528 properties for sale in Saint Michaels, St Michaels town District 2 St Michaels Talbot County Maryland

Welcome to the Bernstein II, a beautifully designed home offering 2 bedrooms, 2 baths, and a 2-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area offers a spacious and functional space for lounging. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoorsperfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owners bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a

Open house, saturday oct 24th from 12-3pm. Direct Marina Views of Castle Harbor Marina. Watch the Boats and Sunsets from your Deck & Balcony. One-of-a-Kind View. End-unit with garage. Nestled in the prestigious Bayside community, this exquisite end-of-row townhouse offers a harmonious blend of contemporary coastal design and luxurious living. With three spacious bedrooms and three and a half elegantly appointed bathrooms, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living, dining, and kitchen areas. The heart of the home features upgraded countertops, a generous kitchen island, and an eat-in space, perfect for casual gatherings. The family room, adorned with a cozy gas fireplace framed by glass doors, creates an intimate atmosphere for relaxation. Recessed lighting and ceiling fans enhance the ambiance, while large windows drench the space in natural light, showcasing the beautiful luxury vinyl plank an

Looking for an interest rate that starts with a 5? If rising rates have you questioning whether you can afford to move, come see 101 Branta Lndg, Stevensville in the community of Ellendale! With an accepted offer by 9/30, the sellers are offering up to $10,000 toward a rate buydown. Ask your lender how. Or call us! This beautifully updated end-unit townhome offers low-maintenance living with approximately $35,000 in improvements over the last 1-2 years. You have nothing to do here but unpack! Freshly painted throughout, it features new flooring in the main living area, kitchen countertops and appliances, an updated primary bath with walk-in shower, refreshed stone fireplace, and more. With 4 bedrooms, 4 bathrooms (2 half & 2 full), a 2-car garage, and a spacious deck, theres plenty of room to live comfortably without the upkeep of a single-family home. As an end unit, youll also enjoy added privacy and natural light. Ellendale offers a pool, clubhouse, playground, walking trail, boat s

Located in the waterfront community of Prospect Bay, residents enjoy golf, swimming pool, boat ramp, tennis courts, and a clubhouse with restaurant. Welcome to this much-loved home, beautifully situated on 1.03 acres with sunset water views on one side and golf course views on the other. Quality built with 2x6 construction, the home features hardwood flooring, Andersen windows, and abundant natural light. The kitchen offers maple cabinetry, a center island, table space, and an open layout connecting to the family room with fireplace and efficient wood-burning insert. Separate living and dining rooms feature bow windows showcasing the water views. A main-level fourth bedroom with built-ins currently serves as a home office. Upstairs, the spacious primary suite features water views, a large bath, and generous walk-in closet, along with two additional bedrooms and a full bath. Enjoy a screened porch overlooking the golf course, a 16' x 12' Amish-built shed, and an oversized two-car garage

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owners suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owners bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales represen

This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities. The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that Tilghman Island has to offer. Whether you're looking for a primary residence, vacation retreat, or investment opportunity, this home provides the perfect setting to experience Maryland's Chesapeake Bay lifestyle. Currently priced significantly under current appraised value!

The Sawgrass is a modern take on the center hall colonial home. Enjoy formal living and dining rooms as well as a huge island kitchen with tons of cabinet space, breakfast area and spacious family room. A main level library or guest room is included. Add a morning room and a three-car garage to increase your space. Upstairs, youll enjoy four spacious bedrooms. Your Owners suite features a sitting room and deluxe bath with tub and shower. Customize your lower level to match your lifestyle needs

Charming 3-Bedroom Home with Sunroom Addition, Wood Stove & Detached Garage with Office Welcome home to this inviting 3-bedroom, 2-full-bath home situated on a beautiful 0.33-acre lot, offering a wonderful combination of indoor comfort, outdoor living, and versatile space. Featuring warm wood accents, hardwood floors, a spacious living room, and a cozy wood stove, this home is full of character and possibilities. The living room provides a welcoming gathering space, while the kitchen features abundant cabinetry, stainless steel appliances, generous counter space, and a large island perfect for meal preparation, casual dining, and entertaining. The sunroom addition boasts impressive 12-foot ceilings, creating an open, airy atmosphere with endless potential for a second living area, hobby space, or relaxing retreat. Enjoy the outdoors with both a front porch, screened-in porch, and open porch, offering plenty of options for relaxing, entertaining guests, or enjoying a quiet morning surro

Welcome to the Taylor, a beautifully designed home offering 2 bedrooms, 2 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoorsperfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owners bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry

Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacksthe last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite countertops and opens to a spacious outdoor deck, perfect for entertaining or relaxing while enjoying the coastal atmosphere. Upstairs, the private primary suite offers a full bath with a spa tub, creating a tranquil retreat. Also on the second level is an expansive open living area complete with a half bath and wet bar, providing exceptional flexibility for entertaining, recreation, a home office, or additional guest accommodations. Recent improvements include a new roof (2026), luxury vinyl plank flooring throughout, a new washer and dryer, a new stove/range, and a new central heating and air

Experience the pinnacle of coastal luxury in this breathtaking top-floor penthouse at K. Hovnanians Four Seasons at Kent Island. This highly coveted'Chester' floor plan delivers unparalleled, sun-drenched resort-style living with spectacular water views from nearly every vantage point. The open-concept layout features a gourmet kitchen with stainless steel appliances, a spacious great room anchored by a cozy fireplace, and an elegant dry bar perfect for entertaining. Retreat to the pristine owner's suite, complete with a dramatic tray ceiling, spa-like bath, and direct access to an expansive waterside balcony where you can watch the boats glide by. Living here feels like a permanent vacation. Enjoy world-class community amenities, including a 24,000 sq. Ft. clubhouse, indoor and outdoor pools with tiki huts, a state-of-the-art fitness center, tennis and pickleball courts, and a community pier. Complete with a private garage and dedicated storage, this lock-and-leave sanctuary offers th

Picture life at 10 Shawnee Road. From the moment you step inside, light-filled, expansive living spaces invite you to relax, entertain, and make lasting memories. Worry free with a brand-new roof along with new major appliances, including a new washer, dryer, stove, and dishwasher. Large kitchen and family room with additional space for dining and living room. The primary bedroom features a spectacular bath with walk in shower and soaking tub. Lots of storage. (Come check out the storage area off the 4th bedroom! )Outside, your private paradise awaitsa spectacular back yard, fully fenced for privacy and kept lush all season long by an underground lawn sprinkler system. Enjoy evenings by the fire pit and listen to the whispering pines. As an added bonus, this home offers deeded community water rights that grant access to the Choptank River and the boat basin on Jenkins Creek. Seller will consider concession for age of heat pump A lot to love here!

Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don

This house has not been built yet! Timberlake Homes Design|Build provided the description of the home and features. Renderings/elevations are not community-specific and may show features/elements/materials that are not offered in your community of choice. Please see your sales manager to confirm the specific house type elevations available. Beech. Discover this new design which offers farmhouse-Craftsman charm and a flexible, open layout. This design features a main-level owners suite, three upstairs bedrooms, and a convenient first-floor laundry off the two-car garage. The spacious great room flows into a large kitchen island and dining space perfect for entertaining, with stainless steel appliances and a walk-in pantry. Customize with an optional fifth bedroom, sunroom, or screened porch, and a versatile flex space perfect for a home office or playroom. The Beech is designed for comfort, versatility, and easy living. FEATURES include: Main level owners suite, Sunroom or screened porc

Welcome to 1305 Marion Quimby Drive in Stevensville, a rare waterfront opportunity offering stunning views, low-maintenance living, and direct access to the best of Kent Islands coastal lifestyle. This beautifully positioned 2-bedroom, 2.5-bath home sits right along the water, delivering breathtaking panoramic views youll enjoy from sunrise to sunset. Whether youre sipping your morning coffee or unwinding in the evening, the peaceful waterfront setting creates the perfect backdrop for everyday living. Step outside and youre immediately connected to the scenic waterfront walking trail ideal for morning jogs, sunset strolls, or simply soaking in the shoreline beauty. For boating enthusiasts, the property also includes a deeded boat slip, making it effortless to get out on the Chesapeake Bay whenever the mood strikes. Inside, youll find a thoughtfully designed layout with two spacious bedrooms, each offering privacy and comfort, plus two full bathrooms and a convenient half bath for guest

Enjoy breathtaking Chester River views from this move-in-ready waterfront condo at Four Seasons at Kent Island. Meticulously maintained by its original owners as a 2nd home, this beautifully customized three-bedroom, two-and-a-half-bath condo combines elegant, low-maintenance living with the exceptional amenities of a premier 55+ community. Enjoy added convenience with Wi-Fi-enabled appliances in both the kitchen and laundry room, all easily controlled through a connected app. The home also features a Wi-Fi-enabled thermostat for convenient remote control of the heating and cooling system. Five-year extended warranties are included on most major appliances. The light-filled, open-concept floor plan features luxury vinyl plank flooring, recessed lighting, and expansive windows that bring the river views into nearly every room. A cozy electric fireplace anchors the spacious living room, which flows seamlessly into the dining area and gourmet kitchenan inviting setting for everyday living

100% Renovated. Welcome to this. Beautiful renovated. 2-bedroom, 2.5-bath townhome nestled in a desirable condo community on Kent Island. This fully updated home shines with thoughtful upgrades and modern touches throughout including new storm doors, 2025 heat pump, new water heater, upgraded electrical system, new blinds, a new Samsung washer and dryer, double-pane windows, and brand-new carpet on the stairs and upper level. The open-concept main floor flows effortlessly to a private outdoor deck, perfect for morning coffee or evening entertaining with a tranquil view. Upstairs, the spacious primary suite features its own private balcony overlooking Thompson Creek, creating a peaceful personal retreat. The second bedroom and beautifully renovated bathrooms provide a flexible living space for guests and family. Enjoy serene water views, a quiet and walkable neighborhood, and easy access to scenic community walking trails. Whether youre savoring the outdoors or relaxing amid a fully ren

Nestled along the shores of the Chesapeake Bay, this exquisite new construction home embodies the essence of luxury living. In a contemporary Farmhouse architectural style, this brand new home offers a perfect blend of elegance and comfort and is set on a generous lot of nearly a half acre surrounded by mature trees. Step inside to discover a thoughtfully designed layout featuring contemporary black steel finishes and fixtures along with crisp whites and warm wide plank flooring. A Bright and open foyer invites you into a formal Dining room with windows looking out to the front and water views beyond. The Kitchen is the heart of the home with its central location in this updated open plan layout. A Breakfast area leads into the generous Family room with sleek sliding doors that open to a large composite deck for outdoor entertaining and leisure activities. Upstairs you will find four spacious bedrooms and two beautifully appointed bathrooms. Laundry is conveniently located in the upper

Welcome to 452 Timber Lane in Grasonville! This inviting 3-bedroom, 2-bath home offers comfortable living spaces along with a unique converted garage that provides additional finished space perfect for entertaining, relaxing, a home gym, game room, or whatever best fits your lifestyle. Step outside and enjoy the nice backyard, offering plenty of room for outdoor entertaining, gatherings, play, or simply relaxing and enjoying your own outdoor space. With its flexible layout, additional finished space, and inviting yard, this home offers plenty of opportunity to make it your own. Come see all that 452 Timber Lane has to offer!

The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space perfect for working from home or quiet retreat. The kitchen is equipped with a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops for a polished finish. Luxury vinyl plank flooring flows throughout the home, with tile flooring in the two full baths for added durability. The owners bath features a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a spa-inspired retreat. For a full list of features for this home, please contact our sales representatives. Photos

Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shores premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, electric fireplace, and dry bar cabinets with top shelf glass doors. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing. Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and ou

New construction in kent island estates being framed now! *. Welcome to 103 Worcester, a brand-new. *Schaefer Homes Monroe model*. Featuring. *4 bedrooms, 2.5 baths and a 2-car garage*, with expected completion in. *early 2027*. Construction is underway, so now is the time to. *come pick your finishes! *. With so many upgrades already included, enjoy the look and feel of a custom home without the custom-home price. The Monroe offers an open main level with a spacious kitchen, dining area and great roomperfect for everyday living and entertainingwith all four bedrooms upstairs, including a private owner's suite with walk in tiled shower and double vanity. Located in. *Kent Island Estates*, where the community association is voluntary, you'll enjoy access to community beaches and plenty of neighborhood social events. The. *South Island Trail, Blue Heron Golf Course, pickleball courts and Romancoke Fishing Pier*. Are all nearby, putting some of the best of Kent Island recreation right out

Nestled in the serene enclave of Mallard Pond, this exquisite manor-style residence offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. Spanning an impressive 3,300 square feet, this home is designed to cater to both relaxation and entertainment, featuring five spacious bedrooms and two full and two half elegantly appointed bathrooms. Step inside to discover a thoughtfully crafted interior that radiates warmth and sophistication. The open floor plan seamlessly connects the family room to the gourmet kitchen, where culinary dreams come to life. Outfitted with stainless steel appliances, including a built-in microwave and range, the kitchen boasts upgraded countertops and a charming breakfast area, ideal for casual dining. The formal dining room invites memorable gatherings, while the cozy family room off the kitchen provides a perfect retreat for everyday living. Natural light floods the home through skylights and large windows, while the ne

This charming ranch-style home, built in 1978, offers a serene retreat on a spacious 0.33-acre lot, perfect for those who appreciate the beauty of nature. With three cozy bedrooms and two full bathrooms, this residence is designed for comfort and ease. The inviting screened porch and deck provide ideal spaces for morning coffee or evening gatherings, allowing you to soak in the tranquil surroundings. The driveway accommodates four or more vehicles, ensuring convenience for you and your guests. Imagine evenings spent enjoying the gentle sounds of nature, or hosting barbecues on the deck. This home is not just a place to live it's where memories are made. Embrace the lifestyle you've always wanted in this delightful property that beautifully blends comfort with the allure of outdoor living. Updated Kitchen Cabinets and appliances. Fresh painting throughout and new carpeting in primary bedroom

Welcome to this beautifully updated 4-bedroom, 3-full-bath split-level home in a desirable water-access community on Kent Island! Offering a versatile floor plan, thoughtful improvements, and plenty of room to spread out, this home is ready for its next owners to move right in and enjoy. Step inside to discover a beautifully renovated kitchen, updated bathrooms, new flooring, and fresh paint throughout. Major improvements include a new roof in 2024, a new HVAC system in 2026, and a newly fenced backyard, providing peace of mind for years to come. The upper level features three comfortable bedrooms and two full bathrooms, while the spacious lower level offers an entirely different level of flexibility. Complete with a fourth bedroom, full bathroom, additional living area, and a second partial kitchen, this space is perfect for extended family, overnight guests, an au pair, or simply creating a private retreat. Outside, the newly fenced backyard offers plenty of space for entertaining, g

Welcome home to 120 Pathfinder Circle in Perry's Retreat! Built in 2023 and meticulously maintained, this 4. Bedroom, 3.5 bath home offers approximately 3,010 sf of beautify designed living space, where thoughtful upgrades, custom touches, and everyday functionality come together. From the moment you walk in, the attention to detail is impossible to miss. The main level showcases a stunning three-sided fireplace topped with a custom walnut mantel. An eye catching centerpiece that makes the living space feel warm, inviting, and distinctly your own. The kitchen is made for gathering, cooking and entertaining, featuring two ovens and custom. Made pendant lighting that adds both function and personality. Throughout the home, an upgraded Craftsman trim package recessed lighting, luxury vinyl plank flooring, and ceiling fans in every room create a polished, comfortable feel. With Ethernet wiring throughout, this home is ready for everything from work from home days to movie nights and stream

Welcome to the Magothy, a beautifully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. This home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owners suite includes a private sitting room and large walk-in closets, offering a spacious and relaxing retreat. The kitchen is designed for both style and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Laminate flooring flows throughout the home, with tile flooring in both full baths. The owners bath is thoughtfully designed with a walk-in shower featuring a seat and handheld shower wand, double sinks, and quartz countertops for added comfort and functionality. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purpo

Discover the perfect blend of modern elegance and comfort in this stunning Colonial-style home located in the desirable Perry's Retreat. Built in 2024, this residence boasts a pristine condition and an array of features designed to enhance your lifestyle. Step inside to find an inviting open floor plan that seamlessly connects the gourmet kitchen, dining area, and family room, creating an ideal space for entertaining and everyday living. The kitchen is a chef's dream, equipped with upgraded countertops, a double oven, built-in microwave, and ample pantry space. With four generous bedrooms and 2.5 baths, this home offers plenty of space for relaxation and privacy. The upper floor laundry adds convenience to your daily routine, while the elegant luxury vinyl plank flooring and tasteful window treatments throughout elevate the aesthetic. Outside, the property features a well-maintained exterior with sidewalks and a concrete driveway leading to a two-car attached garage, ensuring ample par

Welcome to Perrys Retreat, where spacious living meets modern comfort and Eastern Shore charm! *. Built in 2023, this pristine Ryan Homes Lehigh model offers the. *largest floor plan in the community*, featuring over 3,000 square feet of beautifully designed living space, five bedrooms, two-and-a-half bathrooms, and an exceptional open-concept layout. The heart of this home is its expansive main living area, thoughtfully designed for both everyday comfort and effortless entertaining. The open floor plan seamlessly connects the kitchen, dining, and gathering spaces, creating a bright and inviting atmosphere. The spacious kitchen features an oversized center island that serves as the perfect gathering spot for casual meals, entertaining guests, or simply enjoying time together. With generous room to spread out, this main level is truly an entertainers dream! Adding to the home's versatility is a main-level bedroom, ideal for guests or multigenerational living, along with a separate flex

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shores most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the communitys active social calendar. Ideally located on Marylands Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and communityall just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 1