# 23116 GILPIN POINT Road, Preston, MD 21655 > **TL;DR:** 4bd/2ba single family, $374,990 ($199/sqft), built 1989, 1,880 sqft. > A/C. Est. $2,005/mo. Listed 106 days. ## Property at a Glance | Attribute | Value | |-----------|-------| | Price | $374,990 | | Price/sqft | $199 | | Bedrooms | 4 | | Bathrooms | 2 full | | Square Feet | 1,880 | | Year Built | 1989 | | Lot Size | 44,867 sqft (1.03 acres) | | Stories | 1 | | Property Type | Single Family (Single Family Residence) | | Status | Active | | Days on Market | 106 | ## Estimated Monthly Costs | Category | Amount | |----------|--------| | Principal & Interest (20% down, 30-year at 6.5%) | $1,896 | | Estimated Insurance | $109 | | **Total** | **$2,005** | ## Key Amenities - A/C ## Property Highlights - Built in 1989 - 1.03 acre lot - 11 parking spaces ## Description ### Agent Description 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. ## Location - **Address:** 23116 GILPIN POINT Road, Preston, MD 21655 - **County:** CAROLINE - **Neighborhood:** NONE AVAILABLE - **Coordinates:** 38.80039, -75.90391 - **Google Maps:** https://www.google.com/maps?q=38.80039,-75.90391 ## Virtual Tour & Media - **Video Tour:** https://my.matterport.com/show/?m=AS88bbPtKrg ## Listing Agent - **Name:** Angela C Demattia · **License:** 584403 - **Brokerage:** Berkshire Hathaway HomeServices PenFed Realty - **Phone:** (866) 225-5778 - **Broker Phone:** (866) 225-5778 - **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/23116-Gilpin-Point-Rd_Preston_MD_21655_M61857-81264?f=listhub&s=TRENDPA&m=MDCM2007400&c=propsimple) ## Photos ![23116 GILPIN POINT Road - Photo 1](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1315843173r.jpg) ![23116 GILPIN POINT Road - Photo 2](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f127207945r.jpg) ![23116 GILPIN POINT Road - Photo 3](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f4243046248r.jpg) ![23116 GILPIN POINT Road - Photo 4](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3682058969r.jpg) ![23116 GILPIN POINT Road - Photo 5](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2994853885r.jpg) ![23116 GILPIN POINT Road - Photo 6](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f808420223r.jpg) ![23116 GILPIN POINT Road - Photo 7](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f649952944r.jpg) ![23116 GILPIN POINT Road - Photo 8](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f4206359676r.jpg) ![23116 GILPIN POINT Road - Photo 9](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3513690765r.jpg) ![23116 GILPIN POINT Road - Photo 10](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f44960966r.jpg) ![23116 GILPIN POINT Road - Photo 11](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3546728187r.jpg) ![23116 GILPIN POINT Road - Photo 12](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2751114924r.jpg) ![23116 GILPIN POINT Road - Photo 13](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f763028889r.jpg) ![23116 GILPIN POINT Road - Photo 14](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1527241392r.jpg) ![23116 GILPIN POINT Road - Photo 15](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1510422188r.jpg) ![23116 GILPIN POINT Road - Photo 16](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1954777786r.jpg) ![23116 GILPIN POINT Road - Photo 17](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f799697932r.jpg) ![23116 GILPIN POINT Road - Photo 18](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1979868548r.jpg) ![23116 GILPIN POINT Road - Photo 19](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f11701881r.jpg) ![23116 GILPIN POINT Road - Photo 20](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3114985353r.jpg) ![23116 GILPIN POINT Road - Photo 21](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1872470135r.jpg) ![23116 GILPIN POINT Road - Photo 22](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1818628207r.jpg) ![23116 GILPIN POINT Road - Photo 23](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3267802213r.jpg) ![23116 GILPIN POINT Road - Photo 24](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3488834000r.jpg) ![23116 GILPIN POINT Road - Photo 25](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1868733562r.jpg) ![23116 GILPIN POINT Road - Photo 26](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2048955500r.jpg) ![23116 GILPIN POINT Road - Photo 27](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3553166164r.jpg) ![23116 GILPIN POINT Road - Photo 28](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3928639223r.jpg) ![23116 GILPIN POINT Road - Photo 29](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3094271627r.jpg) ![23116 GILPIN POINT Road - Photo 30](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1481259458r.jpg) ![23116 GILPIN POINT Road - Photo 31](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2539796372r.jpg) ![23116 GILPIN POINT Road - Photo 32](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3916212235r.jpg) ![23116 GILPIN POINT Road - Photo 33](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3370072202r.jpg) ![23116 GILPIN POINT Road - Photo 34](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1830951033r.jpg) ![23116 GILPIN POINT Road - Photo 35](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f429052168r.jpg) ![23116 GILPIN POINT Road - Photo 36](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2642234399r.jpg) ![23116 GILPIN POINT Road - Photo 37](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2167302289r.jpg) ![23116 GILPIN POINT Road - Photo 38](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2579185817r.jpg) ![23116 GILPIN POINT Road - Photo 39](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1493168848r.jpg) ![23116 GILPIN POINT Road - Photo 40](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2699253160r.jpg) ![23116 GILPIN POINT Road - Photo 41](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f983828010r.jpg) ![23116 GILPIN POINT Road - Photo 42](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f633995090r.jpg) ![23116 GILPIN POINT Road - Photo 43](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f639203229r.jpg) ![23116 GILPIN POINT Road - Photo 44](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f275800006r.jpg) ![23116 GILPIN POINT Road - Photo 45](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f4228895696r.jpg) ![23116 GILPIN POINT Road - Photo 46](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f65869101r.jpg) ![23116 GILPIN POINT Road - Photo 47](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1040795030r.jpg) ![23116 GILPIN POINT Road - Photo 48](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2608370073r.jpg) ![23116 GILPIN POINT Road - Photo 49](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3831343455r.jpg) ![23116 GILPIN POINT Road - Photo 50](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3221132520r.jpg) ![23116 GILPIN POINT Road - Photo 51](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f334759447r.jpg) ![23116 GILPIN POINT Road - Photo 52](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1287869738r.jpg) ![23116 GILPIN POINT Road - Photo 53](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2190728534r.jpg) ![23116 GILPIN POINT Road - Photo 54](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1610779829r.jpg) ![23116 GILPIN POINT Road - Photo 55](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2310407368r.jpg) ![23116 GILPIN POINT Road - Photo 56](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3930618997r.jpg) ![23116 GILPIN POINT Road - Photo 57](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f948225985r.jpg) ![23116 GILPIN POINT Road - Photo 58](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1666595229r.jpg) ![23116 GILPIN POINT Road - Photo 59](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1761001329r.jpg) ![23116 GILPIN POINT Road - Photo 60](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1569882668r.jpg) ![23116 GILPIN POINT Road - Photo 61](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2099498168r.jpg) ![23116 GILPIN POINT Road - Photo 62](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3125185106r.jpg) ![23116 GILPIN POINT Road - Photo 63](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3035164430r.jpg) ![23116 GILPIN POINT Road - Photo 64](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2695103247r.jpg) ![23116 GILPIN POINT Road - Photo 65](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f932757430r.jpg) ![23116 GILPIN POINT Road - Photo 66](http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3188191769r.jpg) --- **MLS#:** MDCM2007400 | **Updated:** 2026-09-14 **Source:** listhub *Copyright © 2026 Bright MLS. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.* [View on PropertySimple](https://www.propertysimple.ai/listing/23116-gilpin-point-road-preston-md-21655-m2007400) --- ## Structured Data ```json { "@context": "https://schema.org", "@type": "RealEstateListing", "@id": "https://www.propertysimple.ai/listing/23116-gilpin-point-road-preston-md-21655-m2007400#listing", "url": "https://www.propertysimple.ai/listing/23116-gilpin-point-road-preston-md-21655-m2007400", "name": "23116 GILPIN POINT Road, Preston, MD 21655", "description": "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.", "image": [ "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f1315843173r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f127207945r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f4243046248r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3682058969r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2994853885r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f808420223r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f649952944r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f4206359676r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3513690765r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f44960966r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f3546728187r.jpg", "http://lh.rdcpix.com/33d98470e9496c6b9ff8add08163c0b8l-f2751114924r.jpg", 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