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5 Beds
6 Baths
3,960 sqft

$659,000

59 Webb Road, Middletown NY, 10940

Price per sqft$166.41
Built in1800
Property size3,960 sqft
Property typeResidential
Courtesy of Howard Hanna Rand Realty, Lori Kolesar Listing Contact: 845-986-4848

Overview

Active

Listed Oct 15, 2026

Updated 4h ago

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!

$4,384/mo

Est. mortgage payment based on a $659,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
1060361

Interior Features

Bedrooms
5
Bathrooms
6
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
2.9 Acres

Other Property Details

Taxes
$12,203
Tax Frequency
Annually
Garage
Yes
55+/Senior Community
No

Listings courtesy of OneKey MLS as distributed by MLS GRID

All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change or withdrawal. Neither listing broker(s) nor Acard Winograd Team shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless. Properties displayed may be listed or sold by various participants in the MLS.

Based on information submitted to the MLS GRID as of 9:05 AM UTC on 10/16/2026. 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.

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