Talbot County MD Houses for Sale

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  /54

  $1,945,000

  $50K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,906 Sq Ft

  5698 Leeward Ln, Tilghman, MD 21671

  Experience sweeping western-facing views of the Chesapeake Bay from this beautifully renovated waterfront retreat on Tilghman Island. Thoughtfully redesigned and updated in 2023, this exceptional property seamlessly blends refined coastal living with the tranquility and natural beauty of its extraordinary waterfront setting. Offered fully furnished, the home provides a truly turnkey opportunity,

  

  Brian Gearhart

  Benson & Mangold, LLC

  5698 Leeward Ln, Tilghman, MD 21671
• 

  

  

  /35

  $1,095,000

  • 3 Beds
  • 2.5 Baths
  • 2,242 Sq Ft

  100 W Pier St, Oxford, MD 21654

  Waterfront, a deeded boat slip, off-street parking, and a single-car garage with additional storage set the stage for this thoughtfully redesigned coastal retreat in the heart of Oxford. Completely renovated from top to bottom, this 3 bedroom, 2.5 bathroom home blends timeless Eastern Shore charm with luxury finishes and exceptional boating amenities.Every detail has been carefully

  

  Brian Gearhart

  Benson & Mangold, LLC

  100 W Pier St, Oxford, MD 21654
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  /26

  $550,000

  $25K PRICE DROP

  • 4 Beds
  • 2.5 Baths
  • 2,252 Sq Ft

  10490 Longwoods Rd, Easton, MD 21601

  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

  

  Brian Gearhart

  Benson & Mangold, LLC

  10490 Longwoods Rd, Easton, MD 21601
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  /75

  $550,000

  $19K PRICE DROP

  • 5 Beds
  • 3.5 Baths
  • 3,404 Sq Ft

  5559 Trafalgar Cir, Tilghman, MD 21671

  TILGHMAN ISLAND.Welcome to this beautiful and spacious 5-bedroom, 3.5-bath single-family home located in the highly sought-after Tilghman on Chesapeake community. Designed for modern comfort and relaxed island living, this home offers an open-concept floor plan filled with abundant natural light and elegant finishes throughout.The gourmet kitchen is a true centerpiece, featuring

  

  John McGlannan

  Meredith Fine Properties

  5559 Trafalgar Cir, Tilghman, MD 21671
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  /73

  $395,000

  • 3 Beds
  • 2 Baths
  • 1,750 Sq Ft

  11778 Old Skipton Rd, Cordova, MD 21625

  Online Bidding Open: 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

  

  Jane Gharfeh

  Taylor Properties

  11778 Old Skipton Rd, Cordova, MD 21625
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  /39

  $695,000

  $154K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,288 Sq Ft

  803 New Ln, Saint Michaels, MD 21663

  NEW PRICE!! Thoughtfully reimagined from the studs out, this exceptional residence offers the character of an in-town cottage with the quality, comfort, and finishes of a newly constructed home. Every detail has been carefully considered, creating a seamless blend of timeless charm and modern design.A welcoming front porch with a classic porch swing sets the tone before stepping inside to

  

  Larry Brennan

  TTR Sotheby's International Realty

  803 New Ln, Saint Michaels, MD 21663
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  /48

  $925,000

  $30K PRICE INCREASE

  • 4 Beds
  • 3 Baths
  • 2,850 Sq Ft

  4938 Fairbank Rd, Tilghman, MD 21671

  *INCOME PRODUCING* Tucked away in the charming Fairbank community on Tilghman Island a delightful waterfront home captures the very best of Eastern Shore living. Overlooking the serene waters of Blackwalnut Cove with approximately 3’ MLW, the property blends classic cottage character with thoughtful modern enhancements. The original portion of the home reflects its roots as a cozy summer cottage,

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  4938 Fairbank Rd, Tilghman, MD 21671
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  /47

  $513,000

  $27K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 3,506 Sq Ft

  7316 Casey Ave, Easton, MD 21601

  Hillsboro model in the desirable Easton Club East 55+ Community. Corner lot! Over 3000sqft with a thoughtful floor plan. The first floor boasts 2 bedrooms and 2 bathrooms, an office/library, family room off of the eat in kitchen, living and dining room and laundry room. Upstairs is a large loft area with a 3rd bedroom and full bathroom. New HVAC in 2022, New roof in 2023. Seller is offering

  

  Elizabeth Tryon

  Coldwell Banker Realty

  7316 Casey Ave, Easton, MD 21601
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  /28

  $372,000

  Open House 9/26 $18K PRICE DROP

  • 3 Beds
  • 2 Baths
  • 1,880 Sq Ft

  29331 Fourth St, Easton, MD 21601

  Welcome to 29331 Fourth Street! This charming split level 3 bedroom 2 bath house is situated on a well shaded lot perfect for outdoor entertaining. The beautifully updated kitchen has an entire wall of cabinets and eating area. Open living area, with a family room in the basement. Basement also has a large laundry area with great storage. Short walk to the community park!

  

  Elizabeth Tryon

  Coldwell Banker Realty

  29331 Fourth St, Easton, MD 21601
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  /37

  $385,000

  $10K PRICE INCREASE Coming Soon Sep 15

  • 3 Beds
  • 1.5 Baths
  • 1,600 Sq Ft

  33 Mount Pleasant Ave, Easton, MD 21601

  Coming Soon ListingCOMING SOON — LOCATION, LOCATION, LOCATION!Welcome to easy, one-level living in the heart of Downtown Easton! This charming 3-bedroom, 1.5-bath home offers the perfect combination of convenience, comfort, and privacy.Tucked away on a spacious lot, the home features a large, fully fenced backyard — perfect for relaxing, entertaining, gardening, or simply enjoying

  

  Martha Suss

  Coldwell Banker Realty

  33 Mount Pleasant Ave, Easton, MD 21601
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  /68

  $410,000

  • 4 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  21406 Dogwood Cove Rd, Tilghman, MD 21671

  Experience authentic Eastern Shore living in this peaceful Chesapeake Bay retreat, located just steps from historic Dogwood Harbour, home to the Skipjacks—the last working commercial sailing fleet in the United States. This charming home features three first-floor bedrooms and a full bath, providing comfortable one-level living for family and guests. The remodeled eat-in kitchen showcases granite

  

  John McGlannan

  Meredith Fine Properties

  21406 Dogwood Cove Rd, Tilghman, MD 21671
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  /72

  $539,900

  $35K PRICE DROP

  • 2 Beds
  • 1 Bath
  • 1,200 Sq Ft

  204 E Marengo St, Saint Michaels, MD 21663

  Just reduced - Priced to sell! The perfect weekend getaway does exist—and it's more attainable than you might think.Escape the city and discover the charm of St. Michaels, one of the Eastern Shore's most beloved waterfront towns. Known for its picturesque streets, waterfront dining, boutique shopping, wineries, marinas, and laid-back coastal lifestyle, St. Michaels offers the perfect

  

  Gretchen Wichlinski

  Compass

  204 E Marengo St, Saint Michaels, MD 21663
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  /35

  $470,000

  $5K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,072 Sq Ft

  5933 Tilghman Island Rd, Tilghman, MD 21671

  Unique, one-of-a-kind property located in the heart of Tilghman Island, offering unparalleled tranquility and breathtaking water views overlooking Dogwood Harbor.Welcome to your private Eastern Shore retreat! This beautifully updated water-view home captures the essence of coastal living with sweeping views of the harbor and surrounding wildlife. Enjoy stunning sunsets and peaceful

  

  John McGlannan

  Meredith Fine Properties

  5933 Tilghman Island Rd, Tilghman, MD 21671
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  /77

  $799,000

  $26K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 2,648 Sq Ft

  8050 Easton Village Dr, Easton, MD 21601

  Covell custom built home, featuring luxury resort style living in the prestigious waterfront community of Easton Village. This spacious 4-bedroom, 3.5-bath home features a rare dual primary suite layout—with options on both the first and second floors—complemented by a $5,000 cash bonus flooring design credit.The light-filled interior has been freshly painted throughout and features a

  

  Annie Witte Raymond

  Coldwell Banker Realty

  8050 Easton Village Dr, Easton, MD 21601
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  /63

  $995,000

  • 3 Beds
  • 3 Baths
  • 3,853 Sq Ft

  6670 Tilghman Island Rd, Sherwood, MD 21665

  New 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.

  

  Larry Brennan

  TTR Sotheby's International Realty

  6670 Tilghman Island Rd, Sherwood, MD 21665
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  /73

  $5,045,000

  $200K PRICE DROP

  • 4 Beds
  • 4.5 Baths
  • 4,172 Sq Ft

  8051 Leehaven Rd, Easton, MD 21601

  8051 Leehaven Road is the only property of its kind on the Eastern Shore right now — a custom-built waterfront estate move-in ready, and available today. This is not a project. It is not a renovation waiting to happen. It is +/-4,800 square feet of considered, uncompromising construction sitting on a private waterfront lot with direct access to the Chesapeake Bay, a Gunite saltwater pool with

  

  Tracy Higgs-Wagner

  Meredith Fine Properties

  8051 Leehaven Rd, Easton, MD 21601
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  /41

  $704,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 3,118 Sq Ft

  Greenbrier Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012070, Wye Mills, MD 21679
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  /53

  $2,495,000

  • 3 Beds
  • 2.5 Baths
  • 2,472 Sq Ft

  26282 Deep Water Harbor Rd, Easton, MD 21601

  Tucked away on approximately 3 private acres along Plaindealing Creek just off the Tred Avon River, this striking waterfront retreat offers the perfect blend of Mid-Century Modern style, open-concept living, and exceptional Eastern Shore lifestyle amenities. With approximately 5’ MLW, a private dock with boat lift and floating dock, and sweeping water views from nearly every room, this property

  Chuck Mangold Benson & Mangold, LLC

  26282 Deep Water Harbor Rd, Easton, MD 21601
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  /32

  $995,000

  $54K PRICE DROP

  • 4 Beds
  • 3 Baths
  • 2,250 Sq Ft

  109 W Marengo St, Saint Michaels, MD 21663

  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

  Chuck Mangold Benson & Mangold, LLC

  109 W Marengo St, Saint Michaels, MD 21663
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  /101

  $2,895,000

  • 4 Beds
  • 5 Baths
  • 3,589 Sq Ft

  4440 Baildon Rd, Trappe, MD 21673

  Enjoy a Piazza Italian Market lunch at this Public and Broker/Agent open house Thursday 8/6 11am-1pm. With sweeping sunset views, this picturesque estate—perfectly situation on a deepwater point with a private dock on Island Creek just off the Choptank River—offers the rare combination of privacy, acreage, and refined Eastern Shore living. Just ten minutes from Easton, Oxford, and Cambridge, the

  Janet Larson Benson & Mangold, LLC

  4440 Baildon Rd, Trappe, MD 21673
• 

  

  /16

  $689,990

  New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,685 Sq Ft

  Madison Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012050, Wye Mills, MD 21679
• 

  

  /13

  $814,990

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,736 Sq Ft

  Brentwood Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012111, Wye Mills, MD 21679
• 

  

  /25

  $599,900

  $40K PRICE DROP

  • 3 Beds
  • 3 Baths
  • 1,986 Sq Ft

  4794 Sailors Ln, Oxford, MD 21654

  Nestled on 2± acres, this inviting property offers a peaceful setting surrounded by mature trees that provide shade and natural beauty throughout the seasons. A circular driveway creates a welcoming approach and allows for easy access to the home and detached two-car garage, which also offers excellent potential as a workshop, studio, or hobby space.Inside, hardwood flooring extends

  Chuck Mangold Benson & Mangold, LLC

  4794 Sailors Ln, Oxford, MD 21654
• 

  

  /63

  $7,900,000

  • 5 Beds
  • 6 Baths
  • 14,935 Sq Ft

  6010 Shipyard Ln, Easton, MD 21601

  Situated on one of the finest residential parcels in the country, Ship’s Point, is an estate with few rivals anywhere, at any price. The completely private 13+/- acre estate includes a deep water pier, and 270-degree views at the confluence of Trippe’s Creek and the Tred Avon River. The south-west facing manor house has been meticulously renovated by renowned builder Winchester Construction. A

  Chuck Mangold Benson & Mangold, LLC

  6010 Shipyard Ln, Easton, MD 21601
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  /51

  $6,375,000

  • 2 Beds
  • 3 Baths
  • 2,388 Sq Ft

  6150 Oxford Rd, Easton, MD 21601

  Duvall Farm is a rare Eastern Shore offering — a 408± acre farm that blends meaningful conservation efforts with immense easement potential, productive farmland, and refined residential improvements in a location between Easton and Oxford. Significant in both scale and character, the farm is comprised of 20 recorded parcels, presenting long-term value and a wide range of opportunities. The land

  Coard Benson Benson & Mangold, LLC

  6150 Oxford Rd, Easton, MD 21601
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  /44

  $466,990

  New Construction

  • 5 Beds
  • 3 Baths
  • 2,511 Sq Ft

  HAYDEN Plan at Gannon Range, Easton, MD 21601

  The Hayden, a 2,511 square foot unique two-story home, offers five bedrooms, one located on the first floor, three full bathrooms, a flex room, a loft, and a two-car garage.The home’s welcoming foyer offers two coat closets and creates the perfect space to greet your guests. In the front of the home, the flex room with an abundance of natural light could be used as a home office or a

  D.R. Horton Builder

  8749 Harper Way Unit 36203248, Easton, MD 21601
• 

  

  /91

  $5,995,000

  • 6 Beds
  • 6 Baths
  • 9,566 Sq Ft

  27293 Southside Island Creek Rd, Trappe, MD 21673

  Wilderness Estate- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 47± acres, with original structures that are impeccably well-kept and improved with modern amenities, The Wilderness provides a unique opportunity to enjoy the best of the Eastern Shore. Surrounded by open space and preserved farmland with proximity to Oxford, Easton,

  Coard Benson Benson & Mangold, LLC

  27293 Southside Island Creek Rd, Trappe, MD 21673
• 

  

  /20

  $359,800

  • 2 Beds
  • 2 Baths
  • 1,364 Sq Ft

  29336 Hawkes Hill Rd, Easton, MD 21601

  Updated 2-bedroom, 2-bath home featuring a number of improvements and upgrades completed since December 2023. A bright front sunroom provides an inviting entry and features a custom built-in window bench seat. The adjoining living and dining areas offer comfortable everyday living space, accented by a custom stained-glass window. The renovated kitchen features new custom cabinetry, quartz

  Chuck Mangold Benson & Mangold, LLC

  29336 Hawkes Hill Rd, Easton, MD 21601
• 

  

  /48

  $525,000

  • 3 Beds
  • 2.5 Baths
  • 2,729 Sq Ft

  29796 Lyons Dr, Easton, MD 21601

  Welcome to 29796 Lyons Drive, where comfortable elegance, easy living, and the peaceful beauty of Maryland’s Eastern Shore come together. Located in a desirable 55+ community, this beautifully maintained Merion Model offers an inviting floor plan, impressive architectural details, and tranquil surroundings. Adding even more peace of mind, the home features a roof that is only 2 years

  Gwen Eskridge Coldwell Banker Chesapeake Real Estate Company

  29796 Lyons Dr, Easton, MD 21601
• 

  

  /18

  $784,990

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,690 Sq Ft

  Dover Plan at The Preserve at Wye Mills, Wye Mills, MD 21679

  Koch Homes Builder

  13505 Rustling Oaks Dr Unit 41012100, Wye Mills, MD 21679
• 

  

  /46

  $2,500,000

  • 5 Beds
  • 1 Bath

  4108 Saulsbury Ln, Trappe, MD 21673

  Discover one of Talbot Countys rare farms that combines productive farmland, waterfront, and exceptional recreational opportunities. This 105.72 acre agricultural property features approximately 80 acres of tillable ground and is well-suited for continued farming, income production, or long-term land investment. The open farmland is framed by wooded perimeter lines with a mixture of mature

  Casey Kennedy Whitetail Properties Real Estate

  4108 Saulsbury Ln, Trappe, MD 21673
• 

  

  /53

  $2,995,000

  $105K PRICE DROP

  • 4 Beds
  • 4 Baths
  • 3,878 Sq Ft

  26279 Deep Water Harbor Rd, Easton, MD 21601

  Set on 28 private acres overlooking Plaindealing Creek along the desirable Easton–St. Michaels corridor, this beautifully remodeled waterfront home offers 4 bedrooms, 4 full baths, and breathtaking panoramic views stretching across to Oxford, the Choptank River, and beyond. Positioned on an exceptional point of land, the property enjoys a rare combination of expansive water vistas, privacy, and

  Laura Carney TTR Sotheby's International Realty

  26279 Deep Water Harbor Rd, Easton, MD 21601
• 

  

  /72

  $5,995,000

  • 8 Beds
  • 5.5 Baths
  • 9,051 Sq Ft

  8612 Tilghman Island Rd, Wittman, MD 21676

  See listing MDTA2012146 which includes an adjacent 37+-acre waterfront parcel which has a sandy beach and offers additional opportunity, with approvals in place for a seven-bedroom main residence and a three-bedroom guest house. "Bolton Farm", available for the first time in over two decades, is an exceptional offering of rare privacy, including a renovated manor house, historic guest house, new

  Laura Carney TTR Sotheby's International Realty

  8612 Tilghman Island Rd, Wittman, MD 21676
• 

  

  /25

  $459,990

  New Construction

  • 3 Beds
  • 2 Baths
  • 1,892 Sq Ft

  1553 Lake Tahoe Dr, Trappe, MD 21673

  Experience the epitome of modern living in the Matisse. This thoughtfully designed home offers main-level living at its finest, providing unparalleled comfort and flexibility to suit your unique lifestyle. The heart of the home is an open-concept haven, seamlessly blending a gourmet kitchen, dining room, and spacious family room. The kitchen, a chef's dream, features a functional island, abundant

  Brookfield Residential Builder

  1553 Lake Tahoe Dr, Trappe, MD 21673
• 

  

  /25

  $275,000

  $20K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,262 Sq Ft

  21647 Camper Cir, Tilghman, MD 21671

  This well-maintained home offers a peaceful Eastern Shore lifestyle with easy access to boating, fishing, crabbing, local marinas, and waterfront dining. Enjoy the relaxed island atmosphere while still being just a short drive from historic St. Michaels and other nearby amenities.The property features comfortable living spaces, a spacious yard, and the opportunity to enjoy all that

  Heather Brummell Keller Williams Realty

  21647 Camper Cir, Tilghman, MD 21671
• 

  

  /29

  $339,999

  • 3 Beds
  • 1.5 Baths
  • 1,408 Sq Ft

  29245 Corbin Pkwy, Easton, MD 21601

  This move-in-ready Easton rancher offers approximately 1,400 square feet of comfortable one-level living with 3 bedrooms and 1.5 baths. The home features a spacious living area, an open kitchen and dining space, a generously sized primary bedroom, and good natural light throughout. Set on an oversized, nearly half-acre lot, the property offers a large fenced backyard with plenty of room for

  Eddie Mangold Benson & Mangold, LLC

  29245 Corbin Pkwy, Easton, MD 21601
• 

  

  /87

  $5,000,000

  • 3 Beds
  • 4 Baths
  • 5,921 Sq Ft

  5499 Anderby Hall Rd, Royal Oak, MD 21662

  Now offered at an improved price of $5,000,000. Excellent opportunity to own your own private Eastern Shore estate in Royal Oak. Anderby Hall, part of an original 1680 land grant, spans a breathtaking 12+/- acre parcel featuring 3,260’+/- of rip-rapped shoreline. This exceptional property includes a tidal pond, a private cove, and an exclusive island peninsula accessed by bridge. Pass through the

  Valerie Brown Coldwell Banker Realty

  5499 Anderby Hall Rd, Royal Oak, MD 21662
• 

  

  /36

  $429,990

  New Construction

  • 4 Beds
  • 2 Baths
  • 1,774 Sq Ft

  CALI Plan at Gannon Range, Easton, MD 21601

  The Cali is a one-story home that optimizes living space with an open kitchen overlooking the living area and dining room. This 1,774 square foot home offers four bedrooms, two baths, and a two-car garage.As you enter the home from your porch, two guest bedrooms share the same bath and are separated from the living area. Continuing down the hallway, the well-appointed kitchen comes with a

  D.R. Horton Builder

  8749 Harper Way Unit 36203247, Easton, MD 21601
• 

  

  /27

  $598,000

  • 3 Beds
  • 2 Baths
  • 2,348 Sq Ft

  204 Lincoln Ave, Saint Michaels, MD 21663

  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

  Cornelia Heckenbach Long & Foster Real Estate, Inc.

  204 Lincoln Ave, Saint Michaels, MD 21663
• 

  

  /64

  $3,000,000

  • 4 Beds
  • 3 Baths
  • 2,815 Sq Ft

  23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

  Extraordinary waterfront living on 3+ acres with more than 500 feet of stunning water views—offering the privacy of being miles from civilization, yet just 1 mile from famed, historic downtown St. Michaels. Extensively renovated and meticulously cared for, this exceptional one-level living residence provides relaxed comfort, thoughtful design and effortless living in a a resort-like setting. Its

  Carrie Mock Engel & Völkers Annapolis

  23820 Mount Pleasant Landing Cir, Saint Michaels, MD 21663

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