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$140,000
1 Beds 1 Baths
What a privilege to live in this historic circa 1892 late Victorian-era stunning architecture! The 2006 renovation/restoration project created a gorgeously unique residential opportunity to live in this beautiful 19th-century former school ("Public School #25 or "Captain Henry Fleete School") with all the conveniences of the 21st-century! After passing through the secure entrance, just a few steps to the 1st level and you enter this contemporary 1 bedroom condo featuring a chic kitchen w/ 42-inch cabinets, granite counters and stainless steel appliances. The dining/living room combination allows for versatile layout design so you can decide how to best utilize the space! The bright bedroom is spacious enough to host a desk/office area and the recently remodeled bath boasts an oversized walk-in subway tiled shower w/ marble floor, oversized "fogless" mirror plus linen closet. Experience lifestyle ease while being located right in the middle of Fells Point! While inside your quiet urban retreat, plan your next Baltimore adventure and enjoy the best that Baltimore has to offer right outside your door!

511 S Bond St Unit #107, Baltimore

Listing courtesy of Monument Sotheby's International Realty. Contact: 4437087074

$1,789,000
4 Beds 3 Baths
Stunning Victorian on a double lot in the heart of Kensington's historic district. Rare opportunity to own one of the most beautiful historic homes in the heart of Kensington’s historic district. Built in 1898 and in meticulous condition, this is a must see in person! This Queen Anne style architectural gem is beautifully sited on a double, .40-acre lot and has magnificent custom features not found in homes today- fabulous millwork, custom built in china cabinet, pocket doors, original fireplace mantels, gas fireplace, front and back staircases, heart pine floors, transom windows, glass doorknobs, soaring ceilings , historic light fixtures, even a secret room! Tour in person to see all rooms and the special features. The main level features a stately foyer with large coat closet and gorgeous staircase, formal living room with bay window and gas fireplace, family room with fireplace and door to side deck, grand formal dining room large built in china cabinet and door the back porch, full bath, and masterfully renovated kitchen with custom cabinetry, Silestone countertops, stainless steel appliances, tin ceiling, pantry, and back stair to the second floor. The upper level includes four large bedrooms, hall closet, large renovated bath , access to upper porch, and stairs to the attic with lots room for storage and play. The lower level is a wonderful surprise with good ceiling height, ceramic tile floor recreation/guest room areas, full bath , outside egress, and laundry area with front loading washer and dryer. Please see floor plans. The outdoor living areas are amazing- large front porch, side porch , and rear covered porch , and a private brick patio. The established gardens feature more than fifty mature flowering trees and shrubs. Upgrades include a 50 year shingle architectural roof with copper stand seam porch roofs and copper downspouts, new sewer and water lines, electrical 200 amp heavy up and electrical upgrades, relining of chimney flues, newly constructed chimney, new master water valve shut off, new hot water heater in 2023, dual zone AC, exterior recently repainted & more! location, location! Walk to the heart of Kensington and all it has to offer- restaurants, shops, multiple parks, weekly Farmer’s market, Noyes Children’s Library, Babycat Brewery & more. Just minutes to the entertainment and shopping districts of Chevy Chase Lake and Pike and Rose. A commuter’s dream close to two Metro shops, downtown Bethesda and just a mile to the Beltway. You will love the community spirit of Kensington. Prepare to fall in love with this very special home, property, and neighborhood!

3911 Prospect St, Kensington

Listing courtesy of Compass. Contact: (301) 304-8444

$509,900
4 Beds 4 Baths
Open House Sunday August 1st, 12PM - 2PM!Welcome to 1218 W Northern Parkway, an exceptional opportunity to own a beautifully updated home in a prime Mount Washington location! This spacious homes blends classic charm with modern upgrades, offering the perfect balance of character and functionality. Step inside to a bright and inviting main level featuring an open, flowing floorplan ideal for both everyday living and entertaining. The gourmet kitchen is the heart of the home, complete with stylish cabinetry, soft close drawers, sleek countertops, exposed brick, and modern appliances, all opening seamlessly to the dining and living areas. Large windows throughout fill the space with abundant natural light keeping the space airy and bright. On the second level, you’ll find 2 generously sized primary bedroom suites both equipped with luxurious ensuite bathrooms, large closets, and quick access to laundry. The third level features two additional, generously sized bedrooms and shared upgraded full bathroom. No detail has been left out. The lower level features an unfinished space with tall ceilings which could be easily finished and made into another living space. It is currently purposed for storage, recreation, and gaming area. Enjoy outdoor living with a spacious yard and private outdoor space, ideal for relaxing or hosting gatherings. The fenced in backyard and detached 2-car oversized garage is a rare find for city living in Baltimore! Conveniently located just minutes from both downtown Baltimore and Towson, major commuter routes, shopping, fantastic dining, and local parks, this home offers both accessibility and a sought-after city lifestyle. Don’t miss your chance to own a move-in ready home in one of Baltimore’s most convenient locations, schedule your private tour today!

1218 W Northern Pkwy, Baltimore

Listing courtesy of Charis Realty Group. Contact: 3018315099

$1,449,000
5 Beds 4 Baths
75 Shipwright Street is an enchanting Victorian semi-detached home located in the heart of the Historic District of downtown Annapolis. This is a rare opportunity to own a five-bedroom historic home directly across from St. Mary's School (Pre-K-12), allowing students to walk to class while enjoying all that Historic Annapolis has to offer. Built around 1910, this four-level residence offers a blend of original architectural character and modern updates, with significant views of Spa Creek. The property is located in Zone C1 within the historic district, ensuring the preservation of its external architectural integrity. The home features approximately 2,800 square feet of livable space across four finished levels with 5 bedrooms and 3.5 baths, all equiped with eco-friendly bidets. It maintains much of its original Victorian charm, including hardwood floors, moldings, pocket door, and a central hall with high ceilings. The main level boasts a light-filled chef’s kitchen with new quartzite countertops, newer appliances, and a breakfast bar, connecting to a living area with a gas fireplace and a private balcony with wonderful views of Spa Creek. The walk-out basement includes a family room, a full bathroom, and a workshop/laundry area. The new brick patio is surrounded with lush "cottage gardens," providing a private outdoor retreat. A deeded path allows for direct access to the waterfront from your backyard for launching your kayaks and paddleboards. Situated on a secluded street, the property is a short stroll from several major Annapolis landmarks. Residents are just steps from the end of Shipwright Street, where they can catch a water taxi or access slips at the Old Towne Marina. The home is within easy walking distance of the United States Naval Academy, City Dock, and the various shops and restaurants along Main Street. The neighborhood is noted for its tranquil atmosphere while remaining central to the city's vibrant downtown activities. The current owners not only enjoy the property as a second home, they also offer it as a profitable short-term rental, licensed with City of Annapolis. ***Records are available upon request, along with special information pertaining to the current STR license*** This is your chance to own a storied property and a little piece of Annapolis history. Don't miss it! Request your private tour today. ***WATCH THE AERIAL VIDEO TOUR. CLICK THE VIRTUAL TOUR ICON OR VISIT YOUTUBE AND SEARCH "75 Shipwright St Annapolis"***

75 Shipwright St, Annapolis

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

$2,795,000
6 Beds 6 Baths
OPEN HOUSE SUNDAY 7/26 FROM 2 TO 4 PM -- Ask about SUBSTANTIAL tax savings - potentially $1M through preservation easements. Welcome to 10400 Montgomery Avenue, a beautiful family home that is truly the best of Kensington and the best of both worlds – a classic, spacious, and charming Victorian residence fully renovated and updated with a large three-story addition designed by GTM Architects. The home is situated on a large and open 3/4-acre lot with plenty of privacy but located in the center of historic and vibrant Kensington, right next to shops, restaurants, Noyes Library, BabyCat Brewery, the Farmers Market and MARC train station, for an easy commute to DC. Craftsmanship shines throughout the home, featuring high ceilings, large decks and porches, rich woodwork and generous windows that bathe the home with natural light. Completed in 2010, the addition includes a chef’s kitchen, large family room with coffered ceiling, master bedroom suite and finished basement. The spacious kitchen features a Sub-Zero refrigerator, Thermador range and a large center island with two Miele dishwashers. Well-proportioned bedrooms, cozy nooks and thoughtful touches reflect the home's personality and enduring warmth. The finished attic and the basement add lots of additional space for entertaining or home offices. A whole-house audio system adds to the entertainment possibilities. With this rare blend of character, modern comfort, generous lot size and unparalleled convenience, this gem of a home is ready to welcome its next chapter. Please feel free to inquire about any of the furniture or furnishings.

10400 Montgomery Ave, Kensington

Listing courtesy of Keller Williams Capital Properties. Contact:

$649,999
6 Beds 5 Baths
****Neighborhood Grant incentive available**** Welcome to 1526 McCulloh Street — where scale, luxury, and presence converge in the heart of Marble Hill. Situated on the iconic 1500 block, this 4,100+ square foot residence delivers a rare level of grandeur with soaring 15-foot ceilings, sun-drenched interiors through beautiful wood-framed windows, and expansive living spaces designed for both high-end entertaining and everyday comfort. The gourmet kitchen stands as a true centerpiece, featuring premium finishes and a layout that seamlessly blends style and function, while oversized bedrooms and spa-inspired bathrooms elevate the living experience throughout. A standout feature is the fully self-contained lower-level suite with a private entrance and full kitchen, offering unmatched flexibility for guests, multigenerational living, or income potential. Built with substance as much as style, the home includes dual-zone HVAC, all-new electrical, plumbing, and mechanical systems, and the rare convenience of private rear parking. Surrounded by historic architecture and moments from Bolton Hill, Penn Station, and downtown Baltimore, this property isn’t just a home—it’s a statement.

1526 Mcculloh St, Baltimore

Listing courtesy of Keller Williams Legacy. Contact: 4436609229

$1,195,000
5 Beds 6 Baths
Incredible opportunity to own a circa 1875 home in Oxford's Historic District that has been renovated with a separate 2 bedroom apartment with views of Town Creek. Formerly a Bed and Breakfast, it features 2 first floor bedrooms with 1 and 1/2 baths and 3 second floor bedrooms each with its own full bath. Entire exterior has been newly painted and most of the windows have been replaced. A lovely side garden with a fountain, front porch close to Town Park, and a one and one half car garage with room for a workshop compliment the home. The bright, newly renovated kitchen is the center of the house featuring an alcove with a large kitchen table. It overlooks the side garden. Owner prefers 24 hour notice if possible

110 N Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

$2,300,000
4 Beds 3 Baths
"New Scotland Farm" First time offered in decades! This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.

28923 Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,300,000
4 Beds 3 Baths
"New Scotland Farm" First time offered in decades! This special and unique offering includes 100 +/- acres of prime farm and hunting land, encompassing a spacious farmhouse and three additional income producing properties, two ponds, and deeded water access with a dock and slip on LaTrappe Creek. There is the potential for subdivision of 4 lots outside the of the critical area. (buyer to verify) This offering consists of three parcels: Parcel #1 Main House with Rental Properties 21.34 +/- acres improved by a 5BR farmhouse (which includes a separately rented apartment above the garage), two guest cottages that are income producing, and two scenic ponds, one that can be hunted year round. A newly refurbished tennis court and pavilion overlook the second pond. The main house, a Victorian style farmhouse, has a brand new roof , geothermal units and outdoor deck. There is a historic section of the home and an addition built in the 1990’s. The main house also features a separate apartment above the garage for income potential, or ideal for a caretaker. Beautiful setting with mature trees, complete privacy and lovely vistas from several vantage points. Parcel #2 Land 83+/- acres (65 in till) in agriculture. Farm tenant in place. Community Boat Slip (25% interest) 1.424 +/- acres Deeded boat slip and water access on LaTrappe Creek via shared pier with 3 other homes. This is a unique property with an endless potential of uses, from a hunting retreat, private getaway, investment or combination of all.

28923 Island Creek Rd, Trappe

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$415,000
5 Beds 4 Baths
STUNNING VICTORIAN HOME ON HISTORIC WASHINGTON STREET! Welcome to 611 Washington Street, a beautifully restored Victorian home offering five bedrooms, 3.5 bathrooms, and three full levels of living space. Built in 1901 for Congressman Col. George Pearre, this home was designed by Wright Butler, a prominent architect. Located in the historic district, this exceptional home offers breathtaking mountain and city views. From the moment you arrive, the home’s charming curved front porch sets the tone for the character found throughout. Inside, a spacious foyer showcases exquisite woodwork, hardwood floors, and original fireplaces, leading to a formal living room, an elegant dining room, and a library with custom built-in bookcases. The renovated kitchen features stainless steel appliances, a center island, and ample workspace, while a convenient half bath completes the main level. Two staircases lead to the second floor, where you’ll find four bedrooms, two full bathrooms, and a versatile walk-in closet or office space. The fully finished basement offers incredible flexibility with a second kitchen, fifth bedroom, full bathroom, and laundry area. Additional highlights include a walk-up attic, central air, and off-street parking. All within walking distance to downtown Cumberland and with easy access to I-68!

611 Washington St, Cumberland

Listing courtesy of Mountainside Home Realty. Contact: 3017220190

$200,000
4 Beds 4 Baths
Welcome to 3014 Belmont Ave., a beautiful four-bedroom semi-detached townhouse located in the highly desirable Rosemont neighborhood, featuring a 17-foot wide single-car garage and a deck. This inviting home offers an open-concept layout with a bright breakfast area, perfect for both everyday living and entertaining. Charming original details and hardwood floors throughout create a warm blend of character and comfort. The main level includes a convenient half bath and a mudroom, adding both functionality and ease to daily living. Upstairs, you will find four generously sized, light-filled bedrooms, along with a full hallway bath and an additional half bath in the primary bedroom, offering flexibility and comfort for family or guests. The lower level provides a spacious and versatile open area, ideal for a home gym, playroom, office, or additional living space and a half bath. It also includes two dedicated storage areas and a jacuzzi, perfect for unwinding after a long day or post-workout relaxation.

3014 Belmont Ave, Baltimore

Listing courtesy of RLAH @properties. Contact: (301) 652-0643

$284,900
3 Beds 4 Baths
Welcome to this beautifully move-in-ready, updated Baltimore rowhome offering the perfect blend of space, style, and convenience. The main level flows effortlessly—ideal for both everyday living and entertaining—leading into a stylish kitchen with ample cabinetry and room to gather. Upstairs, you’ll find generously sized bedrooms along with 2 full bathrooms, providing comfort and flexibility for any lifestyle. The fully finished basement adds valuable living space, perfect for a guest suite, home office, gym, or entertainment area. Step outside to your private backyard—ideal for relaxing evenings or hosting friends. All of this in a location that truly delivers—just minutes from Patterson Park, the vibrant waterfront at Canton Waterfront Park, and the shops, dining, and nightlife of Fells Point. Whether you're a first-time buyer or looking to invest, this move-in-ready home offers incredible value in one of Baltimore’s most sought-after areas.

129 N Rose St, Baltimore

Listing courtesy of Century 21 Downtown. Contact:

$315,000
3 Beds 2 Baths
NEW PRICE! Folk Victorian home, featuring gingerbread trim and over 2000 sq ft., offers a versatile layout ideal for everyday living and entertaining. Spacious kitchen and family rooms with exposed beams provide warmth and character, while the primary suite and laundry on the main level add convenience. The family room bay window overlooks an adjacent lot for sale, presenting exciting opportunities for expansion, gardening, or added privacy. Outdoors, you have a composite deck where you can enjoy beautiful sunsets and a view of the Chesapeake City bridge, front porch, and fenced, sodded rear yard- perfect for gatherings or relaxing. Shed for added storage. While the home has had updates and repairs, it offers the opportunity to refresh finishes and flooring to make it your own.

320 Cecil St, Chesapeake City

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 879-8080

$900,000
5 Beds 4 Baths
Beautifully maintained and thoughtfully updated 5-bedroom, 3.5-bath residence set on over an acre in the Advocate Hill Farms community. Offering more than 5,500 square feet above grade and over 8,000 total square feet, this home combines scale, craftsmanship, and refined updates throughout. The main level showcases newly refinished wood flooring, soaring ceilings, and an expansive, well-designed layout. Multiple living and entertaining spaces include formal and casual areas, each enhanced by detailed millwork, abundant natural light, and five fireplaces that create warmth and architectural interest. The kitchen is designed for both function and style, featuring a large center island, table space, generous cabinetry, and seamless flow into surrounding gathering areas. French doors and large windows frame views of the property and provide access to outdoor living spaces, including a wraparound porch and rear deck. Upstairs, the primary suite offers a spacious retreat with a fireplace, private bath, and ample closet space. Additional bedrooms are generously sized and supported by well-appointed baths. The full lower level with outside access provides substantial space for storage, recreation, or future customization. Additional highlights include a 3-car attached garage, geothermal heating and cooling, central vacuum system, and private well with septic. The property is set on approximately 1.07 acres with mature landscaping and a tree-lined backdrop, offering a peaceful and expansive setting.

1614 Randallwood Ct, Jarrettsville

Listing courtesy of Next Step Realty. Contact: 4439012200

$499,999
4 Beds 4 Baths
Experience elevated coastal living in this beautiful fully renovated two story home in Cambridge Marylands’ historic district. This home features 3 spacious bedrooms and 3 full bathrooms, includes a detached 1 bedroom, 1 bath Accessory Dwelling Unit complete with its own kitchenette, perfect for guests, extended family, or rental income potential. This property offers stunning river views and a grand wrap-around porch ideal for relaxing evenings or entertaining while enjoying the coastal breeze. Inside, the home has undergone a complete 360 degree transformation with thoughtful, modern updates throughout. Abundant windows fill the home with natural light, creating a bright and airy atmosphere that enhances every living space. The new kitchen showcases new stainless steel appliances, Shaker Cabinetry, quartz countertops and stylish finishes. Every detail has been upgraded to provide comfort, functionality, and contemporary appeal, making this property truly move in ready. Opportunities like this do not come around often. Schedule your private tour today and experience this exceptional coastal property for yourself.

10 W End Ave, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000

$405,000
3 Beds 2 Baths
Huge price drop. You will be amazed at how spacious this home is. This charming Victorian in the heart of Halethorpe has undergone updating by blending classic elegance with modern comforts. With 3 spacious bedrooms and 2 additional bedroom/office spaces and 2 full bathrooms, this residence offers ample space for relaxation and entertaining. The electric has been upgraded and there are new appliances. Convenient to the train and major roads. Let your imagination go to work. Enjoy the convenience of off-street parking and a driveway, ensuring easy access for you and your guests. Nestled in a vibrant community, this home is just moments away from local amenities, providing a perfect balance of tranquility and accessibility. Experience the warmth and charm of this beautifully renovated property, where every detail has been thoughtfully designed to create a welcoming atmosphere. Don't miss the opportunity to make this house your home!

1712 Selma Ave, Baltimore

Listing courtesy of Keller Williams Preferred Properties. Contact:

$349,900
3 Beds 2 Baths
WOW! Seller is motivated and has drastically reduced. Act now while there is plenty of summer left. Chesapeake sunsets and Honga River sunrises. Watermen heading out at dawn. Ospreys, heron, and egrets hunting their dinner. A short walk to crabs harvested that very morning. Everything that makes the Eastern Shore unique -- the Bay, windswept marshes, seafood, its deeply rooted history -- in a magical place where time slows down so you can catch up. Check out the former Airbnb " Hoopers Island Victorian" listing to find out what makes the house and island so special, from the past visitor's reviews. 🏡 The House Cross a breathtaking causeway and you are smack dab in the middle of an island that measures 1/3 of a mile across. this Chesapeake Bay to the west, Honga River to the east, tidal marsh to the north, and a marina to the south. You are surrounded by water and can see it from every room in the house. A spacious Victorian filled with historic details, high ceilings and original hardwood floors. Windows everywhere, all designed to bring in natural light and bay breezes, 3 bedrooms (comfortably sleeps 8), 1.5 baths, all new appliances. 1.4 acres, privacy, outdoor shower, grazing deer and resident Osprey family. Air-conditioning, high-speed internet, 2 fridges. 🔑 Lock and Load All you have to do is move in. Seller has completed extensive renovations. Includes most furniture and lighting, including dining table and chairs, living room couch and chairs, 5 beds, bureaus, TV and 2 refrigerators. Hammock chairs, porch furniture, fishing poles, crab nets and appliances. 🌾 The Island Two miles off Maryland’s Eastern Shore and 45 minutes from historic Cambridge lies Hoopers Island—one of the last inhabited islands in the Chesapeake Bay. Stretching ten miles and made up of three barrier islands, it’s home to pelicans, ospreys, great blue herons, egrets, cormorants, ibis, and only about 500 year‑round residents. Outdoors, the lifestyle truly comes alive--summer firepits under the stars, crisp fall evenings along the shoreline, and kayak adventures just moments way (kayaks included). Each season brings its own rhythm from sun-soaked summer days to the deeply restorative autumn season. 📍 The Region Close to Easton, St. Michaels, and Oxford. Blackwater National Wildlife Refuge offers hiking paths and 17 miles of water trails and a wide variety of local wildlife and scenic views. The Harriet Tubman Museum. a 10-minute drive to Old Salty's Restaurant, an Eastern Shore institution. A 10-minute walk to the freshest crabmeat and steamed crabs. Day trips to Ocean City or Rehoboth Beach, or carve out a half day visit to St Michaels, Oxford or Easton/

1606 Steamboat Wharf Rd, Fishing Creek

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000

$280,000
3 Beds 2 Baths
Investor alert! Well-maintained duplex in convenient location offering strong income potential and flexible living options. Perfect opportunity for an owner-occupant or investor looking to grow a portfolio. Unit A (main level) features 1 bedroom, 1 full bathroom, living room, and kitchen with access to the basement for additional storage. Unit A is currently occupied, providing immediate rental income. Unit B is accessed from the rear of the property via a deck staircase and offers 2 bedrooms, 1 full bathroom, and a kitchen. This unit also includes attic access with additional living space, ideal for a home office, flex space, or storage. Property includes a rear parking lot providing off-street parking for both units. Separate entrances add privacy and functionality. With only one unit currently occupied, this is an excellent opportunity for owner-occupied living while generating rental income, or for an investor seeking a value-add addition to their portfolio. Multifamily MLS# MDCR2032814

71 Bond St, Westminster

Listing courtesy of Real Estate Innovations. Contact:

$345,000
4 Beds 3 Baths
31 Main Street – East New Market, Maryland Step back in time and experience the charm of this 1920 Victorian-style home located in the Historic District of the Town of East New Market. This home showcases many of its original architectural details and period character while offering several important modern updates. Over the years, the property has seen numerous improvements, including a new roof installed approximately five years ago, updated flooring, plumbing improvements, and an electrical upgrade. The furnace was replaced just two years ago, and a new hot water heater has also been installed. The home is currently heated with a pellet stove that conveys with the property, providing an efficient and cozy heating option. While the home does not currently have central air conditioning, a mini-split system could easily be installed to provide modern cooling while preserving the home’s historic character. Located in the heart of the charming Town of East New Market, residents enjoy a strong sense of community and a full calendar of events including Easter celebrations, May Day festivities, the annual Fourth of July celebration, and many other community gatherings throughout the year. The town is also planning a new amphitheater at Friendship Park, which will provide an exciting venue for concerts, educational programs, and community events. East New Market is known for its historic charm, welcoming community, and small-town character, making it a wonderful place to call home. Schedule your private showing today and come see the character and potential this historic home has to offer. Professional photography will be available soon. Important Note: The property tax amount estimated in the listing may not be accurate. Buyers are advised to verify the current tax information with the Dorchester County Tax Office

31 Main Street, East New Market

Listing courtesy of Keller Williams Realty. Contact: (443) 746-2132

$339,000
4 Beds 2 Baths
Live the Tilghman Island lifestyle just steps from the Chesapeake Bay. Perfectly positioned in the heart of historic Tilghman Island, this updated four-bedroom home offers the ability to enjoy one of Maryland's most authentic waterfront communities without the waterfront price tag. Walk to marinas, waterfront restaurants, charter fishing, Tilghman Wharf, and the iconic drawbridge, or spend your days exploring the Chesapeake by boat, kayak, or bicycle. Originally inspired by one of Tilghman's classic "M" homes, the residence blends timeless island character with modern updates. Inside, you'll find a spacious, open floor plan featuring an updated kitchen with granite countertops, stainless steel appliances, and abundant cabinetry, along with beautifully renovated bathrooms, new flooring, and a flexible layout that includes a first-floor bedroom and full bath—ideal for guests or one-level living. Three additional bedrooms and another updated full bath are located upstairs, providing plenty of space for family and friends. A new HVAC system adds year-round comfort, while the generous yard offers room for gardening, entertaining, or simply relaxing after a day on the water. Whether you're searching for a full-time residence, a weekend retreat, or an investment in one of the Eastern Shore's most charming villages, this home delivers exceptional value at an attractive price point. Experience the slower pace, rich maritime heritage, and unmatched sense of community that make Tilghman Island one of the Chesapeake Bay's hidden gems.

21524 Chicken Point Rd, Tilghman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$369,900
4 Beds 2 Baths
Major Reduction! Sellers are ready to move on! Homes like this is what they use for Christmas cards, large wrap around porch, entry foyer, detailed fireplaces, hard wood floors, and so much more. This is waiting for the right owner to continue the 126 years this home has stood. Everything in this home is in grand size. Large rooms, make this an easy home for a large family . The house current owners have the house set up as a six bedroom home. These rooms cannot be considered bedroom's to lack of closets. Located in historic Denton which sits on the Choptank River. A short walk to the 4th Street park with a playground for children , tennis and pickleball for adults and a picnic area. Additional parks are Martinak and Tuckahoe, which offer camping, walking trails, and access to the Choptank River. A public boat ramp is in town as well as in the park. Shopping is minutes away with a vast and fast growing commercial district offering a healthy mix of options. The surrounding area is full of nature lovers options, multiple farmers markets, small entrepreneurial businesses, which includes our local pub, a brewery, a bakery, and a culinary school just to name a few. This really is a special house and a special area. May be subject to a short sale.

112 S 5th Ave, Denton

Listing courtesy of Benson & Mangold, LLC.. Contact: (410) 479-0777

$1,179,000
4 Beds 3 Baths
Beautifully restored Historic Victorian in the heart of Saint Michaels. This charming home has a strong rental history, last tenant was paying $4,500 a month. From the wide, welcoming front porch to the gated, manicured yard—complete with a hammock ideal for long afternoon naps—every space is designed for comfort and relaxation. A brick walkway leads to the custom beveled‑glass entry door and into the warm, inviting family room. Inside, the home features rich pine floors throughout, a cherry kitchen with stainless steel appliances, granite countertops, and an open flow into the charming dining room. The spacious family room includes a propane stove for cozy winter days. The first floor also offers a full laundry room and an ornate powder room. The original staircase leads to the second floor, which includes three bedrooms and a renovated marble‑tile full bath. The private third‑floor primary suite offers a peaceful retreat with its own en‑suite bath. Just one block from the water—with water views from the street—this home captures the best of small‑town living. Enjoy walking access to Saint Michaels’ restaurants, quaint shops, kayaking, swimming, boating, and biking. It’s a special property ready for unforgettable memories with family and friends. Whether you're looking for a proven investment property or a beautiful home for your family, this one stands out.

101 Mulberry St, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$354,900
4 Beds 3 Baths
Back on the market due to buyer falling through, at no fault of the seller! This beautifully renovated Victorian home offers over 2,500 sq. ft. of living space with a perfect mix of character and modern updates. The main level features an open layout with a bright entry sunroom, spacious living and dining areas, and an updated kitchen with granite countertops and stainless steel appliances. A convenient main-level laundry area and half bath complete the space. Upstairs, the primary suite includes a walk-in closet and full bath, along with three additional bedrooms and another full bath. The finished basement provides flexible living or storage space. Enjoy a large rear yard ideal for relaxing or entertaining. The seller is also offering a 1-year home warranty for added peace of mind.

4919 Harford Rd, Baltimore

Listing courtesy of Mr. Lister Realty. Contact: (410) 486-5478