Unobstructed westerly waterfront views, small waterfront access (20+ ft. ESTIMATED) and stunning sunsetsan incredible opportunity to own a Madison Bay cottage at just $250,000. Charming 1930 waterfront cottage set on . 91 acres, this 2-bedroom, 2-bath home offers timeless character and exceptional potential. Inside, you’ll find a sunroom, kitchen, and living room thoughtfully positioned to capture the surrounding water views. Multiple waterside decks provide the perfect setting for relaxing or entertaining while taking in the expansive bay vistas. Additional highlights include public sewer, a newer roof, and an unfinished attic space offering exciting expansion possibilities. With a small stretch of waterfront that isn’t suited for a pier, the property still invites you to enjoy the waterperfect for launching a kayak and taking in the peaceful surroundings. While the property does require further improvements, it presents a rare opportunity to create your ideal full-time residence, weekend retreat, or income-producing property in a truly special waterfront setting. Being sold strictly as is.
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Market trends in 21648, MD
Last updated September 2026
Sale-to-List Price
100.0%
+7.8% MoM
Median sale price
$275K
$57K MoM
Avg. days on market
0d
138 days MoM
Recently sold homes
1
0 MoM
Provided by Redfin
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Rental estimate
Est. $2,042 per month, based on comparable rentals
Sale and tax history for 1250 Old Madison Rd
Sale History
Tax History
Date
Event
Price
BRIGHT MLS #MDDO2013044
Sep 22, 2026
Sold
$275,000
$273/sq ft
Aug 31, 2026
Pending
—
Aug 31, 2026
Listed
$275,000
$273/sq ft
BRIGHT MLS #MDDO2012114
May 19, 2026
Listing Removed
—
Apr 24, 2026
Listed
$250,000
$248/sq ft
BRIGHT MLS #MDDO2011830
Apr 2, 2026
Listing Removed
—
Mar 27, 2026
Listed
$1,600,000
$1,587/sq ft
Public Records
Sep 6, 2019
Sold
$175,000
$174/sq ft
BRIGHT MLS #1005047706
Nov 12, 2010
Sold
$169,000
$168/sq ft
Oct 19, 2010
Listing Removed
—
Oct 18, 2010
Listed
$169,000
$168/sq ft
BRIGHT MLS #1001182246
Jan 22, 2004
Listing Removed
—
Jul 15, 2003
Listed
$495,000
$491/sq ft
Public Records
Feb 16, 1999
Sold
$180,000
$179/sq ft
Public Records
Feb 11, 1987
Sold
$145,000
$144/sq ft
Year
Property tax
Land + Additions
Assessment*
2025
$2,056 (+12.8%)
$75,300 + $107,600
$182,900
2023
$1,824 (+5.3%)
2022
$1,732 (+5.6%)
$75,300 + $83,300
$158,600
2021
$1,641 (+5.9%)
2020
$1,550
2019
$1,550 (−47.1%)
$49,700 + $84,300
$134,000
2018
$2,930 (+3.0%)
2017
$2,843 (+0.8%)
$51,400 + $204,900
$256,300
2015
$2,822 (+3.1%)
2014
$2,738 (+3.2%)
2013
$2,653 (+5.7%)
2012
$2,510
2011
2010
$2,282
2009
$2,282
Public record
Public record
Zoning
Beds
—
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
0.92 Acres
Year renovated
—
Sq. Ft.
1,008
Year built
1930
Style
Single Family Residential
County
Dorchester County
APN
16 001406
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 12, 2026.
RR
Rural Residential District
The Rural Residential District is established to encourage and concentrate low- to medium-density residential development in limited areas of the county, near existing towns or in development corridors where public services can be efficiently provided, thereby helping to preserve Resource Conservation and Agricultural Conservation Districts. Rural Residential Districts are not to be served by public community water or sewer systems.
Permitted uses
Include but are not limited to:
Livestock production
Housing-Single unit
Housing-Student
Bed & breakfast
Public service
Recreation
Communications tower
Agriculture-Cropland
Park & open space
Timberland
Property details
Parking
Parking Information
Driveway
Interior
Bedroom Information
# of Bedrooms On Main Level: 2
Bathroom Information
# of Bathrooms (Full) On Main Level: 2
# of Bathrooms (Full): 2
Interior Information
Interior Features: Master Bath(s), Kitchen - Island
Living Area Sq.Ft. Source: Assessor
Basement Information
Basement: Yes
Drainage System, Connecting Stairway, Full, Poured Concrete, Sump Pump, Unfinished, Water Proofing System
Exterior
Property Information
Total Below Grade Sq. Ft.: 0
Ownership Interest: Fee Simple
Property Condition: Average
Year Built Source: Estimated
Building Information
Construction Materials: Vinyl Siding
Foundation Details: Other
Other Structures: Above Grade, Below Grade
Structure Type: Detached
Lot Information
Lot Features: Level
Has Water View
Water Frontage In Feet: 40
Tidal Water: Yes
Above Grade Information
Finished Sq.Ft.: 1,008
Financial
Tax Information
Tax Assessed Value: $174,800
Tax Year: 2025
Tax Annual Amount: $1,800
Utilities
Utilities Information
Central Air
Cooling Type: Central A/C
Cooling Fuel: Electric
Heat Pump(s)
Heating Fuel: Electric
Hot Water: Electric
Sewer Septic: Public Sewer
Water Source: Private
Location
School Information
School District Name: DORCHESTER COUNTY PUBLIC SCHOOLS
Location Information
Outside City Limits
Directions: Use GPS
Waterfrontage Information
On Waterfront
Water Oriented
Water Body Type: Bay
Water Body Name: Madison Bay
Public facts
Beds: —
Baths: 2.0
Sq. Ft.: 1,008
Stories: 1.0
Lot Size: 0.92 acres
Style: Single Family Residential
Year Built: 1930
Year Renovated: —
County: Dorchester County
APN: 16 001406
Home facts updated by county records on Oct 12, 2026
Around this home
Schools
South Dorchester School
Public PreK-8 • Assigned • 8.1mi
8/10
Cambridge-South Dorchester High School
Public 9-12 • Assigned • 7.4mi
2/10
Provided by GreatSchools
Historical weather
Madison, MD • 21648
Average low and high temperatures (°F)
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43
68
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59
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32
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Feb
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Aug
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Dec
Sun exposure
99/ 100
Exceptional sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
11 hrs
7.1 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$305,000 – $370,000
Sell confidently with a local market expert in Madison.