House Chestertown (United States)by ttr sotheby's international realty

Backto the list : house for Sale at Chestertown

HouseChestertown (United States)
Price :
$325,000
bedrooms4 bathrooms2 land1,902 m²

Name: Chestertown Luxury House for Sale | $325,000
Creator: Le Figaro Properties

A rare opportunity to own a classic two-story split-level home in Chestertown — set on a large, shaded corner lot just a few miles to Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, and only steps to locally loved restaurants and everyday conveniences. This is the kind of home that simply isn't built anymore: classic lines, original details, and the quiet character that comes from decades of careful ownership. Step inside and the home tells its story with original trim, classic proportions and timeless architectural touches. The two-story split-level floor plan offers a thoughtful separation of living and sleeping spaces, with a sun-filled sunroom that works beautifully as a screened porch when the doors are all open or as extra living space during the shoulder seasons. Two of the bedrooms sit on the upper level, while two large bedrooms flow comfortably below. Out back, the large, gently sloped corner lot offers privacy, mature trees, and room to garden, entertain, or simply enjoy a quiet afternoon. The setting feels tucked away, while the rest of Chestertown is just a short jaunt from the front door. The two-bay carport keeps your vehicles safe from the elements in the wide stone driveway. What truly sets this home apart is its condition. It has been maintained impeccably — spotlessly clean, carefully tended, and gently lived in. The HVAC system is new, and the kitchen and laundry appliances are all young as well, giving the next owner the best of both worlds: classic character on the outside, modern mechanicals where it counts. The remaining finishes offer a thoughtful canvas for the next owner to put their own stamp on it, with the confidence that the bones and the care have already been handled. Classic character, pristine condition, and convenience to it all.

Advertiser reference : PFYC8SLe Figaro Properties reference : 107082441

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House Chestertown (United States)

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Liddy Campbell

ttr sotheby's international realty

17 Goldsborough Street21601 Easton (United States) All the listings of this agency

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Chestertown (United States)

Similar listings this house, Chestertown

House Chestertown (United States)

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home set on a large, shaded yard just a few flat blocks from Downtown Chestertown, Washington College, the weekly farmers market, the town's annual festivals, locally loved restaurants, and everyday groceries. The location is the kind that sells itself: leave the car in the driveway and run the day on foot, from morning coffee downtown to an evening stroll after the festivals. Inside, the sun-filled sunroom anchors the home with year-round natural light and a flexible layout that adapts to how you actually live. Use it as a quiet reading nook, a bright home office, an art studio, or simply a place to begin and end each day. The three-bedroom, single-level floor plan delivers true main-level living with no stairs and no wasted square footage, an increasingly rare find in historic Chestertown. The HVAC has been recently updated, providing year-round comfort, modern efficiency, and predictable utility costs for new owners. Step outside to a generous, tree-shaded yard offering a level of privacy and outdoor space uncommon to a home this close to downtown. There's room to garden, host family dinners, let pets roam, or simply enjoy a quiet afternoon in the shade. The setting feels tucked away while the rest of the town is just a short walk from your front door. For weekend owners, the home offers true lock-and-leave simplicity. For full-time residents, it offers the daily rhythm of a small college town with a real cultural calendar, a thriving farmers market, and a walkable downtown filled with independent shops and restaurants. Fiber optic internet is available at the property, supporting fast, reliable connectivity for remote work, streaming, and study without compromise. Single-level, move-in ready, and walkable to it all — a rare combination in this small, storybook college town. The home suits a wide range of buyers, from first-time homeowners and downsizers to weekend retreat owners and anyone seeking a quieter life with genuine connection to community. Schedule your private tour today!

…

$325,000

3bd

land 1,174m²

By Ttr Sotheby's International Realty

House Chestertown (United States)

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

…

$350,000

1bd

By Ttr Sotheby's International Realty

House Chestertown (United States)

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

…

$375,000

2bd

By Ttr Sotheby's International Realty

House Chestertown (United States)

**Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

…

$1,600,000

7bd

By Ttr Sotheby's International Realty

HouseChestertown (United States)
Price :
$325,000
bedrooms4 bathrooms2 land1,902 m²

Its assets

In detail

Energy Performance Certificate

GreenHouse Gas emission

House Chestertown (United States)

Visit this house

Contact an advisor

House Chestertown (United States)

House Chestertown (United States)

House Chestertown (United States)

House Chestertown (United States)

HouseChestertown (United States)Price : $325,000 USDEuro € EURAmerican Dollar ($ USD)British Pound (£ GBP)bedrooms4 bathrooms2 land1,902 m²

Its assets

In detail

House Chestertown (United States)

Visit this house

Contact an advisor

HouseChestertown (United States)
Price :
$325,000
bedrooms4 bathrooms2 land1,902 m²