Experience the best of Eastern Shore Living at this stunning waterfront retreat. Set on 8+ private acres, this solid brick Dutch Colonial offers timeless architecture, exceptional privacy and spectacular waterfrontage on San Domingo Creek. A long tree lined drive welcomes you to over 4400 square feet of thoughtfully designed living space. Additional highlights include a 2 car garage, paved parking, mature landscaping, pool, 4+ mlw water depth and pier. A short 5 minute drive to downtown St. Michaels. Please see notes about the ALARM.
Rio Vista Community – No Town Taxes! Enjoy life in the desirable Rio Vista community, featuring exclusive resident access to a waterfront park on the Miles River. Located just outside historic St. Michaels, this home offers exceptional convenience with a grocery store, hardware store, restaurants, beauty salon, Pilates studio, YMCA, and garden center all just minutes away. This solid ranch-style home is currently tenant-occupied; a minimum of 24 hours' notice is required for showings. Home Features: Hardwood floors throughout Wood cabinetry kitchen with quartz countertops Bright tiled sunroom with a cozy wood stove Attached 2-car garage Comfortable single-level living Whether you're looking for a weekend retreat or a year-round residence, this property offers both comfort and convenience in a sought-after location. Priced below appraised value—an outstanding opportunity!
This thoughtfully designed 4-bedroom, 3-bathroom home features an open-concept floor plan ideal for both everyday living and entertaining. The main-level primary suite provides a private retreat with a spacious walk-in closet and an en-suite bath complete with a double vanity and glass-enclosed shower. The living room is anchored by a cozy gas fireplace and flows seamlessly into the dining area and well-appointed kitchen, featuring a gas stove and stainless steel appliances. Practical amenities include a mudroom with laundry just off the attached two-car garage, a Rinnai tankless water heater, and an efficient dual-zone heat pump system with separate upstairs and downstairs climate controls. The second floor offers additional flexibility with a bedroom, full bathroom, and a large family room—perfect for guests, a home office, media room, or recreation space. Just off the recreation room, a spacious attic provides abundant storage and offers potential for future expansion. Outside, enjoy a beautifully landscaped backyard featuring a stone patio and ample garden space, creating the perfect setting for outdoor dining, gardening, or simply enjoying the peaceful surroundings. Ideally situated in the heart of St. Michaels, this home offers exceptional proximity to the area's most beloved destinations. Located less than 200 feet from the St. Michaels Nature Trail, just 0.2 miles from Chew Street Park, and only 0.2 miles from historic downtown St. Michaels, you'll enjoy convenient access to shopping, dining, waterfront attractions, and community events. Adding to the appeal, plans are underway for the future San Domingo Creek Park at the end of W Marengo Street—a proposed 7.6-acre waterfront park focused on recreation, environmental restoration, and trail connectivity that is anticipated to become the largest waterfront park in St. Michaels. Exceptional proximity to downtown St. Michaels, future recreational amenities, modern comforts, and versatile living spaces make this home a rare opportunity in one of the Eastern Shore's most sought-after communities.
Nestled on a gorgeous waterfront lot just minutes from St. Michaels, this exceptional property offers the perfect blend of privacy, comfort, and convenience. Enjoy an easy bike ride into town while coming home to a peaceful setting surrounded by mature, established trees and beautifully landscaped grounds. Built with quality and designed for comfortable living, the home features two spacious primary suites, including one conveniently located on the first floor. Large walk-in closets provide abundant storage throughout. An attached in-law suite offers flexibility for extended family, guests, or multi-generational living. The impressive foyer welcomes you into a thoughtfully designed floor plan featuring mostly hardwood floors throughout. Enjoy a spacious dining room perfect for large family gatherings, a comfortable living room anchored by a cozy brick fireplace, dedicated office space, and a separate craft room. A large utility room provides exceptional functionality with space for an extra freezer and refrigerator, while multiple HVAC zones ensure comfortable heating and cooling throughout the home. Outdoor amenities are equally impressive. Relax by the pool, entertain on the waterfront, or take advantage of the private dock with approximately 4 feet of mean low water depth. The property also includes a substantial workshop with tractor storage, ideal for hobbyists, boaters, or those needing extra workspace. Recent improvements provide peace of mind, including a roof that is just two years old and a paved driveway completed within the last year. This is a rare opportunity to own a solidly built waterfront retreat offering space, functionality, and timeless Eastern Shore charm just moments from the shops, restaurants, and waterfront attractions of St. Michaels.
The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A What's special The experience of Rose’s Garden unfolds gradually, the way the best properties always do. A long, pine-lined entrance drive carries you toward a first glimpse of Harris Creek ahead — water framed by tall pines, open and still. Then the drive sweeps gently to the left, and then, almost as a surprise, the cottage — modest, elegant, perfectly placed. It makes no attempt to impress. It doesn’t need to. The cottage is quiet and handsome — simply elegant in the way that only genuine character produces. Nothing oversized, nothing imposing. Just a well-proportioned, beautifully maintained home that belongs exactly where it sits. That first view of the house — unhurried, understated, perfectly at home in its setting — tells you everything about what kind of place this is. THE PROPERTY Few waterfront properties in Talbot County can offer what Rose’s Garden delivers: 6.87 private acres along Harris Creek, with approximately 400 feet of rip-rap shoreline in excellent condition. That kind of scale — within the Saint Michaels area — is simply not available anymore. And the west-facing orientation means sunsets over open water every evening, looking out across largely undeveloped land on the opposite shore. The views are clean, natural, and remarkably unspoiled. For a property this close to Saint Michaels, that is genuinely extraordinary. A private dock with 4 feet of water provides direct access to the creek and the Chesapeake Bay beyond. The home has been comprehensively renovated — new roof, refinished hardwood floors, updated kitchen, two fully remodeled baths, and complete HVAC throughout. A buyer arrives to something turnkey, not a project. THE LIFESTYLE Morning coffee on the primary bedroom deck with the creek glassy and still, nothing but natural shoreline across the water. Afternoons in the saltwater pool with the scent of pines and the sound of the water nearby. Evenings at the waterside pavilion as the sky turns orange over Harris Creek — unobstructed, undeveloped, all yours to take in. The rose garden and large, beautiful mature trees spread across the property give the grounds a park-like, tended quality that simply cannot be manufactured — it accumulates over decades, and here it already exists. At night, subtle landscape lighting illuminates those trees from below, casting the grounds in a quiet, warm glow. It is the kind of lighting that enhances rather than announces — a property that is just as inviting after dark as it is at sunset. And yet Saint Michaels — its restaurants, the Chesapeake Bay Maritime Museum, the Miles River Yacht Club — is just minutes away. The seclusion is real. The convenience is too. That combination is what makes Rose’s Garden so difficult to replicate. WHY THIS PROPERTY IS RARE Properties like Rose’s Garden do not come together by accident. The acreage, the frontage, the dock, the unspoiled views, the mature landscape — each of these alone would make a property noteworthy. Together, and this close to Saint Michaels, they represent something that simply does not come to market often. The renovation means a buyer inherits none of the headaches that typically accompany older waterfront homes — the deferred maintenance, the aging systems, the compromises. The work is done and done well. Rose’s Garden is ready for its next chapter. AT A GLANCE 6.87 private acres — Saint Michaels area — Waterside pavilion — Pine-lined entrance drive w/ creek views — New roof — Large mature trees throughout grounds — Primary bedroom deck w/ water views — Subtle up lighting on mature trees — Full HVAC — central + mini-splits — Unspoiled views — largely undeveloped opposite shore — Both baths fully remodeled — 400 ft Harris Creek frontage — Refinished hardwood floors — Rip-rap shoreline — excellent condition — Updated kitchen w/
Want to live close to Historic Saint Michaels in a beautiful and low maintenance setting offering ample first floor living? Welcome to 24375 Widgeon Place, Unit 37, nestled in the picturesque Martingham Community just outside Historic St. Michaels . This desirable END UNIT property is the epitome of style and comfort, encapsulating all the charms of eastern shore coastal living. Featuring 3 stunning bedrooms with 3 full bathrooms, offering generous living spaces and functionality, the property overlooks the beautiful Links of the Perry Cabin Golf Course, blending indoor comfort with outdoor beauty. After you enter the vestibule/covered entryway, you're greeted by the foyer leading into the open living room area, which offers an inviting atmosphere, all new LVP flooring, a convenient wet bar, Bose sound system, and an electric fireplace, then unfolds into the dining area featuring grasscloth wallpaper and is perfect for hosting social gatherings. Off the dining area is a well-appointed kitchen with hardwood floors and outfitted with Bosch stainless steel appliances, solid wood cabinets, ample storage, and a stackable washer and dryer area. The Anderson sliding glass doors are only a few years old and lead to a private patio. It only gets better with two spacious primary bedroom suite options, one on the first floor boasting a private sitting/office area, and the second upstairs featuring its own private balcony with new trex decking, and wonderful views of the golf course. The 3rd bedroom on the second floor is large and spacious as well and storage will never be a problem with a walk-in attic off the large closet to accommodate your needs. NOTE: A portion of the garage was utilized to expand the first floor primary by prior owners, so the garage presently is suitable for storage and/or a golf cart. There is unassigned outdoor parking. If you wish to convert the storage/golf cart sized garage back to a full one car garage, that is feasible without losing a main floor bedroom (ask listing agent for details). Additional upgrades: entire HVAC replaced approximately seven years ago, a roof installed in 2011, two year old spout/gutter guards (gutters are cleaned by HOA), and a lower deck/patio area built approximately eight years ago, and a long list of recent upgrades (past two yrs): Replaced the flooring throughout the condo (except kitchen)--so both levels--with a high quality LVP. The stairs were redone in oak. The kitchen floor is hardwood; Replaced (or added) new overhead light fixtures and ceiling fans throughout the unit, including adding under cabinet lighting in the kitchen and a utility closet light; Upgraded all electric outlets throughout the unit (they were original to the unit and the electrician advised it); Replaced the second floor balcony/deck with new roofing materials (underneath as it's essentially a flat roof so has all the components of roofing except for shingles) and new Trex decking materials;Put in new downspouts off the rear of the unit; Every room was painted in muted coastal colors with the exception of the first floor bathroom which has a nautical stripe wallpaper; Upgraded window treatments (the cellular shades, curtain rods and curtains will convey if the buyers want them). Whether it’s a weekend getaway situated on a golf course and near Historic St Michaels' renowned shops and restaurants or a forever home you seek, this property is a tremendous blend of a vibrant community spirit and a tranquil, coastal life.
Rare opportunity to acquire a well-appointed home with immense views and convenient proximity to St Michaels. Ideally located by land and sea in Chance Hope Farm on the Miles River at the confluence of Eastern Bay, this stunning, classic eastern shore brick colonial has everything the most decerning buyer needs. This Daffin custom-built home features a generous, main-level primary suite featuring a spa-like bath with heated floors, a large soaking tub and separate shower, and two walk-in closets. The kitchen is a chef’s dream, featuring high-end stainless-steel appliances, a wine cooler, a warming drawer, and a massive island. There are also formal living and dining rooms, two office spaces, a recreation room, and a river room that enjoys views of Eastern Bay and beyond. The park-like lot has 220+/- feet of rip-rapped shoreline, a private pier with 3’ of MLW, lush landscaping, and a waterside deck with an outdoor kitchen.
Nestled on 2.3 private acres in the sought-after Martingham neighborhood, this beautifully updated waterfront home offers one level living with the perfect blend of comfort, style, and outdoor living. Overlooking Porter Creek, the property features a private pier with lift and rip-rapped shoreline, where you can enjoy breathtaking sunsets, and endless days enjoying the water. Inside, the open floor plan flows effortlessly from the spacious living areas, open dining area, to the fully renovated kitchen, complete with quartz countertops, custom cabinetry, and modern appliances. The expansive waterside owner’s suite has a luxurious bathroom with heated tile floors, and generous closet space. Two additional bedrooms, plus a den that could serve as a fourth bedroom and custom bathroom. Step outside to a screened porch with awning or lounge beside the tiled gunite heated saltwater pool, Pebblesheen finish and surrounded by a custom deck—perfect for entertaining or quiet relaxation. Additional highlights include a two-car garage with attic storage, a laundry room with utility sink, stacked washer/dryer, and a 4-ton Legacy heat pump for year-round comfort. This is a rare opportunity to own a meticulously maintained home in one of St. Michaels’ most desirable communities, where privacy, luxury, and a waterfront lifestyle come together beautifully. Experience life alongside one of Maryland’s finest golf courses - across the street of the award-winning Links at Perry Cabin Golf Course—a premier golf destination designed by the legendary Pete Dye.
New Price! Transformative renovation in Martingham! This beautifully updated 2-bedroom, 2-bath single-level Gull Wing Villa overlooks the 6th fairway at Links at Perry Cabin, offering a serene golf course setting just minutes from the heart of St. Michaels. Thoughtfully redesigned, the home features new flooring throughout, a fully renovated kitchen and baths, and a reimagined layout that enhances both flow and functionality. The kitchen now opens seamlessly to the living area—ideal for modern living and entertaining. The primary bath has been expanded and now includes a large vanity. The smart design choices resulted in the addition of a generous extra closet in the primary suite. Additional updates include a new roof (2025), providing peace of mind for years to come. Located in the desirable Martingham community, residents enjoy access to a waterfront park with beach which is only about a 15 minute walk away. All of this is just moments from St. Michaels’ renowned shops, restaurants, and harbor.
Situated in the established community of Martingham, and surrounded by the Links at Perry Cabin golf course, this beautifully updated 2-bedroom, 2.5 bath townhome has been thoughtfully renovated with an emphasis on quality craftsmanship, energy efficiency, and long-term durability. The redesigned open floor plan creates a seamless flow throughout the main living areas, complemented by updated cabinetry, granite countertops, and stainless steel appliances in the kitchen. All three bathrooms have been refreshed with new vanities, fixtures, and finishes, offering a clean and modern feel throughout the home. Beyond the cosmetic updates, extensive infrastructure improvements provide peace of mind, including a newer HVAC, upgraded electrical panel, full outlet and switch replacement and enhanced attic efficiency with resealing and R49 insulation installation. Interior finishes have been completely reimagined and updated throughout, including new luxury vinyl plank flooring on the upper level and premium Mohawk carpeting with upgraded padding in the lower bedrooms and on the stairwell (2024). Fresh interior paint throughout the home, along with meticulous restoration of original doors - stripped, primed, and repainted with all new hardware installed in 2024 - add to the home's character and detail. Additional improvements include a new washer and dryer (2024), new sliding glass doors in the bedrooms, and a 60-inch Hunter ceiling fan in the great room. A stand out feature of this unit is the expanded floor plan, offering a more open, functional, and spacious living area not commonly found in similar units. The HOA recently completed significant improvements, including a new roof, decking replacements, and new gutters in 2025. Completely turnkey and thoughtfully upgraded make this property ideal as a full-time residence, weekend retreat or investment property.
Discover this ranch-style home located 1 block to the center of downtown, perfect for those seeking convenience to everything St Michaels has to offer. This 3-bedroom, 2-bathroom residence offers 1,364 sq. ft. of potential, set on a generous 0.17-acre lot. The rails to trails is located right at the end of the street. With a little creativity and vision, this property can be transformed into your dream home. Roof was replaced in 2014, HVAC 2014, hot water heater 2015. Fence panels have been removed, posts remain, they are on the property line. No permit would be needed to add new panels. There is space for a driveway to be added to the left of the home. Embrace the opportunity to invest in a community that values connection and quality of life. Don't miss out on this chance to make it your own!
This sturdy brick ranch sits on a premium lot backing up to The Links at Perry Cabin Golf Course in St. Michaels, MD. A park like setting with mature specimen trees and shrubs. It's a 4 BR, 3 full bath, one level for easy living. New updated flooring. The Martingham Subdivision provides a waterfront community lot to enjoy the Miles River constant boat shows. Wednesday night sailboat races, fourth of July fireworks and thirsty Thursday with your new neighbors. Less than 3 miles to downtown St. Michaels Fine Dining and Shopping. MORE PHOTOS TO COME.
This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering an easy walk or bike ride to the wonderful shops, restaurants and amenities of Historic St. Michaels. The residence features four private bedroom suites, a den, 4.5 spa-like bathrooms and a 2-car garage with an adorable guest residence with outdoor deck above. A 1.5-acre manicured lush, landscaped setting features a beautiful saltwater, waterside pool, substantial outdoor entertaining space and a firepit. The property also features a custom, stone entrance with lighting, a tree lined Belgian block bordered driveway and a fully irrigated sprinkler system. The home enjoys a bright, sunlit, open floor plan, sophisticated finishes, tall ceilings, a main level waterside primary suite, and a beautiful kitchen designed for entertaining that includes quartz counters, a glass subway tile backsplash and stainless appliances. The living room features a fireplace wall with limestone surround, custom cabinetry and floating shelving. The home’s appointments include; high-end bath fixtures and lighting by Restoration Hardware, beautiful bamboo hardwood flooring, custom frameless glass shower enclosures, an upgraded sound system on the main level and pool entertainment deck and automated blinds. The dream garage is temperature controlled, has epoxy flooring and a custom cabinetry and storage system. Enjoy boating on the picturesque San Domingo Creek and the connecting, beautiful tributaries via the dedicated pier that is shared with the adjacent neighbor that features, an approximate 4 feet MLW water depth, a 10,000 lb. boat lift and a floating pier for your kayaks. Your family and guests will enjoy the convenience and lifestyle of this coveted St. Michaels location and the waterfront living experience afforded by this exquisite residence. **See the movie icon for the virtual tour and floor plans.
Known as the William J. Wrightson House, this distinguished circa 1897 residence in the heart of St. Michaels beautifully blends timeless elegance and refined architectural detail with the comforts and conveniences of modern living. Lovingly restored from top to bottom, the home has undergone extensive renovations and improvements, including all new HVAC systems, tankless hot water system, updated wiring, crawlspace encapsulation, new roof and gutters, recessed lighting, high-end appliances, three fully renovated baths, a custom butler’s pantry, complete interior and exterior painting, and new patio grading and drainage, among many others. A full list of improvements is available. Ideally situated just steps from the waterfront, marinas, boutique shops, waterfront dining, and renowned local restaurants, the property offers an exceptional in-town lifestyle in one of the Eastern Shore’s most beloved waterfront communities. Filled with natural light throughout, the beautiful 3BR/3BA residence showcases heart pine and yellow pine flooring, custom millwork, and thoughtfully renovated living spaces designed for both everyday comfort and effortless entertaining. The welcoming living room, anchored by a new gas fireplace/stove, flows seamlessly into a gracious formal dining room ideal for gatherings with family and friends. The gourmet kitchen features quartz countertops, top-tier appliances, abundant cabinetry, and custom built-ins, effortlessly combining style and functionality. At the rear of the home, a stunning sunroom addition serves as a true focal point, featuring vaulted ceilings, a shiplap accent wall, wet bar and custom butler’s pantry with beverage chiller and bar sink, custom built-ins, a renovated full bath, and French doors opening to the picturesque gardens and brick patio beyond. Upstairs, the comfortable primary suite offers a peaceful retreat, complemented by a luxurious bath with a clawfoot soaking tub, Carrara Bella marble flooring (in shower as well), custom antique vanity, and glass-enclosed walk-in shower. Two additional guest bedrooms and a beautifully renovated bath with marble tile flooring, granite-topped vanity, and Perrin & Rowe fixtures provide inviting accommodations for family and guests. The outdoor spaces are equally enchanting, highlighted by a stunning English garden filled with roses, crepe myrtles, and hydrangeas, all enclosed by a charming French Gothic lattice shadowbox fence, creating a private and storybook setting.
Welcome to waterfront living in the heart of St. Michaels. This fully renovated 3-bedroom plus office, 2.5-bath home offers a thoughtful blend of modern updates and coastal charm, all set against expansive views of the Miles River. The first-floor primary suite is a true retreat, featuring a custom California Closet system and a beautifully updated bath with a walk-in shower, freestanding tub, and double vanity. Upstairs, enjoy a private balcony with elevated water views, while the rear composite deck provides the perfect setting for everyday living and entertaining, all overlooking the Miles River. The outdoor space is designed to impress, complete with hardscaped pavers, a gas-connected grill, pizza oven, and propane fire table. A private dock offers direct water access, ideal for boating, kayaking, or simply enjoying the waterfront lifestyle. Additional highlights include new LVP flooring, a new furnace, encapsulated crawlspace, and a newly installed irrigation system to maintain the home’s mature landscaping and hydrangeas. A detached garage and access to a nearby community dock within walking distance further enhance the lifestyle this property offers. Tax record indicates wrong square footage, actual square footage of the home is 3,076 square feet of living space. *** Settlement cannot occur before September 10th, 2026***
PUBLIC OPEN HOUSE: SUNDAY, JUNE 7 from 10AM-12:30PM. BRAND NEW & MOVE-IN READY, this Arts & Crafts home sits on a quaint corner lot in picturesque Saint Michaels, MD and is clad with high end finishes throughout. Step from the covered front porch into the luxurious kitchen which features stylish pistachio and linen cabinetry with satin bronze hardware, Z-Line appliances including a 36" dual fuel 6 burner range with champagne bronze accessories, artisan wood range hood, spacious center island w/breakfast bar, high end d'oro quartz countertops and herringbone tile backsplash. The living room includes a gas fireplace w/shiplap surround, custom coffered ceiling, large picture windows and a four panel Pella slider door which allows abundance of natural light and direct access to the backyard. Rounding out the main level is a flexible multi-purpose space - perfect for a formal dining room, office or a sitting room. On the upper level enjoy 3 bedrooms and two baths, including an owner's suite with walk-in closet and a luxurious spa-like bath with dual vanities, rich blue cabinetry and walk-in shower with dual shower heads and floor-to-ceiling attache calacatta tile. Additional amenities include LVP flooring throughout main level, ceramic or porcelain tile in all baths, custom light fixtures, public water and sewer, 30 year architectural singles, 92% efficient Carrier HVAC, Pella windows, 2x6 framing, R49 insulation in ceiling, R21 insulation in walls, air seal package, covered front porch and much more. All of this in a convenient location adjacent to all historic Saint Michaels has to offer. Loaded with amenities and unbound by an HOA or restrictive covenants, this one of a kind property will not last long! Schedule your private tour today!
This well-maintained duplex in Rio Vista presents an exceptional investment opportunity, featuring two spacious units, each offering 2 bedrooms and 1.5 baths. Ideally situated just moments from the heart of historic downtown St. Michaels, residents enjoy easy access to charming shops, dining, and waterfront attractions—all while benefiting from no town taxes. With both units currently 100% leased, this property provides immediate, reliable income, making it a smart addition to any investment portfolio.
Escape to Swan Road Villa Townhomes — a bright, low-maintenance retreat. This reverse-living 2-bedroom, 2.5-bath townhome features an open floor plan on the second level with a galley kitchen, dining area, and a combined living room that opens to a balcony spanning the entire back of the second floor — perfect for indoor/outdoor living and filled with natural light. The main level includes two bedrooms, two full baths, and a laundry room. Convenient access to golfing(with membership), walking and biking paths, and a waterfront park. Ideal as a first home, second home, primary residence, or investment. Recent upgrades - roof, bathrooms, flooring, HVAC unit, landscaping, and interior painting. *Some images are virtually staged*
Effortless living in the Martingham community. This thoughtfully designed 3-bedroom, 3-bath rancher features a light-filled, easy-flow floorplan with two ensuite bedrooms for added privacy and versatility. The home offers a garage and separate laundry room and opens to a charming backyard deck - ideal for morning coffee or evening gatherings. The spacious backyard provides ample room for a pool, enhancing the home's outdoor living potential. Comfortable, functional and perfectly suited for enjoying the Eastern Shore lifestyle.
Stunning One-Level Luxury Living with Golf Course & Pond Views Perfectly positioned in one of St. Michaels' most desirable communities, this exceptional residence offers effortless one-level living with a private backyard overlooking a tranquil pond and the 4th green of The Links at Perry Cabin. Just minutes from the historic charm, fine dining, boutiques, and waterfront attractions of St. Michaels, residents enjoy exclusive access to a beautiful private waterfront park on the Miles River—a treasured amenity that embodies the best of Eastern Shore living. Meticulously maintained and thoughtfully renovated, this home is truly move-in ready. Recent improvements include a beautifully updated kitchen, renovated bathrooms, fresh interior paint, and a new roof installed in September 2025 featuring 30-year architectural shingles. Additional upgrades and features include: Main HVAC system installed in 2021 with an active service agreement New hot water heater (2024) New dishwasher (2024) Electric vehicle charging station in the garage Invisible pet fence surrounding the yard The serene setting, spectacular views, and extensive updates create a rare opportunity to enjoy a low-maintenance lifestyle in a premier St. Michaels location. Whether relaxing on the patio overlooking the pond and golf course or enjoying the community's private waterfront park, this home offers the perfect blend of luxury, comfort, and convenience. A truly turnkey property where every detail has been thoughtfully updated and impeccably maintained.
This charming, spectacular reimagined home offers refined Eastern Shore living at its very best. Set on beautifully landscaped grounds with views of the Miles River and only steps to the park in a quiet sought after St. Michael’s neighborhood with town restaurants, shops, etc. and Y walking distance away to enjoy without all the noise and congestion of in town living. Thoughtfully designed 1200 sf main level offers beautiful open large living room with fireplace and dining room for entertainment, which leads to fabulous sunroom overlooking the back yard garden. Modern kitchen off the dining room that leads to cozy breakfast room and back porch and patio. The Master suite has a completely remodeled bath with free standing soaker tub, walk in shower, his and hers vanities, as well as laundry. The key to this home is the second floor. This 800 SF space offers unimaginable flexibility. It can be various spaces based on your needs. A private space for your guests when visiting, a space for family and grandchildren, an in-law suite, or as a rental apartment with private entrance. Space is built to accommodate all the above with out any changes required. At present it has a living room, dining room, kitchen, bedroom and full bath with laundry, and under eave storage. The space, with the addition of one wall can add an additional bedroom making the property with all the aforementioned, a 3-bedroom home. In the backyard you will find self-contained workshop with HVAC, hot and cold running water, and attic, a Williamsburg garden shed, and parking for 3-4 cars. Home has encapsulated crawl space, and 2 zoned HVAC system.
Situated on a corner lot just minutes from downtown St. Michaels, this 3-bedroom, 2-bath home offers easy access to local shops, restaurants, and the Maritime Museum. Inside, the living room is filled with natural light from a large bay window and features LVP flooring, recessed lighting, and updated fixtures throughout. The kitchen and dining area provide an open, functional layout with direct access to the backyard through sliding glass doors. Both bathrooms have been remodeled, and additional updates include new electrical outlets and switches, a 2024 electric panel, HVAC (2025), and a 2026 hot water heater. Outside, the fenced yard includes a patio, sodded lawn, professional landscaping, and an irrigation system. A 14’x20’ insulated shed with electric and heating/air offers flexible use as a workshop or studio. The home also features a newer roof, siding, gutters, and downspouts (2 years), plus a 5-year-old encapsulated crawlspace with sump pump and dehumidifier. Complete with a private driveway and well-maintained exterior, this property combines convenience, updates, and location.
A fresh new price – now offered at $699,000. A light-filled entertainer’s dream with soaring vaulted wood ceilings and seamless indoor-outdoor living, this beautifully maintained four-bedroom contemporary is privately situated on a one+ acre lot overlooking the 12th fairway of the Links at Perry Cabin golf course. The inviting interior features a dramatic vaulted living room with fireplace and wood-burning insert, spacious family and dining rooms, and a bright sunroom that opens to a relaxing private deck ideal for entertaining or quiet everyday living. The main level primary ensuite includes two walk-in closets and new carpeting installed in 2024, creating a comfortable private retreat. Significant 2024 improvements include a new roof and gutters, representing approximately $90,000+ in recent upgrades. Double-pane windows throughout enhance energy efficiency and create a peaceful interior environment. Home is supported by three HVAC systems professionally serviced and maintained by Shaw's along with two water heaters for enhanced comfort and efficiency. Nestled within a wooded setting offering both privacy and scenic golf course vistas. The two-car garage provides abundant space for hobbies, storage, or workshop use, while the expansive driveway comfortably accommodates 7+ vehicles. Enjoy quiet golf course living just minutes from historic St. Michaels, restaurants, shops and the waterfront.
Welcome to 203 E Chew Avenue, a residence of exceptional craftsmanship and refined luxury, originally constructed in 2008 and thoughtfully reimagined through comprehensive renovations completed in 2023 and 2024. Encompassing more than 4,700 +/- square feet of finished living space, with 5 bedrooms, this home offers an elevated blend of sophistication, comfort, and timeless Eastern Shore charm— located on East Chew Street, the property is walking distance to the harbor, boutiques, and celebrated dining of St. Michaels. From the moment you enter, the quality is unmistakable. Clean sightlines and an open, interconnected floor plan create an ideal setting for both everyday living and effortless entertaining. Throughout the home, curated lighting, custom millwork, elegant crown molding, custom doors, and redesigned fireplaces reflect a commitment to thoughtful design and enduring craftsmanship. The main level features a primary suite with beautifully updated finishes and refined details, including a fully renovated primary bath. There is a second primary suite on the second level as well with a renovated bath. The main residence offers four ensuite bedrooms; all baths have been renovated each providing privacy and comfort for family and guests alike. A standout feature of the property is the fully independent renovated permitted apartment above the two-car heated garage. Complete with a full kitchen, bath, washer and dryer, office area, and sleeping loft, this versatile space is ideal for extended family, guests, a private studio, home office or potential rental income. At the heart of the home, with secure access to the main house from a two garage, providing off street parking and easy kitchen access, is both functional and thoughtful. The kitchen showcases high-end appliances with gas, exquisite finishes, and custom lighting. The kitchen flows seamlessly into the living and dining areas, where fireplaces add warmth and ambiance. Upstairs, an additional media lounge area, a second upper-level primary suite offers a serene retreat with updated bathroom cabinetry and fixtures, a fireplace, and a beautifully designed custom walk-in closet. A third en-suite bedroom along with a spacious laundry room adjacent to the media room, enhance convenience. The fourth en-suite bedroom is on the third level with additional living space and a renovated bathroom. Outside, professionally newly designed landscaping and a full irrigation system provide year-round beauty, while the blue slate terrace—framed by expertly trained David Austin climbing roses—a grilling area creates a private outdoor sanctuary for entertaining or quiet reflection. Modern conveniences include Wi-Fi broadband, advanced home monitoring systems, and a Hikvision doorbell with remote access, updated HVAC, Renaldi tankless hot water systems both add comfort and peace of mind. A concrete crawlspace with a dehumidification unit is part of this well-built home. Perfectly positioned near the waterfront and within easy reach of Easton and Oxford, this turnkey home is ideal as a full-time residence or a sophisticated weekend retreat. With flawless finishes, flexible living spaces, and an unrivaled location, this property represents the pinnacle of Eastern Shore living. Schedule your private showing and experience its exceptional character firsthand. On a price per sq. ft. basis this property represents an excellent value and the new two-level apartment above the heated garage is an exceptional rental investment opportunity, guest quarters, studio or office.
SNestled in the highly desirable Drum Point neighborhood of St. Michaels, this exceptional waterfront property offers the perfect blend of privacy, comfort, and Eastern Shore charm. Just minutes from the vibrant heart of town, you'll enjoy easy access to renowned restaurants, boutique shopping, cozy cafés, the Classic Motor Museum, and the Chesapeake Bay Maritime Museum. A former successful vacation rental, this beautifully maintained three-bedroom brick home is designed for effortless living and year-round enjoyment. The open floor plan features rich wood flooring, a striking double-sided fireplace, a renovated kitchen, updated bathrooms, and energy-efficient geothermal HVAC. Water views surround you at every turn. Relax in the shade of mature trees by the shoreline, sway in a hammock with refreshing bay breezes, or spend the day enjoying the property's outstanding outdoor amenities. Entertain guests on the spacious deck complete with an outdoor kitchen and hot tub, gather on the charming stone-walled patio, rinse off in the outdoor shower, and cool off with a swim in the pool. Boaters will appreciate the private dock offering approximately 3 feet MLW, a boat lift, and a boat launch for easy access to the water. A detached two-room studio with a covered porch provides additional flexible space for guests, hobbies, or a private retreat while enjoying spectacular water views. Additional highlights include an encapsulated crawl space and numerous upgrades throughout. This is Eastern Shore living at its finest—a rare opportunity to own a waterfront sanctuary in one of St. Michaels' most sought-after locations.T MICHAELS TUCKED AWAY ON DESIRABLE DRUM POINT NEIGHBORHOOD, MINUTES FROM THE
Saint Michaels is located in Maryland. Saint Michaels, Maryland has a population of 3,161. Saint Michaels is less family-centric than the surrounding county with 10.11% of the households containing married families with children. The county average for households married with children is 22.67%.
The median household income in Saint Michaels, Maryland is $71,765. 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 Saint Michaels is 57.4 years.
The average high temperature in July is 87.7 degrees, with an average low temperature in January of 27.9 degrees. The average rainfall is approximately 46.1 inches per year, with 12.5 inches of snow per year.
