4910 GREGORY ROAD

CAMBRIDGE, MD 21613

Beds

4

Baths

3

Square Ft.

3,192

Active Under Contract

Residential

$995,000

Step into the elegance of a 50-acre waterfront estate steeped in timeless charm. Built in 1920, this Neo-Classical Eastern Shore property offers the perfect combination of sophistication and natural beauty. The property is awaiting the perfect buyer who can transform it back to the style and charisma of it's earlier… Read More days. Enjoy a bright, welcoming interior. The main house features a large center hall foyer that leads to a stunning living room with a brick fireplace, custom-built shelving, and dual French doors opening into a sunroom. Bask in serene waterfront views from the sunroom, complete with hardwood flooring and another brick fireplace - a space designed for entertaining or quiet retreats. Create unforgettable dining experiences in a formal dining room highlighted by Black Walnut paneling, tasteful wall sconces, and a custom-built wine glass cabinet. The enclosed side porch, fitted with vintage touches like brick flooring, laundry amenities, and the original farmhouse enamel sink, doubles as a mudroom. Meanwhile, the waterside screened porch invites al fresco dining with picturesque views of Church Creek. The second floor offers practicality and comfort with four bedrooms and two bathrooms, accommodating family and guests with ease. A walk-in cedar lined closet and another walk-in attic closet offer a surprising amount of storage. Enhance your lifestyle with additional perks. A thoughtfully updated guest cottage (2019) offers two bedrooms, one bathroom, a kitchen, a living room, a dining area, and laundry facilities - currently enjoyed as a vacation rental. Wildlife thrives here: expect visits from ospreys, bald eagles, and white-tail deer in an atmosphere guests rave about. Relax poolside with a redesigned in-ground pool (2022) boasting a paver deck, modern landscaping, and fencing - all with views of Church Creek. A 28 x 42 wooden barn with concrete flooring, with space sufficient for garage/vehicle or boat storage, and an upper story is complemented by a four-stall stable and additional sheds. The barn built in 1960 was built using reclaimed wood from old chicken houses. Environmental stewardship defines this property. Placed in an Environmental Trust, the land remains protected, ensuring its use promotes nature and agriculture. Boating lovers will appreciate the creek's access to the Chesapeake Bay, renowned for crabbing, fishing, kayaking, and paddle boarding. Let your vision breathe life into this stunning space. This estate pairs historical allure with limitless possibilities for those ready to turn dreams into reality. Read Less

Courtesy of Sharon Spedden, Sharon Real Estate P.C. [email protected]

Listing Snapshot

Days Online

35

Last Updated

Oct 10, 2025

Property Type

Single Family Residential

Beds

4

Full Baths

2

Partial Baths

1

Square Ft.

3,192

Lot Size

50 Acres

Year Built

1920

MLS Number

MDDO2010050

30 Days Snapshot Of 21613

$339k

+20%

(avg) sold price

23

-11%

homes sold

62

-8%

(avg) days on market

Snapshot

Area Map

Additional Details

Property Access

Boat - Powered, Canoe/Kayak, Fishing Allowed, Personal Watercraft (PWC)

Appliances & Equipment

Dishwasher, Dryer, Oven/Range - Electric, Refrigerator, Washer

Basement

Partial, Sump Pump

Building

3,192 sqft living area, 3,192 sqft above grade (finished), Built in 1920, Structure Type: Detached, Wall & Ceiling Types: Plaster Walls, 2 levels, Cape Cod, Aluminum Siding

Cooling

Electric, None

Doors

French, Storm

Exterior Features

Boat Storage, Outbuilding(s)

Fireplaces

2 fireplaces, Brick, Mantel(s), Wood

Floors

Wood, Tile/Brick

Foundation

Crawl Space

Water Features

Navigable Water, Water Access, Water Body Name: CHURCH CREEK, Water Body Type: Creek, Water Oriented, Waterfront Features: Y, Rip-Rap

Heating

Oil, Radiator

Interior Features

Breakfast Area, Built-Ins, Floor Plan - Traditional, Formal/Separate Dining Room, Wood Floors, Cedar Closet(s), Kitchen - Eat-In, Primary Bath(s), Walk-in Closet(s)

Laundry

Has Laundry, Main Floor

Lot

2,178,000 sqft, 50 acres, Fishing Available, Hunting Available, Partly Wooded, Rip-Rapped, Secluded, Rural, Trees/Wooded

Parking

Circular Driveway, Gravel Driveway

Pool

In Ground

Property

Horse, Horse Amenities: Horses Allowed, Other Structures: Above Grade, Below Grade, Outdoor Living Structures: Porch(es), Screened, View: Creek/Stream, Water, Trees/Woods

Roof

Shingle

Sewer

Septic Exists

Taxes

County Tax: $4,715, County Tax Pymnt Freq: Annually, Tax Annual Amount: $4,715, Tax Year: 2024

Utilities

Hot Water: None, Electric Available, Phone Available

Windows

Wood Frame, Storm

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South Dorchester School 410-901-6934 Public PK-8

Cambridge-South Dorchester High School 410-228-9224 Public 9-12

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This information is provided exclusively for consumers' personal, non-commercial use; that it may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing, and that data is deemed reliable but is not guaranteed accurate by BrightMLS. Information may appear from many brokers but not every listing in BrightMLS is available.
This content last updated on Oct 10, 2025.

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