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Homes for Sale in Chester, MD with 3-Bedrooms

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  • /34

    $443,000

    • 3 Beds
    • 2.5 Baths
    • 1,296 Sq Ft

    200 Newtown Rd, Chester, MD 21619

    NO HOA! Beautifully maintained 2017-built home offering 3 bedrooms and 2.5 baths. Features a fenced yard for kids and pets, screened porch, large yard with concrete pad, and small storage shed. Temperature-controlled concrete crawl space, new sump pump, and septic contract for easy, worry-free living. Conveniently located near shopping and everything Kent Island has to offer.Make sure you see

    Agent Photo

    Linda Moran

    Berkshire Hathaway HomeServices PenFed Realty-WOC

    (410) 650-8215

    200 Newtown Rd, Chester, MD 21619
  • /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, Chester, MD 21619
  • /27

    $858,990 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • /27

    $819,990 New Construction

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

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • /29

    $400,000

    • 3 Beds
    • 2 Baths
    • 1,636 Sq Ft

    1803 Chester Dr, Chester, MD 21619

    Adorable rancher on Kent Island in the community of Harbor View! Featuring 3 beds, 2 baths, and private driveway. Enjoy the large fenced yard with deck, shed, and firepit. The living room has a cozy fireplace with wood stove insert. The primary bedroom has a private bath with tile and stand up shower. Updates include both bathrooms, updated windows, roof 2020. Close to Route 50 for easy access to

    Jennifer Kramer-Dela Cruz Keller Williams Legacy

    1803 Chester Dr, Chester, MD 21619
  • /85

    $779,900 Open Sat 12PM - 2PM

    • 3 Beds
    • 2 Baths
    • 2,394 Sq Ft

    169 Harrier Way, Chester, MD 21619

    Look no further—welcome to the prestigious 55+ resort-style community of Four Seasons at Kent Island, where refined living meets effortless elegance. This exquisitely upgraded Killarney model offers over 2,300 square feet of thoughtfully designed single-level living, featuring an open-concept layout and high-end finishes throughout.At the heart of the home is a stunning gourmet kitchen,

    Dorothea Slaughter Century 21 Redwood Realty

    169 Harrier Way, Chester, MD 21619
  • /23

    $485,000

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft

    1872 Harbor Dr, Chester, MD 21619

    Harbor View Community | Corner Lot | Renovated Rancher with Room to GrowWelcome to 1872 Harbor Drive —a move-in ready ranch-style home that offers the space and updates today’s buyers are searching for. Located in the Matapeake Elementary School district, this home sits on a rare double corner lot with nearly three-quarters of an acre, making it a standout opportunity on Maryland’s Eastern

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • /29

    $387,500

    • 3 Beds
    • 2 Baths
    • 1,204 Sq Ft

    1838 Sherman Dr, Chester, MD 21619

    Nestled in the heart of Chester, Maryland on the beautiful Eastern Shore, this charming rancher offers comfort and convenience. Inside, a bright and inviting interior features neutral tones, modern finishes, and a functional layout ideal for everyday living. The light-filled dining area overlooks the backyard and flows into the galley kitchen, complete with stainless steel appliances, ample

    Bret Merson Keller Williams Realty Centre

    1838 Sherman Dr, Chester, MD 21619
  • /83

    $750,000

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

    2000 Herons Nest Way Unit 401, Chester, MD 21619

    HERE IT IS! This Rare Luxurious Severn Penthouse, available immediately, offers a lifestyle that seamlessly blends comfort and elegance. Built in 2020, this beautifully maintained residence showcases an open floor plan with windows throughout that invite natural light to dance across its spacious interiors, creating a warm, inviting atmosphere. Step into the heart of the home, where a stunning

    Veronica Lawson Real Broker, LLC

    2000 Herons Nest Way Unit 401, Chester, MD 21619
  • /67

    $694,500

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

    230 Switchgrass Way Unit 21, Chester, MD 21619

    --------------------------------------EXCEPTIONAL PANORAMIC VIEWS -------------------------------------Immediate Move In Ready. Nature, water and sunshine abound in this beautifully situated, stunning 3BR corner unit at Four Seasons. Flexible closing available. South, west and north exposures through 17 windows and two sets of sliding doors assure that this condo is drenched in sunshine, water

    Lawrence Doyle Long & Foster Real Estate, Inc.

    230 Switchgrass Way Unit 21, Chester, MD 21619
  • /48

    $479,000

    • 3 Beds
    • 4 Baths
    • 1,899 Sq Ft

    312 Blenny Ln, Chester, MD 21619

    You don't want to miss the opportunity to enjoy Island Living in this maintenance free Pond View End Unit! Come enjoy Island Living in the Bayside Community. Offering Pond Views from every window in this sought after end unit home complete with beautiful landscaping. Relax on your spacious deck overlooking the pond complete with 2 fountains or invite family and friends to enjoy a cookout on your

    Judith Brown EXP Realty, LLC

    312 Blenny Ln, Chester, MD 21619
  • /44

    $479,900

    • 3 Beds
    • 2 Baths
    • 1,750 Sq Ft

    1906 Harbor Dr, Chester, MD 21619

    Experience the epitome of luxury living in this stunning ranch-style home located in the prestigious Harbor View subdivision. This meticulously renovated residence boasts an impressive 1,750 square feet of thoughtfully designed space, perfect for those who appreciate both elegance and functionality. Step inside to discover a harmonious blend of modern sophistication and timeless charm. The

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, Chester, MD 21619
  • /47

    $425,000

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades.Welcome to Bayside living at its finest. This meticulously maintained

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • /37

    $1,100,000

    • 3 Beds
    • 2.5 Baths
    • 1,830 Sq Ft

    1704 Bayside Dr, Chester, MD 21619

    Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautifully renovated 3-bedroom, 2.5 bath home offers an open-concept layout design to capture breathing taking water views that stretch endless across the horizon. Each evening brings magnificent, direct sunset views-- the kind that make you stop, breathe, and take it all in. New pier in 2020! Step inside to

    Alex Hodges Cottage Street Realty LLC

    1704 Bayside Dr, Chester, MD 21619
  • /40

    $489,000

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

    1916 Stevens Dr, Chester, MD 21619

    Come see this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens Dr, Chester, MD 21619
  • /44

    $659,900

    • 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
  • /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
  • /21

    $901,540 New Construction

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

    102 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island & sleek finishes. Dining area with built-in dry bar for easy entertaining. Bright great room with electric fireplace & open layout. Private balcony just off the great room. Owner’s suite with dual walk-in closets for added storage. Sitting room in owner’s suite with direct balcony access. Spa-inspired owner’s bath with dual sinks & glass-enclosed

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

    $1,003,673 New Construction

    • 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
  • /44

    $989,990 New Construction

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

    102 Warbler Way Unit 2934, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2934, Chester, MD 21619
  • /19

    $739,900 New Construction

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

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes Builder
    211 Switchgrass Way Unit 31, Chester, MD 21619
  • /44

    $889,990 New Construction

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

    102 Warbler Way Unit 2921, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home blends modern comfort with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting setting for everyday living and entertaining. The owner’s suite includes a private sitting

    Mary Anne Kowalewski KOVO Realty

    102 Warbler Way Unit 2921, Chester, MD 21619
  • /18

    $949,990 New Construction

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

    110 Boatswain Way Unit 41, Chester, MD 21619

    Welcoming foyer leads into open-concept living spaces. Gourmet kitchen featuring ample cabinetry & seamless connection to the dining area. Dry bar adds a stylish touch, ideal for hosting guests. Spacious great room highlighted by a cozy fireplace. Owner’s suite features a private sitting room & walk-in closet. Owner’s bath showcases a frameless shower door for a modern, elevated feel. Balcony

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 41, Chester, MD 21619
  • /21

    $849,990 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
  • /21

    $749,990 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
  • /22

    $989,990 New Construction

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

    110 Boatswain Way Unit 44, Chester, MD 21619

    Open-concept kitchen, dining area, & great room designed for effortless flow. Gourmet kitchen with ample cabinetry for streamlined storage & prep. Dry bar creates a dedicated space for serving & display. Fireplace adds warmth & character to the great room. Owner’s suite with sitting room, walk-in closet & private bath. Frameless shower door delivers a sleek, spa-like touch in the owner’s bath.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 44, Chester, MD 21619
  • /29

    $979,990 New Construction

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

    307 Kingfisher Ln, Chester, MD 21619

    Welcoming foyer leads to beautiful open concept floorplan. Inviting kitchen featuring white cabinetry, quartz countertops, & center island. Spacious great room with cozy fireplace, perfect for spending time with family. Tranquil primary suite featuring detailed ceiling treatment. Polished primary bath with brushed nickel finishes & generous walk-in closet. Convenient Extra Suite & home office off

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, Chester, MD 21619
  • /44

    $949,990 New Construction

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

    110 Boatswain Way Unit 3041, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3041, Chester, MD 21619
  • /44

    $989,990 New Construction

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

    110 Boatswain Way Unit 3044, Chester, MD 21619

    Welcome to the Severn, a beautifully designed home offering 3 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in November 2026, this home combines modern style with functional living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. The owner’s suite includes a sitting room and large walk-in closets, providing a

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3044, Chester, MD 21619
  • /44

    $849,990 New Construction

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

    110 Warbler Way Unit 3031, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3031, Chester, MD 21619
  • /44

    $749,990 New Construction

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

    110 Warbler Way Unit 3021, Chester, MD 21619

    The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat,

    Mary Anne Kowalewski KOVO Realty

    110 Warbler Way Unit 3021, Chester, MD 21619
  • /21

    $584,990 New Construction

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

    Severn Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Expansive end home condominium with 3 bedrooms. Lavish gourmet kitchen and formal dining area. Huge great room with large corner balcony. Fantastic owner’s suite and sitting room with access to balcony. Extravagant owner’s spa bath with two walk-in closets. Large secondary bedrooms for all of your company. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36503530, Chester, MD 21619
  • /24

    $1,400,000 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    117 Flycatcher Way, Chester, MD 21619

    Formal dining room off the foyer for hosting celebrations. Breathtaking kitchen with stacked grey cabinetry & glass uppers. Sprawling quartz island perfect for prep & dining. Vaulted ceiling with ceiling beams connects dining area and great room. Elegant fireplace and sliding door to screened patio in great room. Private home office for working remotely. Primary suite & bath with dual vanities

    K. Hovnanian Homes Builder
    117 Flycatcher Way, Chester, MD 21619
  • /24

    $1,389,667 New Construction

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

    123 Flycatcher Way, Chester, MD 21619

    Well-equipped kitchen with stacked dark stained cabinetry & glass uppers. Cozy fireplace adds warmth & character to spacious great room. Tranquil primary suite with generous walk-in closet. Productive home office for studying or reading. Private Extra Suite, great for overnight guests. Inviting screened patio for outdoor entertaining. Second floor loft provide addtionial living space.

    K. Hovnanian Homes Builder
    123 Flycatcher Way, Chester, MD 21619

Home Trends in Chester, MD

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$684,900
Median Townhouse Sale Price
$372,500
Median 2 Bedroom Sale Price
$549,900
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$298
Number of Homes for Sale
77
Last 12 months Home Sales
213
Months of Supply
4.30
Median List Price
$676,950
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
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