414 High Street
New Windsor, MD, 21776 $ 449,900
Bedrooms3 Baths2.1 Sq 2,668 Monthly Estimate*
$ 2,770
for $449,900 with 3 bedrooms and 2 full baths, 1 half bath. This 2,668 square foot home was built in 1920 on a lot size of 0.5.
A beautifully updated Colonial offering rare space, character, and major system upgrades all on a halfacre corner lot in the heart of historic New Windsor! This home is the first address included in the upcoming statefunded streetscape project, which will add new sidewalks and pedestrian lighting, enhancing walkability, safety, and curb appeal for the entire neighborhood. Step into timeless elegance in this stately 3bedroom, 3bath home filled with natural light and thoughtful updates. A bright foyer off the welcoming side porch leads to a dining room with builtins and a woodburning insert perfect for gatherings. The powder room features a modern twist on a vintage household staple. The spacious kitchen offers abundant cabinetry and prep space, while the large formal living room includes more builtins and a cozy gas fireplace. Refinished floors and abundant storage add to the homes charm and functionality. Upstairs, the primary suite is a true retreat with a brandnew private balcony, a large office, and an additional walkin closet ideal for working from home. The ensuite bath blends vintage charm with modern comfort, featuring a refinished clawfoot tub. Two additional large bedrooms, a shared bath, and a dedicated laundry room complete the upper level. The basement doubles as a workshop with an electric fireplace, and the walkup attic offers hickory flooring, new windows, and generous storage. Outside, enjoy a brick paver patio, privacy fencing, a garden shed, and a rare detached threecar garage with an additional 600 sq. ft. of attic space ready for your imagination. The long list of recent improvements includes HVAC, water heater, and a fully replaced public water supply line meeting new county requirements. And a home warranty is included for added peace of mind. Recently adjusted price offers due by midnight on 5/17. Dont miss this historic gem with modern upgrades and unbeatable smalltown charm!
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FeaturesGeneralLiving Area 2668
Sewer Public Sewer
Heating Radiator Heat Pump - Electric BackUp
Cooling Central A/C
Possession Immediate
Zoning VILLA
Garage Spaces 3.00
Architectural Style Colonial
Construction Materials Brick
School District CARROLL COUNTY PUBLIC SCHOOLS
Year Built 1920
Levels 2
Tax Year 2025
Ownership Fee Simple
Cool Fuel Electric
Municipality New Windsor
Accessibility None
County CARROLL
New Construction N
Property Type Residential
HOA N
Subdivision Name NEW WINDSOR VISTAS
Garage Y/N Y
Water Access Y/N N
Other Structures Above Grade Below Grade
Full Baths 2
Status ACTIVE
Directions Use GPS but turn up Lambert because the driveways face the back. Park next to the large blue garage on Pilson.
City NEW WINDSOR
Senior Community Y/N N
Lot Size Units Square Feet
Lot Size Square Feet 21597.00
Tax Annual Amount 4232.0
Home Warranty Y/N Y
Structure Type Detached
Condo/Coop Association fee Y/N N
Bathrooms Full Main Level 0
Bathrooms Count Main Level 1.00
Price Per Sq Ft Total AG 168.63
Vacation Rental Y/N N
Standard Status Active
Year Built Source Assessor
Legal Subdivision NEW WINDSOR ELECTION DISTRICT
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InteriorInterior Amenities Attic Built-Ins Cedar Closet(s) Ceiling Fan(s) Formal/Separate Dining Room Pantry Recessed Lighting Wood Floors
Heating Fuel Oil
Basement Daylight Full Connecting Stairway Outside Entrance Sump Pump
Total Fireplaces 3
Fireplace Features Wood Insert Gas/Propane Electric
Hot Water Electric
Basement (Y/N) Y
Heating Y/N Y
Fireplace Y/N Y
Above Grade Finished Area 2668
Half Baths 1
Central Air Y/N Y
Total Bedrooms 3
Room Type Laundry Office
Main Level Bedrooms 0
Laundry Type Upper Floor
Above Grade Finished Area Source Estimated
Above Grade Finished Area Unit Type Square Feet
Total Baths 3
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ExteriorPool No Pool
Fencing Rear Wood
Lot Features Corner
Water Source Public
Garage Features Additional Storage Area Garage Door Opener
Type of Parking Detached Garage Driveway
Foundation Details Stone
Water View Y/N N
Lot Size Acres 0.50
Lot Size Source Assessor
Waterfront Y/N N
Land Assessed Value 99700.00
Navigable Water Y/N N
Water Oriented Y/N N
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* Excluded FeaturesAffordability Calculator
- Monthly Principal & Interest
- $2,770
- Monthly Property Taxes
- $353
- Monthly Home Insurance
- --
Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in New Windsor, MD
Average List Price $675,611
Percent of Sale Price 50%
About New Windsor, MD 1,208 Population
7% Since 2002
$ 76,465 Median Income
42.67 Median Age
25% Households with Children
Trends Information provided by ATTOM Data Solutions.
4518866 Elementary School
3534329 Middle School
Francis Scott Key Senior High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 5/8/2026 | $449,900 | -5.28% | Price Down |
| 4/23/2026 | $475,000 | -4.98% | Price Down |
| 3/19/2026 | $499,900 | | Listed Price |