$650,000

Step into timeless charm without leaving behind today's comforts. This distinctive Painted Lady captures the character, craftsmanship, and gracious proportions that make a home truly memorable, right in the heart of Middletown. Set well back from historic Main Street behind an expansive front lawn, the home has an impressive presence,… Read More with a wide wraparound porch inviting you to sit awhile and enjoy the rhythm of small-town living. Located within the sought-after Middletown school district, this is a home that feels a part of the town's story. Offering over 3,000 finished square feet above grade, the home has been lovingly cared for by the same owners since 1997. Natural light and tall ceilings on every level create a remarkably open and airy feel, while fresh paint complements the beautiful architectural details throughout. An impressive entry foyer sets the tone with original millwork and wood floors, fireplace mantels, pocket doors, a built-in bookcase, and a distinctive split staircase. Stacked bay windows on separate levels feature diamond-pattern divided-light upper sashes and clear glass below - one of the many details that makes this home so special. The spacious front living room features custom built-ins, a fireplace, and pocket doors connecting both the foyer and dining room. The large dining room is ready for holidays, celebrations, and everyday dinners, with a side door opening directly onto the wraparound porch. The updated kitchen blends classic character with modern function, featuring a large center island, wall oven, cooktop, built-in cabinetry, and a charming original pass-through cupboard. A mudroom provides a practical everyday entrance and access to the covered rear porch, while a main-level half bath adds convenience. Upstairs are three generously sized bedrooms, including a spacious primary suite with a private full bath, plus an additional hall bath. An open loft area provides flexible space for an office, study, reading nook, or sitting area. The completely remodeled finished third floor adds another exceptional level of living space, with tall ceilings, abundant natural light, a large recreation room, separate den, and laundry area. Use it as an office, studio, exercise space, media room, hobby room, or private retreat. A unique glass-floor feature allows light to pass through and adds an unexpected architectural element. Outside, there is room to breathe - something increasingly difficult to find right in the heart of town. The large, level property stretches from Main Street to Green Street with access from both streets, offering an expansive front lawn and spacious backyard. A detached one-car garage adds convenience, while eligibility for future subdivision through the Town of Middletown adds another unique dimension. Additional features include air conditioning, radiator heat, updated electrical, a clean unfinished basement for utility and storage, and eligibility for a one-year home warranty. Perhaps what makes this home most memorable is simply the feeling of it - the sunlight, tall ceilings, warmth of the wood floors, beautiful architectural details, and the ability to step onto that wonderful wraparound porch and watch Main Street go by. Filled with charm and personality, yet offering the light, space, and functionality for the way we live today, this gracious Painted Lady is ready for its next chapter. Read Less

Courtesy of Bobbi Prescott, RE/MAX Results 301-698-5005

Listing Snapshot

Days Online

Last Updated

Sep 14, 2026

Property Type

Single Family Residential

Beds

Full Baths

Partial Baths

Square Ft.

3,000

Lot Size

0.6 Acres

Year Built

1913

MLS Number

MDFR2088606

Additional Details

Appliances & Equipment

Stainless Steel Appliances, Refrigerator, Cooktop, Oven - Wall, Dishwasher, Disposal, Washer, Dryer

Basement

Daylight, Partial

Building

Built in 1913, Living area: 3000, Levels: 4, Construction Materials: Wood Siding

Cooling

Central A/C

Accessibility Features

None

Exterior Features

Patio/Porch Features: Porch(es), Sidewalks

Fireplaces

1 fireplace, Corner

Floors

Hardwood

Foundation

Slab

Garage

1 spaces

Heating

Radiator

Interior Features

Built-Ins, Combination Dining/Living, Dining Area, Floor Plan - Traditional, Formal/Separate Dining Room, Kitchen - Island, Primary Bath(s), Upgraded Countertops, Wood Floors

Lot

0.6 acres

Property

Excellent, Other structures: Above Grade

Roof

Slate

Sewer

Public Sewer

Taxes

Annual Amount: $7,550.52, Year: 2027, Zoning: R

Utilities

Water Source: Public

Windows

Bay/Bow

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