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

35 homes

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ABOUT THIS HOME
Vintage Home for sale in Caroline 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

NEW 34 HRS AGO

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Seller Requestes to use Cardinal Title. Sold AS-IS and Priced to Sell! Located on a quiet rural road, this 1-acre property is ideal for investors, homeowners or builders. Major rehab needed or tear down and build your dream home. Great opportunity!

$89,900

3 beds1 bath1,152 sq ft

22415 Hillsboro Rd, Denton, MD 21629

1-acre property • 1 acre lot • Built 1910

(443) 317-8125

NEW 32 HRS AGO

$155,000

3 beds1.5 baths1,393 sq ft

109 Buena Vista Buena Vista Ave, Federalsburg, MD 21632

5,130 sq ft lot • Built 1932

(410) 754-7000

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Charming colonial in the heart of Denton, thoughtfully converted into a two-unit multifamily property. Nestled on a quiet street, this home offers flexible living options with spacious layouts, classic character, and excellent potential for rental income or multigenerational living. A wonderful opportunity to invest or reside in a peaceful in-town setting. Great investment property.

$169,000

3 beds2 baths2,776 sq ft

106 S 6th St, Denton, MD 21629

Investment property • 9,800 sq ft lot • 2 parking spots

(410) 543-4545

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
This charming bungalow, fully renovated in 2020 and move-in ready, blends modern comfort with timeless appeal. Behind the classic covered front porch, an open, light-filled layout offers two bedrooms and two full bathrooms on a single level. The living and kitchen area features a vaulted ceiling with recessed lighting, enhancing the sense of space and adding a clean, modern feel to this efficient floor plan. The living and dining areas flow seamlessly into the fully renovated and completely remodeled kitchen, which was reconfigured during the renovation and now includes new cabinetry, granite countertops, stainless steel appliances, a gas oven/range, built-in microwave, dishwasher, garbage

$258,900

2 beds2 baths606 sq ft

318 Carter Ave, Denton, MD 21629

Covered front porch • Vaulted ceiling • Recessed lighting

(410) 770-9255

Property at 115 Boyce Mill Rd, Greensboro, MD 21639, 3 beds, 1 bath

$219,000

3 beds1 bath1,350 sq ft

115 Boyce Mill Rd, Greensboro, MD 21639

(410) 479-0777

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

$330,000

5 beds2 baths2,574 sq ft

305 Central Ave, Ridgely, MD 21660

(410) 822-9000

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

$296,000

3 beds2 baths1,368 sq ft

229 Oldtown Rd, Goldsboro, MD 21636

(301) 970-2447

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

$289,900

4 beds1.5 baths2,820 sq ft

306 S Main St, Federalsburg, MD 21632

(410) 271-1265

Property at 115 Maple Ave, Goldsboro, MD 21636, 2 beds, 2 baths

$250,000

2 beds2 baths2,048 sq ft

115 Maple Ave, Goldsboro, MD 21636

(410) 770-3600

Property at 215 Academy Ave, Federalsburg, MD 21632, 2 beds, 2 baths

$99,000

2 beds2 baths1,520 sq ft

215 Academy Ave, Federalsburg, MD 21632

(410) 479-3993

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

$325,000

2 beds1 bath1,528 sq ft

506 Park Ave, Ridgely, MD 21660

(302) 360-0300

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 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 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 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 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 2697 Choptank Main St, Preston, MD 21655, 2 beds, 2 baths

$279,000

2 beds2 baths1,104 sq ft

2697 Choptank Main St, Preston, MD 21655

(410) 770-9255

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 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 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 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 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 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 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 35 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 58 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 33 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 4 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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