59 Webb Rd Middletown, NY 10940
59 Webb Rd Middletown, NY 10940 | MLS 1060361 Photo 1
59 Webb Rd Middletown, NY 10940 | MLS 1060361 Photo 2
59 Webb Rd Middletown, NY 10940 | MLS 1060361 Photo 3
59 Webb Rd Middletown, NY 10940 | MLS 1060361 Photo 4
59 Webb Rd Middletown, NY 10940 | MLS 1060361 Photo 5
For more information on this listing, contact us at: (914) 438-5975
Active
$659,000

59 Webb Rd Middletown, NY 10940

Single Family Residence Property Type
5 Beds
5 Full 1 Half Baths
3,960 Sq. Ft.
1800 Year Built
Orange County
View All Property Details
Set on approximately 3 acres, 59 Webb Road is a remarkable circa-1800 Colonial with the kind of charm and presence you simply don't find in newer homes. From the moment you arrive, there is a feeling that this is a home with a story, cared for and enjoyed through generations.

Inside, original character is everywhere you look. Beautiful wide-plank pine floors, hardwood floors with intricate inlay, crown molding, original fireplaces, a charming tin ceiling and built-in cabinetry are just some of the details that make this home so unique. With approximately 3,960 square feet of living space, generously sized rooms and multiple staircases, there is plenty of flexibility for everyday living, entertaining, working from home or simply enjoying the character of an older home.

The kitchen is full of personality, featuring an original brick fireplace, a commercial-grade stove and a new Bosch dishwasher. The formal dining room and living room with fireplace are complemented by a family room, office and additional versatile living space that can be adapted to suit your needs. An oversized sliding glass door opens to the gorgeous patio, creating a natural connection between the home and its beautiful setting.

While its historic character remains at the heart of the home, numerous updates add modern convenience, including a newer roof on the main house, geothermal heating, a whole-house generator, new Andersen windows, a new sliding glass door, blown-in insulation, an updated electrical panel and a whole-house water filtration system. A newer washer and dryer, a charming Dutch door at the side entrance and two upstairs rooms offering additional flexibility add to the home's appeal.

Outside, a U-shaped driveway provides ample parking, while a chicken coop adds to the property's country charm, along with a garden shed, a fenced-in garden and some of the oldest and tallest white pines in the area. Enjoy the space, privacy, and peaceful setting while still being conveniently located near major highways, shopping, restaurants and entertainment, making it easy to enjoy everything the Middletown area has to offer.

This is not a cookie-cutter home, and that is exactly what makes it so special. For someone who appreciates architecture, history and craftsmanship, 59 Webb Road offers a rare opportunity to own a piece of Middletown history, ready for its next chapter!
MLS # 1060361
Monthly Fees N/A
On Site 8 Days
Last Updated 10/17/2026

Location

Contact Agent

Ruth Garcia

Ruth Garcia

(914) 438-5975

Property Details

Community Information

Address 59 Webb Rd, Middletown, NY 10940
County Orange
City Middletown
Zip Code 10940

School Information

School District Middletown
Middle School Monhagen Middle School
Elementary School Maple Hill Elementary School

Architecture

Bedrooms 5
Bathrooms 5 Full / 1 Half
Year Built 1800
Style Colonial
Construction Materials Frame, Vinyl Siding
Basement Bilco Door(s), Crawl Space, Full, Storage Space, Unfinished
Garage Spaces 2

Features / Amenities

Interior Features 1st fl Master Bedroom, First Floor Full Bath, Built-in Features, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Original Details, Storage
Appliances Dishwasher, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Geothermal Water Heater
Equipment Generator
Fireplace Features Decorative, Electric, Wood Burning
Flooring Hardwood, Wood
Laundry Laundry Room
Exterior Features Garden
Accessibility Features Accessible Approach with Ramp
Patio And Porch Covered, Patio, Porch
Parking Features Attached, Driveway, Garage, Oversized
Cooling Central Air, Ductless
Heating Forced Air, Geothermal
Total Rooms 14

Property Features

Lot Size 126,324 Sq. Ft. / 2.9 Acres
Lot Features Back Yard, Front Yard, Level, Part Wooded
Property Attached No
Utilities Trash Collection Private
Sewer Septic Tank
Water Public
Fencing Front Yard, Vinyl

Tax and Financial Info

Tax Year 2026
Tax Annual Amount $12,202.69

Rooms

LevelDescription
Dining RoomFirst
Bedroom 1First
Bathroom 1First
LavatoryFirsthalf bath
LaundryFirst
Family RoomFirst
KitchenFirst
BasementLower
Primary BedroomSecond
Bedroom 2Second
Bedroom 3Second
Bedroom 4Second
OfficeSecond
Bonus RoomSecond
Bathroom 2Second
Bathroom 3Second
Bathroom 4Second
Bathroom 5Second

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59 Webb Rd Middletown, NY 10940 | MLS 1060361
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Listing provided courtesy of Howard Hanna Rand Realty (845-986-4848).
Listings courtesy of Onekey MLS as distributed by MLS GRID.
Based on information submitted to the MLS GRID as of October 22, 2026 6:45 AM EST .
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.

Properties displayed may be listed or sold by various participants in the MLS,” as established by the applicable MLS Governing Documents.
59 Webb Rd Middletown, NY 10940
  • $659,000
  • 5 beds
  • 5 full  1 half baths
  • 3,960 Sq. Ft.