NEW PRICE! RECENTLY REDUCED BY NEARLY $40,000! AN INCREDIBLE OPPORTUNITY TO ENJOY EASTERN SHORE LIVING! Welcome to 23116 Gilpin Point Road in Preston, an updated Eastern Shore rancher offering the perfect blend of one-level living, privacy, history, and a water-oriented lifestyle. Beautifully situated in the historic Gilpin Point area, this inviting home provides a peaceful country backdrop with convenient access to nearby towns, commuter routes, and the Choptank River. Steeped in the heritage of the Gilpin Point estate area, the property offers a special connection to one of the Eastern Shore’s historic riverfront communities. Inside, enjoy the ease and comfort of true one-level living with a thoughtful layout designed for everyday convenience. The spacious living area is an inviting place to gather and unwind, while the eat-in kitchen offers comfortable dining space and easy flow to the main living areas. The private owner’s suite features its own full bath, and additional bedrooms offer flexibility for guests, a home office, craft room, or hobbies. A large laundry and utility area provides valuable storage and practical convenience, all on one level. Generous room sizes and a comfortable layout make this home an appealing choice for buyers seeking convenient living without sacrificing space or charm. Outside, the recently refreshed landscaping enhances the home's welcoming curb appeal and highlights its peaceful Eastern Shore setting. Mature trees, open outdoor space, and room to make the yard your own create opportunities for future flower beds, a vegetable garden, outdoor entertaining, or simply relaxing in the fresh air. Whether you envision a fire pit, boat storage, raising chickens, or space for your favorite projects, this property offers flexibility to suit your lifestyle. Fenced areas, greenhouse space, a storage shed with electric, and additional outbuilding space provide options for recreation, hobbies, and storage. Generous parking and room to spread out complete the setting. Less than five blocks away, Ganey’s Wharf provides access to the beautiful Choptank River, with opportunities for boating, fishing, kayaking, crabbing, picnics, or simply enjoying 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 offers one-level living, generous outdoor space, nearby river access, historic character, and everyday comfort. Conveniently located for 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. An exceptional opportunity to enjoy Eastern Shore living at a newly improved price!
For sale
Price cut: $40K (10/22)
$335,000
23116 Gilpin Point Rd, Preston, MD 21655
4beds
1,880sqft
Single Family Residence
Built in 1989
1.03 Acres Lot
$334,000 Zestimate®
$178/sqft
$-- HOA
What's special
One floor livingFenced areasUpdated eastern shore rancherAdditional outbuilding spaceStorage shed with electricGreenhouse spacePeaceful country backdrop
- 151 days
- 915
- 97
Zillow last checked:
Listing updated:
Listed by:
Angela Demattia 240-687-6677,
Berkshire Hathaway HomeServices PenFed Realty 410-647-8000
Source: Bright MLS,MLS#: MDCM2007400
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 2
- Full bathrooms: 2
- Main level bathrooms: 2
- Main level bedrooms: 4
Rooms
- Room types: Bedroom 2, Bedroom 3, Bedroom 4, Bedroom 1, Bathroom 1, Bathroom 2
Bedroom 1
- Level: Main
Bedroom 2
- Level: Main
Bedroom 3
- Level: Main
Bedroom 4
- Level: Main
Bathroom 1
- Level: Main
Bathroom 2
- Level: Main
Heating
- Heat Pump, Electric
Cooling
- Central Air, Electric
Appliances
- Included: Microwave, Dryer, Dishwasher, Exhaust Fan, Oven/Range - Electric, Refrigerator, Washer, Water Heater, Electric Water Heater
Features
- Bathroom - Stall Shower, Bathroom - Walk-In Shower, Breakfast Area, Ceiling Fan(s), Combination Dining/Living, Entry Level Bedroom, Open Floorplan, Floor Plan - Traditional, Eat-in Kitchen, Kitchen - Table Space, Primary Bath(s), Recessed Lighting, Walk-In Closet(s), Other, Dry Wall
- Flooring: Carpet, Laminate, Vinyl
- Doors: French Doors
- Windows: Screens, Window Treatments
- Has basement: No
- Has fireplace: No
Interior area
- Total structure area: 1,880
- Total interior livable area: 1,880 sqft
- Finished area above ground: 1,880
- Finished area below ground: 0
Property
Parking
- Total spaces: 11
- Parking features: Gravel, Detached Carport, Driveway, Off Street
- Carport spaces: 1
- Uncovered spaces: 10
Accessibility
- Accessibility features: Other
Features
- Levels: One
- Stories: 1
- Patio & porch: Porch
- Exterior features: Lighting, Extensive Hardscape, Flood Lights, Sidewalks, Storage, Other
- Pool features: None
- Has spa: Yes
- Spa features: Bath
- Fencing: Back Yard,Wood,Other,Wire
- Has view: Yes
- View description: Street, Trees/Woods
- Waterfront features: Public Access, River
Lot
- Size: 1.03 Acres
Details
- Additional structures: Above Grade, Below Grade, Outbuilding
- Parcel number: 0608011176
- Zoning: R
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch/Rambler
- Property subtype: Single Family Residence
Materials
- Vinyl Siding
- Foundation: Crawl Space, Block
- Roof: Architectural Shingle
Condition
- New construction: No
- Year built: 1989
Utilities & green energy
- Sewer: On Site Septic
- Water: Well
Community & HOA
Community
- Security: Security System
- Subdivision: None Available
HOA
- Has HOA: No
Location
- Region: Preston
Financial & listing details
- Price per square foot: $178/sqft
- Tax assessed value: $282,633
- Annual tax amount: $3,046
- Date on market: 6/4/2026
- Listing agreement: Exclusive Right To Sell
- Listing terms: Cash,Conventional,USDA Loan,VA Loan,FHA
- Inclusions: Premium Kitchen Appliances, Bathroom Mirrors And Accessories, Ceiling Fans-3, Clothes Washer & Dryer, Drapery / Curtain Rods, Draperies / Curtains, Exhaust Fans-3, Existing Carpet, Satellite Dish, Screens, Shades / Blinds, Storage Sheds-2,
- Ownership: Fee Simple
Estimated market value
$334,000
$317,000 - $351,000
$2,294/mo
Price history
| Date | Event | Price |
|---|---|---|
| 10/22/2026 | Price change | $335,000-10.7%$178/sqft |
Source: | ||
| 9/14/2026 | Listed for sale | $374,990$199/sqft |
Source: | ||
| 6/23/2026 | Contingent | $374,990$199/sqft |
Source: | ||
| 6/4/2026 | Listed for sale | $374,990-6%$199/sqft |
Source: | ||
| 5/27/2026 | Listing removed | $399,000$212/sqft |
Source: | ||
| 5/15/2026 | Price change | $399,000-5.9%$212/sqft |
Source: | ||
| 4/30/2026 | Price change | $424,000-2.3%$226/sqft |
Source: | ||
| 2/27/2026 | Listed for sale | $434,000+14.2%$231/sqft |
Source: | ||
| 9/27/2023 | Sold | $380,000$202/sqft |
Source: | ||
| 8/27/2023 | Pending sale | $380,000$202/sqft |
Source: | ||
| 8/25/2023 | Listed for sale | $380,000+63.8%$202/sqft |
Source: | ||
| 7/19/2019 | Sold | $232,000-6.1%$123/sqft |
Source: Public Record Report a problem | ||
| 3/28/2019 | Listed for sale | $247,000+7.4%$131/sqft |
Source: Meredith Fine Properties #MDCM121748 Report a problem | ||
| 1/21/2010 | Sold | $230,000+31.4%$122/sqft |
Source: Public Record Report a problem | ||
| 5/30/2006 | Sold | $175,000+50.9%$93/sqft |
Source: Public Record Report a problem | ||
| 12/4/2002 | Sold | $116,000+37.3%$62/sqft |
Source: Public Record Report a problem | ||
| 2/24/1997 | Sold | $84,500$45/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2026 | $3,090 +1.5% | $282,633 +3.4% |
| 2025 | $3,046 +7.5% | $273,400 +5.4% |
| 2024 | $2,833 +5.7% | $259,400 +5.7% |
| 2023 | $2,680 +6.1% | $245,400 +6.1% |
| 2022 | $2,527 +7.1% | $231,400 +7.1% |
| 2021 | $2,360 +7.6% | $216,100 +7.6% |
| 2020 | $2,193 +8.2% | $200,800 +8.2% |
| 2019 | $2,026 +1.2% | $185,500 +1.2% |
| 2018 | $2,001 +1.3% | $183,233 +1.3% |
| 2017 | $1,976 -1.5% | $180,967 +1.3% |
| 2016 | $2,006 | $178,700 |
| 2015 | $2,006 | $178,700 |
| 2014 | $2,006 | $178,700 -11.2% |
| 2013 | -- | $201,200 |
| 2012 | -- | $201,200 |
| 2011 | -- | $201,200 -19.5% |
| 2010 | -- | $249,930 +9.8% |
| 2009 | -- | $227,580 +10.9% |
| 2008 | -- | $205,230 +59.6% |
| 2007 | -- | $128,620 +13.3% |
| 2006 | -- | $113,552 +15.3% |
| 2005 | -- | $98,486 +18.1% |
| 2004 | -- | $83,420 +3% |
| 2003 | -- | $80,966 +3.1% |
| 2002 | -- | $78,513 +3.2% |
| 2001 | -- | $76,060 |
Find assessor info on the county website
Monthly payment
Est. payment
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.Climate risks
Neighborhood: 21655
Nearby schools
Schools provided by the listing agent
- District: Caroline County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.




