easternshoremdfineproperties.com Search Results

$995,000

Professional pictures will be uploaded 7/31/26 and Public Open House 8/1/26. Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Full description to follow.

3 Beds ⋅ 3 Baths

Professional pictures will be uploaded 7/31/26 and Public Open House 8/1/26. Extremely well maintained, inside and out, 3 bedroom 2 1/2 bath house with an oversized 2 car detached garage, huge back yard and within walking distance to downtown St. Michael's! Full description to follow.

101 Seymour, Saint Michaels

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$750,000

Extremely private 3 BR 3 1/2 BA house on 4 acres with a pool! This property features a huge, finished bonus/game room over the garage with separate hvac zone, large family room with vaulted ceiling, first floor mater suite with an extremely well-done tile bathroom and absolutely complete privacy!

3 Beds ⋅ 4 Baths

Extremely private 3 BR 3 1/2 BA house on 4 acres with a pool! This property features a huge, finished bonus/game room over the garage with separate hvac zone, large family room with vaulted ceiling, first floor mater suite with an extremely well-done tile bathroom and absolutely complete privacy!

30420 Deep Branch Rd, Trappe

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$325,000

Easton Cape. This 4 bedroom, 2 bath home offers a living room with wood burning brick fireplace, spacious eat-in kitchen, porch/sunroom. Hot water baseboard oil heat, central air on 1st floor, 2 sheds, corner lot with mature plantings. Flooring is carpeted, but wood flooring under carpet (Buyer to confirm). Ready for immediate occupancy. First-time offered in 42 years. Close to downtown Easton and amenities.

4 Beds ⋅ 2 Baths

Easton Cape. This 4 bedroom, 2 bath home offers a living room with wood burning brick fireplace, spacious eat-in kitchen, porch/sunroom. Hot water baseboard oil heat, central air on 1st floor, 2 sheds, corner lot with mature plantings. Flooring is carpeted, but wood flooring under carpet (Buyer to confirm). Ready for immediate occupancy. First-time offered in 42 years. Close to downtown Easton and amenities.

107 Wrightson Ave, Easton

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

$1,595,000

Nestled on Peachblossom Creek in Easton is a property that won’t disappoint if you are one who expects the unexpected. From the one-hundred-year-old oak standing sentinel over the tides to the 42 solar panels creating minimal power bills, this “issue free” home is unexpected, if not actually startling. Ideally located along the desirable Oxford Road corridor, the property offers convenient access to both Easton and Oxford while providing a peaceful waterfront setting. Designed for comfortable one-floor living, with a full second floor, you can expect a lifetime of enjoyment. This home offers 4-bedrooms, 3 full baths, beautiful wood floors throughout, 2 sitting/living room areas, a gas fireplace, an office with built ins, an attractive eat-in kitchen, a beautiful waterside sunroom with separate HVAC, and tons of storage space. There’s even a hot tub! A huge attached garage provides abundant room for vehicles, hobbies, and storage. A yard implemented by an expert environmental gardener (an author on the subject) crafts a haven for birds that is less maintenance—and more attractive to neighbors—than the oh, so very common “all lawn” approach. Watch bluebirds and butterflies while you sip your morning coffee on the expansive Azek deck or large paver patio overlooking the water. Smile at lightning bugs flitting about the yard as you watch the stars come out at night in your private back yard retreat. The open floor plan and large windows keep the home full of light and allow endless views of the water. State-of-the-art solar with 2 large Tesla storage batteries, whole house water purification system and zoned HVAC systems make for healthy living, too. A denitrifying septic system - designed for 4-6 bedrooms - helps keep the Bay clean—in fact, this home's low carbon footprint and thoughtfully designed landscape and rain gardens actually help the environment. Several walk-in storage areas, plus huge unfinished space over the garage. An unforeseen property, even if you expect the unexpected. Don't miss this fabulously easy-care, low maintenance home. All the hard work is done - all that's left is to ENJOY!

4 Beds ⋅ 3 Baths

Nestled on Peachblossom Creek in Easton is a property that won’t disappoint if you are one who expects the unexpected. From the one-hundred-year-old oak standing sentinel over the tides to the 42 solar panels creating minimal power bills, this “issue free” home is unexpected, if not actually startling. Ideally located along the desirable Oxford Road corridor, the property offers convenient access to both Easton and Oxford while providing a peaceful waterfront setting. Designed for comfortable one-floor living, with a full second floor, you can expect a lifetime of enjoyment. This home offers 4-bedrooms, 3 full baths, beautiful wood floors throughout, 2 sitting/living room areas, a gas fireplace, an office with built ins, an attractive eat-in kitchen, a beautiful waterside sunroom with separate HVAC, and tons of storage space. There’s even a hot tub! A huge attached garage provides abundant room for vehicles, hobbies, and storage. A yard implemented by an expert environmental gardener (an author on the subject) crafts a haven for birds that is less maintenance—and more attractive to neighbors—than the oh, so very common “all lawn” approach. Watch bluebirds and butterflies while you sip your morning coffee on the expansive Azek deck or large paver patio overlooking the water. Smile at lightning bugs flitting about the yard as you watch the stars come out at night in your private back yard retreat. The open floor plan and large windows keep the home full of light and allow endless views of the water. State-of-the-art solar with 2 large Tesla storage batteries, whole house water purification system and zoned HVAC systems make for healthy living, too. A denitrifying septic system - designed for 4-6 bedrooms - helps keep the Bay clean—in fact, this home's low carbon footprint and thoughtfully designed landscape and rain gardens actually help the environment. Several walk-in storage areas, plus huge unfinished space over the garage. An unforeseen property, even if you expect the unexpected. Don't miss this fabulously easy-care, low maintenance home. All the hard work is done - all that's left is to ENJOY!

28674 Edgemere Rd, Easton

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

$849,000

The Rose Cottage was first built in 1890 and owned by a waterman. With barely 1,200 square feet, the house served many generations of Oxford families. Fast forward for about 100 years, the house was raised and the foundation was modernized in the late 1990s. With plumbing and electrical upgrades, the house became a modern historical home. When the current owners bought the Cottage in 2004, they continued with upgrades and additions that continued that modernization, culminating with 2 major upgrades and an 800 square foot addition that made the house 2000 square feet and quite comfortable by today’s standards. The first major addition and upgrade was to the living room. Owners added a new fireplace and chimney, 2 new Marvin windows and oak flooring in 2006. The front porch received a new decking with Trex decking in 2005. In 2011 the most significant upgrade came to date, taking a full year to complete. Starting with an architectural review and plan, the owners worked closely with Oxford’s Historical Board and added 800 square feet to the total footprint and much modernization. Here are some of the highlights: GMB Foundation Review New Foundation for “Bump out” addition Extensive teardown of interior walls, exterior siding, back kitchen, suspect framing and much more. New build of the “Bump out” section with 2 levels Rotation of the stairs to the second story with complete rebuild Upgraded kitchen with new appliances, granite countertops and more Widening the living room to dining room entry New wood floors throughout both stories New on-demand water heater Security system and surround sound system Floors in attic for better storage use and foam insulation with an “insulating the shell” approach to the entire house Cementitious product planking on the exterior for superior protection and durability looks like wood planks but won’t need painting for 30 years. Crawl space mitigation with 10mil plastic, closed foam insulation, sump pump and dehumidifier. Continual service and monitoring with termite and pest control. Virtually every square inch of the Rose Cottage has been upgraded and modernized except for the historic front bedroom. Detached shed with upright freezer with workbench and storage The Rose Cottage is now a comfortable, fully modernized home that is practically maintenance free. With off-street parking for two cars and ideally located next to the restored Wesleyan Church, the cottage is ideally located in Oxford’s historic district.

3 Beds ⋅ 2 Baths

The Rose Cottage was first built in 1890 and owned by a waterman. With barely 1,200 square feet, the house served many generations of Oxford families. Fast forward for about 100 years, the house was raised and the foundation was modernized in the late 1990s. With plumbing and electrical upgrades, the house became a modern historical home. When the current owners bought the Cottage in 2004, they continued with upgrades and additions that continued that modernization, culminating with 2 major upgrades and an 800 square foot addition that made the house 2000 square feet and quite comfortable by today’s standards. The first major addition and upgrade was to the living room. Owners added a new fireplace and chimney, 2 new Marvin windows and oak flooring in 2006. The front porch received a new decking with Trex decking in 2005. In 2011 the most significant upgrade came to date, taking a full year to complete. Starting with an architectural review and plan, the owners worked closely with Oxford’s Historical Board and added 800 square feet to the total footprint and much modernization. Here are some of the highlights: GMB Foundation Review New Foundation for “Bump out” addition Extensive teardown of interior walls, exterior siding, back kitchen, suspect framing and much more. New build of the “Bump out” section with 2 levels Rotation of the stairs to the second story with complete rebuild Upgraded kitchen with new appliances, granite countertops and more Widening the living room to dining room entry New wood floors throughout both stories New on-demand water heater Security system and surround sound system Floors in attic for better storage use and foam insulation with an “insulating the shell” approach to the entire house Cementitious product planking on the exterior for superior protection and durability looks like wood planks but won’t need painting for 30 years. Crawl space mitigation with 10mil plastic, closed foam insulation, sump pump and dehumidifier. Continual service and monitoring with termite and pest control. Virtually every square inch of the Rose Cottage has been upgraded and modernized except for the historic front bedroom. Detached shed with upright freezer with workbench and storage The Rose Cottage is now a comfortable, fully modernized home that is practically maintenance free. With off-street parking for two cars and ideally located next to the restored Wesleyan Church, the cottage is ideally located in Oxford’s historic district.

228 South St, Oxford

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

$410,000

Welcome to this spacious Cape Cod home featuring three bedrooms and two and a half bathrooms. Enjoy a welcoming front porch, an attached garage, and a generous yard perfect for outdoor enjoyment. A rear porch provides opportunity for outdoor dining and evening relaxation. Inside, the great room impresses with vaulted ceilings, and the primary bathroom offers a Jacuzzi tub and separate shower. Enjoy this immaculately maintained property, ready to call home. Seller is offering $5,000 credit for floors.

3 Beds ⋅ 3 Baths

Welcome to this spacious Cape Cod home featuring three bedrooms and two and a half bathrooms. Enjoy a welcoming front porch, an attached garage, and a generous yard perfect for outdoor enjoyment. A rear porch provides opportunity for outdoor dining and evening relaxation. Inside, the great room impresses with vaulted ceilings, and the primary bathroom offers a Jacuzzi tub and separate shower. Enjoy this immaculately maintained property, ready to call home. Seller is offering $5,000 credit for floors.

29152 Holly Rd, Easton

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

$325,000

Make your appointment today! <br> Charming, beautifully updated Cape Cod just a short stroll from historic downtown Easton, where you'll enjoy an array of restaurants, boutiques, galleries, and year-round community events. This inviting home blends timeless character with thoughtful modern updates, featuring beautiful hardwood floors, fresh paint, an updated HVAC system, and a bright, welcoming kitchen. The spacious second level offers a large bedroom, a dedicated office or sitting area, a walk-in closet, and abundant additional storage. Outside, relax on the classic front porch complete with a porch swing, or entertain on the new deck and patio overlooking the beautifully landscaped backyard. A large storage shed with convenient attic storage provides plenty of room for tools, hobbies, or outdoor equipment. Perfectly located near shopping, schools, parks, and major commuter routes, this move-in ready home offers the ideal combination of charm, comfort, and convenience in one of Easton's most desirable in-town locations. Make your appointment today!!!

2 Beds ⋅ 1 Baths

Make your appointment today! <br> Charming, beautifully updated Cape Cod just a short stroll from historic downtown Easton, where you'll enjoy an array of restaurants, boutiques, galleries, and year-round community events. This inviting home blends timeless character with thoughtful modern updates, featuring beautiful hardwood floors, fresh paint, an updated HVAC system, and a bright, welcoming kitchen. The spacious second level offers a large bedroom, a dedicated office or sitting area, a walk-in closet, and abundant additional storage. Outside, relax on the classic front porch complete with a porch swing, or entertain on the new deck and patio overlooking the beautifully landscaped backyard. A large storage shed with convenient attic storage provides plenty of room for tools, hobbies, or outdoor equipment. Perfectly located near shopping, schools, parks, and major commuter routes, this move-in ready home offers the ideal combination of charm, comfort, and convenience in one of Easton's most desirable in-town locations. Make your appointment today!!!

347 N Washington St, Easton

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: (410) 544-4000

$179,900

Investor Special with Strong Upside Potential! Opportunity awaits with this 2-bedroom Cape Cod situated on a large fenced lot in Easton. The main level has been opened up to create a spacious layout that's ideal for entertaining, while the sunroom addition provides extra living space and abundant natural light. This property needs renovation and is being offered as a project for investors, flippers, or owner-occupants looking to build equity through improvements. With significant redevelopment activity nearby, including new residential and commercial projects, the location offers excellent long-term potential. Whether you're looking for your next fix-and-flip, a value-add rental property, or a home to customize to your own taste, this property presents a unique opportunity. Due to its condition, the home will not qualify for conventional financing. Cash, hard money, or renovation financing will be required. Sold as-is. Bring your vision and unlock this property's potential!

2 Beds ⋅ 1 Baths

Investor Special with Strong Upside Potential! Opportunity awaits with this 2-bedroom Cape Cod situated on a large fenced lot in Easton. The main level has been opened up to create a spacious layout that's ideal for entertaining, while the sunroom addition provides extra living space and abundant natural light. This property needs renovation and is being offered as a project for investors, flippers, or owner-occupants looking to build equity through improvements. With significant redevelopment activity nearby, including new residential and commercial projects, the location offers excellent long-term potential. Whether you're looking for your next fix-and-flip, a value-add rental property, or a home to customize to your own taste, this property presents a unique opportunity. Due to its condition, the home will not qualify for conventional financing. Cash, hard money, or renovation financing will be required. Sold as-is. Bring your vision and unlock this property's potential!

9604 Cordova Rd, Easton

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact: howardcounty@penfedrealty.com

$309,600

Tucked away in a quiet setting, this 3 bedroom, 2 full bathroom home has a full, unfinished basement, front deck and a large, detached garage with numerous access doors and areas for storage and/or a workshop. Situated on a 0.34 +/- acre parcel that backs to an established tree line, providing privacy in the back yard. Located approximately 10 miles from Easton, 40 miles from Annapolis, 60 miles from Delaware Beach Resorts and 80 miles from Ocean City, MD. Home was constructed prior to 1978 and may contain lead-based paint. Seller may contribute up to 3% of the buyer’s closing costs. HUD Case #241-818350. Equal Housing Opportunity.

3 Beds ⋅ 2 Baths

Tucked away in a quiet setting, this 3 bedroom, 2 full bathroom home has a full, unfinished basement, front deck and a large, detached garage with numerous access doors and areas for storage and/or a workshop. Situated on a 0.34 +/- acre parcel that backs to an established tree line, providing privacy in the back yard. Located approximately 10 miles from Easton, 40 miles from Annapolis, 60 miles from Delaware Beach Resorts and 80 miles from Ocean City, MD. Home was constructed prior to 1978 and may contain lead-based paint. Seller may contribute up to 3% of the buyer’s closing costs. HUD Case #241-818350. Equal Housing Opportunity.

31154 Hunteman Aly, Cordova

Listing courtesy of Brokers Realty Group, LLC. Contact: 8556872765

$429,000

Custom built house in 2002 with first floor master suite, large family room, enclosed sunporch and two car garage. House has hardwood floors, gas fireplace with quality built in shelving, covered front porch and so much more. You won't want to miss this one!

3 Beds ⋅ 2 Baths

Custom built house in 2002 with first floor master suite, large family room, enclosed sunporch and two car garage. House has hardwood floors, gas fireplace with quality built in shelving, covered front porch and so much more. You won't want to miss this one!

29739 Penny Ln, Easton

Listing courtesy of Meredith Fine Properties. Contact: 4108226272

$359,000

Charming and move-in ready, this updated 2-bedroom, 1-bath home with a flexible office space that could easily serve as a third bedroom is perfect for first-time homebuyers, downsizers, or anyone seeking comfortable, low-maintenance living. Major improvements include a new roof and siding completed in 2020, along with a whole-house generator for added peace of mind. Inside, you'll find tasteful updates throughout, creating a warm and inviting atmosphere. The oversized detached 2-car garage offers endless possibilities, providing ample space for vehicles, storage, hobbies, or the ideal workshop. Award winning school district. Conveniently located just minutes from Easton and nearby public boat ramps, this home offers easy access to shopping, dining, and all the outdoor recreation the Eastern Shore has to offer.

2 Beds ⋅ 1 Baths

Charming and move-in ready, this updated 2-bedroom, 1-bath home with a flexible office space that could easily serve as a third bedroom is perfect for first-time homebuyers, downsizers, or anyone seeking comfortable, low-maintenance living. Major improvements include a new roof and siding completed in 2020, along with a whole-house generator for added peace of mind. Inside, you'll find tasteful updates throughout, creating a warm and inviting atmosphere. The oversized detached 2-car garage offers endless possibilities, providing ample space for vehicles, storage, hobbies, or the ideal workshop. Award winning school district. Conveniently located just minutes from Easton and nearby public boat ramps, this home offers easy access to shopping, dining, and all the outdoor recreation the Eastern Shore has to offer.

11994 Cordova Rd, Cordova

Listing courtesy of RE/MAX Advantage Realty. Contact:

$2,175,000

Discover a serene retreat in the heart of Waverly Island Estates, where a major renovation in 2025 breathes new life into this charming Cape Cod home. Spanning 2.77 acres, this property offers a perfect blend of comfort and nature, featuring 4 spacious bedrooms and 2 full and 2 half bathrooms, ideal for both comfort and relaxation . Step inside to find a beautifully maintained interior with hardwood and ceramic tile flooring, complemented by a cozy fireplace that invites warmth and gatherings. Outside, the allure continues with a personal pool and a stunning view of the Tred Avon River. Enjoy the tranquility of waterfront living with 200 feet of river frontage, complete with a private dock site, perfect for boating, fishing, or simply soaking in the picturesque surroundings. The lot features rip-rap for added stability and a peaceful, no-thru street setting that enhances privacy. With ample parking, including a side-entry garage and driveway space for guests, convenience is at your fingertips. Embrace the lifestyle of riverfront living, where you can kayak, swim, or enjoy a leisurely day on the water. This home is not just a property; it’s a sanctuary waiting for you to create lasting memories. Experience the perfect blend of comfort, nature, and adventure in this exceptional residence. Only a few short miles to downtown Historic Easton, YMCA, shopping and parks.

4 Beds ⋅ 4 Baths

Discover a serene retreat in the heart of Waverly Island Estates, where a major renovation in 2025 breathes new life into this charming Cape Cod home. Spanning 2.77 acres, this property offers a perfect blend of comfort and nature, featuring 4 spacious bedrooms and 2 full and 2 half bathrooms, ideal for both comfort and relaxation . Step inside to find a beautifully maintained interior with hardwood and ceramic tile flooring, complemented by a cozy fireplace that invites warmth and gatherings. Outside, the allure continues with a personal pool and a stunning view of the Tred Avon River. Enjoy the tranquility of waterfront living with 200 feet of river frontage, complete with a private dock site, perfect for boating, fishing, or simply soaking in the picturesque surroundings. The lot features rip-rap for added stability and a peaceful, no-thru street setting that enhances privacy. With ample parking, including a side-entry garage and driveway space for guests, convenience is at your fingertips. Embrace the lifestyle of riverfront living, where you can kayak, swim, or enjoy a leisurely day on the water. This home is not just a property; it’s a sanctuary waiting for you to create lasting memories. Experience the perfect blend of comfort, nature, and adventure in this exceptional residence. Only a few short miles to downtown Historic Easton, YMCA, shopping and parks.

7272 Waverly Island Rd, Easton

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

$550,000

Tucked away in a quiet country setting just minutes from downtown Easton and convenient access to Rt. 50, this well-maintained Cape Cod offers the perfect balance of privacy and accessibility. Set on a .63-acre lot backing to open space, the home features a bright and inviting main living area with wood flooring, a wood-burning fireplace, and soaring cathedral ceilings that create an open, airy feel. The layout flows easily into the dining area and kitchen, making it well-suited for both everyday living and entertaining. Offering 4 bedrooms and 2.5 bathrooms, the home also includes a versatile bonus room. Recent updates include a new rear deck, ideal for outdoor dining or relaxing while overlooking the peaceful backyard, as well as a new washer and dryer installed in 2024 and a vapor barrier added in the crawlspace for improved efficiency and maintenance. Additional features include a spacious 2-car garage and a functional layout that offers both comfort and flexibility. Backing to open space and surrounded by a quiet setting, this property delivers a more relaxed pace of living while still being just minutes from Easton’s shops, restaurants, and everyday conveniences.

4 Beds ⋅ 3 Baths

Tucked away in a quiet country setting just minutes from downtown Easton and convenient access to Rt. 50, this well-maintained Cape Cod offers the perfect balance of privacy and accessibility. Set on a .63-acre lot backing to open space, the home features a bright and inviting main living area with wood flooring, a wood-burning fireplace, and soaring cathedral ceilings that create an open, airy feel. The layout flows easily into the dining area and kitchen, making it well-suited for both everyday living and entertaining. Offering 4 bedrooms and 2.5 bathrooms, the home also includes a versatile bonus room. Recent updates include a new rear deck, ideal for outdoor dining or relaxing while overlooking the peaceful backyard, as well as a new washer and dryer installed in 2024 and a vapor barrier added in the crawlspace for improved efficiency and maintenance. Additional features include a spacious 2-car garage and a functional layout that offers both comfort and flexibility. Backing to open space and surrounded by a quiet setting, this property delivers a more relaxed pace of living while still being just minutes from Easton’s shops, restaurants, and everyday conveniences.

10490 Longwoods Rd, Easton

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

$3,249,000

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4 Beds ⋅ 4 Baths

Island Creek Estate — rare total privacy, deep water dockage, meaningful architecture, and superb build quality all intersect at this remarkable, truly one-of-a-kind waterfront offering. Set on approximately 6 acres of park-like grounds with 500± feet of shoreline and 6’± MLW, the property offers exceptional water access along the peaceful expanse of Island Creek. The setting is serene and private, with a gracious approach that complements the estate’s architectural presence. Impeccably built with careful attention to detail, the residence offers 4 bedrooms and 3.5 baths within a thoughtfully designed floor plan that maximizes natural light and water views. The living room, kitchen, and dining area flow comfortably together, creating a spacious central gathering area framed by expansive windows overlooking the creek and anchored by a fireplace. The kitchen is generously sized, featuring a substantial island, quality finishes, and an inviting eat-in area suited for both everyday living and entertaining. Outdoor living is equally compelling, with a screened porch overlooking the water and an in-ground pool set against sweeping creek views. The private pier provides deep water dockage, ideal for boating enthusiasts seeking immediate access to the Chesapeake Bay watershed. A finished rec room above the attached garage offers flexible use as a media room, office, or fitness space. In addition to the attached two-car garage, the property features a substantial detached multi-bay garage equipped with a hydraulic vehicle lift, air compressor, and rough-in for a future bath — an exceptional amenity for car collectors, hobbyists, or workshop space. This exceptional Island Creek estate combines craftsmanship, privacy, and premier waterfront living in a setting that is both refined and enduring.

4346 Southside Ln, Trappe

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

$575,000

Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the kitchen, the expansive family room serves as the heart of the home with a stunning whitewashed fireplace. The first-floor primary bedroom provides convenience, while an additional main-level bedroom, currently used as an office, offers flexibility and the potential to create a larger primary suite. Upstairs, you’ll find two generously sized bedrooms, a full bath and abundant storage including eve storage and walk-in attic space. An attached 2-car garage and large detached shed add even more functionality. Enjoy the private 2-acre setting, ideal for outdoor living, gardening, or play, along with community water access, including a dock for boating, kayaking, and paddleboarding with direct access to the Chesapeake Bay, waterfront dining and some of the area’s best fishing and crabbing around.

4 Beds ⋅ 3 Baths

Nestled on over 2 acres in the desirable water access community of Deep Harbor Farm, this beautiful Cape Cod beams with natural light. The home features over 2,400 sqft with 4 bedrooms and 2.5 baths. The welcoming foyer overlooks a spacious dining room and leads to an open kitchen complete with white cabinetry, stainless steel appliances, breakfast bar and a large table space. Just off the kitchen, the expansive family room serves as the heart of the home with a stunning whitewashed fireplace. The first-floor primary bedroom provides convenience, while an additional main-level bedroom, currently used as an office, offers flexibility and the potential to create a larger primary suite. Upstairs, you’ll find two generously sized bedrooms, a full bath and abundant storage including eve storage and walk-in attic space. An attached 2-car garage and large detached shed add even more functionality. Enjoy the private 2-acre setting, ideal for outdoor living, gardening, or play, along with community water access, including a dock for boating, kayaking, and paddleboarding with direct access to the Chesapeake Bay, waterfront dining and some of the area’s best fishing and crabbing around.

6705 Tilghman Island Rd, Sherwood

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

$511,550

Beautiful home offering 4 generous bedrooms with 2 baths featuring new commercial grade LVP flooring throughout the main floor, custom kitchen cabinets with pantry, automatic under counter lighting, slow close cabinets, luxury tile in bathroom and laundry room, all new stainless steel appliances, custom walk-in shower with bench, new vanity, and multiple shower heads. Second bathroom has been renovated completely to feature a deep soaking tub, with new upgraded hot water tank to soak for hours. Additionally all new upgraded HVAC ductwork and with an additional dampening system which allows your garage to have AC/heat. Freshly painted interior tops it off. Outside there is a fenced yard with an extended patio with a 10 x 13 hard topped gazebo, raised garden beds, fire pit, and a large shed to give you the perfect outdoor oasis with outdoor lighting so the celebrations can continue into the night.This is a must see home on a quiet street in a well desired school district. Square footage is larger than tax record and Seller to find home of choice

4 Beds ⋅ 2 Baths

Beautiful home offering 4 generous bedrooms with 2 baths featuring new commercial grade LVP flooring throughout the main floor, custom kitchen cabinets with pantry, automatic under counter lighting, slow close cabinets, luxury tile in bathroom and laundry room, all new stainless steel appliances, custom walk-in shower with bench, new vanity, and multiple shower heads. Second bathroom has been renovated completely to feature a deep soaking tub, with new upgraded hot water tank to soak for hours. Additionally all new upgraded HVAC ductwork and with an additional dampening system which allows your garage to have AC/heat. Freshly painted interior tops it off. Outside there is a fenced yard with an extended patio with a 10 x 13 hard topped gazebo, raised garden beds, fire pit, and a large shed to give you the perfect outdoor oasis with outdoor lighting so the celebrations can continue into the night.This is a must see home on a quiet street in a well desired school district. Square footage is larger than tax record and Seller to find home of choice

3853 Rumsey Dr, Trappe

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

$845,000

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

3 Beds ⋅ 2 Baths

Renovated waterfront living with room for your fleet! Extensively renovated Cape Cod on Tilghman Island offering exceptional boating access and refined coastal living. This beautifully reimagined 3 BR, 2 BA home features 1,314 sq ft of thoughtfully designed space including two full kitchens with high-end finishes, providing outstanding flexibility for guests or extended living. Bright, upscale interiors blend modern comfort with classic Eastern Shore charm, complemented by a distinctive Standing Seam metal roof and owned solar energy system. Situated along protected waterfront with long water views and four boat slips, offering rare boating convenience and potential income opportunity. A turnkey coastal retreat ideal for full-time living weekend escape.

21560 Chicken Point Rd, Tilghman

Listing courtesy of Chesapeake Bay Real Estate Plus, LLC. Contact:

$499,000

RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012942).EDUCED - REDUCED - DO NOT WAIT TO SEE THIS DESIREABLE RIO VISTA LIVING -MOVE IN ONE

4 Beds ⋅ 4 Baths

RDesirable Rio Vista Duplex – Live in One Unit and Let Rental Income Help Pay Your Mortgage! Opportunities to own one of these sought-after duplexes are rare. Located in the desirable Rio Vista water-access community, this property offers potential dock access (subject to owner approval, application, and applicable fees). The building features two mirror-image units, each offering: A kitchen with a cozy eating area Spacious open-concept living and dining room Two generously sized bedrooms One full bath and one half bath Whether you're looking for an owner-occupied investment property or a fully leased income-producing asset, this duplex presents excellent potential. These units have a strong rental history and are consistently in demand. Both units are currently tenant-occupied. THIS IS WHY WE DO NOT HAVE INTERIOR PICTURES For investors seeking additional opportunities, the neighboring building at 1211 Rio Vista is also available for purchase (MLS #MDTA2012942).EDUCED - REDUCED - DO NOT WAIT TO SEE THIS DESIREABLE RIO VISTA LIVING -MOVE IN ONE

1215 Washington, Saint Michaels

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4107450283

$999,000

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual needs, all while maintaining privacy and a connection to the surrounding natural landscape. Restaurants, shops, seasonal events, waterfront parks, and the charm of the historic district are all close at hand, yet the property feels quietly removed. Approximately three times the size of a typical in-town lot, the parcel allows for thoughtful home placement, outdoor living areas, and driveway access from Miles Avenue, Canton Street, or both, depending on the final plan. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

3 Beds ⋅ 3 Baths

A rare opportunity to combine a half-acre+ wooded in-town setting with a classic Cape Cod–style home concept in the heart of St. Michaels. Concept B illustrates a two-story design featuring 3 bedrooms, 2 full baths, and 1 half bath, along with an attached two-car garage. The proposed layout offers a timeless architectural style with flexible living spaces that can be customized to suit individual needs, all while maintaining privacy and a connection to the surrounding natural landscape. Restaurants, shops, seasonal events, waterfront parks, and the charm of the historic district are all close at hand, yet the property feels quietly removed. Approximately three times the size of a typical in-town lot, the parcel allows for thoughtful home placement, outdoor living areas, and driveway access from Miles Avenue, Canton Street, or both, depending on the final plan. Infrastructure upgrades are already complete, including paved roads, a State-approved gravel extension, town water, county sewer, electric service, and fiber-optic internet—allowing for a smoother path from planning to construction. With the appropriate Town approvals, the parcel also offers future subdivision potential. Adjacent to the scenic Rails-to-Trails corridor and near San Domingo Creek, the Miles River, and multiple neighborhood parks, the location provides access to nature and open space without giving up the benefits of being in town. Architectural concept drawings illustrating one potential approach to the site will convey to the new owner, with the option to continue working with the original architect if desired. A unique chance to create something truly exceptional in one of the Eastern Shore’s most sought-after communities: space, privacy, and the freedom to design a home that reflects your vision. By Vehicle: A portion of Canton St is a one-way and Miles Ave is not a completely through Street from Railroad Ave. It is recommended to head north on Talbot St., turn left on Railroad Ave., then left on Glory Ave (also known as Gloria), and right on Canton St. Proceed a short way to the corner of the lot at Miles Ave. & Canton St.

108 Miles Ave, Saint Michaels

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

$1,099,000

Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

3 Beds ⋅ 3 Baths

Reduced Price! Amazing opportunity to be on the water in Talbot County. Waterfront home situated on Back Creek in Sherwood. Conveniently located near St Michaels and Tilghman Island, the property includes views of sunsets over Poplar Island and is located minutes from restaurants, and shopping. Interior features include hickory hardwood floors, custom built-ins, crown molding, and recessed lighting. The kitchen is equipped with stainless steel appliances, a built-in pantry, and granite countertops. The open floor plan incorporates a gas fireplace and a formal dining room. The primary suite has a walk-in shower, soaking tub, and walk-in closet. An attached three-car garage provides additional space with an upstairs bonus game/theatre room. The backyard is built for fun with a swimming pool, an outdoor kitchen with bar area, gas fire features, a hot tub, and a pool house for storage. The property also includes a 30x30 pole building with concrete floors, as well as a dock. New septic installed in 2025!

6670 Tilghman Island Rd, Sherwood

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

$395,000

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.

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

$8,495,000

NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

6 Beds ⋅ 11 Baths

NEW PRICE! Located minutes from downtown St. Michaels, “Aqua Vitae” the waters of life, sits on 8.6 private acres on Harris Creek, a Chesapeake Bay tributary. This custom-built offering w/ over 400’ of direct water frontage is comprised of 3 magnificent structures: a grand main residence, guest cottage, & “party barn” all highlighted by a waterside pool, pier w/ 4’ MLW, pine grove, putting green, extensive landscaping & incomparable craftmanship. The 12,000 SF main residence, positioned to prioritize water views, welcomes you via prominent double lead-glass doors & a grand 3-story foyer w/ dual-staircase. The “river room” w/ 2-story octagon copula offers 270◦ views of the property & creek. The TV room w/ 3 exposures & gas-burning fireplace offers double French doors on two sides leading to the wrap-around flagstone patio. The stunning gourmet kitchen is a true chefs dream. Offering oversized island, built-in media/storage cabinet, coffered ceiling, fireplace, 3 sinks, double Subzero fridges w/ freezer drawers, 2 beverage drawers, 3 dishwashers, Wolf microwave & a stainless-steel Lacanche range with 6-burners, pot warmer, warming oven, & 2 ovens. Complimenting the kitchen is a large walk-in pantry w/ dishwasher, sink & extra freezer in hall. Off the kitchen is a covered porch w/ gas fireplace & “ghost’ screens, a perfect spot to enjoy evenings. A large open dining room has 2 custom built-in display cases. The grand salon w/ bay window, gas-fireplace & intricate mantel is reminiscent of Paris. Adjoining the salon is the handsome 2-story curly cherrywood library w/ custom display cases & leaded-glass pocket doors. The adjoining climate-controlled wine room has a wet bar & storage for 750+ bottles. Wood floors flow throughout the entire main level. The main level is completed by an office, powder room & laundry to service the pool, 2 additional powder rooms, elevator to all 4 levels, mud/dog room, rear spiral staircase, guest suite w/ ensuite bathroom, & 2-car attached garage. The 2nd level offers a generous primary suite w/ fireplace & full length terrace overlooking the water. Her wing features dressing room w/ custom built-ins, separate sitting room, & a luxurious bathroom w/ marble tile, separate shower, jetted tub, & vanity. His wing offers an office w/ fireplace, paneled closet leading to separate bathroom w/ shower, travertine stone, & vanity. From his office access the 2nd level of library, open to below. Just off of the primary suite is a bar area/kitchen. 3 additional bedrooms, each w/ ensuite bathroom, and a laundry room complete the 2nd level. The 3rd level offers theater/rec room, play area, bedroom w/ ensuite bathroom, powder room, & ample storage. The lower-level houses utilities, storage, & enough room for an exercise area. The charming guest cottage sits amongst extensive landscaping. The main level offers a full kitchen, dining area, living room, sunroom, large family room, 2 bedrooms w/ shared bathroom, additional guest bathroom, & large entertaining room. Upstairs is a full bedroom w/ ensuite bathroom. The unfinished lower level offers storage. The party barn originally built for boat storage was designed to look like an old Pennsylvania barn w/ 4’ of stone around the base. Flanked by 2 garage wings allowing for 4+ cars & capped w/ a cupola, the shingled-style barn has two large doors on either side of the building that allow for a trailered boat or 4+ more cars. The 2nd level is a loft w/ sleeping/living area w/ full bathroom, plumbed for potential kitchenette, front & rear terraces, & a spiral staircase to a crow’s nest w/ amazing views. There is a full property generator & a dog run w/ kennel just off the rear. Outside enjoy the benefits of beautiful shore living amongst the verdant grounds, mature landscaping & exceptional views. The pier offers 4’ MLW & the shoreline is fully rip-rapped w/ natural plantings.

8620 Bozman Neavitt, Saint Michaels

Listing courtesy of Washington Fine Properties, LLC. Contact: info@wfp.com