59 Webb Rd
Middletown, NY 10940
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
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!
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
(914) 438-5975Property Details
Community Information
School Information
School District
Middletown
High School
Middletown High School
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
| Level | Description | |
| Dining Room | First | |
| Bedroom 1 | First | |
| Bathroom 1 | First | |
| Lavatory | First | half bath |
| Laundry | First | |
| Family Room | First | |
| Kitchen | First | |
| Basement | Lower | |
| Primary Bedroom | Second | |
| Bedroom 2 | Second | |
| Bedroom 3 | Second | |
| Bedroom 4 | Second | |
| Office | Second | |
| Bonus Room | Second | |
| Bathroom 2 | Second | |
| Bathroom 3 | Second | |
| Bathroom 4 | Second | |
| Bathroom 5 | Second |
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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.
Properties displayed may be listed or sold by various participants in the MLS,” as established by the applicable MLS Governing Documents.