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$724,900
3 Beds ⋅ 2 Baths
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!

101 Tilghman St, Oxford

Listing courtesy of The Parker Group. Contact: 3022176692
$3,295,000
5 Beds ⋅ 5 Baths
Welcome to this exceptional 4/5 BR/4.5BA waterfront residence overlooking picturesque Town Creek in the historic waterfront town of Oxford. Built in 2023, this home is privately set on 1.71 acres (very rare for Oxford) surrounded by mature trees, extensive landscaping and thoughtfully designed hardscaping that complement the natural beauty of its serene waterfront setting. Designed with extraordinary attention to detail, the home showcases soaring vaulted ceilings, expansive windows, and multiple decks and balconies that capture tranquil water views from nearly every room. The grand living room, anchored by a gas fireplace, flows effortlessly into the dining area and an extraordinary chef’s kitchen featuring a large center island, separate casual dining space, a well-appointed butler’s pantry, and a screened porch just off the kitchen - perfect for outdoor dining and enjoying the peaceful waterfront setting. A private office with an adjacent full bath offers flexibility as a guest suite. The desirable main-level primary suite is a luxurious retreat, complete with a spa-inspired bath, private sitting room, and sliding doors opening to a peaceful screened waterside porch. The second floor offers three additional guest bedrooms, including one with an ensuite bath and two connected by a Jack & Jill bath, providing comfortable accommodation for family and guests. Outdoor living is equally impressive, featuring a waterside slate patio with expansive views, ideal for relaxing or entertaining while enjoying the serene waterfront setting. A new pier with two slips and 4’ MLW provides convenient boating access, while a thoughtfully integrated rainwater harvesting and management system was incorporated as part of the property’s environmental site design. Located just a short stroll from downtown Oxford, this beautiful waterfront home offers the perfect blend of luxury, comfort, and small-town coastal living. *Home built out of flood zone: Elevation certificate available *Room for pool; plans available for pool and pool house.

104 East St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$2,295,000
3 Beds ⋅ 6 Baths
With its central Talbot County location and effortless one‑story layout, this move‑in ready waterfront retreat offers a rare blend of convenience, comfort, and stunning natural beauty. Set on more than two acres on Trippe Creek with 185' of water frontage—directly across from Talbot Country Club—the property enjoys an elevated vantage point with broad water views, a private pier, and a heated pool and hot tub all just minutes from the amenities of both Oxford and Easton. The 3,100‑plus square‑foot home is designed for easy living, with sweeping waterside views and a newly renovated primary suite featuring a luxurious private bath with a steam shower. Two additional bedrooms, a bunkroom plus three full baths provide ample space for guests. The gourmet eat‑in kitchen, formal dining room, large living room with fireplace, separate family room create a warm, flexible layout for everyday living and entertaining. A screened porch offers the perfect spot to enjoy the breeze off the creek. Thoughtful updates throughout the home preserve its beautiful hardwood floors, moldings, and character while introducing a fresh coastal palette, contemporary kitchen and baths, new roof and Hardie board siding, and numerous additional improvements. The grounds are exceptional—one of the most beautiful settings in the county—with mature specimen trees, curated landscaping, full yard and garden sprinkler system, invisible dog fence and uncommon topography that enhances both privacy and views. The dedicated nature preserve directly across the street ensures no future building. A waterfront property of this quality, setting, and convenience with no flood insurance required is a rare find. Added bonus--enjoy a front row seat without leaving your own property to enjoy TCC's incredible 4th of July fireworks! Don’t miss the opportunity to make 5920 Oxford Road your own.

5920 Oxford Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$3,495,000
4 Beds ⋅ 5 Baths
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 recently 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.

28161 Harleigh Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415
$895,000
3 Beds ⋅ 3 Baths
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, 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. Professional photos coming in September

104 Stewart Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$425,000
2 Beds ⋅ 1 Baths
Welcome to this charming Jack’s Point bungalow, where classic style, modern updates, and thoughtfully restored Craftsman details come together in a warm, bright, and inviting home. Tastefully refreshed throughout and fully furnished the residence features newer flooring, a newer roof, and updated appliances, offering modern comfort while maintaining its timeless appeal. The thoughtfully designed floor plan includes two bedrooms, one bathroom, and an open concept living area that is ideal for both everyday living and effortless entertaining. A screened-in porch provides the perfect space to relax and enjoy the outdoors year-round. The open kitchen showcases beautifully restored original pine cabinetry, blending vintage charm with modern functionality. Outside, the yard features a lovely rose garden and plenty of room to garden, unwind, or entertain. Ideally located near Oxfords restaurants, marinas, parks, and scenic trails, this delightful home offers the perfect combination of character, comfort, and convenience.

104 Bonfield Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,095,000
3 Beds ⋅ 3 Baths
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.

100 Pier St W, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$254,900
Location, location, location! It doesn't get much better than this. Nestled on a private, wooded 2.3-acre lot between Easton and Oxford, this property has everything you need to move forward with building your dream home. The sellers are even willing to include their house plans! This perc-approved lot is approved for a 4-bedroom home and is accessed from Almshouse Road via an existing right-of-way. The site has already been cleared and is ready for the permit application process. See documents for the site plan, architectural plans, conservation plan, and stormwater management plan. They aren't making any more land—don't miss this opportunity to secure a beautiful homesite in a sought-after location. Buy now and start building your dream home! Please only go to the lot and not further back the lane as there is a house back there.

Almshouse ( Lot 2) Rd, Oxford

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$1,499,000
3 Beds ⋅ 3 Baths
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

104 Myrtle St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$795,000
3 Beds ⋅ 2 Baths
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 an 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.

228 South St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$599,900
3 Beds ⋅ 3 Baths
Nestled on 2± acres, this inviting property offers a peaceful setting surrounded by mature trees that provide shade and natural beauty throughout the seasons. A circular driveway creates a welcoming approach and allows for easy access to the home and detached two-car garage, which also offers excellent potential as a workshop, studio, or hobby space. Inside, hardwood flooring extends throughout the home, adding warmth and timeless appeal. The living room is filled with natural light from a charming bay window, while the screened porch provides the perfect place to relax and enjoy the tranquil surroundings. Conveniently accessed from both the dining room and family room, the porch creates a seamless connection between indoor and outdoor living spaces. The primary suite serves as a private retreat, featuring a cathedral ceiling that enhances the sense of space along with a well-appointed en-suite bath. Two additional bedrooms each offer their own en-suite bathrooms, providing exceptional comfort and privacy for family members and guests alike. Combining spacious grounds, mature landscaping, and thoughtfully designed living spaces, this Oxford property offers the perfect blend of comfort, character, and Eastern Shore charm.

4794 Sailors Ln, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$159,000
Motivated Seller! Oxford Lot in the heart of town in the Historic District. Lot size .20 acre +/-. Build your ideal home. A few blocks to Town Creek and Tree Avon River, restaurants, ferry dock, park, town market and more. Buyers to perform own feasibility study and due diligence for intended use. You may contact the town of Oxford Planning and Zoning.

105 Tilghman St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$3,995,000
5 Beds ⋅ 4 Baths
Experience refined waterfront living in this stunning Lowcountry-style estate, gracefully set on an exceptional waterfront lot among mature Loblolly pines with a coveted southern exposure. Offering sweeping, unobstructed water views, and a rare sense of privacy, the property is bathed in natural light throughout the day, with breathtaking sunrises and and warm, golden reflections in the evening. This 3,800 square foot main residence is complimented by a beautifully appointed 1,200 sq. foot guest cottage, creating an ideal balance of elegance and hospitality. The guest cottage serves as a private retreat, complete with a comfortable living room, galley kitchen, three bedrooms, and a screened porch for quiet relaxation. Inside, timeless craftsmanship defines every space, from reclaimed oak flooring to granite countertops and a meticulously maintained cedar exterior. Outdoors, the lifestyle continues with resort style amenities, including a sparkling in-ground pool, hot tub, firepit and a private 120 foot pier with approximately 7 feet of depth at mean low water- offering effortless access for boating fishing, and enjoying the very best of waterfront living. A rare offering where exceptional land, elegant design, and an unparalleled coastal lifestyle come together.

4335 World Farm Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$1,250,000
3 Beds ⋅ 4 Baths
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.

115 W Pier St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$629,900
4 Beds ⋅ 3 Baths
Motivated Seller and Improved Pricing ! Make this Charming Oxford Gem your new home. This well-maintained 4-bedroom, 2.5-bath home offers a comfortable blend of classic style and Eastern Shore charm in a prime Oxford location. Whether you're looking for a first home, a retirement retreat, a weekend escape, or an investment property, this inviting residence is designed to fit a variety of lifestyles. Tucked away on a quiet cul-de-sac, it features welcoming indoor and outdoor spaces ideal for year-round living, with plenty of room to transform/grow and make it your own. Inside, the foyer opens to spacious living and dining areas featuring Brazilian cherry hardwood floors, vaulted ceilings, and abundant natural light. French doors lead to a flexible room that can serve as a first floor guest room or home office. The living room flows into a large kitchen with a bright breakfast room and an adjacent dining area, making it ideal for casual mornings and gatherings with family and friends. Just off the kitchen, a half bath and a large family room provide added convenience and direct access to a spacious backyard. Upstairs, the primary suite offers a peaceful retreat with a large walk-in closet and an en-suite bath featuring double sinks, a Jacuzzi tub, and a walk-in shower. Two additional bedrooms share a generous hall bath with double sinks and a tub-shower combination. A second-floor bonus room adds even more flexibility and can be used as a playroom, home gym, game room, or private retreat. Outdoor living is equally appealing, with a front and back decks, patio with fire pit and a fully fenced backyard. One of the largest yards in the neighborhood, with plenty of room for a pool. Located just a short walk from downtown Oxford, the home offers easy access to local shops, restaurants, the waterfront park, Oxford Market, and Scottish Highland Creamery. Move-in ready and full of character, this Eastern Shore gem delivers exceptional value. Move-in ready and full of character, this Eastern Shore gem offers the best of Oxford living at an exceptional value. Recent Upgrades include: A new roof installed in August 2025, Stainless-steel appliances less than two years old, encapsulated crawlspace.

209 Third St, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$1,945,000
Your Custom Dream Waterfront Home Awaits! This rare, build-ready lot offers a blank canvas for you to craft your perfect Eastern Shore estate with spectacular, panoramic views! The 2.9 acre waterfront lot in the Bachelor Pt section of Oxford offers 180 degree panoramic views stretching across the majestic Choptank River. Enjoy the peace of mind of a recently installed rip-rap shoreline over an estimated 569 feet of protected waterfront, providing long-term erosion protection and maintaining your valuable waterfront. The property also includes a new dock setup, featuring a heavy-duty 16,000 lb boat lift and two additional lifts perfect for jet skis. The lot is located within Oxford town limits, offering the advantage of access to public water and sewer hook-ups. Final approval has been given from the Oxford Planning Board for the building plans the current owner proposed providing a massive head start on your construction timeline. Those plans can be included in the sale of the lot and while you may modify them to suit your taste, having approved plans means the property is truly "build-ready." Simply choose your builder and start constructing your dream!

4480 Bachelors Point Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415
$262,000
Exceptional 2.18 acre residential lot. Ready to go with approved 4 Bedroom perc. Locate in the very desirable Sailors Retreat neighborhood with a beautiful setting and high-end homes. This parcel offers a high elevation (Zone X). Build your dream home on this last remaining parcel in this coveted neighborhood. See conceptual house plans and site plan in the photos. House plans are available. Click on the movie camera icon for the Virtual Tour*

Sailors Retreat Rd, Oxford

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