346

Talbot County MD Homes for Sale

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  • /41

    $1,695,000

    • 4 Beds
    • 3.5 Baths
    • 4,102 Sq Ft

    9171 Deepwater Point Rd, Saint Michaels, MD 21663

    Welcome to Saint Micheals Retreat, an extraordinary 6+/- acre waterfront property overlooking the Links at Perry Cabin Golf Course with direct access to the Long Haul Creek and Miles River. Just moments to downtown Saint Michaels, fine dining, shopping, and entertainment, this stunning makeover offers 4,100 +/- sq. ft. of single-story living designed for endless indoor/outdoor entertainment.

    Craig Linthicum Benson & Mangold, LLC

    9171 Deepwater Point Rd, Saint Michaels, MD 21663
  • /88

    $3,690,000

    • 4 Beds
    • 4 Baths
    • 6,374 Sq Ft

    27047 Presquile Rd, Easton, MD 21601

    Originally constructed in 1970 and extensively renovated in 2018, the main residence embodies refined sophistication and modern comfort. The open-concept floor plan seamlessly connects living, dining, and kitchen spaces, highlighted by high-quality hardwood floors, custom built-ins, and shiplap detailing that harmonize timeless charm with contemporary luxury. A chef’s kitchen with premium custom

    Coard Benson Benson & Mangold, LLC

    27047 Presquile Rd, Easton, MD 21601
  • /39

    $3,275,000

    • 7 Beds
    • 10 Baths
    • 7,077 Sq Ft

    28092 Glebe Rd, Easton, MD 21601

    Miles Away on Murphy’s Point – Discover an unparalleled waterfront retreat at 28092 Glebe Rd, Easton, MD, nestled on approximately ±2.7 picturesque acres. Thoughtfully designed for entertaining, relaxation, and convenient living, this luxurious estate offers expansive indoor and outdoor spaces, exceptional waterfront amenities, and easy access to nearby towns, beaches, and metropolitan

    Coard Benson Benson & Mangold, LLC

    28092 Glebe Rd, Easton, MD 21601
  • /51

    $435,000

    • 3 Beds
    • 2 Baths
    • 1,540 Sq Ft

    29345 Greenfield Ave, Trappe, MD 21673

    OPEN HOUSE, Sunday, August 3, from 3 - 4 pm...Huge Price Improvement!...Welcome to your new home with no HOA in the charming town of Trappe, where serenity meets modern comfort! Nestled on a nearly half-acre corner lot, this beautiful ranch home is the perfect blend of spaciousness and light. The open floor plan and vaulted ceilings immediately captivate, creating an inviting and airy atmosphere

    Darlene Winegardner RE/MAX Executive

    29345 Greenfield Ave, Trappe, MD 21673
  • /91

    $8,750,000

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

    27295 Southside Island Creek Rd, Trappe, MD 21673

    Wilderness Estate- REVISED OFFERING INCLUDES 5 PARCELS 6.27.25- This quintessential Eastern Shore farm is located along the Choptank River in Trappe, Maryland. Comprised of 234 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

    Coard Benson Benson & Mangold, LLC

    27295 Southside Island Creek Rd, Trappe, MD 21673
  • /22

    $499,999

    • 2 Beds
    • 2 Baths
    • 1,400 Sq Ft

    295 Bay St, Easton, MD 21601

    "Beautifully renovated townhome within blocks of Downtown Easton" This 2 Bedroom, 2 Bath unit was taken down to the stud and built back with no expenses spared. When you enter the front door, you will be amazed by the spaciousness of the unit given the open floor plan. The living room is very inviting, with a wood burning fireplace, floating “old wood” mantle, and recessed lighting. Wood

    Craig Linthicum Benson & Mangold, LLC

    295 Bay St, Easton, MD 21601
  • /71

    $9,900,000

    • 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
  • /62

    $4,499,000

    • 6 Beds
    • 9 Baths
    • 3,700 Sq Ft

    27473 Westpoint Rd, Easton, MD 21601

    Offered for the first time in nearly forty years, Swan Point is the quintessential Eastern Shore estate. Situated on 4.5 +/- acres, with westerly exposure on the Tred Avon River this estate has it all. Private pier with 4’+/- MLW and 400 +/- of waterfrontage. The main house is classically charming and takes full advantage of the sunset water views. Spacious kitchen is complete with high-end

    Chuck Mangold Benson & Mangold, LLC

    27473 Westpoint Rd, Easton, MD 21601
  • /23

    $419,990 New Construction

    • 3 Beds
    • 2 Baths
    • 1,676 Sq Ft

    Alan Plan at Lakeside at Trappe - Signature, Trappe, MD 21673

    Designed for low-maintenance living, this new single-family home features a convenient, open-concept layout. Two secondary bedrooms frame the foyer to provide peaceful retreats, while down the hallway is the main living area. It showcases a fully equipped kitchen, dining room and a spacious Great Room with direct access to the backyard. In a corner is the owner’s suite with an attached bathroom

    Builder Photo

    Lennar

    Builder

    1258 Lake Michigan Unit 36949654, Trappe, MD 21673
  • /27

    $514,990 New Construction

    • 4 Beds
    • 1.5 Baths
    • 3,241 Sq Ft

    Beckham Plan at Lakeside at Trappe - Single Family Homes Collection at Lakeside at Trappe, Trappe, MD 21673

    Step into the two-story foyer of the Beckham and you’ll feel the unmatched luxury and comfort. The open floorplan creates an atmosphere that is both impressive and inviting. Use the library to work from home and be tucked away in the back of the home or choose to turn this into a main level guest suite. A large gourmet kitchen with center island and pantry are a chef’s delight and flow into the

    Builder Photo

    Brookfield Residential

    Builder

    1254 Lake Michigan Unit 36578896, Trappe, MD 21673
  • /26

    $464,990 New Construction

    • 4 Beds
    • 1.5 Baths
    • 2,340 Sq Ft

    Torrington Plan at Lakeside at Trappe - Single Family Homes Collection at Lakeside at Trappe, Trappe, MD 21673

    Step into refined living with The Torrington – an impeccably designed 2-level residence that seamlessly marries sophistication with functionality. A covered porch extends a gracious welcome. Upon entering is a living room that can be converted into a library or playroom to meet your needs. The heart of this residence lies in its open-concept kitchen, harmoniously connecting the dining room and

    Builder Photo

    Brookfield Residential

    Builder

    1254 Lake Michigan Unit 36578895, Trappe, MD 21673
  • /23

    $439,990 New Construction

    • 3 Beds
    • 1 Bath
    • 1,841 Sq Ft

    Matisse Plan at Lakeside at Trappe - Single Family Homes Collection at Lakeside at Trappe, 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

    Builder Photo

    Brookfield Residential

    Builder

    1254 Lake Michigan Unit 36578892, Trappe, MD 21673
  • /111

    $11,500,000

    • Land
    • 675 Acres
    • $17,037 per Acre

    2924 Ocean Gateway, Trappe, MD 21673

    Currently one of the largest Farm/Residential Estates available in the State of Maryland and a once in a lifetime opportunity to own it. This 662+ acres waterfront property with 1.8 miles of shoreline known as "Middleville" circa 1880 is truly a magnificent landholding. Located in Talbot County the property is improved with 5 Residents. A newly renovated Main Home that boasts Tidewater Colonial

    Jay Phillips

    2924 Ocean Gateway, Trappe, MD 21673
  • /2

    Call for Price

    • Land
    • 1.35 Acres

    12b Mistletoe Dr, Easton, MD 21601

    New Development - Build to suit, variety of uses available in zoning. Adjacent to Easton airport and close proximity to Rt. 50.

    Chuck Jr. Benson and Mangold

    12b Mistletoe Dr, Easton, MD 21601
  • /2

    $549,900

    • Land
    • 4.26 Acres
    • $129,085 per Acre

    28850 Jennings Rd, Easton, MD 21601

    Welcome to an extraordinary opportunity in the heart of the picturesque Eastern Shore! This 4.26-acre building lot, nestled within the esteemed Llandaff at Cookes Hope Subdivision, presents an unparalleled canvas for your dream estate. Perc approved for a 7-bedroom home and has the rare opportunity to include a basement, this expansive parcel offers serene living in a peaceful country setting.

    Chuck Jr. Benson and Mangold

    28850 Jennings Rd, Easton, MD 21601
  • /2

    $995,000

    • Land
    • 5 Acres
    • $181,569 per Acre

    9361 Woodstock Ln, Easton, MD 21601

    Quiet country setting can be yours with this 5.5 +/- acre waterfront lot located in the Woodstock Farm community on Goldsborough Creek is perc approved for 6 bedrooms! Located just minutes to downtown Easton and all of the amenities Easton has to offer from shopping to dining, entertainment at the Avalon Theatre, and the convenience of Easton's Jetport.

    Chuck Jr. Benson and Mangold

    9361 Woodstock Ln, Easton, MD 21601
  • /50

    $1,200,000

    • 4 Beds
    • 2.5 Baths
    • 3,040 Sq Ft

    21477 Island Club Rd, Tilghman, MD 21671

    Welcome to waterfront living at its finest on picturesque Tilghman Island! This beautifully maintained 3,040 sq ft Colonial offers stunning open water views and a lifestyle of comfort, elegance, and ease. Boasting four spacious bedrooms and two and a half baths, this home features a flowing floor plan with natural light, generous living spaces, and a perfect blend of indoor and outdoor

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • /33

    $825,000

    • 4 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    24420 Mallard Place, Saint Michaels, MD 21663

    This stately and well-constructed brick/wood cape cod majestically sits on a prime corner lot in the extremely desirable community of Martingham. The ideal floor-plan features a main floor primary bedroom and 3 second floor guest bedrooms. Beautiful hardwood flooring, custom built-ins, fireplace, 2 story foyer, screened porch , deck, covered front porch, circular driveway with extra parking

    Robert Lacaze TTR Sotheby's International Realty

    24420 Mallard Place, Saint Michaels, MD 21663
  • /56

    $675,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,856 Sq Ft

    510 Tenant Cir, Saint Michaels, MD 21663

    Location! You really can’t beat this spot! Just head a few houses left and you’ll hit the Rio Vista waterfront park on the beautiful Miles River. Go a few houses to the right and you’re at the Rio Vista community dock—super handy if you have a boat. With this water-privileged location, you get easy access to both the park and the dock. This place has gotten some great updates over the years,

    Larry Brennan TTR Sotheby's International Realty

    510 Tenant Cir, Saint Michaels, MD 21663
  • /53

    $940,000

    • 4 Beds
    • 3.5 Baths
    • 2,869 Sq Ft

    11 Brookletts Ave, Easton, MD 21601

    Fabulous Victorian in Historic Easton, Circa 1910Step into timeless elegance just a block from the heart of Easton's vibrant downtown—home to the famous Plein Air Festival, Crackerjacks, The Avalon Theatre, Legal Assets, Doc’s Downtown Grille, Vintage Books, charming boutiques, and art galleries galore.This stunning 4–5 bedroom, 3,800+ sq ft Victorian beauty offers classic

    Martha Suss Coldwell Banker Realty

    11 Brookletts Ave, Easton, MD 21601
  • /41

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 2,424 Sq Ft

    6705 Tilghman Island Rd, Sherwood, MD 21665

    Escape to Eastern Shore Living! Welcome to this spacious 4-bedroom, 2.5-bath gem nestled in a sought-after water-access community. Enjoy an open-concept layout flooded with natural light, perfect for entertaining or relaxing. The kitchen features stainless steel appliances, while the cozy living room includes a fireplace for year-round comfort and a bedroom on the main level. Three additional

    Bean Rehbein The KW Collective

    6705 Tilghman Island Rd, Sherwood, MD 21665
  • /45

    $750,000

    • 3 Beds
    • 3 Baths
    • 2,660 Sq Ft

    4957 Bar Neck Rd, Tilghman, MD 21671

    Secure and Secluded Luxury Living with Bay Views & Resort-Style BackyardProperty is located in FEMA Zone X, has never had water on the property and seller is not required to have flood insuranceTucked away at the end of a private Crepe Myrtle-lined drive, this well-maintained luxury retreat offers the perfect blend of tranquility, style, and function—without the constraints of an HOA.

    Danny Martin Keller Williams Flagship

    4957 Bar Neck Rd, Tilghman, MD 21671
  • /44

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,092 Sq Ft

    26604 E Bonfield Rd, Oxford, MD 21654

    Located in one of the county’s most coveted areas along the Oxford Corridor, this 4-bedroom, 3.5-bathroom custom home offers a spacious layout with a flexible design for modern living. The open floor plan seamlessly connects the kitchen, dining area, and vaulted-ceiling living room with fireplace, creating a functional space ideal for everyday living and entertaining. The updated kitchen features

    Chuck Mangold Benson & Mangold, LLC

    26604 E Bonfield Rd, Oxford, MD 21654
  • /48

    $659,000

    • 3 Beds
    • 2 Baths
    • 1,891 Sq Ft

    6524 Oxford Rd, Easton, MD 21601

    Gracious, one-level brick home located along the 5th fairway of the Talbot Country Club golf course. This 3-bedroom, 2-bath residence is thoughtfully designed for entertaining and everyday comfort, with spacious formal living and family rooms, a dedicated dining area, and French doors opening to the rear patio from the kitchen, living room, and primary suite.Features include a newer kitchen,

    Debbie Lipscomb Benson & Mangold, LLC

    6524 Oxford Rd, Easton, MD 21601
  • /51

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 2,246 Sq Ft

    8629 Unionville Rd, Easton, MD 21601

    BRAND NEW AND READY FOR IMMEDIATE OCCUPANCY! Property will be Active and ready for showings on Wednesday, July 16. This spacious 2200+ square foot new build features a main level owners suite and is clad with high end appointments throughout. Step into the main level and enjoy an open concept layout including a spacious family room with gas fireplace, formal office with cathedral ceiling,

    Adam Ellison Long & Foster Real Estate, Inc.

    8629 Unionville Rd, Easton, MD 21601
  • /47

    $625,000

    • 3 Beds
    • 2 Baths
    • 2,052 Sq Ft

    506 Goldsborough St, Easton, MD 21601

    Located in Historic Easton and rightfully historic as well, Caldwells Brick Cottage T459. Caldwell was the Station Master for the Easton Railroad and built 506 Goldsborough Street along with several houses in 1861. The house is listed with Maryland Historic Trust and given the number T459. It can be seen in the Talbot Public Library's History room along with further references. A thoughtful

    Kelly Showell Benson & Mangold, LLC

    506 Goldsborough St, Easton, MD 21601
  • /42

    $675,000

    • 3 Beds
    • 2.5 Baths
    • 2,350 Sq Ft

    9560 Martingham Cir, Saint Michaels, MD 21663

    Located in the popular Martingham community just beyond historic St. Michaels, this well-built one-level home has a prime location, with The Links at Perry Cabin golf course right behind it. The open, spacious floor plan features a large primary suite at one end and two bedrooms and bath at the other for maximum privacy. The owners added a sunroom with a grilling deck off the side. The kitchen

    Debra Crouch Benson & Mangold, LLC

    9560 Martingham Cir, Saint Michaels, MD 21663
  • /51

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 2,786 Sq Ft

    28602 Clubhouse Dr, Easton, MD 21601

    Easton Club. One owner custom built home. The open floor plan features a great room with gas fireplace and built-ins, dining room/sitting room combo, kitchen with center island, sunroom, primary suite, 2 additional guest bedrooms and full bath plus half bath and laundry. 2 car side-load garage, deck and expandable walk-up attic. Community pool and tennis/pickleball court. This established

    Judy Moore Benson & Mangold, LLC

    28602 Clubhouse Dr, Easton, MD 21601
  • /56

    $599,000

    • 3 Beds
    • 2 Baths
    • 1,761 Sq Ft

    8000 Bozman Neavitt Rd, Bozman, MD 21612

    Nestled along the peaceful waters of Swan Cove with access to Harris Creek, this circa 1890 farmhouse is full of Eastern Shore character and charm. Set on 1.38 private acres, the property offers the peace and serenity you’re seeking. The spacious enclosed front porch is accented with wood floors and a wood ceiling setting the tone of this charming home. The inviting foyer features original

    Kim Crouch Ozman Benson & Mangold, LLC

    8000 Bozman Neavitt Rd, Bozman, MD 21612
  • /53

    $368,500

    • 2 Beds
    • 3 Baths
    • 1,800 Sq Ft

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663

    Martingham, a golf course and waterfront community just a mile outside of Historic St. Michaels with all of its amenities. This Widgeon Place condo is a two-story condo with two en-suite bedrooms and a half bath on the first floor. Living room and dining room are an open floor plan with hardwood floors and fireplace. From the sunroom you can step onto a brick patio which looks out to treed

    Jane Baker Benson & Mangold, LLC

    24362 Widgeon Place Unit 4, Saint Michaels, MD 21663
  • /60

    $709,000

    • 3 Beds
    • 3.5 Baths
    • 3,288 Sq Ft

    13474 Rustling Oaks Dr, Wye Mills, MD 21679

    Recent price improvement! Welcome to your dream home in The Preserve at Wye Mills! This beautiful move-in-ready colonial offering designer touches and exceptional outdoor living sits on nearly an acre and offers the perfect blend of classic charm and modern upgrades. This home features nine-foot ceilings and hardwood floors throughout the main level excluding the bonus room which can be used

    Janet Powers Berkshire Hathaway Homeservice Homesale Realty

    13474 Rustling Oaks Dr, Wye Mills, MD 21679
  • /58

    $589,500

    • 3 Beds
    • 2.5 Baths
    • 2,233 Sq Ft

    8357 Gannon Cir, Easton, MD 21601

    Very beautiful home on a large one-acre lot in the sought-after neighborhood of Crofton -- very rare a home goes on market here. This beautiful rancher has been totally renovated kitchen stainless steel appliances, cabinets, farm sink with all the attachments, microwave, dishwasher, pantry, large island with gorgeous light will seat 5-6, new granite countertops, recessed lighting and window

    Bonnie Duley Long & Foster Real Estate, Inc.

    8357 Gannon Cir, Easton, MD 21601
  • /61

    $699,000 Open Sat 1PM - 3PM

    • 4 Beds
    • 2.5 Baths
    • 2,616 Sq Ft

    703 S Morris St, Oxford, MD 21654

    Major Price Reduction. Motivated seller. Seller will entertain reasonable offers. Welcome to Oxford, a storybook town where the streets are quiet, the air smells like salt and summer, and neighbors wave as you pass by. Tucked along the peaceful Tred Avon River, this beloved waterfront community invites you to slow down and enjoy life’s simple pleasures-sunset walks by the marina, weekend

    Christie Bishop Northrop Realty

    703 S Morris St, Oxford, MD 21654
  • /31

    $695,000

    • 2 Beds
    • 2.5 Baths
    • 2,528 Sq Ft

    28622 Clubhouse Dr, Easton, MD 21601

    Spacious One-Level Living in the Desirable Easton Club Community - New Roof coming in August, 2025! - New HVAC in 2023! - Welcome to this meticulously maintained home featuring a highly sought-after, single-level floor plan with lofty ceilings. The expansive kitchen is equipped with brand-new stainless steel appliances, an island with seating, and a generous dining area—perfect for everyday

    Clifford Meredith Meredith Fine Properties

    28622 Clubhouse Dr, Easton, MD 21601
  • /46

    $675,000

    • 4 Beds
    • 3.5 Baths
    • 3,510 Sq Ft

    13443 Blackberry Ln, Wye Mills, MD 21679

    Beautiful home on a cul-de-sac in the sought after neighborhood 'The Preserve at Wye Mills'! Spacious, two story family room with hardwood floors, gas fireplace, and lots of natural light. Large kitchen with oversized island with built in gas cooktop, double ovens, lots of cabinets and counter space. First floor office could also work as a guest room. Four large bedrooms with three and a

    Keith Hensley Meredith Fine Properties

    13443 Blackberry Ln, Wye Mills, MD 21679
  • /89

    $585,000

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

    7371 Michael Ave, Easton, MD 21601

    Welcome to Easton Club East — a vibrant 55+ community offering the perfect blend of comfort, convenience, and coastal charm on Maryland’s Eastern Shore.This beautifully maintained Merion model features 3 bedrooms, 2.5 baths, and a thoughtfully designed layout ideal for those looking to downsize without compromising quality or space. This home is also situated on one of the premier lot locations

    Coard Benson Benson & Mangold, LLC

    7371 Michael Ave, Easton, MD 21601
  • /58

    $699,000

    • 3 Beds
    • 2 Baths
    • 1,500 Sq Ft

    204 W Chew Ave, Saint Michaels, MD 21663

    Big things come in small packages! A St. Michaels treasure! Absolutely charming, completely renovated historic property only steps to the waterfront park & a block into town. This beautiful home has been renovated from top to bottom & has been designed to offer style & historic charm. Featuring a new, lifetime blue metal roof, gardens, patios, & relaxing, covered front porch to watch the world

    Kate Koeppen Chesapeake Bay Real Estate Plus, LLC

    204 W Chew Ave, Saint Michaels, MD 21663
  • /43

    $695,000

    • 3 Beds
    • 2.5 Baths
    • 2,496 Sq Ft

    24749 Swan Rd, Saint Michaels, MD 21663

    Located in Martingham, home of the newly redesigned Pete Dye golf course, The Links at Perry Cabin. This 3BR/2.5BA Colonial style home is situated on an open 1.13ac lot with a tree lined backyard for privacy. Inside you will enjoy a spacious floor plan, and updated island kitchen, and a large family room highlighted by a wood burning fireplace and a beam ceiling. Upstairs you will find the

    Steve Bealefeld Benson & Mangold, LLC

    24749 Swan Rd, Saint Michaels, MD 21663
  • /31

    $695,000

    • 2 Beds
    • 2 Baths
    • 1,720 Sq Ft

    103 Richardson St, Oxford, MD 21654

    Oxford, Unique Carriage House sits on large, high lot, with plenty of off street parking. Located on the quiet side of Town, this 2-BR, 2-Bath house offers open living plan with views of Town Creek. Nestled in a Maritime Community, that offers a feeling of privacy but puts you close to Marinas and a short walk to the center of Town. This is the perfect weekend or retirement house, with the

    Ray Stevens Benson & Mangold, LLC

    103 Richardson St, Oxford, MD 21654
  • /8

    $675,000

    • 4 Beds
    • 2 Baths
    • 1,740 Sq Ft

    9236 Chapel Rd, Easton, MD 21601

    Incredibly rare opportunity just minutes from downtown Easton—17.48+ acres with three deeded lots. This unique offering includes a two-story farmhouse (circa 1900) ready for renovation, along with two additional parcels currently leased for farming. The land is cleared, open, and scenic—perfectly positioned for a future estate, family compound, or investment.Enjoy exceptional proximity to

    Julie Stevenson Shore Living Real Estate

    9236 Chapel Rd, Easton, MD 21601

Showing Results 41 - 80, Page 2 of 9

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