135

Talbot County MD Homes for Sale with Pool

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  • /50

    $989,000

    • 4 Beds
    • 4.5 Baths
    • 2,623 Sq Ft

    27939 Waverly Rd, Easton, MD 21601

    Set on 2.8± private acres along the highly sought-after Oxford Corridor, this spacious residence offers the perfect blend of comfort, space, and timeless Eastern Shore appeal. A welcoming rocking-chair front porch, huge fenced rear yard with expansive rear deck perfect for entertaining with a custom retractable awning, , paver patio, and in-ground saltwater pool create an ideal setting for

    Barbara Watkins Benson & Mangold, LLC

    27939 Waverly Rd, Easton, MD 21601
  • /32

    $572,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    Kerr Plan at Four Seasons at Easton, Easton, MD 21601

    HovHall with valet and closet conveniently located between 3-car tandem garage and extended foyer.Beautiful kitchen with walk-in pantry and large island off great room for a sense of connection.Dining area thoughtfully positioned beside kitchen through cased opening to create a balance between open-concept living and more traditional zones, ideal for entertaining.Serene first-floor

    K. Hovnanian Homes Builder
    29434 Dutchmans Ln Unit 37862413, Easton, MD 21601
  • /70

    $2,995,000

    • 4 Beds
    • 3.5 Baths
    • 3,088 Sq Ft

    5837 Irish Creek Rd, Royal Oak, MD 21662

    Absolutely stunning mid-century contemporary estate offering a private , park-like setting, with heated swimming pool, pavilion, luxurious fully equipped outdoor- kitchen, outdoor shower, in -ground hot tub ,tennis court, and maintenance -free Azek pier with new 30K lb. boat lift. Meticulously maintained inside and out! Professionally landscaped with WiFi controlled front/rear irrigation

    Robert Lacaze TTR Sotheby's International Realty

    5837 Irish Creek Rd, Royal Oak, MD 21662
  • /26

    $379,990

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 1,990 Sq Ft

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

    This new two-story home features an inviting open-concept layout on the first floor, blending the kitchen, living and dining areas to maximize interior space. A spacious loft provides a shared living area on the second floor near three secondary bedrooms and the lavish owner’s suite, complete with a spa-inspired bathroom and generous walk-in closet.

    Lennar Builder
    1258 Lake Michigan Unit 36949688, Trappe, MD 21673
  • /23

    $429,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,570 Sq Ft

    Spring Lake II Plan at Four Seasons at Easton, Easton, MD 21601

    Cozy kitchen open to dining area, great room, and sunny covered patio. Beautiful primary suite with dual-sink vanity in bathroom and large walk-in closet. Versatile and secluded home office. Hall bath ideal for guests and conveniently near bedroom 2. Laundry room away from living spaces to help keep your home clean, quiet, and organized. Spacious 2-car garage.

    K. Hovnanian Homes Builder
    29434 Dutchmans Ln Unit 37862410, Easton, MD 21601
  • /27

    $599,990

    New Construction
    • 3 Beds
    • 3.5 Baths
    • 2,963 Sq Ft

    Franklin Plan at Four Seasons at Easton, Easton, MD 21601

    Formal dining room off foyer for entertaining guests.Spacious and beautiful kitchen with walk-in pantry and large island.Open and airy great room featuring vaulted ceiling with optional beams and slider to covered patio.Luxurious primary suite with triple windows and gorgeous primary bath with optional freestanding tub and walk-in closet.Bedrooms 2 and 3 with en suite bathrooms

    K. Hovnanian Homes Builder
    29434 Dutchmans Ln Unit 37862401, Easton, MD 21601
  • /14

    $565,000

    • 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
  • /19

    $279,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,798 Sq Ft

    Devonshire Front Load Garage Plan at Lakeside at Trappe - Townhomes, Trappe, MD 21673

    This new townhome offers three stories of elegant living and entertainment space. Beyond the foyer is a recreation room that provides numerous possibilities, along with a convenient garage. The open-concept main level features a central kitchen with a dining area and a welcoming family room. The topmost level includes two-bedroom suites located at opposite ends of the hallway, each with an

    Lennar Builder
    1258 Lake Michigan Unit 36949728, Trappe, MD 21673
  • /19

    $366,540

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,600 Sq Ft

    1690 Lake Placid Dr, Trappe, MD 21673

    This newly built two-story home offers an expansive open-concept main level, where the kitchen, living, and dining areas come together to create a seamless and flexible living space. Upstairs, two secondary bedrooms and a luxurious owner’s suite are thoughtfully positioned around a versatile loft, ideal for a variety of uses. A two-car garage adds both convenience and functionality to complete

    Lennar Builder
    1690 Lake Placid Dr, Trappe, MD 21673
  • /4

    $309,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,254 Sq Ft

    Elmwood Front Load Garage Plan at Lakeside at Trappe - Townhomes, Trappe, MD 21673

    This three-story home features a first-floor a recreation room, ideal for entertaining guests, with access to an outdoor space. Upstairs is an open layout shared among the kitchen, dining area and Great Room, creating the perfect space for hosting special gatherings. On the top floor are two secondary bedrooms, along with the luxe owner’s suite with an en-suite bathroom and walk-in closet.

    Lennar Builder
    1258 Lake Michigan Unit 36949687, Trappe, MD 21673
  • /47

    $559,000

    $16K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,548 Sq Ft

    28642 Clubhouse Dr, Easton, MD 21601

    Discover this inviting home in The Easton Club along the desirable Oxford Corridor. Photos coming soon. Welcome to a beautifully designed two‐level residence in the sought‐after Easton Club community. Built in 1995, this home blends timeless style with an open, light‐filled layout that offers both comfort and flexibility. The main level features a spacious primary suite with a luxury en suite

    Jana Meredith Meredith Fine Properties

    28642 Clubhouse Dr, Easton, MD 21601
  • /25

    $399,990

    New Construction
    • 4 Beds
    • 3 Baths
    • 2,170 Sq Ft

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

    This new two-story home has a smart layout that offers ample space and functionality. The first floor is occupied by the living area, which includes an open Great Room, dining room and kitchen. A bedroom on the same level can be used as a home office. The three remaining bedrooms are tucked away upstairs to ensure better privacy and center around a versatile loft. The spacious owner’s suite comes

    Lennar Builder
    1258 Lake Michigan Unit 36949708, Trappe, MD 21673
  • /14

    $639,990

    New Construction $30K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,493 Sq Ft

    29405 Jobes St, Easton, MD 21601

    Home office with sliding doors off the foyer.Great room & dining area connect by striking vaulted ceiling.Elegant fireplace with hearth adds charm to the great room.Kitchen with Ash Grey cabinetry & pendant lights.Screened patio extends living space outdoors.Primary suite & private bath with dual freestanding vanities.Attached 3-car garage for added storage & parking.

    K. Hovnanian Homes Builder
    29405 Jobes St, Easton, MD 21601
  • /41

    $399,900

    $35K PRICE DROP
    • 4 Beds
    • 2.5 Baths
    • 2,700 Sq Ft

    29181 Superior Cir, Easton, MD 21601

    Significant price improvement 5/18/26! Spacious four bedroom 2700+ fsf end unit town home in Easton's prized Lakelands subdivision 5 minutes from downtown and all its' amenities. New roof 2025, granite kitchen with stainless appliances,1st floor primary suite with private bath & large walk-in closet, living room w/fireplace, dining, area, powder room, 1st floor light filled den/office, two car

    Janet Larson Benson & Mangold, LLC

    29181 Superior Cir, Easton, MD 21601
  • /13

    $502,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,939 Sq Ft

    Bogart Plan at Four Seasons at Easton, Easton, MD 21601

    Extended foyer leading into heart of the home: the great room and dining area, featuring vaulted ceiling and access to covered patio.Stunning kitchen with island, plenty of counter space, and large walk-in pantry.Serene primary suite with private bath and spacious walk-in closet.HovHall off laundry room connecting foyer to 2-car garage.

    K. Hovnanian Homes Builder
    29434 Dutchmans Ln Unit 37862405, Easton, MD 21601
  • /57

    $489,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,523 Sq Ft

    1553 Lake Tahoe Dr, Trappe, MD 21673

    Brande New Single Level Matisse is now Ready for Move In at Lakeside at Trappe! This home is highlighted by impressive 10-foot ceilings throughout. The kitchen is designed with white and grey cabinets, Carrara Morro quartz countertops, a gourmet stainless steel appliance package and opens to the family room and dining area which leads to the rear screened porch.The primary suite offers a

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    1553 Lake Tahoe Dr, Trappe, MD 21673
  • /49

    $385,000

    • 3 Beds
    • 2.5 Baths
    • 2,520 Sq Ft

    29049 Superior Cir, Easton, MD 21601

    Welcome home to Lakelands! This beautifully maintained townhome offers an impressive 2,520 square feet of living space, featuring an open-concept floor plan designed for comfortable everyday living and entertaining. The spacious main-level primary suite includes a large walk-in closet, while the inviting second floor loft provides the perfect space to relax, read, or enjoy hobbies. You'll also

    Rick Parreco RE/MAX Executive

    29049 Superior Cir, Easton, MD 21601
  • /58

    $2,175,000

    • 4 Beds
    • 4 Baths
    • 2,741 Sq Ft

    7272 Waverly Island Rd, Easton, MD 21601

    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

    Barbara Watkins Benson & Mangold, LLC

    7272 Waverly Island Rd, Easton, MD 21601
  • /50

    $1,150,000

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

    21477 Island Club Rd, Tilghman, MD 21671

    PRICE IMPROVEMENT*** 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

    Cheri Bruce-Phipps TTR Sotheby's International Realty

    21477 Island Club Rd, Tilghman, MD 21671
  • /91

    $8,750,000

    $50K PRICE DROP
    • 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
  • /34

    $599,990

    New Construction $60K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    29339 Blackiston St, Easton, MD 21601

    Beautiful kitchen with Chestnut Brown cabinetry & quartz countertops.Inviting great room featuring cozy fireplace & stained ceiling beams.Serene primary suite with stylish feature wall.Refreshing primary bath with dual vanities & matte black finishes.Private Extra Suite for overnight guests.Functional laundry room with washer & dryer included.Peaceful screened patio for

    K. Hovnanian Homes Builder
    29339 Blackiston St, Easton, MD 21601
  • /51

    $492,440

    New Construction $40K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 2,340 Sq Ft

    231 Silver Lake Ln, Trappe, MD 21673

    Brand‐new Torrington with a main‐level primary bedroom—now under construction and available for a fall move‐in!This thoughtfully designed home offers 4 bedrooms and 3.5 bathrooms and presents a rare opportunity to personalize your interior selections while construction is underway. Choose your own cabinetry, countertops, and flooring and create a home that truly reflects your style.The

    Elizabeth Ellis Brookfield Mid-Atlantic Brokerage, LLC

    231 Silver Lake Ln, Trappe, MD 21673
  • /25

    $479,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 1,570 Sq Ft

    29474 Mason Ln, Easton, MD 21601

    Kitchen with Ash Grey cabinetry & quartz central island for prep & hosting.Great room & dining area with stunning ceiling treatment.Fireplace creates a cozy focal point in the great room.Screened patio for quiet mornings or evening unwind.Primary bath with dual sinks & luxe shower for a spa-like touch.Two-car garage with space for vehicles & everyday essentials.

    K. Hovnanian Homes Builder
    29474 Mason Ln, Easton, MD 21601
  • /24

    $799,000

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,413 Sq Ft

    Lot 119 Easton Village Dr, Easton, MD 21601

    Carrigan Homes introduces our newest model, the “Talbot II”, a 2400 sqft 3 bedroom, 2.5 bath customhome with a 1st floor primary suite, gourmet kitchen, 2nd floor bonus family room and oversized garage.This home is packed with generous standard and energy-saving features, and is to be built on one of the last remaining lots in Easton Village. Buy now, make every selection and color choice and

    Melissa Tippett TTR Sotheby's International Realty

    Lot 119 Easton Village Dr, Easton, MD 21601
  • /42

    $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
  • /3

    $369,390

    New Construction
    • 3 Beds
    • 2 Baths
    • 2,254 Sq Ft

    1418 Lake Geneva Dr, Trappe, MD 21673

    This three-story home features a first-floor a recreation room, ideal for entertaining guests, with access to an outdoor space. Upstairs is an open layout shared among the kitchen, dining area and Great Room, creating the perfect space for hosting special gatherings. On the top floor are two secondary bedrooms, along with the luxe owner’s suite with an en-suite bathroom and walk-in closet.

    Lennar Builder
    1418 Lake Geneva Dr, Trappe, MD 21673
  • /47

    $724,900

    • 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
  • /19

    $369,490

    New Construction $7K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    1469 Lake George Ln, Trappe, MD 21673

    This new two-story home is host to a spacious and flexible open-concept layout on the first floor, blending the kitchen, living and dining areas to maximize interior space. On the second level, two bedrooms and a luxurious owner’s suite surround a versatile and inviting loft. A two-car garage completes the home.

    Lennar Builder
    1469 Lake George Ln, Trappe, MD 21673
  • /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
  • /49

    $499,888

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,710 Sq Ft

    5654 Trafalgar Cir, Tilghman, MD 21671

    Kim Crouch Ozman Benson & Mangold, LLC

    5654 Trafalgar Cir, Tilghman, MD 21671
  • /22

    $359,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

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

    This new two-story home is host to a spacious and flexible open-concept layout on the first floor, blending the kitchen, living and dining areas to maximize interior space. On the second level, two bedrooms and a luxurious owner’s suite surround a versatile and inviting loft. A two-car garage completes the home.

    Lennar Builder
    1258 Lake Michigan Unit 36949695, Trappe, MD 21673
  • /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 115-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
  • /60

    $8,495,000

    • 6 Beds
    • 11 Baths
    • 17,402 Sq Ft

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663

    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,

    Doc Keane Washington Fine Properties, LLC

    8620 Bozman Neavitt Rd, Saint Michaels, MD 21663
  • /43

    $2,595,000

    • 4 Beds
    • 3.5 Baths
    • 3,345 Sq Ft

    3770 Leonard Cove Ln, Trappe, MD 21673

    Timeless Tidewater Colonial-inspired waterfront estate set on 3.5± private acres with 870± feet of shoreline and panoramic water views. A rare offering combining classic architecture, thoughtful upgrades and exceptional outdoor living in one of Talbot County’s most desirable waterfront settings, with a seamless indoor-outdoor flow and water views from nearly every room. Featured in Coastal

    Kathy Christensen TTR Sotheby's International Realty

    3770 Leonard Cove Ln, Trappe, MD 21673
  • /16

    $399,990

    New Construction
    • 3 Beds
    • 2 Baths
    • 1,385 Sq Ft

    29500 Cromwell Ln, Easton, MD 21601

    Welcome to the Pacifica II, a thoughtfully designed 1,385 sq. ft. home offering 2 bedrooms, 2 bathrooms, and a 2-car garage. The lovely kitchen flows seamlessly into the airy dining area and spacious great room, with access to the covered patio—perfect for indoor-outdoor living. A secluded primary suite features a beautiful private bath and walk-in closet, providing a true retreat. At the front

    Mary Anne Kowalewski KOVO Realty

    29500 Cromwell Ln, Easton, MD 21601
  • /108

    $6,995,000

    • 7 Beds
    • 5.5 Baths
    • 8,478 Sq Ft

    24390 Deep Neck Farm Ln, Royal Oak, MD 21662

    Welcome to Deep Neck Farm Lane, a stately waterfront farm overlooking Broad Creek with sweeping west and southwest views that stretch over the Choptank River to the Western Shore. This extraordinary estate captures dramatic sunsets, summer breezes, and shelter from northern winds, all from an unrivaled vantage point. Built in 2006 by a builder for their family, the 8,500± square foot residence

    Coard Benson Benson & Mangold, LLC

    24390 Deep Neck Farm Ln, Royal Oak, MD 21662
  • /103

    $2,449,000

    Open Sat 11AM - 1PM
    • 4 Beds
    • 4.5 Baths
    • 3,300 Sq Ft

    962 San Domingo Ct, Saint Michaels, MD 21663

    This exquisite in-town St. Michaels coastal-style waterfront is a designer’s dream home. The 3,300 sq, ft. residence shows like a new model home with an unparalleled quality of finishes and level of design. Located in desirable San Domingo Cove, the community enjoys protected natural open space, beautiful water features and immediate access to the ever-popular St. Michaels Nature Trail offering

    Eugene Smith TTR Sotheby's International Realty

    962 San Domingo Ct, Saint Michaels, MD 21663
  • /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

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