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  • 414 High Street, New Windsor, MD 21776 Main Photo

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BEDS3 BATHS2 full 1 partial SQUARE FEET2,522 MLS#MDCR2033324
STATUSACTIVE PROPERTY TYPEResidential - Single Family SUBDIVISIONNEW WINDSOR VISTAS SCHOOLCARROLL COUNTY PUBLIC SCHOOLS

Property 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!

414 High Street | MLS# MDCR2033324

This single family home located at 414 High Street, New Windsor, MD 21776 is currently listed for sale with an asking price of $499,900. This property was built in 1920 and has 3 bedrooms and 2 full and 1 partial baths with 2522 sq. ft. High Street is located in the NEW WINDSOR VISTAS subdivision within the CARROLL COUNTY PUBLIC SCHOOLS school district. Search NEW WINDSOR VISTAS real estate on www.freeman4realestate.com today.

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Open House Sunday March 29th, 11:00am - 2:00pm
Open House Saturday April 4th, 11:00am - 1:00pm
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Property Features

Property Type: Residential - Single Family
Basement: Yes
Basement: Daylight, Full, Connecting Stairway, Outside Entrance, Sump Pump
Cooling: Central A/C
Fireplaces: 3
Fuel Type: Oil
Garage: 3
Heating: Radiator, Heat Pump - Electric BackUp
Home Style: Colonial
Lot Size: 0.50 Acres
Stories: 2.0
Taxes: $4,232
Year Built: 1920

Feature Descriptions

Additional Structures: Above Grade, Below Grade
Exterior: Brick
Lot Dimensions: 0.50 Acre(S)
Municipality: New Windsor
Parking Notes: 6 Total Parking Spaces
Rooms: Laundry, Office
Sewer: Public Sewer
SQFT Above Finished: 2522
SQFT Total Finished: 2522
Structure Type: Detached
Total Garage/Parking Spaces: 6
Water: Public

Local Schools

School District: CARROLL COUNTY PUBLIC SCHOOLS

Listed By / Shown By

Listed By

Agency Name: Epique Realty
Agency Phone: 8888933537

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Estimated Payment

$ 1,611.03 per month $1,112.56 Principal & Interest $352.67 Property Tax $145.80 Homeowner's Insurance

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Disclaimer: All information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) or information provider(s) shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Listing(s) information is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information on this site was last updated 03/29/2026. The listing information on this page last changed on 03/29/2026. The data relating to real estate for sale on this website comes in part from the Internet Data Exchange program of Delta Media Group MLS (last updated Sun 03/29/2026 12:03:26 AM EST) or Bright MLS (last updated Sat 03/28/2026 11:56:30 PM EST). Real estate listings held by brokerage firms other than Berkshire Hathaway HomeServices Homesale Realty may be marked with the Internet Data Exchange logo and detailed information about those properties will include the name of the listing broker(s) when required by the MLS. All rights reserved.
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Edward (Ed) Freeman & Teri Lutz Freeman 

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