104-108 Highland Avenue Middletown, NY 10940
Listing by: ONEKEY as distributed by MLS GRID / Howard Hanna | Rand Realty / Jo Ann Maxwell - Contact:  845-294-3100

  104-108 Highland Avenue Middletown, NY 10940

Coming Soon (1 Days)
$568,000 (USD)
7
BED
5
BATH
3,592
SQFT

Description

Historic Elegance Meets Modern-Day Convenience in this circa 1860 home in the heart of Middletown, NY. Pristinely positioned back from the road, set on just shy of an acre, this historic gem offers 3500+ square feet of timeless character and space. From the moment you enter, soaring ceilings, rich hardwood floors, built-ins and detailed crown molding set the tone. The expansive dining room, living room and formal parlor are thoughtfully connected by solid wood pocket doors - perfect for both grand entertaining and intimate gatherings. A full bath just off the parlor adds flexibility, making it ideal as a playroom or guest space. A true standout, the wood paneled library/den exudes warmth and sophistication, complete with its own powder room, an ideal retreat or home office. The light-filled kitchen offers everyday functionality and leads to a spacious back covered porch overlooking the level backyard and detached 2 car garage. Upstairs, the primary suite is complemented by private office/bedroom and beautifully renovated (2026) bath with Signature Hardware vanity. Three additional bedrooms include a Jack-and-Jill bath, plus another full bath, a dedicated laundry room, and a charming music room offering space for every need. The detached garage has new garage doors with electric opener and plenty of storage with loft area. Adding to its rich history, the home was once owned by an individual connected to the story of the Titanic - an intriguing piece of its past that enhances its timeless allure. Commuter-friendly with easy access to Metro-North and Shortline Bus, along with a vibrant, revitalized downtown filled with dining and shopping. Nearby Garnet Health Medical Center, Touro College of Osteopathic Medicine, SUNY Orange, recreational parks, golf, and so much more.

MLS #:
980025
Taxes
$13,001(2025)
Lot Size
0.91 acres
Type
Single-Family Home
Year Built
1860
Style
Colonial
School District
Middletown
County
Orange County

Listed By

Jo Ann Maxwell, Howard Hanna | Rand Realty, Contact: 845-294-3100
Source
ONEKEY
Last checked Apr 11 2026 at 5:59 PM EDT
Bathroom Details
  • Full Bathrooms: 4
  • Half Bathroom: 1
Interior Features
  • Cathedral Ceiling(s)
  • Storage
  • Washer/Dryer Hookup
  • High Ceilings
  • Original Details
  • First Floor Bedroom
  • Formal Dining
  • First Floor Full Bath
  • Laundry: Laundry Room
  • Built-In Features
  • Crown Molding
  • Primary Bathroom
  • Natural Woodwork
Kitchen
  • Dishwasher
  • Dryer
  • Microwave
  • Refrigerator
  • Washer
  • Gas Range
Lot Information
  • Cleared
  • Near Public Transit
  • Near School
  • Near Shops
  • Back Yard
  • Front Yard
Heating and Cooling
  • Natural Gas
  • None
Basement Information
  • Unfinished
Flooring
  • Hardwood
Utility Information
  • Utilities: Cable Available, Trash Collection Public, Electricity Connected, Natural Gas Connected, Sewer Connected, Water Connected
  • Sewer: Public Sewer
School Information
  • Elementary School: Presidential Park Elementary
  • Middle School: Middletown Twin Towers Middle Sch
  • High School: Middletown High School
Parking
  • Shared Driveway
  • Detached
  • Driveway
  • Garage
  • Garage Door Opener
Living Area
  • 3,592 sqft
Additional Information: Goshen | 845-294-3100
Location
   
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Disclaimer: Square footage is based on information available to agent, including County records. Information has not been verified by agent and should be verified by buyer.
Based on information submitted to the MLS GRID as of 4/11/2026 13:59. All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.