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Enjoy the charm of Oxford at 105 E. Pier Street! This inviting three-bedroom, two-bathroom home features a kitchen with an eat-in area and three spacious bedrooms, including a primary bedroom with vaulted ceilings and a large walk-in closet. Relax on the front porch beneath the shade of a beautiful oak tree, or unwind on the back porch overlooking the town park, with basketball, pickleball, and tennis courts, a large field for soccer, and a walking trail right outside your door. Oxford’s walkable setting makes it easy to enjoy local favorites, from Doc’s Restaurant to the Highland Creamery, along with the Strand, waterfront park, dog park, and community garden. Several marinas and docking locations throughout town offer options for keeping your boat nearby, subject to availability. A wonderful opportunity to enjoy the relaxed lifestyle of this waterfront town!

3 Beds ⋅ 2 Baths

Enjoy the charm of Oxford at 105 E. Pier Street! This inviting three-bedroom, two-bathroom home features a kitchen with an eat-in area and three spacious bedrooms, including a primary bedroom with vaulted ceilings and a large walk-in closet. Relax on the front porch beneath the shade of a beautiful oak tree, or unwind on the back porch overlooking the town park, with basketball, pickleball, and tennis courts, a large field for soccer, and a walking trail right outside your door. Oxford’s walkable setting makes it easy to enjoy local favorites, from Doc’s Restaurant to the Highland Creamery, along with the Strand, waterfront park, dog park, and community garden. Several marinas and docking locations throughout town offer options for keeping your boat nearby, subject to availability. A wonderful opportunity to enjoy the relaxed lifestyle of this waterfront town!

105 Pier, Oxford

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$499,000

Embrace an effortless coastal lifestyle in the heart of Oxford, where days are shaped by the water and some of the town’s most beloved destinations are just a short stroll from home. Ideally located near beach access, waterfront dining, marinas, tennis and pickleball courts, and a local church, this beautifully refreshed cottage offers a rare combination of walkability, privacy, and Eastern Shore charm. Set on a generous 16,988+/- square foot lot, the 1,200+/- square foot, two bedroom, two full bath residence has been thoughtfully updated with a fresh coastal sensibility. The remodeled kitchen features new stainless steel appliances, while renovated baths, new luxury vinyl plank flooring throughout, windows and doors, custom window treatments, and efficient ductless heating and cooling create a polished, comfortable interior designed for easy living. A wooden deck extends the living space outdoors, providing a relaxed setting for morning coffee, meals with friends and family, and evening relaxation after a day on the water. The grounds offer room to entertain and enjoy the outdoors, complemented by ample parking and a two story outbuilding with electricity, offering potential with exceptional storage and versatility. Additional improvements include a new hot water heater and French drain installation, while affordable utility costs add to the home’s low maintenance appeal. A history of short term rental income provides additional flexibility for buyers seeking a coastal retreat with income potential. What truly distinguishes this property is its location. From 705 S. Morris Street, the waterfront lifestyle of Oxford is within easy reach. Walk to the beach, stroll to enjoy dinner overlooking the river, head to the marina for an afternoon on the Chesapeake, or spend the morning on the tennis and pickleball courts and many walking paths. Situated in sought after Talbot County, Oxford offers the understated elegance and slower pace that have long made Maryland’s Eastern Shore a coveted destination. Conveniently positioned between Washington, D.C. and the Atlantic Ocean, this inviting cottage presents an opportunity to enjoy a refined yet relaxed coastal escape in one of the Shore’s most charming waterfront towns.

2 Beds ⋅ 2 Baths

Embrace an effortless coastal lifestyle in the heart of Oxford, where days are shaped by the water and some of the town’s most beloved destinations are just a short stroll from home. Ideally located near beach access, waterfront dining, marinas, tennis and pickleball courts, and a local church, this beautifully refreshed cottage offers a rare combination of walkability, privacy, and Eastern Shore charm. Set on a generous 16,988+/- square foot lot, the 1,200+/- square foot, two bedroom, two full bath residence has been thoughtfully updated with a fresh coastal sensibility. The remodeled kitchen features new stainless steel appliances, while renovated baths, new luxury vinyl plank flooring throughout, windows and doors, custom window treatments, and efficient ductless heating and cooling create a polished, comfortable interior designed for easy living. A wooden deck extends the living space outdoors, providing a relaxed setting for morning coffee, meals with friends and family, and evening relaxation after a day on the water. The grounds offer room to entertain and enjoy the outdoors, complemented by ample parking and a two story outbuilding with electricity, offering potential with exceptional storage and versatility. Additional improvements include a new hot water heater and French drain installation, while affordable utility costs add to the home’s low maintenance appeal. A history of short term rental income provides additional flexibility for buyers seeking a coastal retreat with income potential. What truly distinguishes this property is its location. From 705 S. Morris Street, the waterfront lifestyle of Oxford is within easy reach. Walk to the beach, stroll to enjoy dinner overlooking the river, head to the marina for an afternoon on the Chesapeake, or spend the morning on the tennis and pickleball courts and many walking paths. Situated in sought after Talbot County, Oxford offers the understated elegance and slower pace that have long made Maryland’s Eastern Shore a coveted destination. Conveniently positioned between Washington, D.C. and the Atlantic Ocean, this inviting cottage presents an opportunity to enjoy a refined yet relaxed coastal escape in one of the Shore’s most charming waterfront towns.

705 S Morris St, Oxford

Listing courtesy of Meredith Fine Properties. Contact:

$599,999

Motivated Seller and Improved Pricing! Whether seeking a year-round residence or a peaceful Eastern Shore getaway, Oxford offers a truly special place to call home. Discover this home and the exceptional opportunity to enjoy life in historic Oxford, Maryland. This inviting three- to four-bedroom home is located on a quiet cul-de-sac in the Jacks Point neighborhood, just a short distance from the waterfront. Vaulted ceilings and an open-concept layout create a bright, airy feel, while continuous Brazilian cherry hardwood floors add warmth and character throughout. The first-floor living space offers a generous foyer, flexible office or guest space, a separate dining room, a living room, a half bath, and an eat-in kitchen. The main second floor includes three bedrooms and two full baths, while a separate staircase provides access to a bonus room that can serve as a playroom, entertainment space, or private retreat. Beyond these rooms, a garage conversion completed before the current owner’s 2007 purchase expands the home with a large, light-filled family room and a separate storage area with interior and exterior access, providing ample room for lawn, garden, athletic, and marine equipment. The well maintained 28-year-old home has received steady updates, including a new roof in 2025, new appliances in 2024, first-floor HVAC system replacement in 2022, an encapsulated crawlspace, and more. It is move-in ready and priced to give the next owner flexibility to personalize the finishes and pursue future updates. Set on a quarter-acre lot with a fully fenced yard, the property offers ample space for outdoor living, a swimming pool, a shed, or an expanded garden. Endless possiblities! Just steps from the Oxford Community Center, Jacks Point Marina, Play Ball Dog Park, and the town center, the home also places shops, cafés, the museum, library, ice cream shop, yacht club and ferry within easy reach. The relaxed rhythm of Oxford life begins just beyond your front door.

4 Beds ⋅ 3 Baths

Motivated Seller and Improved Pricing! Whether seeking a year-round residence or a peaceful Eastern Shore getaway, Oxford offers a truly special place to call home. Discover this home and the exceptional opportunity to enjoy life in historic Oxford, Maryland. This inviting three- to four-bedroom home is located on a quiet cul-de-sac in the Jacks Point neighborhood, just a short distance from the waterfront. Vaulted ceilings and an open-concept layout create a bright, airy feel, while continuous Brazilian cherry hardwood floors add warmth and character throughout. The first-floor living space offers a generous foyer, flexible office or guest space, a separate dining room, a living room, a half bath, and an eat-in kitchen. The main second floor includes three bedrooms and two full baths, while a separate staircase provides access to a bonus room that can serve as a playroom, entertainment space, or private retreat. Beyond these rooms, a garage conversion completed before the current owner’s 2007 purchase expands the home with a large, light-filled family room and a separate storage area with interior and exterior access, providing ample room for lawn, garden, athletic, and marine equipment. The well maintained 28-year-old home has received steady updates, including a new roof in 2025, new appliances in 2024, first-floor HVAC system replacement in 2022, an encapsulated crawlspace, and more. It is move-in ready and priced to give the next owner flexibility to personalize the finishes and pursue future updates. Set on a quarter-acre lot with a fully fenced yard, the property offers ample space for outdoor living, a swimming pool, a shed, or an expanded garden. Endless possiblities! Just steps from the Oxford Community Center, Jacks Point Marina, Play Ball Dog Park, and the town center, the home also places shops, cafés, the museum, library, ice cream shop, yacht club and ferry within easy reach. The relaxed rhythm of Oxford life begins just beyond your front door.

209 Third St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact:

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