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

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ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
This charming ranch-style home, nestled in the desirable Denton area, offers a perfect blend of comfort and functionality. With 1,858 square feet of thoughtfully designed living space, this residence features four bedrooms, ideal for guests or multi-generational living. The heart of the home is the spacious eat-in kitchen. The kitchen is equipped with essential appliances, including a stove, refrigerator, ensuring that daily tasks are a breeze. The traditional floor plan offers a warm and welcoming atmosphere, the full bathroom features a tub shower. Step outside to discover your own personal oasis on 1.44 acres, complete with a private pool-ideal for summer fun and relaxation. The property

$340,000

4 beds1 bath1,858 sq ft

25900 Shore Hwy, Denton, MD 21629

Private pool • 1.44 acres • Ranch style home

(410) 822-6665

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Nestled in the charming TOWN OF GREENSBORO, this beautifully renovated residence offers a perfect blend of classic elegance and modern luxury. Originally built in 1910, this home has undergone a major transformation, with renovations completed in 2026, ensuring that every detail reflects contemporary sophistication while maintaining its timeless appeal. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas, creating an ideal space for both relaxation and entertaining. The rich hardwood flooring flows throughout, adding warmth and character to the home. Recessed lighting enhances the ambiance, illuminating the space with a soft glo

$349,900

3 beds2 baths1,092 sq ft

13243 Greensboro Rd, Greensboro, MD 21639

Hardwood flooring • Open floor plan • Renovated residence

(301) 445-1395

OPEN SUN, 1PM TO 3PM

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Adorable curb appeal, major updates, and room to make it your own! This charming 4-bedroom, 1-bath home at 522 Denton Road offers a great opportunity for buyers looking to add their personal touch without tackling all the big-ticket projects! The seller has already done much of the heavy lifting with remodeling, a new roof, new windows, and a brand-new septic system to be installed prior to settlement. Outside, you'll find two pergolas and a detached one-car garage, adding even more possibilities to this property. With its inviting exterior, important improvements, and plenty of potential left to make it your own, this home is ready for its next chapter. The hard work has started, now bring

$215,000

4 beds1 bath1,446 sq ft

522 Denton Rd, Federalsburg, MD 21632

New septic system • Major updates • Two pergolas

(302) 360-0300

$239,900

3 beds2 baths1,064 sq ft

233 Oldtown Rd, Goldsboro, MD 21636

4,506 sq ft lot • 2 parking spots • Built 1900

(301) 970-2447

ABOUT THIS HOME
Vintage Home for sale in Caroline County, MD:
Step into a charming piece of history with this beautiful Colonial home in the desirable Denton area. Built in 1900, this 2,759-square-foot residence offers the character and craftsmanship of a bygone era while providing the space and conveniences today's buyers desire. From the moment you arrive, the large wrap-around front porch with beautiful wood decking welcomes you home. It's the perfect spot to enjoy your morning coffee, relax on a summer evening, or simply take in the charm of small-town living. And with local festivals, parades, and community events passing right by your front porch, you'll have a front-row seat to all that makes Denton special! Inside, you'll find four spacious

$290,000

4 beds2 baths2,759 sq ft

105 S 5th Ave, Denton, MD 21629

Separate office • Large dining room • Cozy fireplace

(410) 643-4663

Property at 306 Sunrise Ave, Ridgely, MD 21660, 4 beds, 2 baths

$319,900

4 beds2 baths1,539 sq ft

306 Sunrise Ave, Ridgely, MD 21660

(301) 854-2155

Property at 215 N Main St, Federalsburg, MD 21632, 3 beds, 2 baths

$215,000

3 beds2 baths1,096 sq ft

215 N Main St, Federalsburg, MD 21632

(877) 366-2213

Property at 533 Gay St, Denton, MD 21629, 4 beds, 2 baths

$270,000

4 beds2 baths1,288 sq ft

533 Gay St, Denton, MD 21629

(410) 643-4663

Property at 216 S 3rd St, Denton, MD 21629, 3 beds, 2 baths

$250,000

3 beds2 baths1,254 sq ft

216 S 3rd St, Denton, MD 21629

(443) 215-4663

Property at 1115 Market St, Denton, MD 21629, 2 beds, 1 bath

$224,900

2 beds1 bath788 sq ft

1115 Market St, Denton, MD 21629

(443) 274-1900

Property at 200 Maple Ave, Greensboro, MD 21639, 3 beds, 2 baths

$205,000

3 beds2 baths1,306 sq ft

200 Maple Ave, Greensboro, MD 21639

(410) 814-2400

Property at 105 Park Ave, Ridgely, MD 21660, 3 beds, 2 baths

$239,000

3 beds2 baths1,620 sq ft

105 Park Ave, Ridgely, MD 21660

(410) 479-3993

Property at 305 Old Denton Rd, Federalsburg, MD 21632, 2 beds, 1 bath

$89,900

2 beds1 bath600 sq ft

305 Old Denton Rd, Federalsburg, MD 21632

(410) 677-0909

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

$440,000

4 beds2 baths1,986 sq ft

25699 Auction Rd, Federalsburg, MD 21632

(410) 228-0800

Property at 104 Riverton Ave, Denton, MD 21629, 3 beds, 2 baths

$467,900

3 beds2 baths2,318 sq ft

104 Riverton Ave, Denton, MD 21629

(410) 479-3993

Property at 6132 Harmony Rd, Preston, MD 21655, 2 beds, 1 bath

$150,000

2 beds1 bath1,080 sq ft

6132 Harmony Rd, Preston, MD 21655

(240) 623-3948

Property at 105 Noble Ave, Preston, MD 21655, 3 beds, 2 baths

$299,000

3 beds2 baths2,034 sq ft

105 Noble Ave, Preston, MD 21655

(302) 360-0300

Property at 522 Market St, Denton, MD 21629, 4 beds, 2 baths

$225,000

4 beds2 baths2,448 sq ft

522 Market St, Denton, MD 21629

(888) 860-7369

Property at 2766 Veterans Dr, Federalsburg, MD 21632, 2 beds, 1 bath

$299,900

2 beds1 bath1,284 sq ft

2766 Veterans Dr, Federalsburg, MD 21632

(410) 745-0415

Property at 13166 Oakland Rd, Ridgely, MD 21660, 3 beds, 2 baths

$395,000

3 beds2 baths2,408 sq ft

13166 Oakland Rd, Ridgely, MD 21660

(410) 934-3478

Property at 4 N Maryland Ave, Ridgely, MD 21660, 4 beds, 2.5 baths

$375,000

4 beds2.5 baths2,552 sq ft

4 N Maryland Ave, Ridgely, MD 21660

(302) 360-0300

Property at 310 Central Ave, Federalsburg, MD 21632, 3 beds, 1.5 baths

$72,000

3 beds1.5 baths1,408 sq ft

310 Central Ave, Federalsburg, MD 21632

(410) 432-1223

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

$225,000

3 beds2 baths1,840 sq ft

158 Wright St, Preston, MD 21655

(302) 360-0300

Property at 104 Chambers St, Federalsburg, MD 21632, 3 beds, 2.5 baths

$299,800

3 beds2.5 baths1,212 sq ft

104 Chambers St, Federalsburg, MD 21632

(410) 822-6665

Property at 305 Caroline Ave, Ridgely, MD 21660, 2 beds, 1 bath

$224,000

2 beds1 bath840 sq ft

305 Caroline Ave, Ridgely, MD 21660

(410) 304-2011

Property at 5820 Bell Creek Rd, Preston, MD 21655, 2 beds, 1 bath

$490,000

2 beds1 bath1,292 sq ft

5820 Bell Creek Rd, Preston, MD 21655

(888) 860-7369

Property at 156 Main St, Preston, MD 21655, 3 beds, 1.5 baths

$199,900

3 beds1.5 baths1,694 sq ft

156 Main St, Preston, MD 21655

(410) 822-6665

Property at 407 W Sunset Ave, Greensboro, MD 21639, 5 beds, 2 baths

$280,000

5 beds2 baths1,884 sq ft

407 W Sunset Ave, Greensboro, MD 21639

(410) 432-1223

Property at 202 Central Ave, Ridgely, MD 21660, 3 beds, 3 baths

$465,900

3 beds3 baths2,713 sq ft

202 Central Ave, Ridgely, MD 21660

(410) 479-3993

Property at 612 Market St, Denton, MD 21629, 4 beds, 2 baths

$325,000

4 beds2 baths2,172 sq ft

612 Market St, Denton, MD 21629

(410) 778-3779

Property at 222 S 2nd St, Denton, MD 21629, 5 beds, 2 baths

$319,000

5 beds2 baths1,800 sq ft

222 S 2nd St, Denton, MD 21629

(410) 479-4663

Property at 412 N Main St, Greensboro, MD 21639, 3 beds, 2 baths

$359,900

3 beds2 baths2,160 sq ft

412 N Main St, Greensboro, MD 21639

(302) 677-0020

Property at 208 W 2nd St, Ridgely, MD 21660, 3 beds, 1 bath

$155,000

3 beds1 bath1,015 sq ft

208 W 2nd St, Ridgely, MD 21660

(410) 583-0400

Property at 506 Central Ave, Ridgely, MD 21660, 3 beds, 1 bath

$385,000

3 beds1 bath1,370 sq ft

506 Central Ave, Ridgely, MD 21660

(301) 970-2447

Property at 306 Caroline Ave, Ridgely, MD 21660, 3 beds, 2 baths

$320,000

3 beds2 baths1,680 sq ft

306 Caroline Ave, Ridgely, MD 21660

(410) 643-4663

Property at 1210 Market St, Denton, MD 21629, 2 beds, 1 bath

$249,000

2 beds1 bath908 sq ft

1210 Market St, Denton, MD 21629

(410) 221-8000

Property at 112 S 5th Ave, Denton, MD 21629, 4 beds, 1.5 baths

$359,000

4 beds1.5 baths2,885 sq ft

112 S 5th Ave, Denton, MD 21629

(410) 479-0777

Property at 3894 Old Denton Rd, Federalsburg, MD 21632, 2 beds, 1 bath

$230,000

2 beds1 bath1,108 sq ft

3894 Old Denton Rd, Federalsburg, MD 21632

(302) 856-1458

Property at 108 N Academy St N, Greensboro, MD 21639, 4 beds, 2 baths

$269,000

4 beds2 baths1,950 sq ft

108 N Academy St N, Greensboro, MD 21639

(410) 479-3993

Property at 126 Maple Ave, Preston, MD 21655, 3 beds, 1.5 baths

$220,000

3 beds1.5 baths1,828 sq ft

126 Maple Ave, Preston, MD 21655

(410) 754-7000

Property at 310 Park Ave, Federalsburg, MD 21632, 2 beds, 1.5 baths

$199,000

2 beds1.5 baths812 sq ft

310 Park Ave, Federalsburg, MD 21632

(410) 643-4663

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Vintage Homes for Sale in Caroline County

There are currently 54 vintage homes for sale in Caroline County at a median listing price of $331K. 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 78 days and receive 2 offers. This map is refreshed with the newest listings in Caroline County every 15 minutes.

In the past month, 32 homes have been sold in Caroline County. In addition to houses in Caroline County, there was also 1 condo, 9 townhouses, and 2 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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