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Homes for Sale in 21666

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  • /31

    $790,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 32, Chester, MD 21619

    Gourmet kitchen with central island for prep & dining. Home office with double doors adds privacy & style. Dining area enhanced by a convenient dry bar. Great room centered around an electric fireplace. Balcony extends living space off the great room. Owner’s suite with private balcony access for relaxation. Spa-like owner’s bath with dual sinks & sleek finishes.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 32, Chester, MD 21619
  • /19

    $979,990 New Construction

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

    110 Boatswain Way Unit 34, Chester, MD 21619

    Gourmet kitchen with spacious central island. Convenient dry bar in dining area makes hosting easy. Great room features an electric fireplace. Balcony extends off of the great room. Owner’s suite with dual walk-in closets. Private sitting room with balcony access. Luxurious owner’s bath with dual sinks.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 34, Chester, MD 21619
  • /31

    $789,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Exquisite dining area with dry bar, perfect for entertaining. Gorgeous great room with cozy electric fireplace. Sophisticated owner's suite with triple windows. Stunning owner's spa bath featuring split vanities. Beautiful balcony has access through primary suite & great room.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 33, Chester, MD 21619
  • /18

    $929,990 New Construction

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

    110 Boatswain Way Unit 31, Chester, MD 21619

    Home office with double doors for privacy. Great room with an electric fireplace for warmth & charm. Large central island anchors the gourmet kitchen. Dry bar in dining area creates a perfect hosting space. Owner’s suite with a serene sitting room & balcony access. Dual walk-in closets for organized living. Owner’s bath with sleek dual sinks & spacious layout.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 31, Chester, MD 21619
  • /18

    $829,990 New Construction

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

    110 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island. Dining area includes a convenient dry bar. Great room features an electric fireplace. Beautiful balcony extends off of the great room. Owner’s suite with dual walk-in closets. Private sitting room with balcony access. Luxurious owner’s bath with dual sinks.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 21, Chester, MD 21619
  • /18

    $675,000 Coming Soon

    • 3 Beds
    • 3 Baths
    • 2,306 Sq Ft

    440 Moorings Cir, Stevensville, MD 21666

    OPEN SATURDAY & SUNDAY, FEB 14 & 15, 1:00–3:00! AVAILABLE FOR SHOWINGS STARTING FEBRUARY 13! Welcome to Bay Bridge Cove, a premier 55+ community on beautiful Kent Island. This sought-after Laurel model sits on a premier lot and offers the largest floor plan in the community, filled with natural light from a wall of exterior windows. Upgrades include an expanded layout with over 2,700 square feet,

    Deborah Laggini Long & Foster Real Estate, Inc.

    440 Moorings Cir, Stevensville, MD 21666
  • /46

    $689,900

    • 3 Beds
    • 3 Baths
    • 2,284 Sq Ft

    222 Topside Dr, Stevensville, MD 21666

    Welcome to effortless Eastern Shore living in this beautifully appointed 3-bedroom, 3-bath Oxford model, located in one of Kent Island’s premier and coveted active adult communities, Bay Bridge Cove. Perfectly positioned on a large, premium lot, this home offers a low-maintenance lifestyle paired with thoughtful upgrades, flexible living spaces, and access to outstanding community amenities.

    DJ Dauses Coldwell Banker Waterman Realty

    222 Topside Dr, Stevensville, MD 21666
  • /2

    $525,000 Coming Soon

    • 5 Beds
    • 3 Baths
    • 1,908 Sq Ft

    610 Elm St, Stevensville, MD 21666

    Eduardo Martinez Daboud Homeview Real Estate

    610 Elm St, Stevensville, MD 21666
  • /48

    $519,000

    • 5 Beds
    • 3 Baths
    • 1,080 Sq Ft

    200 Orchid St, Stevensville, MD 21666

    Beautiful recently updated home offering just over 2,000 sq ft of living space. This unique setup offers a living area on both levels, each with its own Kitchen and Full Bath and Bedrooms for a total of Five. Great for those who have inlaws, elderly parents or any other additional needs. You could even rent out a level and let them help pay your mortgage. A super large deck with a spot view of

    Michael Rosendale Rosendale Realty

    200 Orchid St, Stevensville, MD 21666
  • /6

    $439,000

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

    211 State St, Stevensville, MD 21666

    Situated in Stevensville; this beautiful Cape Cod, 3 bed, 2 bath, 1248 sq ft home is located in a community known for its convenient access to shopping, parks, schools, and local amenities. This home combines neighborhood charm with practical convenience. Easy commuting to nearby Annapolis, Kent Island, and the Chesapeake Bay area adds to the appeal. Whether you’re looking for a move-in-ready

    Jarnell Foster Benson & Mangold, LLC

    211 State St, Stevensville, MD 21666
  • /30

    $849,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 33, Chester, MD 21619

    Gourmet kitchen with central island for prep & gathering. Home office with French doors for focused work. Dining area with built-in dry bar for easy entertaining. Great room with fireplace as a cozy focal point. Balcony off the great room extends living space outdoors. Owner’s suite with spacious walk-in closet. Owner’s spa bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 33, Chester, MD 21619
  • /9

    $679,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    176 Flagstaff Way Unit 12, Chester, MD 21619

    Welcoming foyer leads to open concept living spaces. Efficient gourmet kitchen featuring designer cabinetry & wall oven. Vast center island overlooking dining area with dry bar. Electric fireplace adds warmth & character to great room. Private owner's suite for rest & relaxation. Pristine owner's spa bath featuring framless shower door. Organized home office with lited double doors. Versatile

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 12, Chester, MD 21619
  • /31

    $999,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 43, Chester, MD 21619

    Central island anchors the gourmet kitchen for everyday use. Home office with lited French doors add character. Dining area includes a convenient dry bar for hosting. Fireplace highlights the great room’s inviting design. Private balcony off the great room for outdoor relaxation. Owner’s suite features a generous walk-in closet. Spa-inspired owner’s bath with dual sinks & glass-enclosed shower.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 43, Chester, MD 21619
  • /9

    $649,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    176 Flagstaff Way Unit 11, Chester, MD 21619

    Gourmet kitchen featuring designer cabinetry & center island. Spacious great room with electric fireplace. Inviting dining area featuring lovely dry bar. Pristine owner's suite & spa bath with walk-in closet. Versatile outdoor patio, perfect for spending time with friends. Productive home office with lited double doors. Functional laundry room for added convenience.

    K. Hovnanian Homes Builder
    176 Flagstaff Way Unit 11, Chester, MD 21619
  • /48

    $1,069,000 Open Sat 12PM - 2PM

    • 5 Beds
    • 3.5 Baths
    • 2,600 Sq Ft

    101 Beachside Dr, Stevensville, MD 21666

    NOW, Priced 50K below recent Appraisal! Owner has found home of choice, please bring offers. You can install new bulkhead and fishing pier. Boat ramp is directly across the street. Nantucket meets the Bay in this 5 bedrooms, 3.5 baths Carriage style home. The Coastal charmer has views from nearly every room, with the house wrapping around both creek and bay views. Recent improvements include true

    Candice Friday Coastal Realty Maryland

    101 Beachside Dr, Stevensville, MD 21666
  • /10

    $275,000

    • Land
    • 0.56 Acre
    • $491,071 per Acre

    346 Oregon Rd, Stevensville, MD 21666

    This is a wonderful, shaded lot offering over a quarter acre and incredible views of Price Creek and the Chesapeake Bay, and a 2 minute walk to the community beach on public sewer. This is listed and offered individually along with two other adjoining lots listed at $205,000 and $249,000 to make three awesome Kent island building sites in a row. If you walk these lots, you will want them ALL !!

    Michael Rosendale Rosendale Realty

    346 Oregon Rd, Stevensville, MD 21666
  • /20

    $205,000

    • Land
    • 0.28 Acre
    • $732,143 per Acre

    0 Bay Dr Unit MDQA2016060, Stevensville, MD 21666

    This is a wonderful shaded lot offering .26 acre and incredible views of Price Creek and the Chesapeake Bay, and a 2 minute walk to the community beach on public sewer. This is listed and offered individually along with two other adjoining lots listed at $249,000 and $275,000 to make three awesome Kent island building sites in a row. If you walk these lots, you will want them ALL !!

    Michael Rosendale Rosendale Realty

    0 Bay Dr Unit MDQA2016060, Stevensville, MD 21666
  • /20

    $329,999

    • 3 Beds
    • 1 Bath
    • 1,119 Sq Ft

    126 State St, Stevensville, MD 21666

    Located in the heart of Stevensville, this 3-bedroom, 1-bath rancher offers a prime opportunity for renovation, investment, or potential redevelopment. The property is within close distance to local schools, parks, and downtown Stevensville, and is approximately 1⁄2 mile from the Cross Island Trail, providing convenient access to miles of paved walking and biking paths across Kent Island.

    Jarnell Foster Benson & Mangold, LLC

    126 State St, Stevensville, MD 21666
  • /16

    $249,000

    • Land
    • 0.55 Acre
    • $452,727 per Acre

    0 Bay Dr Unit MDQA2016058, Stevensville, MD 21666

    This is a wonderful shaded lot offering over a HALF ACRE and incredible views of Price Creek and the Chesapeake Bay, and a 2 minute walk to the community beach on public sewer. This is listed and offered individually along with two other adjoining lots listed at $205,000 and $275,000 to make three awesome Kent island building sites in a row. If you walk these lots, you will want them ALL !! This

    Michael Rosendale Rosendale Realty

    0 Bay Dr Unit MDQA2016058, Stevensville, MD 21666
  • /25

    $999,990 New Construction

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

    141 Redstart Dr, Chester, MD 21619

    First-floor Extra Suite offers flexible guest accommodations. Home office with sliding barn doors adds charm. Kitchen with white stacked cabinetry & glass-front uppers. Fireplace anchors the great room as a warm focal point. Screened patio off the great room for relaxed outdoor living. Primary suite with decorative feature wall & ceiling treatment. Primary bath with dual freestanding vanities.

    K. Hovnanian Homes Builder
    141 Redstart Dr, Chester, MD 21619
  • /11

    $824,990 New Construction

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    259 Redstart Dr, Chester, MD 21619

    Kitchen with stacked white cabinetry & glass-front uppers. Great room with fireplace creates a warm focal point. Covered patio off the great room for outdoor living. Primary suite with ceiling treatment adds refined detail. Primary bath with dual freestanding vanities. Home office tucked away for quiet work time. Second-floor loft open to the great room below.

    K. Hovnanian Homes Builder
    259 Redstart Dr, Chester, MD 21619
  • /3

    $400,500 Coming Soon

    • 2 Beds
    • 2.5 Baths
    • 1,161 Sq Ft

    1205 Marion Quimby Dr, Stevensville, MD 21666

    100% Renovated:))Welcome to this *BEAUTIFUL RENOVATED* 2-bedroom, 2.5-bath townhome nestled in a desirable condo community on Kent Island.This fully updated home shines with thoughtful upgrades and modern touches throughout — including new storm doors, a 2025 heat pump, a new water heater, an upgraded electrical system, new blinds, a new Samsung washer and dryer, double-pane windows, and

    Rita Cordova Taylor Properties

    1205 Marion Quimby Dr, Stevensville, MD 21666
  • /21

    $2,788,000 Open House 2/28

    • 5 Beds
    • 8 Baths
    • 6,148 Sq Ft

    414 Bay Dr, Stevensville, MD 21666

    Designed by YSA Homes and Simply Wesley Interior Design of Annapolis, this extraordinary brand-new modern coastal farmhouse style smart-home offers over 6,148 square feet of thoughtfully designed living space, where every tile throughout the home was handpicked and expertly curated using top-of-the-line luxury selections. The kitchen is outfitted with premium, top-tier appliances including Wolf,

    Caroline Nowell Cummings & Co. Realtors

    414 Bay Dr, Stevensville, MD 21666
  • /9

    $479,000 Open House 2/15

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

    109 Carroll Rd, Stevensville, MD 21666

    KENT ISLAND - Nestled in charming Kent Island Estates, this delightful ranch-style home offers a perfect blend of comfort and modern living. With 1,800 sq. ft. of thoughtfully designed space, this residence features 3 spacious bedrooms and 2 full bathrooms, ideal for relaxation and privacy. The heart of the home is a welcoming combination kitchen and dining area, perfect for gatherings, while the

    Suzanne Hitt Coldwell Banker Waterman Realty

    109 Carroll Rd, Stevensville, MD 21666
  • /29

    $799,500 Open House 2/15

    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    528 Warbler Way, Stevensville, MD 21666

    Like-new luxury living in Four Seasons at Kent Island.Completed in August and only lightly lived in, this 2,800 sq ft home offers 4 bedrooms and 3 baths with a pristine, move-in-ready feel. Highlights include luxury vinyl plank flooring, quartz countertops, and over $20,000 in custom window treatments, can you say "plantation shutters". Professionally decorated throughout—with the option to

    Jennifer Thomas RE/MAX Executive

    528 Warbler Way, Stevensville, MD 21666
  • /10

    $375,000 Coming Soon

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    217 Ackerman Dr, Stevensville, MD 21666

    Gorgeous, move in ready rancher! Large double lot with detached building. LVP floors, white cabinets, freshly painted with large screened in porch. Get ready!

    Crystal Smith RE/MAX Executive

    217 Ackerman Dr, Stevensville, MD 21666
  • /43

    $445,000 Open Sun 1PM - 3PM

    • 3 Beds
    • 2 Baths
    • 1,604 Sq Ft

    515 Love Point Rd, Stevensville, MD 21666

    Open House canceled. Welcome to 515 Love Point Road — a beautifully renovated traditional-style home just steps from charming downtown Stevensville. This property seamlessly blends historic character with the confidence of modern construction and upgraded systems.The home features a brand-new kitchen with granite countertops and stainless-steel appliances, 3 spacious bedrooms, and 2 elegantly

    Alex Hodges Cottage Street Realty LLC

    515 Love Point Rd, Stevensville, MD 21666
  • /23

    $255,000 Open Sun 11AM - 1PM

    • 2 Beds
    • 1.5 Baths
    • 968 Sq Ft

    2 Mariners Way Unit 2, Stevensville, MD 21666

    This charming 2-bedroom, 1.5-bathroom townhouse offers a blend of modern comfort and community living. The interior features luxury vinyl plank and carpet and ceramic tile flooring in selected areas, complemented by a traditional floor plan. Enjoy cooking in the well-equipped kitchen with stainless steel appliances, including a dishwasher and microwave, and a convenient pantry. The main floor

    Agent Photo

    Deborah Shiley

    Long & Foster Real Estate, Inc.

    (410) 538-1240

    2 Mariners Way Unit 2, Stevensville, MD 21666
  • /30

    $275,900

    • 2 Beds
    • 1.5 Baths
    • 968 Sq Ft

    2 Mariners Way Unit 17-2, Stevensville, MD 21666

    This charming two-bedroom, one-and-a-half-bath townhouse is designed for comfortable everyday living within a friendly, family-oriented community setting. A thoughtfully designed traditional floor plan showcases engineered flooring, carpeting, and ceramic tile in select areas, creating a warm interior. The well-appointed kitchen features coordinating appliances, including a dishwasher and

    Kenny Smith Up-County Realty, Inc.

    2 Mariners Way Unit 17-2, Stevensville, MD 21666
  • /100

    $2,000,000

    • 5 Beds
    • 4.5 Baths
    • 4,182 Sq Ft

    122 Queen Anne Rd, Stevensville, MD 21666

    Fully gutted and exquisitely restored maintaining original brick exterior, then thoughtfully expanded in 2012-2013 by Blue Heron Contracting, this 18th-century waterfront estate offers sweeping, unobstructed views of Eastern Bay. Set on 1.3 acres in Kent Island Estates, this remarkable 1778 home blends historic character with refined modern upgrades. Reclaimed pine floors, four brick wood-burning

    Creig Northrop Northrop Realty

    122 Queen Anne Rd, Stevensville, MD 21666
  • /26

    $1,995,000

    • 3 Beds
    • 2.5 Baths
    • 3,216 Sq Ft

    301 John Kallis Ln, Stevensville, MD 21666

    Commanding an exceptional waterfront setting, this timeless historic property offers an increasingly rare opportunity to own a generational retreat defined by land, water, and view. Encompassing 35 acres and approximately 599 feet of shoreline, the property unfolds to a private beach and panoramic vistas across the Bay, where dramatic sunsets and iconic views of the Bay Bridge create a daily

    Brad Kappel TTR Sotheby's International Realty

    301 John Kallis Ln, Stevensville, MD 21666
  • /45

    $465,000

    • 3 Beds
    • 3 Baths
    • 1,419 Sq Ft

    932 Kimberly Way, Stevensville, MD 21666

    Welcome to this charming and beautifully updated rancher located in the sought-after, water-access community of Cloverfields. This thoughtfully renovated home offers three bedrooms and three full bathrooms, with tasteful updates throughout the remodeled kitchen, great room, and baths. The light-filled great room is a true centerpiece, featuring vaulted ceilings with exposed rafters and an

    Barbara McCaffrey Redfin Corp

    932 Kimberly Way, Stevensville, MD 21666
  • /52

    $849,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 2433, Chester, MD 21619

    The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2433, Chester, MD 21619
  • /52

    $999,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    176 Flagstaff Way Unit 2443, Chester, MD 21619

    The Chester at Lot 2443 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it a great opportunity for buyers planning ahead. This home includes 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Highlighted features include a dedicated home office with lighted French doors, a stylish dry

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2443, Chester, MD 21619
  • /49

    $449,000

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

    119 Liam Thomas Ln, Stevensville, MD 21666

    This meticulously maintained Ellendale townhome with pond views offers modern living with premium location. The entry level features vinyl flooring and a flexible open space—perfect as an office, den, gym or playroom and internal access to the two-car garage. The main level impresses with 9-foot ceilings and an open-concept layout. A gourmet eat-in kitchen boasts granite countertops, a breakfast

    Max Singer Gans Realty

    119 Liam Thomas Ln, Stevensville, MD 21666
  • /58

    $349,000

    • 3 Beds
    • 1 Bath
    • 907 Sq Ft

    410 Stafford Rd, Stevensville, MD 21666

    Welcome to your storybook cottage in Bay City, Stevensville—just steps from the shimmering waters of the Chesapeake. This isn’t just a house; it’s a lifestyle.Imagine morning coffee on the inviting, breezy front porch, evening strolls by the pier, and sunsets that look like they belong on a postcard.Bay City is one of Kent Island’s most sought-after neighborhoods for a reason. Enjoy two

    Agent Photo

    Petra Quinn

    Realty Navigator

    (410) 593-3667

    410 Stafford Rd, Stevensville, MD 21666
  • /63

    $679,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    176 Flagstaff Way Unit 2412, Chester, MD 21619

    The Magothy at Lot 2412 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2412, Chester, MD 21619
  • /63

    $649,990 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    176 Flagstaff Way Unit 2411, Chester, MD 21619

    The Magothy at Lot 2411 delivers a thoughtfully designed layout with modern comforts and refined details, offering a projected settlement of August 2026. This inviting home features 2 bedrooms, 2.5 baths, and a 1-car garage, making it an ideal blend of style and functionality. Standout features include a dedicated home office with lighted French doors, a stylish dry bar perfect for entertaining,

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2411, Chester, MD 21619
  • /40

    $555,555 Coming Soon

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

    511 Chesapeake Ave, Stevensville, MD 21666

    Discover the perfect blend of coastal living and everyday comfort in this spacious 4-bedroom, 3-bath single-family home located in the lovely area of Stevensville. Set on a generous 0.39-acre private fully fenced in lot. Ideal for those who enjoy entertaining, recreation, gardening or simply rest and relaxation with the Chesapeake Bay in your own backyard. Inside, you’ll find a bright and

    Catalina Sandoval RE/MAX Realty Centre, Inc.

    511 Chesapeake Ave, Stevensville, MD 21666
  • /42

    $3,495,000

    • 4 Beds
    • 5 Baths
    • 5,900 Sq Ft

    200 Mallard Cove Ln, Stevensville, MD 21666

    Welcome to 200 Mallard Cove, a rare 15-acre waterfront estate on Maryland’s Eastern Shore, just 23 miles from Annapolis and moments from the Bay Bridge. This private coastal retreat offers an extraordinary blend of refined living, panoramic Chesapeake Bay views, and the wide-open feeling that defines life on the Shore. A long, tree-lined, 1/4-mile paved driveway leads you through acres of

    Brad Kappel TTR Sotheby's International Realty

    200 Mallard Cove Ln, Stevensville, MD 21666

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