BACK ACTIVE and offering another opportunity to make this special Eastern Shore property your own! Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one-floor living, privacy, history, and a water-oriented lifestyle. Beautifully situated on a spacious setting in the historic Gilpin Point area, this inviting home provides a peaceful country backdrop while still offering convenient access to nearby towns, commuter routes, and the gorgeous Choptank River. Steeped in the rich heritage of the Gilpin Point estate area, this property offers a special connection to one of the Eastern Shore’s most historic riverfront communities. Inside, this updated rancher offers the ease and comfort of true one-level living with a thoughtful layout designed for everyday convenience. The spacious living area creates an inviting place to gather, relax, and unwind, while the eat-in kitchen provides excellent functionality with comfortable dining space and easy flow to the main living areas. The private owner’s suite offers a peaceful retreat with its own full bath, while the additional bedrooms provide wonderful flexibility for family, guests, a home office, craft room, or hobby space. A large laundry and utility area adds valuable storage and practical convenience, keeping everything easily accessible on one level. With generous room sizes, a comfortable layout, and no stairs to navigate, this home is ideal for buyers seeking low-maintenance living without sacrificing space, privacy, or charm. The exterior setting is one of the true highlights of this special property. Surrounded by mature trees and open outdoor space, the home offers a peaceful Eastern Shore setting with established garden areas, fruit-bearing trees, and plenty of room to enjoy outdoor living. Whether you envision gardening, entertaining, relaxing around a fire pit, storing a boat, raising chickens, creating a hobby space, or simply enjoying the quiet surroundings, this property delivers wonderful flexibility. Fenced areas, greenhouse space, a storage shed with electric, and additional outbuilding space add tremendous value for those who enjoy outdoor projects, recreation, or extra storage. With easy access, generous parking, and room to spread out, the property feels private and tucked away while still remaining convenient. Less than five blocks away, Ganey’s Wharf provides access to the beautiful Choptank River, creating an incredible opportunity for boating, fishing, kayaking, crabbing, picnics, or simply enjoying peaceful waterfront views. This is more than a home—it is an Eastern Shore lifestyle. Private, peaceful, updated, and full of Eastern Shore charm, 23116 Gilpin Point Road is an incredible opportunity for buyers seeking true one-level living, generous outdoor space, nearby river access, historic character, and everyday comfort. Ideally located with convenient access to Easton, Denton, Cambridge, Annapolis, Baltimore, Washington, D. C. , Middletown, Dover, Dover Air Force Base, Routes 50 and 301, the Bay Bridge, Kent Island, and Delaware shopping, this property delivers an exceptional combination of privacy and regional accessibility. A wonderful value and an amazing opportunity to enjoy the very best of Eastern Shore living.
Single-familyProperty Type
1989Year Built
1.03 acresLot Size
$199Price/Sq.Ft.
11 spacesParking
Listed by Angela Demattia• Berkshire Hathaway HomeServices PenFed Realty
Discover the epitome of comfortable countryside living with this delightful 3-bedroom rancher nestled on a serene 1.03 +/- acre lot in Preston, MD, less than a mile from Ganey's Wharf public boat ramp. This meticulously maintained home provides the ideal setting for your tranquil escape and easy, one-level living. With an inviting layout, a large primary suite with a walk-in closet, separate office great for remote working, a dedicated laundry room with storage, and abundant outdoor space, this property caters to all your needs. This home has been freshly painted, newly manicured landscaping, and has plenty of parking with a large storage shed. Give us a call to schedule your private showing before it's gone!
BRIGHT MLS #MDCM121748
Jun 28, 2019
Sold
$232,000
$123/sq ft
Jun 1, 2019
Pending
—
Jun 1, 2019
Contingent
—
May 14, 2019
Relisted
—
Apr 22, 2019
Pending
—
Mar 28, 2019
Listed
$247,000
$131/sq ft
Public Records
Jan 15, 2010
Sold
$230,000
$122/sq ft
BRIGHT MLS #1008734304
Sep 11, 2009
Listing Removed
—
Jan 26, 2009
Listed
$249,000
$132/sq ft
Public Records
May 30, 2006
Sold
$175,000
$93/sq ft
Public Records
Dec 4, 2002
Sold
$116,000
$62/sq ft
Public Records
Feb 24, 1997
Sold
$84,500
$45/sq ft
Year
Property tax
Land + Additions
Assessment*
2026
$3,090 (+1.5%)
2025
$3,046 (+5.3%)
2024
$2,893 (+5.6%)
$65,100 + $208,300
$273,400
2023
$2,740 (+5.9%)
2022
$2,587 (+6.9%)
2021
$2,420 (+7.4%)
$65,100 + $166,300
$231,400
2020
$2,253 (+8.0%)
2019
$2,086 (+1.2%)
2018
$2,061 (+1.2%)
2017
$2,036 (+1.3%)
2016
$2,011 (+1.8%)
$60,100 + $118,600
$178,700
2015
$1,975 (−9.3%)
$60,100 + $118,600
$178,700
2014
$2,177 (+4.8%)
$70,100 + $131,100
$201,200
2013
$2,076 (+3.5%)
2012
$2,006 (−19.3%)
2011
$2,484 (+15.1%)
2010
$2,158 (+7.1%)
2009
$2,015
Public record
Public record
Permits
Beds
—
Baths
2
Stories
1
Lot width
—
Lot depth
—
Lot size
1.03 Acres
Year renovated
—
Finished Sq. Ft.
1,880
Unfinished Sq. Ft.
—
Total Sq. Ft.
1,880
Year built
1989
Style
Single Family Residential
County
Caroline County
APN
8 11176
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Oct 8, 2026.
Oct 4, 2016 • Final
Addition
Addition
Remodel
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
8/10 Heat Factor
7 days above 105° expected this year, 16 days in 30 years
6/10 Wind Factor
55% chance of strong winds in next 30 years
2/10 Air Factor
1 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Preston, MD • 21655
Average low and high temperatures (°F)
39
23
44
28
61
40
69
48
74
57
86
65
88
70
81
62
78
61
70
48
59
39
46
29
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
67/ 100
Moderate sunlight
Sunscore
There appears to be some shading by surrounding buildings, terrain, and vegetation.
8 hrs
4.2 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 23116 Gilpin Point Rd
$374,219
$771 under list price of $375K
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $330K to $414K.