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$369,000
2 Beds 1 Baths
Welcome to 5116 Ocean Gateway, a thoughtfully updated rancher in Trappe offering Eastern Shore charm, comfortable one-level living, 1.5 acres, and an exceptional detached workshop and four-car garage. Conveniently located along Route 50, the property provides easy access to Easton, Cambridge, Oxford, St. Michaels, shopping, dining, waterfront destinations, and everyday conveniences, with Ocean City approximately one hour away. From the moment you arrive, the property makes a memorable impression with its established perennial gardens, expansive landscape, flagpole, security doors, new windows installed in 2022, and a brand-new roof completed in 2026. A 12-by-24 hobby shed with an upper storage level provides even more room for lawn equipment, seasonal items, projects, or recreational gear. Inside, a brand-new, fully insulated 225-square-foot sunroom completed in 2026 expands the home’s living space and creates a bright, inviting place to relax, entertain, or enjoy views of the surrounding property throughout the year. A new whole-house split system installed in 2026 provides energy-efficient heating and air conditioning in addition to the home’s existing baseboard heat. The renovated kitchen combines style, character, and everyday functionality with new cabinetry, granite countertops, a farmhouse sink, recessed lighting, a large island with a Boos Block butcher-block countertop, built-in pot filler, range hood, and a brand-new 36-inch Cosmo gas range. A mudroom, pantry, and butler’s pantry add valuable storage and help keep the home organized. The updated bathroom offers a spa-inspired retreat with a soaking tub, dual-sink vanity, built-in shelving, and a spacious walk-in shower with a built-in bench. The standout feature of this property is the hand-built 24-by-36 heated workshop, barn, and four-car garage. Designed for vehicle access, equipment, hobbies, and serious project space, the building features handcrafted 10-by-10 Ipe wood carriage doors, a rear 8-by-7 roll-up garage door, concrete flooring, a water hookup, high-intensity lighting, 120- and 230-volt receptacles, and 120/230-volt electrical service supported by a 60-amp subpanel. The generous layout provides space for multiple vehicles, boat or RV storage, woodworking equipment, tools, recreational gear, or a dedicated creative workspace. With major improvements, flexible storage, an updated one-level home, a beautiful new sunroom, and a substantial four-car garage and workshop, this unique Trappe property offers a rare combination of comfort, land, character, and utility. Schedule your private tour and experience everything 5116 Ocean Gateway has to offer.

5116 Ocean Gateway, Trappe

Listing courtesy of Keller Williams Flagship. Contact:

$459,000
3 Beds 3 Baths
VIRTUAL STAGING. Nestled in the charming Wye Mills community, this delightful Colonial-style home offers a perfect blend of comfort and functionality, ideal for those seeking a serene retreat. Built in 1995, this well-maintained residence boasts 1,984 square feet of inviting living space, thoughtfully designed to cater to modern lifestyles. Step inside to discover an open floor plan that seamlessly connects the living areas, creating an inviting atmosphere for gatherings and everyday living. The heart of the home features a cozy country kitchen, complete with a breakfast area that invites leisurely mornings. The dining area is perfect for hosting dinner parties, while the spacious living room, highlighted by a warm wood stove, provides a welcoming space to unwind after a long day. This home offers three generously sized bedrooms, including a primary suite with an en-suite bath, ensuring privacy and comfort. Outside, the property is a true oasis. Set on a sprawling 2-acre lot, it backs to lush trees, providing a sense of tranquility and privacy. The beautifully landscaped yard is perfect for outdoor activities, while the in-ground pool invites you to relax and enjoy sunny days. Multiple outdoor spaces, including a deck and porch, offer ideal spots for entertaining or simply enjoying the peaceful surroundings. For those who appreciate nature, the proximity to the Wye River adds an extra layer of charm. Just blocks away, you can enjoy leisurely walks by the water or engage in various water activities. The property also features an attached two-car garage and ample off-street parking, ensuring convenience for you and your guests. With sidewalks lining the neighborhood, this home encourages a sense of community and outdoor exploration. Whether you're looking for a peaceful retreat or a place to create lasting memories, this Wye Mills gem is ready to welcome you home. Experience the perfect blend of comfort, style, and nature in this inviting residence.

13415 Wye Landing Ln, Wye Mills

Listing courtesy of Powerhouse Realty, LLC.. Contact: 4109958386

$465,000
Fully leased duplex in-town Easton. Each unit (104 & 106) offers 3 bedrooms, 1 full bath, and 1 half bath, along with a living room, dining room, and kitchen. Bedrooms are located on the second floor, with walk-up attic access above for additional storage. Each unit has a basements with interior access, basements house the washer/dryer, oil furnaces, and hot water heaters. Interior features include a mix of wood and tile/laminate flooring. Each unit also has front porch and a rear kitchen entrance that leads to a shared backyard. On-street parking is available, along with two detached outbuildings/garages accessed from the alley. Heating is oil-fired with separate systems for each unit. Both units are tenant-occupied. Conveniently located near Idlewild Park and Easton’s Rails-to-Trails.

104/106 Stewart St, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 770-9255

$4,395,000
4 Beds 6 Baths
Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted 4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort and efficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an inviting elegance. Enjoy formal living and dining areas, chef’s kitchen with an island, quartz countertops, and a scenic waterside dining nook for informal meals. The family room, with its soaring cathedral ceilings and gas fireplace, flows through a light-filled hallway with cozy seating, offering direct views of the river. New roof installed in 2026. The main-level primary suite features a cathedral ceiling, built-ins, and a private patio, while its spa-like en-suite includes abundant natural light, a jetted soaking tub, marble accents, and two generous walk-in closets. The home also features a newly encapsulated basement and crawlspace, ensuring a well- maintained environment year-round. The professionally landscaped grounds set the stage for a well-equipped pool house complete with a guest room, kitchenette, sitting area, and bathroom. The outdoor space also boasts an in-ground pool with a spacious patio, outdoor shower, and grill area. A private pier with a boat lift offers approximately 4' +/- MLW, a 300' +/- shoreline, and a private beach. For added convenience, the main house includes attic storage and a storage shed, while the 3-car detached garage features a bonus room—perfect for an office or rec room—with kitchenette. All of this is just a short drive from Easton’s dining, shopping, and airport access.

27029 Miles River Rd, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$2,000,000
4 Beds 3 Baths
PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A dedicated space for a future elevator adds thoughtful flexibility for years to come. Outside, the possibilities are as expansive as the land itself- 19.5 private acres with pastures suited for up to eleven Horses, plus a car barn for storage, hobbies, or collections. Agricultural and livestock production also permitted (buyers should confirm specifics with Easton P&Z). Notably, 5.75 wooded acres are enrolled in the DNR's Forest Stewardship Plan, preserving the agricultural tax discount without the requirement to grow crops or house livestock.

7909 Church Neck, Saint Michaels

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

$7,950,000
7 Beds 9 Baths
Presquile Manor House, originally built by the Lloyd Family circa 1800 as one of their three Plantation Houses, sits up high on the Wye River with due West Exposure. The Main House has recently gone through a two-year renovation process from top to bottom by West & Callahan Construction and Peter Zimmerman Architects Inc, with much thought and care to keep all of the historic attributes that this property deserves. The grounds are improved by a pool, tennis court, covered boat house with deep water, formal gardens, magnificent mature trees and a detached 1,670 sq ft caretaker's house. The main parcel is 10.48 acres with an additional 7.1-acre tree lined drive with a perpetual easement. This is a one-of-a-kind property and a true Talbot County piece of History. Furniture is negotiable.

26546 Presquile Dr, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$399,900
3 Beds 2 Baths
Set on nearly an acre in the heart of Wittman, this cedar shake–sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in shelving. The kitchen has been refreshed with new flooring, afarmhouse sink, updated butcher block countertops, and a new refrigerator—bright, functional, and well-suited for daily life while preserving the home’s original character. Outdoors, the spacious 0.86-acre lot is dotted with mature trees and beautiful landscaping, offering plenty of room to add a deck or fence. A covered front porch and outdoor shower enhance the home’s easygoing coastal feel. An oversized two-car garage with attic storage and a large driveway provide ample parking and storage. Located just 0.1 miles from Wittman Community Park, 0.3 miles from Wittman Wharf, and only 7 miles from historic downtown St. Michaels, this property offers peaceful small-town living with convenient access to waterfront amenities, dining, and shopping. A rare opportunity to enjoy space, charm, and location on Maryland’s Eastern Shore.

22582 Pot Pie Rd, Wittman

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

$699,000
3 Beds 3 Baths
Broker and Public Open 4/23 from 10am to Noon! OCCUPANCY PERMIT in hand, move right in! Nestled in the charming town of Easton Maryland, this exquisite new construction offers a perfect blend of modern luxury and traditional elegance. The sixth of Sandy Lane's ten total homes to be built, this design is the first two story that includes a first-floor primary suite with gorgeous en-suite bath and a huge walk-in closet. There are two additional bedrooms up and a 320sf family room, providing a second spacious gathering place for tv watching, reading, homework, pool table, games, the works! It is a thoughtfully designed custom layout providing plenty of space for privacy, relaxation and entertainment. Step inside to discover an inviting open floor plan that seamlessly connects the gourmet kitchen to the dining and living areas. The kitchen as designed is a cook's dream, with an island providing ample workspace and seating for four. The kitchen is equipped with custom cabinetry and elegant countertops as well as stainless appliances. The kitchen island serves as a focal point for gatherings, while recessed lighting and ceiling fans enhance the ambiance throughout the home. The interior is fitted with luxurious vinyl plank flooring and carpeting, creating a warm and comfortable atmosphere. The first-floor primary suite features a huge walk-in closet and a private, beautifully finished bathroom with a custom-tiled shower. Next to the interior entrance to the garage, you will find a convenient, dedicated laundry room and private powder room. Outside, the property is equally impressive. The extensive hardscape and beautifully landscaped front yard create a picturesque setting, with a rear patio and front porch perfect for outdoor entertaining or quiet evenings spent enjoying the neighborhood views. In addition to an encapsulated and climate-controlled crawl space, features include energy-efficient double-pane windows, Certified IECC Energy Efficient insulation (R-49 ceiling, R 21 walls), exterior lighting, and a well-designed gutter system, ensuring both functionality and aesthetic appeal. Whether you are retired, work from home or have a growing family, this flexible floorplan will suit your needs. Parking is a breeze with an attached garage with electric car charger, driveway space for two vehicles, and additional on-street parking available. Located on a cul-de-sac, this home offers a sense of privacy while still being in the heart of downtown, where the vibrant community life of Easton awaits. You can experience the luxury of modern living in a prime downtown Easton location, where every detail has been meticulously crafted to provide comfort and elegance. Don't miss the opportunity to make this stunning residence your own and enjoy the exclusive lifestyle offered on Sandy Lane. Sandy Lane homes are subject to recorded Covenants and Restrictions (attached in docs) but there is no HOA or fees. Developer: Sandy Lane, LLC, MHBR 9512. Builder: Stansbury and Sons Home Improvement Inc., MHBR 8351. BUILDER CONTRACT REQUIRED.

18 Sandy Ln, Easton

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 745-0415

$1,150,000
4 Beds 3 Baths
PRICE IMPROVEMENT*** Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor living. Enjoy your morning coffee while watching boats drift by, or relax in the evening with views that will take your breath away. The home is located in a sought-after waterfront community offering fantastic amenities including a clubhouse, pool, and marina—perfect for boating, entertaining, and leisure. Whether you’re looking for a peaceful full-time residence or a weekend retreat, this home checks all the boxes. Just bring your boat and your dreams! NEW ROOF & FIREPLACE 2024, NEW APPLIANCES 2019

21477 Island Club Rd, Tilghman

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

$395,000
3 Beds 2 Baths
Online Bidding Open: https://www.auction.com/details/11778-old-skipton-rd-cordova-md-1921078 High Visibility Corner Property on Busy Route 50 - Perfect for Living & Business! Exceptional Opportunity in Cordova, MD! This stunning corner property boasts almost 1.5 acres of land on Route 50, offering high visibility and traffic flow. This renovated home is perfect for owner living and operating a good-sized low profile retail business, such as a real estate, insurance agency, law firm, veterinarian, doctor, travel agency, potential billboard signage, solar panels, agricultural products sales, backyard appliances & furniture, sheds, construction and show room co. Renovated from Top to Bottom 2021-2025* - New Roof - New Windows - Modern Kitchens - Updated Bathrooms - New Electrical Fixtures - Top-of-the-Line Appliances - And much more! Land and Zoning: - Plenty of room for parking and outdoor displays - Prime Location: - Corner of Old Skipton Rd and Ocean Gateway - Across from Councell Farms, a well-known agricultural landmark - High traffic flow on Route 50 Don't Miss Out! This property offers endless possibilities for entrepreneurs and families alike. Contact us today to schedule a viewing and make this exceptional property yours! Additional Details: - Property Size: Approximately 1.34 acres - Zoning: A2. We look forward to working with you to attain a mutually beneficial sale.

11778 Old Skipton Rd, Cordova

Listing courtesy of Taylor Properties. Contact: 3019702447