Chestertown
5
bedrooms
bedrooms
4
bathrooms
bathrooms
5,241
build ft2
build ft2
59,242
land ft2
land ft2
About This Property
Chesapeake Bay Waterfront with Breathtaking Views. Experience exceptional waterfront living in this custom-built 5,240 sq ft residence, beautifully situated on an elevated bluff in the sought-after Great Oak Community of Chestertown, Maryland. Offering 5 bedrooms and 3.5 baths, this remarkable home captures sweeping Chesapeake Bay views and unforgettable sunsets from nearly every room. The property features 150 feet of riprap-protected shoreline and direct water access via a brand-new private 140ft pier complete with lighting, water service in four locations, a 12,000-lb boat lift, and two jet ski lifts—perfect for boating and waterfront recreation. Inside, the home impresses with 9-foot ceilings and hardwood floors throughout most of the main level. Designed for entertaining, the gourmet kitchen showcases luxury appliances, a distinctive chef’s cutting-board countertop, and new LVP flooring. The grand great room is a true showpiece, featuring a floor-to-ceiling brick wood-burning fireplace, vaulted shiplap pine ceiling, exposed beams, and views of the Bay! Additional living spaces include an elegant formal dining room, a spacious gathering room, and a casual dining area highlighted by a gas fireplace. The first-floor primary suite offers privacy and comfort with a walk-in closet and an updated bath featuring new flooring, a corner soaking tub, and dual vanities. Two additional bedrooms, a full bath, and a laundry room complete the main level. The second floor provides two generously sized bedrooms, a large living area, a full bath, and an 18’ x 22’ unfinished bonus room/man cave with a separate staircase offering access to the garage or exterior—ideal for future expansion or customization. Notable features include a new roof, an oversized two-car garage with workbench, a small basement housing a state-of-the-art temperature- and humidity-controlled wine cellar, a Culligan whole-house water filtration system, and two hot water heaters. One of the home’s most captivating spaces is the expansive screened-in porch, stretching across much of the waterfront side of the home. With three ceiling fans and panoramic Chesapeake Bay views, it offers the perfect setting for relaxing or entertaining year-round. Whether you’re seeking a serene waterfront retreat or a home designed for memorable gatherings, this exceptional coastal property delivers. Just minutes from historic Chestertown, home to Washington College, waterfront dining, farmers’ markets, parks, festivals, and river cruises. Conveniently located near Safe Harbor Great Oak Marina and approximately 90 minutes from Washington, D.C. and Philadelphia. Schedule your private showing and experience Chesapeake Bay living at its finest
Listing Agent: Lona Sue Todd. Taylor Properties 410-310-0222 lstodd11@outlook.com
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Property Features
Location Information
County:
Subdivision: GREAT OAK ESTATES
Interior Features
Appliances: Built-In Range, Commercial Range, Dishwasher, Dryer, Energy Efficient Appliances, Microwave, Range Hood, Refrigerator, Stainless Steel Appliances, Six Burner Stove, Washer - Front Loading, Water Conditioner - Owned, WaterHeater
Interior: Breakfast Area, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Bathroom - Stall Shower, Walk-in Closet(s), Window Treatments, Wine Storage, Wood Floors
Laundry:
Furnished: None
Flooring:
Water: Private
Interior: Breakfast Area, Ceiling Fan(s), Dining Area, Entry Level Bedroom, Family Room Off Kitchen, Floor Plan - Open, Formal/Separate Dining Room, Kitchen - Eat-In, Kitchen - Gourmet, Kitchen - Island, Primary Bath(s), Primary Bedroom - Bay Front, Recessed Lighting, Bathroom - Stall Shower, Walk-in Closet(s), Window Treatments, Wine Storage, Wood Floors
Laundry:
Furnished: None
Flooring:
Water: Private
Cooling: Central A/C
Heating: Heat Pump(s)
Fireplaces: 2
Windows: Energy Efficient, DoublePaneWindows, Screens
Utilities: Electric Available, Propane, PhoneConnected
Sewer: PrivateSewer
Heating: Heat Pump(s)
Fireplaces: 2
Windows: Energy Efficient, DoublePaneWindows, Screens
Utilities: Electric Available, Propane, PhoneConnected
Sewer: PrivateSewer
Rooms
Room Type: Bedroom 4
Features: Flooring - Carpet
Level: Upper 1
Features: Flooring - Carpet
Level: Upper 1
Room Type: Bedroom 5
Features: Flooring - Carpet
Level: Upper 1
Features: Flooring - Carpet
Level: Upper 1
Room Type: 2nd Stry Fam Rm
Level: Upper 1
Level: Upper 1
Room Type: Bonus Room
Features: Attic - Floored
Level: Upper 1
Features: Attic - Floored
Level: Upper 1
Room Type: Kitchen
Features: Double Sink, Kitchen - Propane Cooking, Island
Level: Main
Features: Double Sink, Kitchen - Propane Cooking, Island
Level: Main
Room Type: Dining Room
Features: Flooring - HardWood
Level: Main
Features: Flooring - HardWood
Level: Main
Room Type: Foyer
Level: Main
Level: Main
Room Type: Bedroom 3
Level: Main
Level: Main
Room Type: Family Room
Features: Fireplace - Wood Burning, Flooring - HardWood, Cathedral/Vaulted Ceiling
Level: Main
Features: Fireplace - Wood Burning, Flooring - HardWood, Cathedral/Vaulted Ceiling
Level: Main
Room Type: Bedroom 2
Features: Flooring - Carpet
Level: Main
Features: Flooring - Carpet
Level: Main
Room Type: Primary Bedroom
Features: Flooring - Carpet
Level: Main
Features: Flooring - Carpet
Level: Main
Room Type: Living Room
Features: Flooring - HardWood, Fireplace - Gas
Level: Main
Features: Flooring - HardWood, Fireplace - Gas
Level: Main
Room Type: Other
Features: Flooring - Concrete
Level: Lower 1
Features: Flooring - Concrete
Level: Lower 1
Exterior Features
Year Built: 1997
Legal Subdivision: Great Oak Estates
Subdivision Name: Great Oak Estates
Exterior Features: Exterior Lighting, Outbuilding(s)
Parking: Circular Driveway, Stone Driveway
Garage Spaces: 2.0
Legal Subdivision: Great Oak Estates
Subdivision Name: Great Oak Estates
Exterior Features: Exterior Lighting, Outbuilding(s)
Parking: Circular Driveway, Stone Driveway
Garage Spaces: 2.0
Schools
Elementary School: None
Junior High School: None
Junior High School: None
High School: None
Listing Courtesy of Lona Sue Todd. Taylor Properties 410-310-0222 lstodd11@outlook.com
Property Photos [Click to enlarge]
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