$659,000

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,… Read More 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! Read Less

Listing Courtesy of Howard Hanna Rand Realty.

Listing Snapshot

Days Online

Last Updated

Oct 18, 2026

Property Type

Single Family Residence

Beds

Full Baths

Partial Baths

Square Ft.

3,960

Lot Size

2.9 Acres

Year Built

1800

Property Tax

$12,203

MLS Number

1060361

Additional Details

Appliances & Equipment

Dishwasher, Microwave, Oven, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Geothermal Water Heater, Other equipment: Generator

Basement

Bilco Door(s), Crawl Space, Full, Storage Space, Unfinished

Building

Built in 1800, Living area: 3960, Construction Materials: Frame, Vinyl Siding

Cooling

Central Air, Ductless

Accessibility Features

Accessible Approach with Ramp

Exterior Features

Patio/Porch Features: Covered, Patio, Porch, Garden

Fence

Front Yard, Vinyl

Fireplaces

Decorative, Electric, Wood Burning

Floors

Hardwood, Wood

Garage

2 spaces

Heating

Forced Air, Geothermal

Interior Features

First Floor Bedroom, First Floor Full Bath, Built-in Features, Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entrance Foyer, Original Details, Storage

Laundry

Laundry Room

Lot

2.9 acres, Back Yard, Front Yard, Level, Part Wooded

Parking

Attached, Driveway, Garage, Oversized

Sewer

Septic Tank

Taxes

Parcel Number: 335200-069-000-0001-037.000-0000, Annual Amount: $12,202.7, Assessed Value: $71,300, Year: 2026

Utilities

Trash Collection Private, Water Source: Public

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