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

79 homes

Sort:

Recommended

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
Well built and lovingly maintained 3 bedroom, 2 bath rancher on 1 acre. New roof installed 2024. Nice open yard with established shade trees around the house. Small barn at rear of the property.

$359,000

3 beds2 baths1,642 sq ft

4215 Preston Rd, Preston, MD 21655

1 acre lot • 4 parking spots • Built 1959

(410) 479-2000

$100,000

3 beds1 bath1,224 sq ft

2530 Toddville Rd, Toddville, MD 21672

Spacious yard • Outdoor recreation • Water access

(410) 304-2011

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
THE ORIGINAL HOME OF "CAPTAIN JOHNNIE" BUILT IN 1920 AND TOTALLY RESTORED. EXPANSIVE WATER-VIEWS WITH 300 FEET OF RIP RAP/BULK HEADING. PERFECT FOR YEAR ROUND LIVING, WEEKLY VACATION RENTAL OR VACATION HOME . BEAUTIFUL HARDWOOD FLOORS, FULLY EQUIPPED EAT IN KITCHEN, HUGE FAMILY/GREAT ROOM WITH WALL MOUNTED TV . HOME IS FULLY FURNISHED AND EXCEPTIONALLY EQUIPPED - EVERYTHING EXCEPT POOL/CARD TALBE CONVEYS. DIRECT TV AND HUGHES INTERNET. NIT-RED SEPTIC SYSTEM, HAS BEEN A SUCCESSFUL VACATION RENTAL - CAN PROVIDE DOCUMENTATION. LARGE OUTBUILDING HOUSING BIKES, CANOES AND KAYAKS THAT ALL CONVEY FABULOUS ON LINE ARTICLE AND PICTURES OF HOOPERS ISLAND AND LOCATION "ONLYINYOURSTATE

$699,900

7 beds2.5 baths2,204 sq ft

1632 Steamboat Wharf Rd S, Fishing Creek, MD 21634

Water views • Rip rap bulk heading • 2.49 acre lot

(866) 987-3937

OPEN DEC 13, 11AM TO 1PM

$235,000

2 beds1 bath972 sq ft

409 Oakley, Cambridge, MD 21613

6,909 sq ft lot • Built 1932 • Listed 4 days

(302) 360-0300

ABOUT THIS HOME
Vintage Home for sale in Dorchester County, MD:
Discover the perfect blend of character and functionality in this spacious classic home, ideally situated half a block from the Robbins Family YMCA. Nestled in an established neighborhood, this property offers the best of both worlds—tranquil residential living with easy access to Gerry Boyle Park at Great Marsh and a short stroll to downtown Cambridge. The traditional floor plan provides versatility with a welcoming living room, family room, formal dining room, and kitchen on the main level. The convenient first-floor primary suite allows for single-level living, while three additional bedrooms and a full bath upstairs offer plenty of space for family or guests. A generous cedar-line

$250,000

4 beds2 baths1,953 sq ft

113 Talbot Ave, Cambridge, MD 21613

0.31 acre lot • 3 parking spots • Built 1930

(410) 543-4545

Property at 2238 Pig Neck Rd, Cambridge, MD 21613, 3 beds, 2 baths

$1,495,000

3 beds2 baths3,344 sq ft

2238 Pig Neck Rd, Cambridge, MD 21613

(410) 643-4663

Property at 5904 Harvey St, East New Market, MD 21631, 4 beds, 2 baths

$329,000

4 beds2 baths1,388 sq ft

5904 Harvey St, East New Market, MD 21631

(202) 313-2590

Property at 2603 Toddville Rd, Toddville, MD 21672, 2 beds, 1 bath

$49,000

2 beds1 bath768 sq ft

2603 Toddville Rd, Toddville, MD 21672

(410) 543-4545

Property at 3241 Robbins Rd, Crapo, MD 21626

$239,000

— beds— baths1,260 sq ft

3241 Robbins Rd, Crapo, MD 21626

(410) 304-2011

Property at 909 Pine St, Cambridge, MD 21613, 2 beds, 1 bath

$124,900

2 beds1 bath672 sq ft

909 Pine St, Cambridge, MD 21613

(410) 822-6272

Property at 1604 Steamboat Wharf Rd, Fishing Creek, MD 21634, 3 beds, 1 bath

$140,000

3 beds1 bath3,144 sq ft

1604 Steamboat Wharf Rd, Fishing Creek, MD 21634

(410) 330-9933

Property at 201 Buena Vista Ave, Cambridge, MD 21613, 3 beds, 2 baths

$389,700

3 beds2 baths1,172 sq ft

201 Buena Vista Ave, Cambridge, MD 21613

(410) 677-0909

Property at 901 Talisman Ln, Cambridge, MD 21613, 3 beds, 2 baths

$269,400

3 beds2 baths1,453 sq ft

901 Talisman Ln, Cambridge, MD 21613

(304) 645-7700

Property at 107 Rambler Rd, Cambridge, MD 21613, 3 beds, 1.5 baths

$254,900

3 beds1.5 baths1,912 sq ft

107 Rambler Rd, Cambridge, MD 21613

(410) 822-6665

Property at 409 Bayly Ave, Cambridge, MD 21613, 3 beds, 1 bath

$284,950

3 beds1 bath1,200 sq ft

409 Bayly Ave, Cambridge, MD 21613

(410) 221-8000

Property at 402 Oakley St, Cambridge, MD 21613, 2 beds, 1 bath

$199,000

2 beds1 bath1,202 sq ft

402 Oakley St, Cambridge, MD 21613

(410) 221-8000

Property at 800 Wood St, Cambridge, MD 21613, 2 beds, 1 bath

$160,000

2 beds1 bath720 sq ft

800 Wood St, Cambridge, MD 21613

(410) 822-9000

Property at 311 E Appleby Ave, Cambridge, MD 21613, 2 beds, 3 baths

$265,000

2 beds3 baths1,348 sq ft

311 E Appleby Ave, Cambridge, MD 21613

(410) 749-4663

Property at 430 Leonards Ln, Cambridge, MD 21613, 2 beds, 1 bath

$167,000

2 beds1 bath756 sq ft

430 Leonards Ln, Cambridge, MD 21613

(410) 543-4545

Property at 109 Mill St, Cambridge, MD 21613, 4 beds, 1.5 baths

$385,000

4 beds1.5 baths2,520 sq ft

109 Mill St, Cambridge, MD 21613

(410) 228-2525

Property at 807 Pine St, Cambridge, MD 21613, 3 beds, 1 bath

$164,900

3 beds1 bath1,000 sq ft

807 Pine St, Cambridge, MD 21613

(410) 548-5484

Property at 1318 Bell Ln, Woolford, MD 21677, 3 beds, 2 baths

$875,000

3 beds2 baths2,120 sq ft

1318 Bell Ln, Woolford, MD 21677

(410) 673-3344

Property at 405 Leonards Ln, Cambridge, MD 21613, 4 beds, 2 baths

$234,000

4 beds2 baths1,608 sq ft

405 Leonards Ln, Cambridge, MD 21613

(410) 271-1265

Property at 2145 Farm Creek Rd, Wingate, MD 21675, 1 bed, 1 bath

$65,000

1 bed1 bath528 sq ft

2145 Farm Creek Rd, Wingate, MD 21675

(410) 860-6800

Property at 613 School House Ln, Cambridge, MD 21613, 6 beds

$100,000

6 beds— baths1,728 sq ft

613 School House Ln, Cambridge, MD 21613

(443) 324-6001

Property at 2404 Hoopers Island Rd, Fishing Creek, MD 21634, 3 beds, 2 baths

$515,000

3 beds2 baths2,664 sq ft

2404 Hoopers Island Rd, Fishing Creek, MD 21634

(410) 729-7700

Property at 4909 Ravenwood Rd, Vienna, MD 21869, 3 beds, 2 baths

$299,900

3 beds2 baths1,638 sq ft

4909 Ravenwood Rd, Vienna, MD 21869

(410) 543-4545

Property at 309 S Main St, Hurlock, MD 21643, 6 beds, 2 baths

$200,000

6 beds2 baths6,970 sq ft

309 S Main St, Hurlock, MD 21643

(410) 220-5745

Property at 802 Allen St, Cambridge, MD 21613, 2 beds, 1.5 baths

$240,000

2 beds1.5 baths784 sq ft

802 Allen St, Cambridge, MD 21613

(240) 965-0053

Property at 206 Maryland Ave, Cambridge, MD 21613, 5 beds

$224,900

5 beds— baths2,484 sq ft

206 Maryland Ave, Cambridge, MD 21613

(302) 846-7839

Property at 5936 Newhart Mill Rd, Rhodesdale, MD 21659

$158,900

— beds— baths— sq ft

5936 Newhart Mill Rd, Rhodesdale, MD 21659

(410) 934-3478

Property at 306 Belvedere Ave, Cambridge, MD 21613, 4 beds, 2 baths

$434,900

4 beds2 baths2,816 sq ft

306 Belvedere Ave, Cambridge, MD 21613

(410) 543-4545

Property at 809 Truman St, Cambridge, MD 21613, 3 beds, 2 baths

$204,999

3 beds2 baths1,066 sq ft

809 Truman St, Cambridge, MD 21613

(855) 450-0442

Property at 2703 Toddville Rd, Toddville, MD 21672, 3 beds, 1 bath

$189,000

3 beds1 bath808 sq ft

2703 Toddville Rd, Toddville, MD 21672

(410) 822-6272

Property at 511 High St, Cambridge, MD 21613

$55,000

— beds— baths792 sq ft

511 High St, Cambridge, MD 21613

(410) 754-7000

Property at 400 Robbins St, Cambridge, MD 21613, 3 beds, 2 baths

$160,000

3 beds2 baths1,248 sq ft

400 Robbins St, Cambridge, MD 21613

(410) 822-9000

Property at 122 Vue De Leau St, Cambridge, MD 21613, 4 beds, 2 baths

$379,000

4 beds2 baths2,148 sq ft

122 Vue De Leau St, Cambridge, MD 21613

(410) 228-2525

Property at 5611 Galestown Rd, Seaford, MD 19973, 3 beds, 2 baths

$132,000

3 beds2 baths1,716 sq ft

5611 Galestown Rd, Seaford, MD 19973

(410) 228-2525

Property at 314 Belvedere Ave, Cambridge, MD 21613, 3 beds, 3.5 baths

$399,000

3 beds3.5 baths2,617 sq ft

314 Belvedere Ave, Cambridge, MD 21613

Property at 5210 Wilson Rd, Cambridge, MD 21613, 5 beds, 3 baths

$849,000

5 beds3 baths2,636 sq ft

5210 Wilson Rd, Cambridge, MD 21613

(410) 304-2011

Property at 1308 Town Point Rd, Cambridge, MD 21613, 4 beds, 4 baths

$899,000

4 beds4 baths2,900 sq ft

1308 Town Point Rd, Cambridge, MD 21613

(410) 228-0800

Viewing page 1 of 2

Vintage Homes for Sale in Dorchester County

There are currently 79 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 90 days and receive 1 offers. This map is refreshed with the newest listings in Dorchester County every 15 minutes.

In the past month, 32 homes have been sold in Dorchester County. In addition to houses in Dorchester County, there were also 14 condos, 35 townhouses, and 2 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.

More real estate resources for Dorchester County, MD

Cities

Nearby Counties

Nearby Counties with Vintage Homes

Nearby Cities with Vintage Homes

More to explore in Dorchester County, MD

How to buy a house in Dorchester County, MD

How much house can I afford?

How to buy a house in 10 steps

First-time homebuyer's guide

See more home buying guides

Popular Markets in Maryland

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Why Redfin?

Community Impact

Diversity & Inclusion

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.