spacious

Cindy Martin Samson Properties

1419 Shady Rest Rd, Shady Side, MD 20764
/31
$381,000 Sold Jan 09, 2026

1208 Oak Ave, Shady Side, MD 20764
- 3 Beds
- 2 Baths
- 1,062 Sq Ft
- Built 1981
Last Sold Summary
- $359/SF
- 22 Days On Market
Current Estimated Value $372,939

Last Listing Agent Ray Mudd Schwartz Realty, Inc.

1208 Oak Ave, Shady Side, MD 20764

/42
Est $361,739 Not Listed For Sale

4737 Chesapeake Ave, Shady Side, MD 20764
- 2 Beds
- 1 Bath
- 800 Sq Ft
- Built 1940
4737 Chesapeake Ave, Shady Side, MD 20764

Last Sold Summary
- 1% Above List Price
- $449/SF
- 60 Days On Market
Last Sold Price $359,000

Last Listing Agent Ray Mudd Schwartz Realty, Inc.

/17
$349,870 Pending
- Land
- 0.15 Acre
- $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
/20
$310,000 Sold May 30, 2025

4871 Avery Rd, Shady Side, MD 20764
- 2 Beds
- 1 Bath
- 836 Sq Ft
- Built 1940
Last Sold Summary
- $371/SF
- 4 Days On Market
Current Estimated Value $336,694

Last Listing Agent Melanie Montague EXP Realty, LLC

4871 Avery Rd, Shady Side, MD 20764

/38
Est $450,247 Not Listed For Sale

1195 Bayview Ave, Shady Side, MD 20764
- 3 Beds
- 2 Baths
- 1,824 Sq Ft
- Built 1960
1195 Bayview Ave, Shady Side, MD 20764

Last Sold Summary
- 2% Above List Price
- $242/SF
- 31 Days On Market
Last Sold Price $441,000

Last Listing Agent Alissa Bond Berkshire Hathaway HomeServices Homesale Realty

/39
$460,000 Open Sat 12PM - 2PM
- 4 Beds
- 3 Baths
- 1,632 Sq Ft
5191 Spring Ave, Shady Side, MD 20764

Welcome to 5191 Spring Avenue in the charming, water-oriented community of Cedarhurst on the Bay. Just steps from the water and community marina, this delightful Cape Cod captures the relaxed essence of coastal cottage living. Situated on a spacious corner lot, the property comes alive in the spring with mature plantings and established landscaping that surround the home, creating a colorful and

Elizabeth Gould Long & Foster Real Estate, Inc.

5191 Spring Ave, Shady Side, MD 20764
/90
$1,100,000 Sold Oct 15, 2025

1323 Jordan Dr, Shady Side, MD 20764
- 5 Beds
- 3 Baths
- 2,671 Sq Ft
- Built 1940
Last Sold Summary
- $412/SF
- 2 Days On Market
Current Estimated Value $1,080,899

Last Listing Agent Karlton Morris Long & Foster Real Estate, Inc.

1323 Jordan Dr, Shady Side, MD 20764

/22
Est $387,522 Not Listed For Sale

1170 Maple Ave, Shady Side, MD 20764
- 3 Beds
- 2 Baths
- 1,120 Sq Ft
- Built 1980
1170 Maple Ave, Shady Side, MD 20764

Last Sold Summary
- 6% Above List Price
- $326/SF
- 10 Days On Market
Last Sold Price $365,000

Last Listing Agent Alexandra McDowell Compass

/2
$25,000
- Land
- 0.57 Acre
- $43,860 per Acre
0 Haile Pkwy Unit MDAA2127474, 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 MDAA2127474, Shady Side, MD 20764
/33
$925,000 Sold Aug 08, 2025

4927 Hine Dr, Shady Side, MD 20764
- 4 Beds
- 2.5 Baths
- 3,445 Sq Ft
- Built 1993
Last Sold Summary
- $269/SF
- 127 Days On Market
Current Estimated Value $960,068

Last Listing Agent William Whitman Long & Foster Real Estate, Inc.

4927 Hine Dr, Shady Side, MD 20764

/39
Est $618,305 Not Listed For Sale

1004 Hawk Channel Ct, West River, MD 20778
- 4 Beds
- 3.5 Baths
- 2,566 Sq Ft
- Built 1989
1004 Hawk Channel Ct, West River, MD 20778

Last Sold Summary
- 3% Above List Price
- $234/SF
- 138 Days On Market
Last Sold Price $599,900

Last Listing Agent Kara Leddy Coldwell Banker (NRT-Southeast-MidAtlantic)

/20
$304,000 Pending
- 3 Beds
- 2.5 Baths
- 1,500 Sq Ft
4908 Aspen St, Shady Side, MD 20764

Welcome to this 2-story home nestled in the serene Avalon Shores community. This home features 3 bedrooms, 2 full baths, and 1 half bath. Eat in kitchen with additional room for table space. The exterior boasts multi-level decks ideal for outdoor entertaining, a shady yard offering privacy, and spacious 2 car garage. Located in the peaceful Avalon Shores subdivision, this home is close to Anne

Brenda Sarver Maryland Realty Connection

4908 Aspen St, Shady Side, MD 20764
/27
$449,950 Sold Oct 16, 2025

1192 Oak Ave, Shady Side, MD 20764
- 3 Beds
- 2 Baths
- 1,224 Sq Ft
- Built 1988
Last Sold Summary
- $368/SF
- 8 Days On Market
Current Estimated Value $450,242

Last Listing Agent Ronald Watson Flag Real Estate Inc.

1192 Oak Ave, Shady Side, MD 20764

/23
Est $476,789 Not Listed For Sale

4961 Filbert St, Shady Side, MD 20764
- 3 Beds
- 2.5 Baths
- 1,568 Sq Ft
- Built 1995
4961 Filbert St, Shady Side, MD 20764

Last Sold Summary
- 11% Above List Price
- $274/SF
- 3 Days On Market
Last Sold Price $430,000

Last Listing Agent Rick Gloekler RE/MAX

/5
$145,000 Pending
- Land
- 0.17 Acre
- $852,941 per Acre
5314 Al Jones Dr, Shady Side, MD 20764

Beautiful Chesapeake Bay property for sale! Don’t miss this rare opportunity to build your dream home in the quaint, gated community of Columbia Beach, a serene neighborhood offering breathtaking bay views. Enjoy coastal living with a private pier, boat ramp, playground, tennis and basketball courts, and pickleball. Perfect for boating, fishing, sailing, kayaking, or simply relaxing by the water

Niesha Thomas NextHome Mims Realty Group

5314 Al Jones Dr, Shady Side, MD 20764
/10
$255,000 Sold Jan 21, 2026

5162 Cedarlea Dr, West River, MD 20778
- Land
- 15.59 Acres
- $16,357 per Acre
Last Sold Summary
- 7 Days On Market
Current Estimated Value $216,500

Last Listing Agent Edith Marie Simpson Long & Foster Real Estate, Inc.

5162 Cedarlea Dr, West River, MD 20778

/47
Est $1,105,080 Not Listed For Sale

4816 Atwell Rd, Shady Side, MD 20764
- 4 Beds
- 3.5 Baths
- 3,040 Sq Ft
- Built 2005
4816 Atwell Rd, Shady Side, MD 20764

Last Sold Summary
- 17% Above List Price
- $312/SF
- 48 Days On Market
Last Sold Price $948,000

Last Listing Agent John Freeman Coldwell Banker (NRT-Southeast-MidAtlantic)

/5
$150,000
- Land
- 4.03 Acres
- $37,221 per Acre
0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764

This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

Sam Tanner Keller Williams Flagship

0 Shady Side Rd Unit MDAA2113156, Shady Side, MD 20764
/4
$420,000 Sold Oct 10, 2025

5196 Chesapeake Ave, Shady Side, MD 20764
- 2 Beds
- 2 Baths
- 934 Sq Ft
- Built 1986
Last Sold Summary
- $450/SF
- 0 Days On Market
Current Estimated Value $420,312

Last Listing Agent Joshua Shapiro Douglas Realty, LLC

5196 Chesapeake Ave, Shady Side, MD 20764

/34
Est $349,450 Not Listed For Sale

4912 Beech St, Shady Side, MD 20764
- 2 Beds
- 2 Baths
- 864 Sq Ft
- Built 1989
4912 Beech St, Shady Side, MD 20764

Last Sold Summary
- 9% Above List Price
- $370/SF
- 5 Days On Market
Last Sold Price $320,000

Last Listing Agent Mark Frisco Century 21 New Millennium

/9
$90,000 Pending
- 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
/32
$450,000 Sold May 16, 2025

1233 Juniper St, Shady Side, MD 20764
- 4 Beds
- 2.5 Baths
- 1,899 Sq Ft
- Built 2007
Last Sold Summary
- $237/SF
- 0 Days On Market
Current Estimated Value $469,010

Last Listing Agent Nicki Palermo RE/MAX One

1233 Juniper St, Shady Side, MD 20764

/23
Est $494,690 Not Listed For Sale

6039 Shady Side Rd, Shady Side, MD 20764
- 3 Beds
- 2.5 Baths
- 1,748 Sq Ft
- Built 2007
6039 Shady Side Rd, Shady Side, MD 20764

Last Sold Summary
- 15% Above List Price
- $245/SF
- 122 Days On Market
Last Sold Price $429,000

Last Listing Agent Robyn Day RE/MAX

/49
$419,900
- 3 Beds
- 2 Baths
- 1,456 Sq Ft
4721 Girton Ave, Shady Side, MD 20764

Perfect time to buy this updated home with a detached garage in the beautiful Chesapeake Bay front communnity of Idlewilde! Main level bedroom and full bathroom, waterview from front second level bedroom, and off street parking. This home has been completely updated with the main level having luxury vinyl flooring and fresh paint. The spacious kitchen has granite countertops, wood cabinets, and

Sheri Stevens Samson Properties

4721 Girton Ave, Shady Side, MD 20764
/12
$185,000 Sold Jul 11, 2025

1344 E West Shady Side Rd, Shady Side, MD 20764
- Land
- 2.86 Acres
- $64,685 per Acre
Last Sold Summary
- 91 Days On Market
Current Estimated Value $187,410

Last Listing Agent Bill Beam Beam Realty Group, Inc.

1344 E West Shady Side Rd, Shady Side, MD 20764

/20
Est $357,838 Not Listed For Sale

1206 Holly Ave, Shady Side, MD 20764
- 2 Beds
- 1 Bath
- 1,083 Sq Ft
- Built 1950
1206 Holly Ave, Shady Side, MD 20764

Last Sold Summary
- 15% Above List Price
- $286/SF
Last Sold Price $310,000

Last Listing Agent Jerry Kline Keller Williams Flagship

/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

Joan Stansfield Samson Properties

1436 Haile Pkwy, Shady Side, MD 20764
/47
$875,000 Sold May 02, 2025

5070 Lerch Dr, Shady Side, MD 20764
- 5 Beds
- 3 Baths
- 2,598 Sq Ft
- Built 1956
Last Sold Summary
- $337/SF
- 78 Days On Market
Current Estimated Value $869,480

Last Listing Agent Doc Keane Washington Fine Properties, LLC

5070 Lerch Dr, Shady Side, MD 20764

/24
Est $396,696 Not Listed For Sale

1172 Maple Ave, Shady Side, MD 20764
- 3 Beds
- 1.5 Baths
- 1,040 Sq Ft
- Built 1979
1172 Maple Ave, Shady Side, MD 20764

Last Sold Summary
- 6% Above List Price
- $362/SF
- 13 Days On Market
Last Sold Price $376,000

Last Listing Agent Bita Dayhoff Compass

/2
$65,000 Under Contract
- 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., is

Joan Stansfield Samson Properties

1408 & 1410 Haile Pkwy, Shady Side, MD 20764
/42
$465,000 Sold Sep 26, 2025

1216 Grove Ave, Shady Side, MD 20764
- 5 Beds
- 2.5 Baths
- 2,051 Sq Ft
- Built 1965
Last Sold Summary
- $227/SF
- 37 Days On Market
Current Estimated Value $475,592

Last Listing Agent Paul Lee Long & Foster Real Estate, Inc.

1216 Grove Ave, Shady Side, MD 20764

/75
Est $1,169,636 Not Listed For Sale

1326 W River Rd, Shady Side, MD 20764
- 4 Beds
- 3 Baths
- 2,617 Sq Ft
- Built 1966
1326 W River Rd, Shady Side, MD 20764

Last Sold Summary
- 11% Below List Price
- $501/SF
- 1 Day On Market
Last Sold Price $1,310,000

Last Listing Agent Nicki Palermo RE/MAX One

/2
$150,000
- Land
- 4.03 Acres
- $37,221 per Acre
0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764

This beautiful four acre lot is heavily wooded, flat and level. Approximately 1,000' off the main road makes it very private and secluded. It abuts an additional four acre lot also available for sale. It is believed that because some of the property is in non-tidal wetlands that it cannot be subdivided but buyers should investigate with a civil engineer of choice to confirm. The access

Sam Tanner Keller Williams Flagship

0 Shady Side Rd Unit MDAA2113166, Shady Side, MD 20764
/40
$385,999 Sold Feb 27, 2026

4937 Aspen St, Shady Side, MD 20764
- 2 Beds
- 2 Baths
- 886 Sq Ft
- Built 1939
Last Sold Summary
- 2% Above List Price
- $436/SF
- 14 Days On Market
Current Estimated Value $371,507

Last Listing Agent Pedro Paz Coldwell Banker Realty

4937 Aspen St, Shady Side, MD 20764

/33
Est $447,519 Not Listed For Sale

1016 Cosimano Place, West River, MD 20778
- 3 Beds
- 2.5 Baths
- 1,714 Sq Ft
- Built 1989
1016 Cosimano Place, West River, MD 20778

Last Sold Summary
- 5% Above List Price
- $248/SF
- 8 Days On Market
Last Sold Price $425,000

Last Listing Agent Julie Katcef Engel & Völkers Annapolis

/51
$389,000 Sold Aug 15, 2025

4977 Lerch Dr, Shady Side, MD 20764
- 3 Beds
- 1 Bath
- 1,407 Sq Ft
- Built 1940
Last Sold Summary
- $276/SF
- 21 Days On Market
Current Estimated Value $392,177

Last Listing Agent Suebina Wong Douglas Realty, LLC

4977 Lerch Dr, Shady Side, MD 20764

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