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Kent Island, MD Homes for Sale

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  • /2

    $495,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 1,580 Sq Ft

    107 Trequassin Dr, Stevensville, MD 21666

    Welcome to 107 Trequassin Dr in the sought-after Kent Island community of Stevensville, Maryland—a spacious and well-appointed 4-bedroom, 3-bathroom home offering comfort, flexibility, and coastal charm. Nestled in a water-oriented community on Kent Island, this home offers the perfect blend of relaxed coastal living and everyday convenience. This thoughtfully designed home features a versatile

    Christine Leonard Redfin Corp

    107 Trequassin Dr, Stevensville, MD 21666
  • /13

    $770,000

    Coming Soon
    • 3 Beds
    • 2.5 Baths

    212 Switchgrass Way Unit 34, Chester, MD 21619

    Professional photos coming! Experience elevated Eastern Shore living in this beautifully appointed corner residence overlooking the Chester River in the sought-after 55+ waterfront community of K. Hovnanian’s Four Seasons at Kent Island. Just one year old and impeccably maintained, this spacious three-bedroom, two-and-a-half-bath home offers more than 2,600 square feet of upscale living with the

    Jennifer Thomas RE/MAX Executive

    212 Switchgrass Way Unit 34, Chester, MD 21619
  • /2

    $459,000

    Coming Soon
    • 4 Beds
    • 3 Baths
    • 1,800 Sq Ft

    708 Dixon Dr, Stevensville, MD 21666

    Coming soon in the desirable Cloverfields community! This spacious four-bedroom, three-bath split foyer home offers an open-concept living area with durable vinyl plank flooring throughout the living room, dining room, and kitchen—perfect for everyday living and entertaining. The upper level features three comfortable bedrooms, including a primary suite with a private bath, all with cozy

    Deborah Shiley Long & Foster Real Estate, Inc.

    708 Dixon Dr, Stevensville, MD 21666
  • /52

    $839,000

    $36K PRICE DROP
    • 5 Beds
    • 3 Baths
    • 2,970 Sq Ft

    111 Holly Ct, Stevensville, MD 21666

    Perfectly situated in the sought-after community of Queen Anne Colony, this exceptional home backs to the Executive Golf Course and is just a short walk to the Cross Island Trail. Inside, you will find numerous upgrades, including beautifully renovated bathrooms and a stunning oversized kitchen with a large center island. The quaint living room is full of character, featuring a stacked-stone

    Dee Dee McCracken Coldwell Banker Realty

    111 Holly Ct, Stevensville, MD 21666
  • /45

    $945,000

    $50K PRICE DROP
    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

    Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • /44

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    200 Harrier Way Unit 21, Chester, MD 21619

    Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile

    shannon Gompers Long & Foster Real Estate, Inc.

    200 Harrier Way Unit 21, Chester, MD 21619
  • /61

    $780,000

    • 4 Beds
    • 2.5 Baths
    • 2,111 Sq Ft

    407 Five Farms Dr, Stevensville, MD 21666

    Welcome to Kent Island luxury living in the sought-after community Queen Anne Colony. This home is where major upgrades, high-end finishes, and effortless coastal lifestyle come together. From the moment you arrive, you’ll notice the peace of mind that comes with big-ticket updates already DONE. With over 2100 sq ft, a new roof (2023), siding (2026), garage door (2025), water heater & softener

    Crystal Smith RE/MAX Executive

    407 Five Farms Dr, Stevensville, MD 21666
  • /64

    $470,000

    $35K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,698 Sq Ft

    132 Pennick Dr, Stevensville, MD 21666

    Welcome to 132 Pennick Drive in Stevensville, where easy one-level living meets the relaxed charm of a water-oriented community. This lovely rancher offers a thoughtful layout with two spacious bedrooms featuring their own ensuite bathrooms, plus a third bedroom and a full hallway bath, giving everyone their own space and comfort. Inside, you will find beautiful hardwood and luxury vinyl plank

    Ruth Anne Strauss Hyatt & Company Real Estate, LLC

    132 Pennick Dr, Stevensville, MD 21666
  • /32

    $434,900

    $24K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    208 Blenny Ln Unit 100, Chester, MD 21619

    PRICE REDUCTION! Just like NEW! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully refreshed from top to bottom! Step inside to find the main level that boasts new carpet and new LVP flooring, a new half bath, new paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home

    Pamela Ackermann-Doll RE/MAX Executive

    208 Blenny Ln Unit 100, Chester, MD 21619
  • /33

    $239,900

    • 3 Beds
    • 2 Baths
    • 949 Sq Ft

    1603 Marion Quimby Dr, Stevensville, MD 21666

    Rarely available first floor condominium centrally located on Kent Island and in the Thompson Creek Community. Enjoy all the amenities of this water access community including the pool, tennis courts, clubhouse, and within a short walking distance to the water where you sit in a quiet community of proud homeowners. As you arrive, you will notice the peace and tranquility this community offers.

    Daniel Register Northrop Realty

    1603 Marion Quimby Dr, Stevensville, MD 21666
  • /81

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    190 Harrier Way Unit 24, Chester, MD 21619

    Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 square feet of comfort, space, and resort-style amenities. The open living, dining, and kitchen layout is ideal for everyday living and entertaining.Enjoy peaceful views of three ponds from the beautiful porch, with limited views of the Chester River. The kitchen features 42-inch cabinets, white quartz

    Dee Dee McCracken Coldwell Banker Realty

    190 Harrier Way Unit 24, Chester, MD 21619
  • /73

    $712,000

    $38K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,870 Sq Ft

    266 Peregrine Dr, Stevensville, MD 21666

    Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner and priced well below the new construction models. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this

    Edward Beres RE/MAX Executive

    266 Peregrine Dr, Stevensville, MD 21666
  • /45

    $2,375,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 3,280 Sq Ft

    107 Petrie Way, Stevensville, MD 21666

    Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along

    Brad Kappel TTR Sotheby's International Realty

    107 Petrie Way, Stevensville, MD 21666
  • /25

    $825,000

    • 3 Beds
    • 2.5 Baths
    • 2,170 Sq Ft

    10554 Miracle House Cir, Claiborne, MD 21624

    Quality construction throughout. This Custom Coastal Home has all the bells and whistles ..... hardwood cherry floors, masonry fireplace, 1st floor primary suite, double porches to enjoy the sunsets over Eastern Bay. Gourmet kitchen with stainless steel appliances. Two screened in porches for dining or sleeping. Very private with professional landscaping. Easy walk to Claiborne boat ramp, beach

    Dawn Lednum Chesapeake Bay Real Estate Plus, LLC

    10554 Miracle House Cir, Claiborne, MD 21624
  • /13

    $819,990

    New Construction $52K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    711 Warbler Way, Chester, MD 21619

    Beautiful kitchen with white cabinetry & glass-front uppers.Vast island & countertops for preparing meals.Elegant dining area for hosting special dinners.Incredible great room featuring stunning fireplace.Serene primary suite with gorgeous ceiling moulding.Lavish primary bath featuring freestanding white vanities.Screened patio off the great room extends living space

    K. Hovnanian Homes Builder
    711 Warbler Way, Chester, MD 21619
  • /16

    $859,990

    New Construction $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft

    719 Warbler Way, Chester, MD 21619

    Polished kitchen with white cabinets & glass-front uppers.Vast island & quartz countertops for prep & dining.Welcoming great room featuring elegant fireplace.Screened patio with direct access to the great room.Charming dining area for mealtime enjoyment.Lavish primary suite & bath with dual vanities & feature wall.Private home office for leisure activities.

    K. Hovnanian Homes Builder
    719 Warbler Way, Chester, MD 21619
  • /38

    $809,990

    New Construction $30K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    711 Warbler Way, Stevensville, MD 21666

    Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the

    Mary Anne Kowalewski KOVO Realty

    711 Warbler Way, Stevensville, MD 21666
  • /27

    $439,900

    • 3 Beds
    • 2 Baths
    • 1,248 Sq Ft

    1340 Queen Anne Dr, Chester, MD 21619

    PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • /17

    $110,000

    • Land
    • 16,988 Sq Ft
    • $282,051 per Acre

    0 Ackerman Dr, 4, Kent Island, MD 21666

    Wooded lot on Ackerman Drive! The community of Romancoke on the Bay featuers water access, boat ramp. beach and club house nearby.

    Jen Holden Compass

    0 Ackerman Dr, 4, Kent Island, MD 21666
  • /45

    $2,375,000

    New Construction
    • 4 Beds
    • 4 Baths
    • 3,280 Sq Ft

    119 Petrie Way, Stevensville, MD 21666

    Welcome to Sunset Wharf, a refined waterfront enclave set within the picturesque Bay Bridge Marina, where coastal living is defined by sweeping views and effortless sophistication. This fully completed residence is one of just a select offering within the initial collection of three buildings, each thoughtfully designed with only two residences each, creating an intimate and private setting along

    Brad Kappel TTR Sotheby's International Realty

    119 Petrie Way, Stevensville, MD 21666
  • /51

    $949,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    540 Warbler Way, Stevensville, MD 21666

    Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened

    Mary Anne Kowalewski KOVO Realty

    540 Warbler Way, Stevensville, MD 21666
  • /41

    $464,900

    $35K PRICE DROP
    • 4 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    *PRICE IMPROVEMENT!* Welcome to this beautifully renovated ranch-style home offering 4 bedrooms, 2 full bathrooms, and a spacious open floor plan designed for modern living. Completely remodeled from top to bottom, this move-in ready property combines style, comfort, and functionality in every detail. The stunning kitchen features sleek quartz countertops, stainless steel appliances, and a large

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • /57

    $723,400

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,210 Sq Ft

    109 Placek's Ln, Stevensville, MD 21666

    One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs

    George Bailey Keller Williams Flagship

    109 Placek's Ln, Stevensville, MD 21666
  • /102

    $529,900

    $9K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    111 Marshgrass Way Unit 22, Chester, MD 21619

    Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart

    Sharon Blaszczak Long & Foster Real Estate, Inc.

    111 Marshgrass Way Unit 22, Chester, MD 21619
  • /52

    $829,990

    New Construction $20K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 2933, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office

    Mary Anne Kowalewski KOVO Realty

    102 Boatswain Way Unit 2933, Chester, MD 21619
  • /106

    $749,000

    • 3 Beds
    • 2 Baths
    • 2,230 Sq Ft

    301 Penny Dr, Stevensville, MD 21666

    Welcome to refined coastal living in the highly sought-after Cove Creek Club on Kent Island. Situated on approximately one acre, this beautifully maintained 3-bedroom, 2-bath home offers space, comfort, and an effortless Eastern Shore lifestyle. Upon entry, you’re greeted by a formal living room, while a second living area flows seamlessly into the open-concept kitchen and dining space, perfect

    Jarnell Foster Benson & Mangold, LLC

    301 Penny Dr, Stevensville, MD 21666
  • /49

    $464,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    1906 Stevens Dr, Chester, MD 21619

    Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfortable one-level living. This versatile layout features 3 bedrooms and 2 full baths, including a large bonus room that can easily function as a fourth bedroom, home office, or second living area. A welcoming front porch sets the tone, while the screened back porch provides the perfect space to relax or

    Terri Murray RE/MAX Executive

    1906 Stevens Dr, Chester, MD 21619
  • /12

    $629,990

    New Construction $34K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study. Gourmet kitchen with central island at the heart of the home. Dining area with dry bar for easy entertaining. Great room with electric fireplace for a cozy focal point. Patio off the great room with direct access to the owner's suite. Owner's suite with dual closets for added storage. Owner's bath with dual sinks & glass shower enclosure. Bedroom 2

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • /64

    $1,167,890

    New Construction
    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

    *****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • /40

    $475,000

    • 3 Beds
    • 2.5 Baths
    • 1,728 Sq Ft

    1916 Stevens Dr, Chester, MD 21619

    Now offered at a new and improved price, this beautifully updated and meticulously maintained home delivers exceptional value in the highly desirable Harbor View community—just two miles east of the Chesapeake Bay Bridge. Set on a picturesque 0.35‐acre corner lot, this 3‐bedroom, 2 full and 1 half bath home blends comfort, quality, and an unbeatable location.Inside, you’ll love the bright,

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • /49

    $949,900

    New Construction $15K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    307 Columbia Ln, Stevensville, MD 21666

    Luxurious new construction that must be seen to be fully appreciated! This thoughtfully designed home showcases exceptional craftsmanship and high-end finishes throughout. A bluestone walkway and inviting front porch set the tone, complemented by durable Hardiplank siding. Inside, you’ll find soaring 10’ ceilings, impressive 8’ doors, and custom trim work that elevates every space. The gourmet

    DJ Dauses Coldwell Banker Waterman Realty

    307 Columbia Ln, Stevensville, MD 21666
  • /13

    $969,000

    New Construction
    • 4 Beds
    • 2.5 Baths
    • 2,656 Sq Ft

    416 5 Farms Dr, Stevensville, MD 21666

    STUNNING NEW CONSTRUCTION – Experience the pinnacle of modern luxury in this exquisite "Farmhouse Chic" masterpiece, perfectly situated in a highly coveted Kent Island community near the shores of the Chesapeake Bay. Offering over 2,600 square feet of meticulously crafted living space, this residence features 4 spacious bedrooms, 2.5 designer baths, and a versatile retreat living space tailored

    Joanna Dalton Coldwell Banker Realty

    416 5 Farms Dr, Stevensville, MD 21666
  • /2

    $849,000

    Open House 5/30 Coming Soon
    • 3 Beds
    • 3.5 Baths
    • 3,570 Sq Ft

    10494 Rich Neck Rd, Claiborne, MD 21624

    PICTURES COMING SOON! Built in the early 1900s and thoughtfully renovated over the past 20 years, this charming home beautifully combines historic character with modern amenities. Situated on a half-acre lot, the property features 3 bedrooms with the potential for a 4th bedroom, along with 3.5 bathrooms. Each bedroom includes its own private bath, and the bedrooms offer access to relaxing

    Laurie Renshaw Coldwell Banker Chesapeake Real Estate Company

    10494 Rich Neck Rd, Claiborne, MD 21624
  • /21

    $969,990

    New Construction $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • /46

    $489,000

    $11K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,072 Sq Ft

    117 Bay Dr, Stevensville, MD 21666

    PRICE REDUCED $10,000 and a NEW 50 YEAR WARRANTY ROOF JUST INSTALLED. Welcome to your new home in one of Stevensville’s water-oriented communities. This 3-bedroom, 3-bath home has much to offer. Additional unfinished space to add up to 2 additional bedrooms. The spacious living areas are perfect for entertaining. Lower-level family room with fireplace and wet bar. Also, an indoor hot tub.

    Jeff Bridegum RE/MAX One

    117 Bay Dr, Stevensville, MD 21666
  • /35

    $829,990

    New Construction $35K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island. Spacious great room featuring electric fireplace. Charming dining area with dry bar for efficient serving. Serene owner's suite & spa bath with frameless shower door. Convenient home office for working remotely. Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • /62

    $459,900

    • 3 Beds
    • 2 Baths
    • 1,548 Sq Ft

    109 Birch Rd, Stevensville, MD 21666

    Welcome to this beautifully renovated and remodeled 3-bedroom, 2-bath home offering the perfect blend of modern style, comfort, and location. Designed with today’s lifestyle in mind, this home features a bright open floor plan with spacious living and dining areas that flow seamlessly into the stunning gourmet kitchen. The kitchen is a true showstopper with elegant quartz countertops, a large

    Gregory Bennett Jr. Five Star Real Estate

    109 Birch Rd, Stevensville, MD 21666
  • /28

    $971,395

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

    540 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry & glass-front uppers.Vast center island, perfect for prepping family meals.Stunning fireplace adds character & warmth to spacious great room.Lavish primary suite & bath featuring bath barn door.Secluded Extra Suite for overnight guests.Functional home office for leisure activities.Cozy screened patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    540 Warbler Way, Chester, MD 21619
  • /11

    $774,990

    New Construction
    • 2 Beds
    • 2 Baths
    • 2,143 Sq Ft

    Kelly Plan at Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private home office for working from home. Spacious great room with slider to covered patio. Beautiful kitchen with large island and roomy pantry. Luxurious primary suite with triple windows. Relaxing primary bath with spacious shower and walk-in closet. Convenient covered patio with screen patio option.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • /59

    $624,900

    • 3 Beds
    • 3 Baths
    • 2,074 Sq Ft

    222 Moorings Cir Unit 126, Stevensville, MD 21666

    Welcome home to refined coastal living on Maryland’s Eastern Shore in this beautifully designed 3-bedroom, 3-bath home located in the premier 55+ community of Bay Bridge Cove in Stevensville, Maryland.This lovely and well-maintained home was built in 2022 and offers 2,074 square feet over two levels. The home blends light-filled spaces with effortless, low-maintenance living just minutes from

    Terri Kulp Coldwell Banker Chesapeake Real Estate Company

    222 Moorings Cir Unit 126, Stevensville, MD 21666

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