USAMDNew WindsorNone Available414 High St
414 High St | Image 1
Open House
414 High St | Image 2
414 High St | Image 3
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$499,900

For Sale

19 days ago

414 High St, New Windsor, MD

House

MLS® MDCR2033324

3 Bed

3 Bath

2668 sqft

3 Parking

Open House
Sat Apr 11, 7:00-9:00 PM UTCSun Apr 12, 8:00-10:00 PM UTC
  • Key Facts
  • Description
  • Rooms
  • Map

Key Facts

Type Single Family Residence
Levels Residential
Size 2668 sqft
Garage Yes
Taxes $4,232
Days Active 19
Lot Size 
Approx. Age 1920
Avg. Price Per Sqft $187
MLS® Number MDCR2033324

Property Address: 414 High St, NEW WINDSOR, MD, 21776-8921

Average square foot calculated using Size range provided by listing agent.

Description

Gorgeous! Step into timeless elegance at 414 High Street, a beautifully updated Colonial in the heart of historic New Windsor! This stately 3-bedroom, 2.5-bath home brimming with character and modern comforts sits on a generous half-acre corner lot. Exciting news: This address is included in an upcoming state streetscape project, which will add brand-new sidewalks and pedestrian lighting—enhancing walkability, safety, and curb appeal for the entire neighborhood! Entering a foyer off of the long side porch, you'll find a welcoming dining room with plenty of built-ins, a wood-burning insert—perfect for gatherings—and a spacious kitchen with ample cabinetry, recessed lighting, and a handy pantry. Check out the powder room where you'll see a modern twist on an antique that was once the heartbeat of every household! The formal living room has more built-ins and a cozy gas fireplace. Notice the original oil lamp hardware in the family room and all of the beautifully refinished floors. Upstairs, the primary suite is a true retreat, featuring a brand-new private balcony off of a large walk-in closet with plenty of room for an office — ideal for working from home or unwinding in style. Vintage charm meets modern luxury in the suite’s private bath featuring a refinished clawfoot tub. More large bedrooms and a shared bath along with a dedicated laundry room complete the upper level. The basement doubles as a workshop and features an electric fireplace, making it a versatile space for hobbies or relaxation. A brick paver patio, privacy fencing, dedicated garden shed, and a rare detached three-car garage are perfect offer a rare combination of modern utility and historic charm in the heart of town. Recent upgrades include newer windows and roof, a new boiler and HVAC system, water heater, and a fully replaced public water supply line to meet county requirements—giving you peace of mind for years to come. Don’t miss your chance to own this historic gem with modern upgrades and unbeatable small-town charm!
MLS® NumberMDCR2033324
Laundry LevelUpper
Central VacNo
FireplaceNo
Acreage
Exterior
GarageYes
Approx. Age1920
BasementDaylight, Full, Connecting Stairway, Outside Entrance, Sump Pump
DrivewayDetached Garage, Driveway
Garage Spaces
Heat
A/C
Heating Fuel

Extras

Rooms

Change to metres

Laundry:Not available
Office:Not available

Price History

-End Date
Not Sold YetSold Price

For Sale

Mar 19, 2026List Date
$499,900List Price
Nov 3, 2025End Date
$280,000Sold Price

Sold

Sep 27, 2025List Date
$279,900List Price

Home Appraisal

This property is estimated to sell between: $401,000 and $550,000.
Similar properties in this area sold on average for: $401,150
Expected to sell in 42 days. Similar properties sold in 61 days. This home has been on eXp Realty for 19 days.

The estimated sale price does not take into account many variables such as recent renovations, type of appliances, school district etc. To get a more accurate estimate please contact agent.

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414 High St, New Windsor, MD

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