414 High Street • New Windsor, MD 21776

$499,900 Beds: 3 • Baths: 2 full 1 partial • Sq. Feet: 2522 • MLS ID: MDCR2033324 • Subdivision: NEW WINDSOR VISTAS • School Dist: CARROLL COUNTY PUBLIC SCHOOLS
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! View this listing at: http://freeman4realestate.com/mls=MDCR2033324

Property Features

  • Garage: 3
  • Taxes: $4,232
  • Basement: Yes
  • Exterior: Brick
  • Parking Notes: 6 Total Parking Spaces
  • Lot Size: 0.50 Acres
  • Lot Dimensions: 0.50 Acre(S)
  • Heating: Radiator,Heat Pump - Electric BackUp
  • Fuel Type: Oil
  • Cooling: Central A/C
  • Year Built: 1920
  • Fireplaces: 3
  • Water: Public
  • Sewer: Public Sewer
  • Stories: 2.0
  • Municipality: New Windsor
  • Additional Structures: Above Grade,Below Grade
  • Structure Type: Detached
  • Total Garage/Parking Spaces: 6
  • Rooms: Laundry,Office
  • Basement: Daylight, Full,Connecting Stairway,Outside Entrance,Sump Pump
  • SQFT Total Finished: 2522
  • SQFT Above Finished: 2522

School Information

  • School District: CARROLL COUNTY PUBLIC SCHOOLS
Printed March 29, 2026


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.
Privacy Policy / DMCA Notice / ADA Accessibility
Federal Housing Equal Opportunity Realtor
Corporate Office - 215 S Centerville Rd. Lancaster, PA 17603
James J Hafer - West Virginia Broker of Record

©2026 BHH Affiliates, LLC. An independently owned and operated franchisee of BHH Affiliates, LLC. Berkshire Hathaway HomeServices and the Berkshire Hathaway HomeServices symbol are registered service marks of Columbia Insurance Company, a Berkshire Hathaway affiliate. Equal Housing Opportunity.


Agent License Information: 
Licensed in Pennsylvania
Edward (Ed) Freeman & Teri Lutz Freeman 

955 Berkshire Boulevard, Suite 100, Wyomissing, PA 19610
610-372-3200