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

36 homes

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ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
This Craftsman style home offers a blank canvas for your vision of classic architectural elements for the discerning buyers. This property presents excellent investment potential. The solid construction provides a strong foundation for future appreciation. With thoughtful updates, this home could significantly increase in value while maintaining its distinctive character. The exterior storage shed adds practical value and additional storage capacity, enhancing the property's appeal to potential buyers. This feature provides convenient space for tools, equipment, or seasonal items, making the home more functional and attractive in the marketplace.

$89,900

2 beds1 bath960 sq ft

11584 Greensboro Rd, Greensboro, MD 21639

Solid construction • Craftsman style home • 0.86 acre lot

(410) 479-3993

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Needs Work. sold as is - large home in need of updating/TLC - 2-story 3 car garage

$225,000

3 beds1.5 baths2,817 sq ft

22060 Main St, Hillsboro, MD 21641

0.49 acre lot • Built 1900 • Listed 5 days

(410) 320-6785

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
For The Love Of Old Homes!! This big and bold 1900s landmark is bursting with soul and charm. Spanning over 2700+ square feet and boasting 6-7 bedrooms / 3 full baths across three stories, it’s the ultimate setting for grand entertaining or quiet relaxation. From the welcoming foyer to the third-floor retreat, every inch exudes character. It’s move-in ready but invites your creative TLC to truly shine. The home offers large rooms with high ceilings, hardwood floors and some expected original features. Included on the main level is a kitchen, living room, dining room, playroom/office/versatile space, full bathroom and a large laundry/mudroom. There are two staircases leading to t

$349,900

7 beds3 baths2,729 sq ft

210 Old Line Rd, Goldsboro, MD 21636

Third floor retreat • Outbuilding • Welcoming foyer

(410) 827-4663

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
This Colonial home features timeless architecture and thoughtful design. The property offers solid construction and classic appeal, making it an excellent opportunity for discerning buyers. This distinctive property presents an outstanding opportunity for transformation and value creation. The established neighborhood setting combines small-town charm with practical accessibility to essential services.

$135,000

3 beds2 baths1,488 sq ft

103 Chamber St, Preston, MD 21655

Solid construction • Classic appeal • 0.33 acre lot

(410) 479-3993

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Charming Colonial-style farmhouse set on 9 scenic acres, offering a rare blend of historic character, pastoral beauty, and endless potential. Ideal for animal lovers or those seeking a peaceful weekend retreat, the home features hardwood floors, exposed ceiling beams, and three wood-burning stoves that add warmth and timeless appeal. Large Spacious bedrooms, a screened porch and rear patio provide tranquil spaces to relax and enjoy the surrounding countryside. The property includes multiple pastures and an array of outbuildings, including a barn, and tool shop—perfect for animals, hobbies, or small-scale farming. Multiple Fruit & Nut trees: Pear, Apple, Fig, Sour Cherry, Mulberr

$475,000

3 beds2 baths2,038 sq ft

27329 Iron Gate Rd, Federalsburg, MD 21632

Screened porch • Wood burning stoves • Hardwood floors

(410) 271-1265

Property at 318 Carter Ave, Denton, MD 21629, 2 beds, 2 baths

$214,900

2 beds2 baths606 sq ft

318 Carter Ave, Denton, MD 21629

(410) 770-9255

Property at 106 S 6th St, Denton, MD 21629, 3 beds, 2 baths

$159,000

3 beds2 baths2,776 sq ft

106 S 6th St, Denton, MD 21629

(410) 543-4545

Property at 113 Maple Ave, Goldsboro, MD 21636, 3 beds, 2 baths

$230,000

3 beds2 baths1,448 sq ft

113 Maple Ave, Goldsboro, MD 21636

(410) 643-4663

Property at 305 Central Ave, Ridgely, MD 21660, 5 beds, 2 baths

$299,000

5 beds2 baths2,574 sq ft

305 Central Ave, Ridgely, MD 21660

(410) 822-9000

Property at 804 Gay St, Denton, MD 21629, 2 beds, 1 bath

$99,000

2 beds1 bath956 sq ft

804 Gay St, Denton, MD 21629

(410) 479-2000

Property at 229 Oldtown Rd, Goldsboro, MD 21636, 3 beds, 2 baths

$265,000

3 beds2 baths1,368 sq ft

229 Oldtown Rd, Goldsboro, MD 21636

(301) 970-2447

Property at 4215 Preston Rd, Preston, MD 21655, 3 beds, 2 baths

$359,000

3 beds2 baths1,642 sq ft

4215 Preston Rd, Preston, MD 21655

(410) 479-2000

Property at 306 S Main St, Federalsburg, MD 21632, 4 beds, 1.5 baths

$269,900

4 beds1.5 baths2,820 sq ft

306 S Main St, Federalsburg, MD 21632

(410) 271-1265

Property at 207 Bloomingdale Ave, Federalsburg, MD 21632, 3 beds, 2 baths

$247,500

3 beds2 baths1,684 sq ft

207 Bloomingdale Ave, Federalsburg, MD 21632

(302) 217-6692

Property at 2766 Veterans Dr, Federalsburg, MD 21632, 3 beds, 1 bath

$299,000

3 beds1 bath1,284 sq ft

2766 Veterans Dr, Federalsburg, MD 21632

(410) 479-4663

Property at 24800 Pealiquor Rd, Denton, MD 21629, 4 beds, 3.5 baths

$1,295,000

4 beds3.5 baths4,496 sq ft

24800 Pealiquor Rd, Denton, MD 21629

(304) 645-7700

Property at 506 Park Ave, Ridgely, MD 21660, 2 beds, 1 bath

$298,000

2 beds1 bath1,528 sq ft

506 Park Ave, Ridgely, MD 21660

(302) 360-0300

Property at 206 Academy St, Greensboro, MD 21639, 3 beds, 1.5 baths

$239,999

3 beds1.5 baths1,565 sq ft

206 Academy St, Greensboro, MD 21639

(302) 217-6692

Property at 25699 Auction Rd, Federalsburg, MD 21632, 4 beds, 2 baths

$500,000

4 beds2 baths1,986 sq ft

25699 Auction Rd, Federalsburg, MD 21632

Property at 4 S 1st St S, Denton, MD 21629, 3 beds, 3 baths

$699,000

3 beds3 baths2,756 sq ft

4 S 1st St S, Denton, MD 21629

(410) 479-4663

Property at 511 Bernard Ave, Greensboro, MD 21639, 3 beds, 1 bath

$245,000

3 beds1 bath1,385 sq ft

511 Bernard Ave, Greensboro, MD 21639

(410) 827-4663

Property at 208 Main St, Federalsburg, MD 21632, 4 beds, 1.5 baths

$150,000

4 beds1.5 baths2,668 sq ft

208 Main St, Federalsburg, MD 21632

(410) 754-7000

Property at 3540 Houston Branch Rd, Federalsburg, MD 21632, 2 beds, 1 bath

$279,000

2 beds1 bath1,140 sq ft

3540 Houston Branch Rd, Federalsburg, MD 21632

(410) 822-1415

Property at 321/323 S Main, Federalsburg, MD 21632, 6 beds, 2 baths

$129,000

6 beds2 baths2,400 sq ft

321/323 S Main, Federalsburg, MD 21632

(410) 543-4545

Property at 21948 Main St, Hillsboro, MD 21641, 3 beds, 1 bath

$189,900

3 beds1 bath1,904 sq ft

21948 Main St, Hillsboro, MD 21641

(410) 479-3993

Property at 212 Main St, Preston, MD 21655, 5 beds, 3 baths

$320,000

5 beds3 baths2,122 sq ft

212 Main St, Preston, MD 21655

(888) 860-7369

Property at 204 Academy Ave, Federalsburg, MD 21632, 2 beds, 1 bath

$24,500

2 beds1 bath1,024 sq ft

204 Academy Ave, Federalsburg, MD 21632

(410) 677-0909

Property at 22005 Main St, Hillsboro, MD 21641, 3 beds, 3 baths

$545,000

3 beds3 baths3,088 sq ft

22005 Main St, Hillsboro, MD 21641

(410) 778-9319

Property at 158 Wright St, Preston, MD 21655, 3 beds, 2 baths

$245,000

3 beds2 baths1,840 sq ft

158 Wright St, Preston, MD 21655

(410) 822-9000

Property at 227 Burnite Mill Rd, Harrington, DE 19952, 3 beds, 1.5 baths

$280,000

3 beds1.5 baths2,026 sq ft

227 Burnite Mill Rd, Harrington, DE 19952

(302) 360-0300

Property at 310 Main St, Marydel, MD 21649, 9 beds

$620,000

9 beds— baths3,600 sq ft

310 Main St, Marydel, MD 21649

(410) 524-6400

Property at 501 Lincoln St, Denton, MD 21629, 3 beds, 1.5 baths

$135,000

3 beds1.5 baths1,664 sq ft

501 Lincoln St, Denton, MD 21629

(410) 479-2000

Property at 28035 Possum Hill Rd, Federalsburg, MD 21632

$125,000

— beds— baths2,168 sq ft

28035 Possum Hill Rd, Federalsburg, MD 21632

(703) 538-1113

Property at 26355 Marydel Rd, Marydel, MD 21649, 1 bed, 1 bath

$155,000

1 bed1 bath512 sq ft

26355 Marydel Rd, Marydel, MD 21649

(410) 479-3993

Property at 23547 Jonestown Ln, Preston, MD 21655

$25,000

— beds— baths728 sq ft

23547 Jonestown Ln, Preston, MD 21655

(410) 972-4000

Property at 10440 Burrsville Branch Rd, Denton, MD 21629

$89,000

— beds— baths— sq ft

10440 Burrsville Branch Rd, Denton, MD 21629

(443) 988-0483

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Vintage Homes for Sale in Caroline County

There are currently 36 vintage homes for sale in Caroline County at a median listing price of $320K. Some of these homes are "Hot Homes," meaning they're likely to sell quickly. Most homes for sale in Caroline County stay on the market for 73 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 30 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 5 townhouses, and 4 multi-family units for sale in Caroline County last month. Find your dream home in Caroline 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 Caroline County are local experts and are ready to answer your questions about properties, neighborhoods, schools, and the newest listings for sale in Caroline County. If you're looking to sell your home in the Caroline County area, our listing agents can help you get the best price. Redfin is redefining real estate and the home buying process in Caroline 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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Vintage homes for sale & real estate in Caroline County, MD

Vintage Homes for Sale in Caroline County

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