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Colonial Homes for Sale in Talbot County MD

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  • /14

    $459,000

    $106K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,984 Sq Ft

    13415 Wye Landing Ln, Wye Mills, MD 21679

    VIRTUAL STAGING. Nestled in the charming Wye Mills community, this delightful Colonial-style home offers a perfect blend of comfort and functionality, ideal for those seeking a serene retreat. Built in 1995, this well-maintained residence boasts 1,984 square feet of inviting living space, thoughtfully designed to cater to modern lifestyles. Step inside to discover an open floor plan that

    Antoine Johnson Powerhouse Realty, LLC.

    13415 Wye Landing Ln, Wye Mills, MD 21679
  • /80

    $480,000

    $10K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,342 Sq Ft

    7449 Kevin Ave, Easton, MD 21601

    Located in the sought-after Easton Club East community and not restricted to 55+, this well-maintained home offers 3 bedrooms, 3 full baths, and a flexible layout designed for comfortable everyday living.Recent updates include fresh interior paint, new carpet, a new roof (2025), and a new HVAC system (2022). The main-level primary suite features a custom walk-in closet and private bath, while

    Coard Benson Benson & Mangold, LLC

    7449 Kevin Ave, Easton, MD 21601
  • /52

    $4,395,000

    • 4 Beds
    • 5.5 Baths
    • 5,062 Sq Ft

    27029 Miles River Rd, Easton, MD 21601

    Irish Tides offers a quintessential Eastern Shore retreat with luxury and style. This beautifully crafted4-bedroom, 5.5-bath main house provides captivating views of the Miles River from almost every room. The main level has been enhanced with a new HVAC system and ductwork, ensuring comfort andefficiency throughout. Exquisite crown moldings, hardwood floors, and custom built-ins add an

    Chuck Mangold Benson & Mangold, LLC

    27029 Miles River Rd, Easton, MD 21601
  • /47

    $699,000

    $26K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 2,208 Sq Ft

    10118 Hiners Ln, Easton, MD 21601

    Beautiful 4-bedroom, 2-bathroom home on a 1+/- acre parcel with an additional 12.45+/- acre lot included—ideal for expansion, equipment storage, or future investment. The 48' x 60' pole barn features three overhead doors, providing ample space for tools, vehicles, and materials. Outside, enjoy an in-ground pool and a fully fenced backyard. The property is currently served by well and septic, but

    Jim Corson Benson & Mangold, LLC

    10118 Hiners Ln, Easton, MD 21601
  • /119

    $1,945,000

    $50K PRICE DROP
    • 6 Beds
    • 6 Baths
    • 4,089 Sq Ft

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663

    Check out the NEW aerial photos! An exceptional opportunity in The Homes at Perry Cabin -- a rare double residence offering approximately 4,000 square feet, six bedrooms, and six full baths in a premier Saint Michaels waterfront community. adjacent to the renowned Inn at Perry Cabin and overlooking Fogg Cove just off the Miles River. This turnkey home features expansive living areas and a

    Maureen McHugh Chesapeake Bay Real Estate Plus, LLC

    228 Perry Cabin Dr Unit 228 / 226, Saint Michaels, MD 21663
  • /38

    $695,000

    • 3 Beds
    • 3 Baths
    • 3,050 Sq Ft

    32930 Oyster Bank Terrace, Easton, MD 21601

    Discover the perfect blend of privacy in this spacious three bedroom, 3 full bath , Colonial located in the sought-after High Banks community. Set on over 4 acres in the water-privileged section with access to the Choptank River, this home offers a bright open floor plan, durable LVP flooring, wood stove insert with marble hearth, crown molding, and a nice open kitchen with a center island ideal

    Barbara Watkins Benson & Mangold, LLC

    32930 Oyster Bank Terrace, Easton, MD 21601
  • /61

    $1,379,800

    New Construction
    • 4 Beds
    • 3.5 Baths
    • 3,332 Sq Ft

    7865 Pea Neck Rd, Saint Michaels, MD 21663

    Under construction by Laine Street Homes, this exceptional property offers over 3,300 sq ft of finished living space plus an additional 480 sq ft of covered outdoor living. Set on approximately 2 acres with mature trees and located just minutes from the heart of historic St. Michaels, the home blends privacy, luxury, and convenience. Designed with a main-level primary suite, the floor plan

    Jana Meredith Meredith Fine Properties

    7865 Pea Neck Rd, Saint Michaels, MD 21663
  • /41

    $795,000

    • 4 Beds
    • 4 Baths
    • 2,900 Sq Ft

    28713 Emanuel St, Easton, MD 21601

    This two-story Charleston-style Colonial is located in the desirable Cooke’s Hope Village community and sits on an oversized lot with a fenced side and rear yard. The property includes a spacious entry-level side porch, second-level balcony, lush seasonal gardens, and a private fenced brick courtyard with built-in speakers for music and a retractable awning—perfect for outdoor entertaining.

    Chuck Mangold Benson & Mangold, LLC

    28713 Emanuel St, Easton, MD 21601
  • /76

    $7,900,000

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

    8612 Tilghman Island Rd, Wittman, MD 21676

    "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 four stall horse barn, pool and tennis. Originally known as Quaker Kemp Farm, dating back to 1790, this remarkable 114+-acre waterfront estate with two deeded lots has breathtaking western views across the Chesapeake Bay. A gated

    Laura Carney TTR Sotheby's International Realty

    8612 Tilghman Island Rd, Wittman, MD 21676
  • /33

    $399,900

    $30K PRICE DROP
    • 3 Beds
    • 1.5 Baths
    • 1,556 Sq Ft

    22582 Pot Pie Rd, Wittman, MD 21676

    Set on nearly an acre in the heart of Wittman, this cedar shake–sided home offers space, character, and a relaxed Eastern Shore lifestyle. Built in 1900, the 3-bedroom, 1.5-bath residence blends timeless charm with thoughtful updates for comfortable everyday living. Hardwood flooring runs throughout, complemented by a sun-filled dining room and a cozy living room with a gas fireplace and built-in

    Chuck Mangold Benson & Mangold, LLC

    22582 Pot Pie Rd, Wittman, MD 21676
  • /81

    $1,100,000

    • 4 Beds
    • 4.5 Baths
    • 6,043 Sq Ft

    13446 Blackberry Ln, Wye Mills, MD 21679

    Built in 2006 and meticulously maintained, this exceptional home offers 6,553 square feet of living space, including 4,463 square feet above grade and an additional 2,090 square feet in the finished walk-out basement with both interior and exterior access. Inside, a dramatic two-story foyer and soaring family room create an impressive sense of openness, while oversized windows fill the home with

    Dee Dee McCracken Coldwell Banker Realty

    13446 Blackberry Ln, Wye Mills, MD 21679
  • /27

    $399,000

    $11K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 1,698 Sq Ft

    331 Hollis Cir, Easton, MD 21601

    Nestled on a desirable corner lot in Easton, this charming 3-bedroom, 2.5-bath home offers the perfect blend of comfort, convenience, and location. Just a short distance from a scenic walking trail, it’s ideal for those who enjoy outdoor strolls, morning jogs, or peaceful evenings surrounded by nature. Inside, the home features a functional and inviting layout with spacious living areas, perfect

    Wes Russum Coldwell Banker Chesapeake Real Estate Company

    331 Hollis Cir, Easton, MD 21601
  • /49

    $895,000

    • 5 Beds
    • 3.5 Baths
    • 3,400 Sq Ft

    8020 Easton Village Dr, Easton, MD 21601

    Effortless Lifestyle — Deeded Boat Slip with Lift in Easton VillageTucked into one of Talbot County’s most coveted waterfront community, 8020 Easton Village Drive delivers what Eastern Shore buyers search for: a deeded boat slip with electric lift on the Tred Avon, a turn-key home, and close proximity to historic downtown Easton. This 5-bedroom, 3.5-bath Colonial offers a wraparound covered

    Chuck Mangold Benson & Mangold, LLC

    8020 Easton Village Dr, Easton, MD 21601
  • /56

    $475,000

    $30K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,342 Sq Ft

    7344 Casey Ave, Easton, MD 21601

    Chesapeake By Del Webb. Popular 2 story Wittman model. Great room with gas fireplace, dining room, large eat-in kitchen with breakfast nook and center island, sunroom, office, 1st floor primary suite with walk-in closet and bath with walk-in shower and soaking tub, guest bedroom, hall bath and laundry. 2nd floor is perfect for guests with a loft, bedroom and bath. Features a 2 car rear loading

    Judy Moore Benson & Mangold, LLC

    7344 Casey Ave, Easton, MD 21601
  • /130

    $6,495,000

    • 4 Beds
    • 5 Baths
    • 6,731 Sq Ft

    24679 Deep Neck Rd, Royal Oak, MD 21662

    Irish Creek Waterfront EstateSet along more than 1,000 +/- feet of pristine, navigable waterfront on Irish Creek, this remarkable 22.14 +/- acre waterfront estate captures the very essence of luxury living on Maryland’s Eastern Shore. Surrounded by sweeping southwest-facing water views and unspoiled natural beauty, the property offers exceptional privacy and scale just minutes from the

    Chuck Mangold Benson & Mangold, LLC

    24679 Deep Neck Rd, Royal Oak, MD 21662
  • /36

    $455,000

    $25K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,800 Sq Ft

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663

    Set within the sought-after Martingham community of Quail Hollow, backing to the top rated golf course The Links at Perry Cabin, this fully updated 3-bedroom, 3-bath townhome offers stylish, low-maintenance living just minutes from downtown St. Michaels. Extensive renovations completed between 2022 and 2024 make this home truly turnkey. The main level welcomes you with beautiful wood floors, a

    Barbara Watkins Benson & Mangold, LLC

    9518 Quail Hollow Dr Unit 702, Saint Michaels, MD 21663
  • /72

    $1,195,000

    • 4 Beds
    • 3.5 Baths
    • 4,500 Sq Ft

    28711 Hope Cir, Easton, MD 21601

    Approximately 4400 square feet +/- , 3 Level, newly updated, 4 bedroom, Federal style home on a quiet circle. Newer kitchen and first floor owner's en suite, new sun room and finished third floor office/bedroom. Second floor includes two spacious bedrooms, two baths (both en suite); plus, large bonus/storage room which could easily be converted to a 5th bedroom or in-law suite. Perfect for

    Brian Petzold Benson & Mangold, LLC

    28711 Hope Cir, Easton, MD 21601
  • /40

    $799,900

    $79K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 3,740 Sq Ft

    29583 Skipton Estates Dr, Cordova, MD 21625

    Brand new roof just completed! Extremely well maintained Skipton Estates colonial situated on a wooded 2 acre lot which offers loads of privacy and plenty of bird watching. Upon entering this spacious home you are greeted by a bright, open 2 story foyer with hardwood flooring that's open to the office/study and formal dining room. Continuing into the home features a generous family room that has

    Bryan Wieland Benson & Mangold, LLC

    29583 Skipton Estates Dr, Cordova, MD 21625
  • /5

    $484,900

    Coming Soon
    • 4 Beds
    • 2.5 Baths
    • 2,060 Sq Ft

    29803 Standish St, Easton, MD 21601

    Beautifully maintained two-story Colonial in Matthewstown Run. Situated on a large lot that backs to a farm with a peaceful spring fed pond, offering privacy and picturesque views, offering endless possibilities for a pool and outdoor living, from entertaining and gardening to play areas and recreation. There are 4 bedrooms, 21⁄2 updated bathrooms, and a beautifully renovated kitchen This is the

    Connie Loveland Benson & Mangold, LLC

    29803 Standish St, Easton, MD 21601
  • /62

    $509,000

    • 3 Beds
    • 3 Baths
    • 2,342 Sq Ft

    7432 Karen Ave, Easton, MD 21601

    Chesapeake by Del Webb. Nicely sited for maximum sunshine , this handsome and beautifully cared for two story Wittman model awaits you. Recent upgrades include luxury Vinyl flooring throughout the entire house ( even the stairs ! ) , entire house repainted neutral tones, custom blinds, enhanced lighting and fans, architectural roof, new high quality kitchen appliances including washer/dryer,

    Kelly Showell Benson & Mangold, LLC

    7432 Karen Ave, Easton, MD 21601
  • /50

    $2,000,000

    $600K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 4,492 Sq Ft

    7909 Church Neck Rd, Saint Michaels, MD 21663

    PRICE IMPROVEMENT.... PRIVATE Estate Living Minutes from Historic St. Michaels... Escape to nearly twenty acres of unspoiled countryside just moments from the charm and waterfront allure of historic St. Michaels. This 4,492-square-foot home offers refined comfort with four bedrooms, two and a half baths, and a gourmet kitchen designed for both everyday living and effortless entertaining. A

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    7909 Church Neck Rd, Saint Michaels, MD 21663
  • /67

    $1,080,000

    $20K PRICE DROP
    • 4 Beds
    • 4 Baths
    • 2,000 Sq Ft

    140 S Washington St, Easton, MD 21601

    Looking for the ideal downtown Easton location? This beautifully renovated Colonial offers a rare opportunity—perfect as a high‐end investment property or as your personal residence with an income‐producing second unit. This stunning building features two fully updated 1,000 sq. ft. units, each finished with high‐quality materials and thoughtful design. First‐Floor Unit2 bedrooms, 2 baths

    Jana Meredith Meredith Fine Properties

    140 S Washington St, Easton, MD 21601
  • /38

    $415,000

    $14K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,028 Sq Ft

    3868 Marvel Dr, Trappe, MD 21673

    Welcome Home to a beautifully maintained home tucked away on a quiet cul-de-sac in an established neighborhood conveniently located within minutes of RT50 for easy commuting to Easton, Cambridge or the beach. This spacious 4 Bedroom, 3 Full Bath home offers the flexibility todays buyer's are looking for with a potential 5th main level bedroom thanks to a dining room with closet access and

    Joanie Hynes EXP Realty, LLC

    3868 Marvel Dr, Trappe, MD 21673
  • /38

    $729,500

    $46K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,819 Sq Ft

    28959 Jasper Ln, Easton, MD 21601

    Nestled in the prestigious Cooke's Hope community, this exquisite end-of-row townhouse embodies the perfect blend of elegance and comfort. Built in 2004, this Colonial-style residence boasts a timeless brick façade that invites you into a world of refined living. Spanning 2,819 square feet, this home features three spacious bedrooms and two and a half luxurious bathrooms, designed to cater to

    Bill Wieland Benson & Mangold, LLC

    28959 Jasper Ln, Easton, MD 21601

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