Refine Search
Sort by
3 Beds 2 Baths
Custom designed and built to perfection, this home features high-end finishes, exquisite workmanship, and premium materials throughout. Upon entry, you're greeted by a stunning compass rose inlaid in the cherry wood floors, setting the tone for the nautical theme that carries into the den/library, reminiscent of a well-fitted yacht's interior. The open kitchen, equipped with a marble-topped island and top-rated Wolf and Subzero appliances, flows seamlessly into the living room, which boasts a fireplace and sliding doors leading to an outdoor deck. This deck overlooks a beautiful patio, perfect for alfresco dining or enjoying a cozy firepit. The property includes two additional structures: a charming garden shed and a versatile boat house. The boat house, previously accommodating a 36' boat, now serves as a shop, storage, and exercise area and can accommodate a boat up to 40' in length. It features a powder room and is heated and air-conditioned. Situated on high elevation with extensive landscaping, this home offers luxury living with unique nautical touches.

104 E Pier St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

5 Beds 4 Baths
Nestled along the quiet waters of Boone Creek, this 5 bedroom, 3.5 bath home has beautiful water views, incredible custom woodwork and is in impeccable condition. Nice paver patio overlooking the Creek. Dock with boat lift and access to Tred Avon and Choptank Rivers. Close to Oxford activities, restaurants, and marinas. Various types of hardwood wide plank floors, living room has custom fireplace surround with enclosure above. Sliding doors to patio, screen porch off of breakfast room, large primary suite on first floor. On the second floor, one bedroom is an en-suite plus large additional bath to serve the other two bedrooms. The 5th bedroom upstairs is currently set up as an office. Lots of storage space. Two car attached garage w/built in stairway to large storage attic. Large garden shed. Bilco door access to concrete floored crawl space.

26226 Langs Landing Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

3 Beds 2 Baths
Quaint 3 bedroom 2 bathroom bungalow on quiet street that is one block from beach access to Tred Avon River. Wildlife love the yard as eastern screech owls, great crested flycatchers, bluebirds and mockingbirds have all created new generations at 102 Riverview. Screened in porch overlooks large fenced-in yard and new hot tub. Eight new trees planted since 2020! Whole-house Culligan water system has the water tasting and smelling fresh. The oldest appliance in the house is from 2020, including HVAC. New woodstove installed for cozy winter evenings. Two outbuildings can house all your bikes, kayaks, paddleboards, wood, and lawn-care equipment. Make the Port of Oxford your home away from home! House is part of Oxford's new FEMA Grant to raise houses in town, which is transferable.

102 Riverview Ave, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

3 Beds 3 Baths
Discover waterfront living at its finest! Located between Easton and Oxford on 2+ acres this absolutely gorgeous one level waterfront home features 400’+ of waterfrontage on Trippe Creek, a deep water pier, a huge in-ground swimming pool, and waterside deck. Meticulously renovated from bottom to top with top-of-the-line features through-out! Full of natural light, the open floor plan has breathtaking views from almost every angle. Beautiful wood flooring, waterside great room with cozy fireplace, fabulous gourmet kitchen with high end appliances, and large center island. Impressive waterside owner’s suite complete with a luxurious custom bathroom and walk in closet. Two additional bedrooms plus full bathroom. Newly paved driveway and attached two car garage. Beautifully landscaped grounds with lush plantings and mature trees. Experience tranquility and privacy with the added bonus of being situated across from a nature preserve. This home has the perfect blend of luxury and tranquility. 2015 new denitrification septic system, 2016 HVAC replaced, 2016 extensive hardscaping, 2023 new asphalt driveway. Buyer to confirm water depth.

5728 Pirates Cove Rd, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

5 Beds 5 Baths
Osprey Point is a one-of-a kind, highly crafted composition of nature, architecture and art. A private, serene Eastern Shore retreat or family compound with spectacular sunsets, deep-water pier and approximately 1500 feet of shoreline. The manageable 6.69+/-acre park-like setting features west and southwest exposure of Island Creek with prevailing, cooling summer breeze, exceptional panoramic water views, a multitude of beautiful, specimen trees and gardens, sweeping lawns, protective living-shoreline, and small, stone revetment jetties. An additional adjacent , 2.32+/-acre waterfront lot with high elevation and deep water is listed separately and can not be sold prior to sale of house . Designed by Pamela Gardner and built by Peter Hanlon in 1996, this architecturally distinctive yet elegant and classic 5,828 square foot home with two turrets, gorgeous exposed-beams, stunning woodwork and ten foot ceilings offers light-filled, water views from every room. The warm, open and inviting interior spaces lend to relaxation and enjoyment of the outdoors from within. The waterside pool, patios and porches are wonderful for entertaining guests and the stately entrance and vast, manicured lawns are welcoming. Grand entry within the front turret showcases its beauty with up-lighting. Rear turret includes a scenic third floor overlook with kitchenette for an additional private space to unwind. The first floor includes a large open kitchen featuring hand-painted, ceramic tiles depicting the wonderful wildlife of Chesapeake Bay, a walk-in wine cellar or larder and a separate pantry, the primary bedroom suite with two walk-in closets, a very large office or additional 5th bedroom, great room with wood burning fireplace, cathedral ceiling and large bar area, the family room with gas fireplace and dining area. The formal dining room is located across the hall from the kitchen. There are many hand-crafted built-ins throughout and additional attic storage on the second floor and above garage. Oversized three car garage has fourth bay for boat and outdoor toy storage. Four-zoned heat pumps with gas back up cool and heat the residence and there is also a back-up generator. Osprey Point is situated perfectly between Oxford and Easton. By water, this address also provides quick access to some nearby, locally known beaches, restaurant and ice cream establishments of Oxford as well as the Hyatt Regency Chesapeake Bay Golf Resort, Spa and Marina.

28080 Brick Row Dr, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-6665

5 Beds 5 Baths
202 N. Morris St is located in the center of Oxford's Historic District, An easy walk to the Town Park, several marinas, coffee shop, restaurants and stores. Located on high ground with hi speed internet available, this prime parcel of land extends in an east west direction with the front facing Morris St and the rear facing Factory St. The property is fully irrigated with lush landscaping, uplighting and has a heated gunite pool. There is an outdoor shower and outdoor kitchen and lovely garden areas surrounding a pergola. There is a two car garage with storage above with off street parking for an additional 3 cars. The home was built in 1883 and is known as the "Parsons House". There was a renovation in 2005 followed by updates in 2017 and again, by it's present owners in 2020. It has high ceilings, a primary bedroom suite on the first floor and 4 bedrooms and 2 baths on the second floor. There is a well appointed office or great room on the second floor plus a small sitting room perfect for reading or quiet time. The construction and finish are exquisite. No expense was spared in the last renovation and the home is ready to be moved into. The kitchen is state- of- the- art with Wolf stove, double ovens, a Sub Zero refrigerator and extra freezer. There is a kitchen bar plus eat in area. Also a beautiful dining area off the kitchen. There is more than ample storage throughout the house. Sit by the pool, or in the shade of the pergola or on your front porch and watch the people and dogs walk by. This is an extraordinary home that will take your breath away.

202 N Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

6 Beds 12 Baths
Nestled along the picturesque Tred Avon River, this extraordinary estate comprises two expansive waterfront parcels totaling 11 acres. A masterpiece of luxury living, the centerpiece is a magnificent 3-level palatial brick home with 6 bedrooms, 7 full baths, 5 half baths, and 7 gas fireplaces set on nearly 7 acres, complemented by an adjoining 4-acre vacant lot. Enjoy the private dock boasting approximately 3 feet of mean low water (MLW), complete with 2 boat lifts, 4 jet ski lifts, and a floating pier to launch your kayaks. The residence is a grand architectural marvel featuring a 2,300+ square foot primary suite with sitting room, breakfast bar, two bathrooms, two walk-in closets, and a spacious, private terrace. Revel in the epitome of entertainment with tons of outdoor terrace space, a built-in barbecue, an indoor pool, spa, and sauna, and a finished, daylight lower level equipped with a wine cellar, second kitchen, and built-in bar. The property is adorned with a pavered driveway, offering a stately approach to this waterfront oasis. Conveniently located between Easton and Oxford and just minutes from a country club, jet airport, theatres, fine dining, shopping, and healthcare, this property is approximately 2 hours from Philadelphia and 1.5 hours from DC and Baltimore. **Click on the Movie Camera for Video Tour**

5369 Morgans Point Dr, Oxford

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

3 Beds 3 Baths
Enjoy "the land of pleasant living" at this unique property in Oxford, one of the Eastern Shore's most sought after towns. Gorgeous lush landscaping with minimal upkeep! The property has two high-quality houses (both easily rentable, and licensed for same) that satisfy contemporary requirements for comfortable living. Restaurants, marinas, the Town Park (dating back to the 17th Century), community beach, tennis and pickle ball courts, Community Center, bank, post office, museum, and food/wine market all close by. Some of the frames of the houses are 100 years old, but both houses were totally remodeled in 2003/2004, including high, sealed crawl spaces. The main house has a first story bedroom with tiled bath, plus a large second story bedroom and bath. The dining area is off the modern kitchen, and the living room (with gas fireplace) is open to the dining area. The screened porch and raised deck provide additional living and dining areas. Downstairs flooring appears to be antique chestnut, while upstairs is antique yellow pine. The second house is one story and features Living Room (16 x 8); Kitchen (9 x 8); Dining Area (8 x 6); Bedroom 10 x 10; tiled bath with stack washer/dryer; screened porch (18 x 9); pine floors, electric heat and central air conditioning, ceiling fan and vaulted ceiling. Each house has off-street parking for two cars. July 2021 property inspection report can be made available to buyer. HVAC is via Mitsubishi "Mr. Slim" through-the-wall split system heat pump in the big house, and regular heat pump in the little house. Electric baseboard back-up heat in the big house. High speed WI-FI internet for both houses is from Breezeline. Electric is Delmarva Power. The furnishings are available for purchase.

200 Tilghman St, Oxford

Listing courtesy of Shoreline Realty. Contact: 410-822-7556

3 Beds 3 Baths
Luxurious Oxford townhouse boasting three spacious bedrooms and three bathrooms. Enjoy the cozy ambiance of the large living room featuring a charming gas-burning fireplace, seamlessly flowing into the dining area and well-appointed kitchen. The first floor hosts a convenient guest bedroom and bath, while a delightful deck with storage space awaits on the backside of the house, accessible from the kitchen. Upstairs, indulge in the comfort of the primary bedroom suite, alongside another inviting guest bedroom with bath and a versatile office space. Stay comfortable year-round with the efficient heating and cooling provided by the heat pump. Ample paved off-street parking and a driveway enhance convenience and accessibility.

102 J L Thompson St Unit #2B, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415

7 Beds 8 Baths
Explore the allure of this hidden jewel in Oxford where refined luxury merges effortlessly with coastal charm. Nestled across 20+ elevated acres, spend your days meander through covered walkways, cobblestone paths, ornamental trees, scenic gardens, and panoramic point-of-land views that captivate the senses. Originally constructed in 1938, Widgeon Point has undergone a complete transformation by skilled artisans and architects, resulting in a stunning residence with guest house, pool house and detached garage with apartment above. Upon entering the main home, the attention to detail is on full display through the intricate millwork, meticulously laid hardwoods, heated Tennessee stone floors, and finely crafted fireplaces. Whether you're working, unwinding, dining or entertaining, this thoughtfully designed home accommodates your needs with unparalleled ease. The provincial kitchen offers professional-grade appliances, a farmhouse sink, and plentiful custom cabinets with granite-topped counters, all chef approved for facilitating the creation of cherished meals. The adjacent dining room, with wet bar, sets the stage for celebrations big and small, while enclosed gazebos and expansive outdoor patios offer perfect settings for gatherings with views of yachts and unforgettable sunsets. At the end of the day, retreat to four bedrooms, each offering perfect accommodations with privacy, and bathrooms adorned with hand-selected stone. The primary bedroom suite boasts, cozy fireplace, spa-like bath and tranquil sunroom overlooking the estate with panoramic views of Trippe Creek. The secondary Primary bedroom suite offers over 1000 sqft of comfy respite, fireplace, and bay window. Guests will appreciate the added option of the two-bedroom guest house and fully independent over-garage apartment. Embrace the outdoors by lounging around the saltwater pool and the pool house with conveniently located kitchen and bathroom, perfect for summer relaxation. And don't forget to explore the 2 private ponds including one with serene island only accessible by a charming footbridge , the caretaker cottage, boathouse, three-car garage, and two barns. The deep-water dock beckons you to launch cruises to discover endless watershed adventures in the surrounding coves, rivers, and sanctuaries that cater to the boating enthusiast or spend the day exploring nearby historic townships like Oxford and Easton, with their plethora of restaurants, golf courses, artful shops, and annual festivals. This exceptional property invites you to experience a lifestyle where refined living seamlessly merges with coastal tranquility. Welcome Home!

5808 Widgeon Point Ln, Oxford

Listing courtesy of TTR Sotheby's International Realty. Contact: (410) 280-5600

3 Beds 4 Baths
Originally built in the late 1800s, this home was totally and beautifully renovated in the 1990s. With amazing sunset views over the Tred Avon River, this beautiful 3 bedroom home has 4 fireplaces, elevator, carport, swimming pool, and garage. The custom moldings and attention to detail in design are incredible. The architectural elements are reminiscent of a London Row house with very high ceilings, tall windows, significant moldings, and wide plank floors. A butternut paneled study with a hidden room, stenciled wood floors, and a hand painted mural in the entryway present images of the Eastern Shore to visitors. Large windows in all rooms allow a bright and happy feeling, yet all very sophisticated. This home truly has to be seen to be appreciated.

212 S Morris St, Oxford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 822-1415