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.
For sale
$374,990
23116 Gilpin Point Rd, Preston, MD 21655
4beds
1,880sqft
Single Family Residence
Built in 1989
1.03 Acres Lot
$370,900 Zestimate®
$199/sqft
$-- HOA
What's special
One floor livingFenced areasUpdated eastern shore rancherAdditional outbuilding spaceStorage shed with electricGreenhouse spacePeaceful country backdrop
- 103 days
- 112
- 19
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: $199/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
$370,900
$352,000 - $389,000
$2,297/mo
Price history
| Date | Event | Price |
|---|---|---|
| 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 |
|---|---|---|
| 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.




