Experience the best of waterfront living on picturesque Trippe Creek, where breathtaking sunsets and sweeping views of the neighboring nature conservancy create an idyllic setting. Nestled in the private Pirates Cove community of Oxford, Maryland, this peaceful retreat offers exceptional privacy, tranquility, and abundant wildlife. {Please refer to agent remarks RE: community association/shared road agreement/community restrictions. etc.} Designed for effortless one-level living, this inviting 4-bedroom home features beautiful hardwood and brick flooring, 3 fireplaces (one double sided so feels like 4), and expansive water views. A waterside screened porch provides the perfect setting to relax and enjoy the natural surroundings, while the saltwater pool overlooking the creek offers a wonderful space for outdoor entertaining. Capital improvements to the property 2019 - installed new septic system, enclosed 1-bay of the garage and converted into a finished office/studio. 2020 - installed a new driveway, reset the patio bricks on the back porch. 2021 - completed substantial pool renovation, including both the pool and surround improvements, reset the front walkway/patio brickwork, upgraded the HVAC system. 2023 - new refrigerator. 2024 - new wine refrigerator, constructed a new walkway. 2025 - installed brand new roof, replaced all toilets throughout the home. Through the years of ownership continuously invested in extensive landscaping and site improvements. Boating enthusiasts will appreciate the private pier with approximately 3 feet of mean low water (MLW), providing convenient access to the beautiful waterways of the Eastern Shore. A two-car garage plus a workspace for a studio adds everyday convenience. Offered turnkey with most furnishings included, this exceptional waterfront property also could convey with a 17-foot Scout center console boat with acceptable offer—allowing you to begin enjoying the Eastern Shore lifestyle from day one. Whether you're seeking a full-time residence or a relaxing weekend escape, this special property offers the perfect combination of waterfront recreation, natural beauty, and peaceful coastal living.
Located at the end of Market Street in sought-after Oxford, this distinctive waterfront estate on Town Creek combines Victorian elegance, boating amenities, and the convenience of a downtown setting. Designed by Linda Serabian of SOMA Architects, the property offers privacy and expansive creek views just moments from local restaurants, boutique shops, the park, and marinas. The four-bedroom, three-and-a-half-bath main house showcases timeless architecture and thoughtful craftsmanship, with extensive custom millwork, warm wood floors, and four gas fireplaces. A grand tiled foyer with radiant heated floors welcomes you into the home. The well-appointed kitchen and inviting living spaces overlook the pool and Town Creek, while the second-floor deck offers elevated views of the water. Recent improvements include new Marvin windows and French doors, updated HVAC components, fresh interior and exterior paint, and a remodeled full bath. The guest house offers two bedrooms and two full baths, providing a private and versatile extension of the property. Custom millwork, three hidden Murphy beds throughout and a newly updated kitchenette make hosting family and friends effortless. Recent improvements include a new HVAC system, water heater, encapsulated crawl space, and refreshed rear patio. The grounds are equally impressive, with a gunite pool featuring an electric cover, a refreshed poolside patio, and extensive landscaping. Along Town Creek, a well-protected dock accommodates three boats, with water and electric service and mean low water of four feet or greater. A brick driveway, two-car garage with generous shop and storage space, and inviting outdoor gathering areas complete the offering. With its distinctive architecture, separate guest accommodations, dock with three slips, and coveted in-town Oxford location, this is a rare opportunity to experience the best of Eastern Shore waterfront living.
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!
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.
Oxford. One owner 2,858 sq. ft home, built in 2006 is just off the Strand only a block from the Tred Avon River. Features living room and dining rooms, den, family room with woodburning fireplace off open kitchen with island and granite countertops, powder room. Second floor offers 3 spacious bedrooms including a primary suite with walk-in closet and 2 guest bedrooms and guest bath. Exterior offers 2 balconies/porches with River views, HardiPlank siding, paver driveway and more on a .18 acre lot. Hardwood flooring throughout most of the home (except 2 guest bedrooms) and 2 energy efficient heat pumps. Located in the Oxford’s historic district. This home preserves the historic character while offering a modern floor plan with 9’ ceilings and modern upgrades. Home is ready for immediate occupancy.
Beautifully crafted, turn-key "Oxford Cottage" built in 2023 offering high-end finishes and classic Eastern Shore charm with NO HOA! Step off the welcoming front porch into a light-filled open-concept main level featuring hardwood floors throughout. The generous-sized eat-in kitchen boasts custom cabinetry, upgraded countertops, stainless steel appliances, and a seamless transition out to a spacious screened-in sunroom—ideal for outdoor dining and entertaining. The main floor offers an entry-level full bath and a versatile flex room perfect for a primary bedroom, home office, or den. Upstairs features two generous-sized bedrooms with dramatic vaulted ceilings, a full bath, and a dedicated laundry area. Outside, cedar-raised flower beds frame the home alongside a low-maintenance 0.11-acre lot and a detached frame garage with ample room for vehicles, water toys, or a workshop. Located just blocks from the Strand beach, waterfront parks, local dockside dining, the historic Oxford-Bellevue Ferry, and the Scottish Highland Creamery!
Holly Point on prestigious World Farm Road offers an unparalleled waterfront lifestyle. This charming three bedroom, two and a half bath Eastern Shore Cape Cod features an open floorplan, a main-floor primary suite, two ensuite bedrooms and a loft area on the second floor, and breathtaking, broad views across Island Creek. Outdoor amenities include an oversized waterside pool and a deep-water dock with 6 feet MLW. Additionally, the property boasts private guest quarters situated above a detached garage, ensuring ample space for visitors. Located in a highly desirable, protected shoreline setting, this rare gem requires no flood insurance.
Located at the end of a private, gated, park-like lane, mid-way between Easton and Oxford: This gracious home is situated on one of the premier sites in Talbot County, MD...2.3-acre point of land, providing Westerly (SUNSET) views looking directly down Trippe Creek toward the Tred Avon River. The tastefully updated brick home provides exceptional water views from most rooms, especially from the living room, dining room and brick-floored glassed "River Room." The floor plan (see downstairs and upstairs plans in the attached photos) features 2-bedrooms down stairs (including a "Primary" Bedroom) and 2 bedrooms upstairs (Including another "Primary" - take your pick!). A total of four large bedrooms, four bathrooms and one half-bath. Lots of living and entertaining spaces downstairs, including a spacious living room, family room, library and River Room. Recent updates include a new BAT septic system; encapsulated crawl space; refinished wood floors throughout; fresh paint inside and out; new kitchen countertops; new kitchen appliances; updated bathrooms and more. This is a true "turn-key" home. For boating, there is a substantial private pier (6' x 135') which provides 6+ ft of depth at low tide (MLW). By boat, the town of Oxford and the open waters of the Choptank River are just a short, scenic 5-mile boat ride downstream. By car, this prime location is conveniently located approx. 5-miles to Easton or 5-miles to Oxford. The Talbot Country Club is less than 2-miles away. A new survey confirms there is room to install a swimming pool. There is a perfect future pool site, providing views of the dock and Trippe Creek.
Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities. Every detail has been carefully curated, from the new hardwood flooring and fresh paint throughout to the completely remodeled gourmet kitchen featuring high-end appliances, quartz and soapstone countertops, custom cabinetry, and a butler's pantry connecting the kitchen and dining room. The dining room is anchored by a beautiful masonry fireplace with a gas insert, while the custom "Wine Snug" offers built-in wine racks, a wine refrigerator, and handcrafted wrought iron doors. Designed to maximize its setting, the home captures water views from both the front and rear, with sightlines straight through the home to the water. Upstairs, the primary suite opens to a private balcony overlooking the harbor, and the conveniently located second-floor laundry adds everyday functionality. For boating enthusiasts, the property includes a deeded 40’ boat slip accommodating with approximately 5’ MLW. Ideally located just moments from downtown Oxford, you'll enjoy easy access to marinas, the Oxford Ferry, waterfront parks, and local favorites like Doc's Sunset Grille with frequent live music. Whether you're searching for a full-time residence, weekend getaway, or luxury second home, 100 W. Pier Street offers the perfect blend of water views, boating access, modern updates, and the relaxed Eastern Shore lifestyle.
Major Price Improvement! Western sunsets and timeless waterfront living define this beautifully restored home on Town Creek in Oxford. A waterside pool, expansive entertaining deck, gazebo and private pier create an exceptional setting for enjoying life on the water. Fabulous gourmet kitchen and inviting family room with a custom built-in bar anchor the home, while warm pine floors add warmth and character throughout. Three bedrooms and three full baths include a spacious waterfront primary suite with a private second-story deck overlooking Town Creek—the perfect place to unwind while taking in spectacular western sunsets. Just moments from Oxford's waterfront park, marina, restaurants and the Oxford-Bellevue Ferry, this distinctive property is privately sited outside the Historic District and features a private pier with approximately 4 + feet of mean low water, providing easy access for boating, kayaking and paddleboarding. Sold As Is
Rose Cottage — The Home You Discover After a Perfect Day on the Water. A sailor arriving in Oxford often falls in love twice: first with the town, and then with the home that feels like it belongs to their journey. Rose Cottage is that home — a beautifully renovated, expanded Eastern Shore retreat nestled near marinas, Town Park, restaurants, and the quiet charm of Town Creek. After tying up at the Tred Avon Yacht Club, or one of several highly rated Oxford marinas, it’s an easy, scenic meander beneath shade trees and by historic cottages to your new home. That’s when Rose Cottage appears — welcoming, warm, and unmistakably connected to the sailing lifestyle. A Sailor’s Location — Everywhere That Matters. Rose Cottage sits in one of Oxford’s most desirable corridors: ? Short distance to the Tred Avon Yacht Club — ideal for regattas, junior sailing, or evening socials ? Minutes from Town Park, where sailors relax under the oaks after a day on the water ? Short promenade to Oxford’s marinas, boatyards, and waterfronts ? Close to local restaurants — from casual bites to fine dining ? Serene Town Creek views just a glance away, capturing the quiet beauty that makes Oxford unforgettable This is the rare home where you can finish a sail and be at your front door in minutes. Historic Charm, Modern Comfort. Inside, Rose Cottage blends its original character with a full structural renovation and a Christine Dayton designed 800 sq ft expansion completed in 2011–2012. The extended roofline, new primary bedroom, updated systems, and all-new flooring create a turnkey home that feels fresh, bright, and thoughtfully designed. The preserved street-facing windows maintain the cottage’s historic personality, while the newer windows and cementitious siding ensure long-term durability. A Home That Fits the Oxford Lifestyle. For sailors, cruisers, and anyone who loves the water, Rose Cottage offers something rare: a modernized home in a historic sailing town, near to everything that makes Oxford special. It’s the kind of place buyers don’t just choose — they discover.
A very exciting, well-built (stick built by Mister Construction-1996), open floor plan waterfront home in Oxford. Amazing broad South facing with river views. Three bedrooms on second floor, each with private bath, elevator to 3rd floor, full attic storage, 2 car garage, new roof in 2022, waterside deck, 2 enclosed waterfront sitting rooms, spacious first floor rooms for entertaining! First floor sitting room is large enough to use as 4th bedroom with full bath on first floor.
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.
Oxford is located in Maryland. Oxford, Maryland has a population of 862. Oxford is less family-centric than the surrounding county with 7.87% of the households containing married families with children. The county average for households married with children is 22.67%.
The median household income in Oxford, Maryland is $71,464. The median household income for the surrounding county is $79,349 compared to the national median of $69,021. The median age of people living in Oxford is 64 years.
The average high temperature in July is 89.1 degrees, with an average low temperature in January of 28.2 degrees. The average rainfall is approximately 46.1 inches per year, with 10.2 inches of snow per year.
