Vintage homes for sale & real estate in 21663, MD

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ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
INVESTOR SPECIAL – PRIME IN-TOWN ST. MICHAELS OPPORTUNITY! Bring your contractor, vision, and renovation plans to 105 W Marengo St. This circa-1890 home offers approximately 1,656 square feet and presents an excellent value-add opportunity for an investor, renovator, or buyer looking for a substantial project in highly desirable St. Michaels. The property is ready for renovation, providing an opportunity to restore its character while updating the home for today's buyer. Whether your strategy is renovate and resell, hold as an investment, or create a distinctive personal residence, the location makes this one worth a serious look. Enjoy an in-town St. Michaels location convenient to d

$349,000

3 beds1 bath1,656 sq ft

105 Marengo St, St Michaels, MD 21663

In-town location • 5,520 sq ft lot • Built 1890

(410) 544-2931

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Experience the quintessential coastal lifestyle in this historic gem, situated on one of the most sought-after streets in the St. Michaels historic district. Featuring timeless charm and character, this stately property perfectly blends classic architectural details (such as multiple built-ins and four working fireplaces) with modern convenience, all just a stone's throw from the town's vibrant harbor, boutique shops, and award-winning restaurants. Enter from the wide, covered front porch - ideal for morning coffee or greeting neighbors - into a grand, elongated foyer that sets a welcoming tone. The interior features gorgeous hardwood floors throughout, seamlessly connecting the bright livi

$1,195,000

4 beds4 baths3,528 sq ft

114 W Chestnut St, St Michaels, MD 21663

Covered front porch • Historic gem • Multiple built-ins

(410) 745-2596

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Opportunity awaits! This 4-bedroom, 2-bathroom, two-level home offers a functional layout and plenty of potential for its next owner. The main level features beautiful hardwood floors, a galley kitchen, a separate dining room, and comfortable living spaces. Outside, you'll find a spacious yard with a storage shed, providing plenty of room for outdoor activities, gardening, or future improvements. This home is in need of some TLC and is priced accordingly, making it an excellent opportunity for investors, renovators, or buyers looking to add their own personal touches and build equity. With great bones and endless possibilities, this property is ready to be transformed into something special

$399,000

4 beds2 baths1,743 sq ft

214 Madison Ave, St Michaels, MD 21663

Spacious yard • Galley kitchen • Separate dining room

(410) 266-0600

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
This beautiful historic house is located in the heart of Saint Michaels Historic District, within walking distance of waterfront parks, the harbor, shops, restaurants, the Maritime Museum, public boat ramp & more. Known as the "Keithley House, " the original dwelling was built in 1786, followed by additions believed to be added in the 1860-1870 time span. This home is beautifully updated while managing to keep & restore much of the original valued features, lending to its incredible charm & comfort. Extensive trim, exposed beams, hand huned wood, 4 fireplaces (3 wood burning, 1 electric), antique fixtures, heart pine floors & more. In addition to a lovel

$1,399,000

3 beds2.5 baths1,938 sq ft

104 Mulberry St, Saint Michaels, MD 21663

Waterfront parks • Historic house • Extensive trim

(410) 224-4400

FLOOR PLAN

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Since the owner purchased this house there has been a primary first floor master addition, all new windows throughout, updated stainless appliances, professional interior designer decorating, all new extensive landscaping with full irrigation and so much more!

$995,000

3 beds2.5 baths2,091 sq ft

101 Seymour, St Michaels, MD 21663

0.25 acre lot • 2 garage spots • Built 1947

(410) 822-6272

Property at 202 E Chestnut St, St Michaels, MD 21663, 3 beds, 3 baths

$1,250,000

3 beds3 baths2,052 sq ft

202 E Chestnut St, St Michaels, MD 21663

(410) 745-0415

Property at 803 New Ln, St Michaels, MD 21663, 3 beds, 2 baths

$695,000

3 beds2 baths1,288 sq ft

803 New Ln, St Michaels, MD 21663

(410) 745-2596

Property at 8090 Bozman Neavitt Rd, Bozman, MD 21612, 3 beds, 2 baths

$939,000

3 beds2 baths1,362 sq ft

8090 Bozman Neavitt Rd, Bozman, MD 21612

(410) 822-6665

Property at 8000 Bozman Neavitt Rd, Bozman, MD 21612, 3 beds, 2 baths

$439,000

3 beds2 baths1,761 sq ft

8000 Bozman Neavitt Rd, Bozman, MD 21612

(410) 745-0415

Property at 101 Mulberry St, St Michaels, MD 21663, 4 beds, 2.5 baths

$1,129,000

4 beds2.5 baths1,500 sq ft

101 Mulberry St, St Michaels, MD 21663

(410) 822-6272

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ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
NEW PRICE - Mc Daniel Rancher - This 3 Bedroom and 2 Bathroom rancher in the community of Mc Daniel, is conveniently located approximately 5 miles to St. Michaels. Close to half an acre of land, this property offers plenty of space for gardening and relaxing or grilling on the back deck. Just over 1400 square feet of living space, the dining room opens to the living room creating a generous space for gathering or entertaining. Newer vinyl plank flooring in bedrooms, living and dining rooms. Being sold "as is" condition.

$285,000

3 beds2 baths1,496 sq ft

9745 Tilghman Island Rd, Mcdaniel, MD 21647

Half an acre of land • Back deck • 0.47 acre lot

(410) 745-8060

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Offered for the first time in nearly 30 years, this charming waterfront bungalow on Duck Cove has been lovingly maintained and thoughtfully improved by its current owners. Filled with warmth and character, the home showcases beautiful original woodwork, hardwood floors, and a cozy wood-burning fireplace that creates an inviting atmosphere year-round. The main level features a spacious kitchen, convenient separate laundry room large dining area perfect for family dinners or entertaining. Plus a half bath, making everyday living easy and comfortable. A standout feature is the completely renovated 12' x 27' screened porch, where you can relax and enjoy peaceful views overlooking Duck Cove. Out

$849,900

3 beds1.5 baths1,176 sq ft

6355 Bozman Neavitt, Neavitt, MD 21652

Spacious kitchen • Large dining area • Original woodwork

(410) 770-9255

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
The perfect renovated, water view cottage, dating back to circa 1890. Has been meticulously maintained and thoughtfully expanded over the years. Located in the waterfront Village of Neavitt (+/- 70 homes). Move-in mint condition with numerous recent upgrades. First floor primary bedroom, first floor renovated full bathroom, two additional bedrooms and full bathroom upstairs. Outdoor Living: A large screened porch and deck extend the living space outdoors, providing opportunities to enjoy views of the large backyard and breezes off the water. Detached garage/shed with electric for storage of boats in addition to space for a workshop. Solar panels on roof are owned and convey. They substanti

$425,000

3 beds2 baths1,520 sq ft

6390 Bozman Neavitt Rd, Neavitt, MD 21652

0.38 acre lot • Built 1890 • Listed 180 days

(410) 822-6665

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Just 12 miles from St Michaels, this house is in a quiet community of 60+ homes at the end of a lovely peninsula. A public landing is at the end of Bozman Neavitt Road, and a community center and park are in the heart of the village. This property has been renovated and updated from the studs out. Features now include 2-3 Bedrooms 2 Full baths Living room with built-ins Light-filled kitchen with cathedral ceiling Large landscaped lot with patio A Short-term Rental application is underway. Ask owner for details. Some furniture conveys

$499,000

2 beds2 baths1,570 sq ft

6394 Bozman Neavitt Rd, Neavitt, MD 21652

Wrap around porch • Brick patio • Large private garden

(410) 745-2596

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Located in the waterfront village of Wittman, close to the public landing and county park, this beautifully crafted two-story cottage blends charm and character with thoughtful design. The home features 2 bedrooms, 1.5 baths, multiple living areas and 2 office spaces . Open beams, wood floors, and architectural details create a warm, inviting atmosphere throughout. Meticulous renovations by a master carpenter include elevating the home, new foundation and accessible crawl space. This unique property offers a perfect blend of craftsmanship and Chesapeake lifestyle. Enjoy the nearby amenities of St. Michaels, Tilghman Island and Easton - restaurants, shops, museums, galleries and more. If yo

$375,000

2 beds1.5 baths1,364 sq ft

8805 Cummings Rd, Wittman, MD 21676

0.28 acre lot • Built 1900 • Listed 299 days

(410) 745-0415

ABOUT THIS HOME
Vintage Home for sale in 21663, MD:
Rental Opportunity in Wittman, MD Positioned in the desirable community of Wittman, this 3 bedroom, 2 bath home situated on 0.84± commercially zoned acreage and premier road frontage presents a compelling opportunity for investors seeking potential rental income in Talbot County. The property offers comfortable living space, a rural Eastern Shore setting, and proximity to key employment, recreation, and service hubs. In addition to the primary residence, the property includes two detached outbuildings. One is ideal for storage or retail use, and another is suited for workshop or auto repair. The lot provides open space with ample parking and a private setting while remaining convenie

$295,000

3 beds2 baths3,924 sq ft

22314 Pot Pie Rd, Wittman, MD 21676

Minutes to dining • Minutes to marinas • Private setting

(410) 822-6272

Property at 6403 Bozman Neavitt Rd, Neavitt, MD 21652, 3 beds, 2 baths

$399,000

3 beds2 baths1,834 sq ft

6403 Bozman Neavitt Rd, Neavitt, MD 21652

(410) 745-2596

Vintage Homes for Sale in 21663

There are currently 10 vintage homes for sale in 21663 at a median listing price of $995K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in 21663 stay on the market for 118 days. This map is refreshed with the newest listings in 21663 every 15 minutes.

In the past month, 6 homes have been sold in 21663. In addition to houses in 21663, there were also 0 condos, 12 townhouses, and 1 multi-family unit for sale in 21663 last month. Find your dream home in 21663 using the tools above. Use filters to narrow your search by price, square feet, beds, and baths to find homes that fit your criteria. Our top-rated real estate agents in 21663 are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in 21663. If you're looking to sell your home in the 21663 area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in 21663 with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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