Vintage homes for sale & real estate in Dorchester County, MD

80 homes

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ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
Classic Historic Tidewater Colonial with 525+/- feet on the banks of Fishing Creek overlooking the Little Choptank River with a short ride to the Chesapeake Bay. Close to some of the best fishing spots on the Bay. This Historic Tidewater Colonial w/ two bedrooms, living room, den, family room, dining room, kitchen, scenic three season porch, utility room, and two car garage make the Bay and its tributaries a wonderful playground for anyone interested in living on Maryland's Eastern Shore. The property also consists of a guest house with two bedrooms, bath, living room and workshop on the first floor with roll-up doors for easy access, as well as, along with a separate expansive two car gara

$899,000

4 beds4 baths2,900 sq ft

1308 Town Point Rd, Cambridge, MD 21613

6.36 acre lot • 4 garage spots • Built 1820

(410) 228-0800

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
NEW PRICE Swan’s Nest: A Premier Waterfront Estate & Retreat Discover Swan’s Nest, a sprawling 8.310-acre private waterfront estate that seamlessly blends rustic charm with modern luxury. This magnificent property features a beautifully restored, fully furnished farmhouse, complemented by a unique deep-water marina perfect for boating enthusiasts. Nestled just 10 minutes from town and the renowned Hyatt Regency Resort, this estate is a haven for those seeking an exceptional hunting, fishing, and crabbing retreat. Whether you're looking for a peaceful getaway or a thriving business opportunity, Swan's Nest has it all, with a successful track record as a vacation rental and

$849,000

5 beds3 baths2,636 sq ft

5210 Wilson Rd, Cambridge, MD 21613

8.31 acre lot • Garage • Built 1932

(410) 304-2011

3D WALKTHROUGH

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
Beautifully renovated farmhouse offering versatile living space on just under three-quarters of an acre. Thoughtfully updated inside and out, this 3-bedroom, 2-bath home blends classic Eastern Shore architecture with high ceilings and large, airy windows with modern comforts designed for today’s lifestyle. The first floor features a spacious living area and a private office that could easily serve as a fourth bedroom if desired. Upstairs, the third-floor loft provides an additional private retreat; ideal for a rec room, home office, or guest space. Outdoor living features include a large deck, pool, hot tub, and an impressive 20x26 ft pool house, all enhanced by garden and security li

$449,900

3 beds2 baths2,098 sq ft

4904 Ravenwood Rd, Vienna, MD 21869

Renovated farmhouse • Large deck • Private office

(410) 822-6665

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
* * Property Description: Waterfront Brick Rancher with Stunning Sunsets * * Welcome to your dream waterfront retreat! This charming brick rancher features 3 spacious bedrooms and 2 full baths, perfect for a vacation rental or your forever home. As you step inside, you'll be greeted by stunning hardwood floors that flow throughout the home. The inviting living room boasts a brick wood-burning fireplace and picturesque views of Jenkins Creek, creating a cozy atmosphere for relaxation. Enjoy breathtaking sunsets from the comfort of your living space as the day winds down. The den, complete with built-in shelves, offers a great space for reading or a home office. Enjoy formal dining in the

$1,300,000

3 beds2.5 baths2,195 sq ft

2202 Jenkins Creek Rd, Cambridge, MD 21613

In-ground pool • Screened porch • Updated kitchen

(443) 225-4100

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
Welcome to 116 Oakley Street, a spacious and soulful home located on the coveted 100's block of Cambridge’s Historic West End. The updated kitchen blends functionality with flair, boasting generous cabinetry, and a butler-style pantry. A first floor primary suite offers convenience not often found in homes of this era. A full staircase—accented by charming built-ins—leads to the second and third floors, where creative spaces and flexible rooms await. Upstairs, the sun-drenched primary bedroom includes a walk-in closet and laundry center and connects to a third bedroom currently used as a studio or workspace. A freshly renovated bathroom and two additional bedrooms offer sp

$374,000

5 beds3 baths2,931 sq ft

116 Oakley St, Cambridge, MD 21613

8,400 sq ft lot • 4 parking spots • Built 1918

(410) 228-2525

Property at 2208 Horns Point Rd, Cambridge, MD 21613, 5 beds, 4.5 baths

$1,300,000

5 beds4.5 baths4,272 sq ft

2208 Horns Point Rd, Cambridge, MD 21613

(410) 228-0800

Property at 610 Washington St, Cambridge, MD 21613, 3 beds, 2 baths

$125,000

3 beds2 baths1,088 sq ft

610 Washington St, Cambridge, MD 21613

(410) 228-2525

Property at 205 Byrn St, Cambridge, MD 21613, 4 beds, 3 baths

$299,900

4 beds3 baths1,314 sq ft

205 Byrn St, Cambridge, MD 21613

(410) 228-2525

Property at 817 Locust St, Cambridge, MD 21613, 4 beds, 2 baths

$300,000

4 beds2 baths2,316 sq ft

817 Locust St, Cambridge, MD 21613

(302) 539-0800

Property at 506 Robbins St, Cambridge, MD 21613, 3 beds, 1 bath

$89,900

3 beds1 bath1,448 sq ft

506 Robbins St, Cambridge, MD 21613

(410) 228-9333

Property at 2136 Hoopersville Rd, Fishing Creek, MD 21634, 3 beds, 2 baths

$194,000

3 beds2 baths1,286 sq ft

2136 Hoopersville Rd, Fishing Creek, MD 21634

(301) 703-8169

Property at 603 Roslyn Ave, Cambridge, MD 21613, 3 beds, 1 bath

$349,000

3 beds1 bath1,572 sq ft

603 Roslyn Ave, Cambridge, MD 21613

(410) 228-0800

Property at 109 Gay St, Vienna, MD 21869, 2 beds, 1 bath

$224,900

2 beds1 bath1,615 sq ft

109 Gay St, Vienna, MD 21869

(855) 204-2400

Property at 706 Locust St, Cambridge, MD 21613, 5 beds, 3.5 baths

$295,000

5 beds3.5 baths3,119 sq ft

706 Locust St, Cambridge, MD 21613

(410) 822-6665

Property at 511 Pine St, Cambridge, MD 21613, 8 beds

$99,000

8 beds— baths2,892 sq ft

511 Pine St, Cambridge, MD 21613

(215) 627-3500

Property at 112 West End Ave, Cambridge, MD 21613, 3 beds, 2 baths

$258,000

3 beds2 baths1,873 sq ft

112 West End Ave, Cambridge, MD 21613

(410) 228-9333

Property at 1622 Town Point Rd, Cambridge, MD 21613, 3 beds, 2.5 baths

$450,000

3 beds2.5 baths2,194 sq ft

1622 Town Point Rd, Cambridge, MD 21613

(410) 228-9333

Property at 2527 Old House Point Rd, Fishing Creek, MD 21634, 2 beds, 2 baths

$299,000

2 beds2 baths1,104 sq ft

2527 Old House Point Rd, Fishing Creek, MD 21634

(410) 822-6272

Property at 201 Washington St, Cambridge, MD 21613, 3 beds, 1 bath

$179,000

3 beds1 bath1,642 sq ft

201 Washington St, Cambridge, MD 21613

(410) 429-7425

Property at 401 N Main St, Hurlock, MD 21643, 6 beds, 4 baths

$390,000

6 beds4 baths3,854 sq ft

401 N Main St, Hurlock, MD 21643

(443) 992-4990

Property at 5 Willis St, Cambridge, MD 21613, 3 beds, 2 baths

$309,000

3 beds2 baths1,863 sq ft

5 Willis St, Cambridge, MD 21613

(410) 822-1415

Property at 601 Edlon Park Dr, Cambridge, MD 21613, 3 beds, 2.5 baths

$290,000

3 beds2.5 baths1,860 sq ft

601 Edlon Park Dr, Cambridge, MD 21613

(410) 271-1265

Property at 2539 Old House Point Rd, Fishing Creek, MD 21634, 2 beds, 1.5 baths

$189,000

2 beds1.5 baths1,152 sq ft

2539 Old House Point Rd, Fishing Creek, MD 21634

(410) 673-3344

Property at 3 Talbot Ave, Cambridge, MD 21613, 3 beds, 2 baths

$390,999

3 beds2 baths1,508 sq ft

3 Talbot Ave, Cambridge, MD 21613

(703) 242-0005

Property at 1008 Phillips St, Cambridge, MD 21613, 3 beds, 1 bath

$110,000

3 beds1 bath976 sq ft

1008 Phillips St, Cambridge, MD 21613

(410) 228-2525

Property at 408 Bayly Ave, Cambridge, MD 21613, 2 beds, 1 bath

$249,000

2 beds1 bath1,004 sq ft

408 Bayly Ave, Cambridge, MD 21613

(410) 429-7425

Property at 722 Glasgow St, Cambridge, MD 21613, 3 beds, 2 baths

$185,000

3 beds2 baths1,592 sq ft

722 Glasgow St, Cambridge, MD 21613

(410) 304-2011

Property at 2835 Crocheron Rd, Crocheron, MD 21627, 2 beds, 1 bath

$59,000

2 beds1 bath1,128 sq ft

2835 Crocheron Rd, Crocheron, MD 21627

(410) 822-6665

Property at 212 S Main St, Hurlock, MD 21643, 4 beds, 2 baths

$150,000

4 beds2 baths1,732 sq ft

212 S Main St, Hurlock, MD 21643

(410) 543-4545

Property at 2 South Main St, East New Market, MD 21631, 4 beds, 3.5 baths

$449,900

4 beds3.5 baths2,178 sq ft

2 South Main St, East New Market, MD 21631

(410) 228-9333

Property at 1105 Holland Ave, Cambridge, MD 21613, 2 beds, 1 bath

$215,000

2 beds1 bath752 sq ft

1105 Holland Ave, Cambridge, MD 21613

(410) 822-6665

Property at 904 & 906 Oakley Ter, Cambridge, MD 21613, 2 beds, 1 bath

$449,900

2 beds1 bath1,768 sq ft

904 & 906 Oakley Ter, Cambridge, MD 21613

(410) 228-9333

Property at 5631 Cedar Grove Rd, East New Market, MD 21631, 3 beds, 1 bath

$680,000

3 beds1 bath984 sq ft

5631 Cedar Grove Rd, East New Market, MD 21631

(443) 856-2211

Property at 9 W End Ave, Cambridge, MD 21613, 3 beds, 2 baths

$499,000

3 beds2 baths2,064 sq ft

9 W End Ave, Cambridge, MD 21613

(410) 429-7425

$725,000

— beds— baths— sq ft

Farm Crk, Wingate, MD 21675

(410) 822-9000

Property at BTW 800-802 Center St, Cambridge, MD 21613

$15,000

— beds— baths— sq ft

BTW 800-802 Center St, Cambridge, MD 21613

(443) 324-6001

Property at 300 Muir St, Cambridge, MD 21613

$449,900

— beds— baths— sq ft

300 Muir St, Cambridge, MD 21613

(410) 822-6665

Property at 301 & 303 Dorchester Ave, Cambridge, MD 21613

$89,000

— beds— baths— sq ft

301 & 303 Dorchester Ave, Cambridge, MD 21613

(410) 228-2525

Property at Petersburg Rd, Hurlock, MD 21643

$230,000

— beds— baths— sq ft

Petersburg Rd, Hurlock, MD 21643

(410) 479-4663

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Vintage Homes for Sale in Dorchester County

There are currently 80 vintage homes for sale in Dorchester County at a median listing price of $325K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Dorchester County stay on the market for 85 days and receive 1 offers. This map is refreshed with the newest listings in Dorchester County every 15 minutes.

In the past month, 40 homes have been sold in Dorchester County. In addition to houses in Dorchester County, there were also 13 condos, 35 townhouses, and 3 multi-family units for sale in Dorchester County last month. Find your dream home in Dorchester County 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 Dorchester County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Dorchester County. If you're looking to sell your home in the Dorchester County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Dorchester County with industry-leading technology, full-service agents, and lower fees that provide a better value for Redfin buyers and sellers.

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