22040 Main Street, Hillsboro, MD 21641 - Photo 1

1/1

$365,000

Sold
Closed
Single Family
4 Beds
1 Full Bath
1 Partial Bath
2,276 Sq. Ft.
5 Car Garage

1/1

Property Description

OFFER DEADLINE- please submit all highest and best offers by 5:30 pm on 8/4. Welcome to this stunning Victorian gem built in 1900, gracefully resting on three combined lots totaling .76 acres of mature, beautifully planted grounds. From the moment you arrive, the home's presence is unmistakable; a sweeping wrap-around front porch invites you in, while a fully enclosed back porch offers a quiet retreat overlooking the private backyard. Step inside to discover soaring high ceilings and generously proportioned rooms that speak to a bygone era of craftsmanship. Original hardwood floors, pocket doors, and period fixtures and hardware remain lovingly preserved throughout, offering that rare, authentic character today's buyers dream of. Two separate staircases lead to the second floor, where you'll find four spacious bedrooms and a beautifully updated full bathroom. The home has been thoughtfully modernized where it counts most- a stylishly updated kitchen anchors the main level, complemented by a fully updated main-floor bathroom, so timeless charm meets everyday comfort. Recent mechanical updates provide additional peace of mind, including new heat pumps installed in 2020 and 2021, a new roof in 2022, chimney repairs completed in 2022, new washer and dryer in 2025 and a new pressure tank in 2026. Outdoor space is just as impressive as the home itself. The grounds include two outbuildings- a small horse barn with stall and a versatile storage shed with workshop area- along with an expansive 5-bay garage/shop, perfect for cars, boats, hobbies, or storage of every kind. This is a rare opportunity to own a true piece of history, thoughtfully updated for modern living, on nearly three-quarters of an acre of storybook grounds. Homes with this much land, character, and versatility simply don't come along often. Welcome home.

Full Property Details

Full Property Details for 22040 Main St

General

Sold For: $365,000
Taxes: $2,823 (2024)
Status: Closed
Type: Single Family
Source: BrightMLSMidAtlantic
MLS ID: MDCM2007636
Added to Site: 65 day(s) ago

Interior

Interior Features: Additional Stairway, Bathroom - Tub Shower, Ceiling Fan(s), Dining Area, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Country, Wood Floors
Fireplace: Yes
Number of Fireplaces: 2
Flooring: Wood

Rooms

Bathrooms

Total Bathrooms: 2
Full Bathrooms: 1
Half Bathrooms: 1
Upper Floor Baths: 1
Upper - Full Baths: 1
Main Floor Baths: 1
Main - 1/2 Baths: 1

Bedrooms

Total Bedrooms: 4
Bedrooms Upper: 4

Exterior

Porch/Patio/Deck: Porch(es), Wrap Around

Parking

Garage: Yes
Garage Spaces: 5
Total Spaces: 10
Parking Type: Driveway, Detached Garage
Garage Description: Additional Storage Area

Location

Municipality: Hillsboro
County: CAROLINE
Driving Directions: Please use GPS
City Limits: Yes

School Information

School District: Caroline County Public Schools

Heating & Cooling

Cooling Type: Heat Pump(s)
Cooling Fuel: Electric
Heating Type: Heat Pump(s), Zoned, Radiator
Heating Fuel: Electric, Oil
Water Heater: Oil

Utilities

Sewer: Septic Exists
Water: Well

Structural Information

Architectural Style: Victorian
Structure Type: Detached
Construction: Aluminum Siding
Basement: Yes
Basement Desc.: Poured Concrete, Interior Access
Foundation: Crawl Space
Stories Description: Main, Upper 1
Square Feet: 2,276
Sq. Ft. Source: Estimated
Living Area: 2,276 Sq. Ft.
Finished Above Grnd: 2,276 Sq. Ft.
Year Built: 1900
Year Built Source: Estimated

Additional Structures

Other Structures: Shed, Wood/Metal Shed

Lot Features

Lot Size (Acres): 0.78
Lot Size (Sq. Ft.): 33,816
Lot Size Source: Estimated
Zoning: R

Financial Considerations

Price Per Sq. Ft.: $160.37
Assessment Year: 2024
City/TownTax: $463
City/TownTax Freq: Annually
County Tax: $2,300
County Tax Freq: Annually
Tax w/Assessment: $210,600
Tax Amount: $2,823
Tax Year: 2024
Terms: Standard Sale

Disclosures and Reports

Ownership: Fee Simple
Section: 1

Listed by Engel & Volkers Annapolis, Kathleen Moore
Sold by Benson & Mangold, LLC, Denis A Gasper

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Listing agent

— 22040 Main St —

Kathleen Moore

Engel & Volkers Annapolis

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Schools

Schools serving 22040 Main St

School District:Caroline County Public Schools, Denton, MD

Name	Grades	Distance
Ridgely Elementary School 118 North Central Avenue, Ridgely, MD 21660	PK-5	3.9 mi
Lockerman Middle School 410 Lockerman Street, Denton, MD 21629	6-8	6.4 mi
North Caroline High School 10990 River Road, Ridgely, MD 21660	9-12	5.4 mi

Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 22040 Main St

Date

Details

Price

Change

Source

9/14/2026

Sold

$365,000

—

MLS

8/10/2026

Price Increased

$365,000

4.29%

MLS

7/29/2026

Listed

$350,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

24882 Riverview Way, Ridgely, MD 21660 - Photo 1

Just Listed

$429,000

24882 Riverview Way Ridgely, MD 21660

Single Family
Active
Updated 2 days ago

3
Beds
3
Total Baths
1,542
Sq. Ft.

Listed by Benson & Mangold, LLC, Edwin M Matthews

[Address not provided], Ridgely, MD 21660 - Photo 1

Just Listed

$529,000

[Address not provided] Ridgely, MD 21660

Single Family
Active
Updated 3 days ago

3
Beds
2
Total Baths
1,344
Sq. Ft.

Listed by Eastern Shore Real Estate, LLC, Bernard J Kilby

306 Sunrise Ave, Ridgely, MD 21660 - Photo 1

Just Listed

$319,900

Open House

306 Sunrise Ave Ridgely, MD 21660

Single Family
Active
Updated 4 days ago

4
Beds
2
Total Baths
2,778
Sq. Ft.

Listed by Samson Properties, Vincent F DeLorenzo

23171 Tuckahoe Springs Dr, Denton, MD 21629 - Photo 1

Just Listed

$499,000

23171 Tuckahoe Springs Dr Denton, MD 21629

Single Family
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,824
Sq. Ft.

Listed by Eastern Shore Real Estate, LLC, Bernard J Kilby

11920 Central Ave, Ridgely, MD 21660 - Photo 1

Price Reduced

-$1,000 (-0.56%)

$179,000

11920 Central Ave Ridgely, MD 21660

Lots/Land
Active
Updated 3 days ago

Listed by Proplocate Realty, Sam Benkirane

306 Caroline Ave, Ridgely, MD 21660 - Photo 1

Price Reduced

-$20,000 (-5.88%)

$320,000

306 Caroline Ave Ridgely, MD 21660

Single Family
Active
Updated 9 hours ago

3
Beds
2
Total Baths
1,680
Sq. Ft.

Listed by Chesapeake Real Estate Associates, LLC, Roger M Boyce

11509 Reed Cir, Ridgely, MD 21660 - Photo 1

Price Reduced

-$14,000 (-3.12%)

$435,000

11509 Reed Cir Ridgely, MD 21660

Single Family
Active
Updated 6 days ago

3
Beds
2
Total Baths
1,392
Sq. Ft.

Listed by Keller Williams Realty, Samantha Kay Jackson

305 Caroline Ave, Ridgely, MD 21660 - Photo 1

Price Reduced

-$5,000 (-2.18%)

$224,000

305 Caroline Ave Ridgely, MD 21660

Single Family
Active
Updated 7 hours ago

2
Beds
1
Total Bath
840
Sq. Ft.

Listed by Eastern Shore Real Estate, LLC, Bernard J Kilby

10280 Log Cabin Rd, Denton, MD 21629 - Photo 1

Sold

$349,000

10280 Log Cabin Rd Denton, MD 21629

Single Family
Closed
Updated 13 days ago

3
Beds
2
Total Baths
1,748
Sq. Ft.

Listed by Brenton Realty Group, Kathleen M Brenton
Sold by Berkshire Hathaway Homeservice Homesale Realty, Dawn M Williams

11139 Central Ave, Ridgely, MD 21660 - Photo 1

Sold

$399,900

11139 Central Ave Ridgely, MD 21660

Single Family
Closed

3
Beds
2
Total Baths
1,120
Sq. Ft.

Listed by Eastern Shore Real Estate, LLC, Bernard J Kilby
Sold by Cummings & Co Realtors, Mark M Novak

1 Sunrise Ave, Ridgely, MD 21660 - Photo 1

Sold

$399,000

1 Sunrise Ave Ridgely, MD 21660

Single Family
Closed
Updated 11 days ago

4
Beds
3
Total Baths
1,768
Sq. Ft.

Listed by RE/MAX Executive, Crystal M Smith
Sold by Keller Williams Select Realtors of Cambridge, Katie Mister

3 Sunrise Ave, Ridgely, MD 21660 - Photo 1

Sold

$364,000

3 Sunrise Ave Ridgely, MD 21660

Single Family
Closed

3
Beds
2
Total Baths
1,292
Sq. Ft.

Listed by Amy Betts
Sold by EXP Realty, LLC, DanYelle Batts

22040 Main Street, Hillsboro, MD 21641 (MLS# MDCM2007636) is a Single Family property that was sold at $365,000 on September 14, 2026. Want to learn more about 22040 Main Street? Do you have questions about finding other Single Family real estate for sale in Hillsboro? You can browse all Hillsboro real estate or contact a Coldwell Banker agent to request more information.

22040 Main St Hillsboro, MD 21641