414 HIGH STREET, NEW WINDSOR, MD 21776 - PenFed Realty Mid-Atlantic

$475,000

Wow! A beautifully updated Colonial with rare space, character, and major system upgrades - all on a half2011;acre corner lot! Recently adjusted price - seller will review all offers on May 4th. Make history and almost instant equity in the heart of historic New Windsor: this home is the first… Read More address included in the state-funded streetscape project, which will add brand new sidewalks and pedestrian lighting, enhancing walkability, safety, and curb appeal for the entire neighborhood. Step into timeless elegance at this stately 3-bedroom, 3-bath home brimming with character and modern comforts. Entering a bright foyer off of the welcoming side porch, you'll find a dining room with plenty of built-in cabinets, a wood-burning insert - perfect for gatherings. Check out the powder room where you'll see a modern twist on an antique that was once the heartbeat of every household! The spacious kitchen has plenty of countertops and cabinetry. The large, formal living room has more built-in shelving and a cozy gas fireplace. Notice all of the multi-use space and beautifully refinished floors. Upstairs, the primary suite is a true retreat, featuring a brand-new private balcony off of a large office with an additional walk-in closet 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. The walk-up attic has hickory flooring, new windows, and plenty of storage. A brick paver patio, privacy fencing, dedicated garden shed, and a rare detached three-car garage offer a rare combination of modern utility and historic charm. Use your imagination in the garage attic, which adds an additional 600 square feet of space. A long list of recent improvements is attached, including HVAC, water heater, and a fully replaced public water supply line to meet new county requirements. All of this and a home warranty is included, 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! Read Less

Courtesy of Karen Brenner, Epique Realty 888-893-3537

Listing Snapshot

Days Online

Last Updated

May 4, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

2,668

Lot Size

0.5 Acres

Year Built

1920

MLS Number

MDCR2033324

Additional Details

Basement

Daylight, Full, Connecting Stairway, Outside Entrance, Sump Pump

Building

Built in 1920, Built in 2026 (effective), Living area: 2668, Levels: 2, Construction Materials: Brick

Cooling

Central A/C

Accessibility Features

None

Fence

Rear, Wood

Fireplaces

3 fireplaces, Wood, Insert, Gas/Propane, Electric

Foundation

Stone

Garage

3 spaces

Heating

Radiator, Heat Pump - Electric BackUp

Interior Features

Attic, Built-Ins, Cedar Closet(s), Ceiling Fan(s), Formal/Separate Dining Room, Pantry, Recessed Lighting, Wood Floors

Lot

0.5 acres, Corner

Property

Other structures: Above Grade, Below Grade

Sewer

Public Sewer

Taxes

Annual Amount: $4,232, Year: 2025, Zoning: VILLA

Utilities

Water Source: Public

Find The Perfect Home

'VIP' Listing Search

Whenever a listing hits the market that matches your criteria you will be immediately notified.

Join The List

Schools In The Area

School attendance zone boundaries and ratings are provided by a third party. The information is not guaranteed to be accurate, up-to-date, or complete. Check with the applicable school district prior to making a decision based on these boundaries. In addition, the ratings, and the metrics used by the third party to arrive at the ratings, should not be the only factor used in selecting the right school for your family.

414 HIGH STREET

'VIP' Listing Search

Schools In The Area

Similar Listings

Find My Dream Home

1. Neighborhoods

2. Home Type

3. Send