414 High St, New Windsor, MD 21776
Local realty services provided by:ERA OakCrest Realty, Inc.
414 High St,New Windsor, MD 21776
$499,900
- 3 Beds
- 3 Baths
- - sq. ft.
- Single family
- Coming Soon
Listed by: karen brenner
Office: epique realty
MLS#:MDCR2033324
Source:BRIGHTMLS
Price summary
- Price:$499,900
About this home
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 sits on a generous half-acre corner lot, offering nearly 2,900 sq ft of living space brimming with character and modern comforts.
Inside, you’ll find a welcoming formal living room with decorative wood accents and a cozy gas fireplace, a grand dining room with a wood-burning insert—perfect for gatherings—and a spacious kitchen with ample cabinetry, recessed lighting, and a handy pantry. The kitchen connects to a mudroom for added convenience.
Upstairs, the luxurious primary suite is a true retreat, featuring a brand-new private balcony, a large walk-in closet, and an attached office—ideal for working from home or unwinding in style. The suite’s private bath and additional upstairs bedrooms offer comfort and flexibility for any lifestyle. A convenient laundry room completes the upper level.
The finished basement doubles as a workshop and features an electric fireplace, making it a versatile space for hobbies or relaxation.
Enjoy outdoor living with a brick paver patio, privacy fencing, a garden shed, and a rare detached three-car garage—perfect for vehicles, storage, or projects. Recent upgrades include a new 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.
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!
All this, just steps from New Windsor’s charming town center and local favorites like New Windsor Liquor and Deli.
Don’t miss your chance to own this historic gem with modern upgrades and unbeatable small-town charm!...
Contact an agent
Home facts
- Year built:1920
- Listing ID #:MDCR2033324
- Added:1 day(s) ago
- Updated:March 20, 2026 at 05:42 AM
Rooms and interior
- Bedrooms:3
- Total bathrooms:3
- Full bathrooms:2
- Half bathrooms:1
- Basement:Yes
- Basement Description:Connecting Stairway, Daylight, Full, Outside Entrance, Sump Pump
Heating and cooling
- Cooling:Central A/C
- Heating:Heat Pump - Electric BackUp, Oil, Radiator
Structure and exterior
- Year built:1920
- Architectural Style:Colonial
- Construction Materials:Brick
- Foundation Description:Stone
- Levels:2 Stories
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$499,900
- Tax amount:$4,232 (2025)
Features and amenities
- Laundry features:Laundry
Parking
- Parking description:Additional Storage Area, Detached Garage, Garage Door Opener
- Garage:Yes
- Garage spaces:3
New listings near 414 High St
- Open Sun, 1 to 3pmNew
$499,000Active3 beds 3 baths2,050 sq. ft.118 S Clear Ridge Rd, NEW WINDSOR, MD 21776
MLS# MDCR2033246Listed by: CUMMINGS & CO. REALTORS
$335,000Pending3 beds 2 baths1,504 sq. ft.3007 Merle Ct, NEW WINDSOR, MD 21776
MLS# MDCR2033196Listed by: RE/MAX SOLUTIONS- New
$430,000Active3 beds 3 baths1,892 sq. ft.3190 Vista Ct, NEW WINDSOR, MD 21776
MLS# MDCR2033178Listed by: LPT REALTY, LLC
$199,900Active5.87 AcresParcel # 22 Sams Creek Rd, NEW WINDSOR, MD 21776
MLS# MDCR2032994Listed by: WINNING EDGE
$699,900Active4 beds 3 baths2,568 sq. ft.3895 Buffalo Rd, NEW WINDSOR, MD 21776
MLS# MDFR2078036Listed by: RE/MAX DISTINCTIVE REAL ESTATE, INC.
$1,214,317Pending4 beds 3 baths3,118 sq. ft.Bowersox Rd, NEW WINDSOR, MD 21776
MLS# MDCR2032738Listed by: KELLER WILLIAMS REALTY CENTRE
$375,000Active3 beds 2 baths936 sq. ft.1038 Green Valley Rd, NEW WINDSOR, MD 21776
MLS# MDCR2031660Listed by: CORNER HOUSE REALTY
$549,000Pending4 beds 3 baths1,584 sq. ft.1589 Smiley Dr, NEW WINDSOR, MD 21776
MLS# MDCR2032790Listed by: EXP REALTY, LLC
$439,500Active3 beds 3 baths1,500 sq. ft.14844 Toll Rd, NEW WINDSOR, MD 21776
MLS# MDFR2077350Listed by: SAMSON PROPERTIES