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2-Bedroom Homes for Sale in Chester, MD

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  • 47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    /45

    $598,000 Open House 9/28

    • 2 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    47 D Queen Anne Way, Chester, MD 21619

    Enjoy resort style living every day in the gorgeous waterfront condo. 42' boat slip w/ water/electric & 25K lb magnum lift conveys - WOW!! Watch the sun & moon rise as you sip your favorite beverage or entertain as everyone will want to come visit you now. Professional pics coming soon. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner has

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 623-7650

    47 D Queen Anne Way, Chester, MD 21619
  • 34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    34 Queen Anne Way, Chester, MD 21619
    /57

    $469,000

    • 2 Beds
    • 2.5 Baths
    • 1,104 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Price Improvement on this CHESTER RIVER WATERFRONT Eastern Shore! Nestled within the water-privileged resort-style community of Queen's Landing, along the scenic Chester River and Macum Creek off the Chesapeake Bay. Step into the light-filled foyer and head up the stairs to the main level, you will find this lovely 2 bedroom, 2.5 bath condominium is move in ready. Just bring your patio chairs,

    Agent Photo

    Lona Todd

    Taylor Properties

    (667) 291-8898

    34 Queen Anne Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    /24

    $661,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, Chester, MD 21619

    Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split vanities. Convenient HovHall off garage for keeping home tidy.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $474,990 New Construction

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

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

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $742,900 New Construction

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

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

    Secluded bedroom 2 and bath off foyer for overnight guests. Stylish home office off foyer for working from home. Open & airy great room with adjacent dining area. Striking kitchen with island & tons of cabinet space. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with roomy shower. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    /43

    $415,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54A Queen Caroline Ct, Chester, MD 21619

    Price Improvement...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits!Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s dream, boasting granite countertops, stainless steel

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • 170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    /71

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • 190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    190 Harrier Way Unit 11, Chester, MD 21619
    /32

    $540,000

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

    190 Harrier Way Unit 11, Chester, MD 21619

    Luxury 55+ Living at Four Seasons on Kent Island – Move-In Ready & Priced to Sell!Welcome to the resort-style lifestyle of Four Seasons on Kent Island, an amenity-rich 55+ waterfront community where luxury, comfort, and convenience meet. Inside, you'll find open-concept layouts filled with natural light, gourmet kitchens with quartz countertops, GE Profile stainless steel

    Jennifer Thomas RE/MAX Executive

    190 Harrier Way Unit 11, Chester, MD 21619
  • 170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    170 Harrier Way Unit 22, Chester, MD 21619
    /73

    $510,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    For a limited time, $4000 credit towards Capital Contribution Fee for full price offer.When I asked the seller what is the best part of living here, she said......"the best things about my place is the balcony and view !! Unobstructed. No buildings directly between my unit and the river". Easy place to live !! Lock the door and leave everything to someone else !!

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • 1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    1000 Herons Nest Way Unit 32, Chester, MD 21619
    /26

    $499,000

    • 2 Beds
    • 2 Baths

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Priced to Sell! Seller is ready for their next adventure! Move in, in May! Enjoy low-maintenance living in the amenity-rich, 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers comfortable one-level living with an open layout, perfect for entertaining or relaxing. The property includes a 1-car garage with additional storage units—ideal for keeping your home organized

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 630 Warbler Way Unit 11, Chester, MD 21619
    630 Warbler Way Unit 11, Chester, MD 21619
    630 Warbler Way Unit 11, Chester, MD 21619
    /10

    $573,365 New Construction

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

    630 Warbler Way Unit 11, Chester, MD 21619

    Efficient gourmet kitchen featuring designer cabinets & vast center island.Open concept living areas featuring electric fireplace & dry bar.Spacious owner's suite & spa bath for relaxation.Organized home office, perfect for working remotely.Inviting outdoor patio for spending time with friends.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 11, Chester, MD 21619
  • 312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    /14

    $305,000

    • 2 Beds
    • 2 Baths
    • 1,073 Sq Ft

    312 Teal Ct Unit F, Chester, MD 21619

    This is a highly sought-after location on Kent Island, known for its limited availability.Sellers have updated shiplap in the living room, paint throughout the house. This second-floor condo offers breathtaking views of the pond. You will enjoy an updated backsplash in the kitchen, featuring granite countertops and stainless steel appliances. Hardwood flooring is throughout the house. The

    Mary Rice Engel & Völkers Ocean City

    312 Teal Ct Unit F, Chester, MD 21619
  • 1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    /34

    $479,000 Open Sun 1PM - 3PM

    • 2 Beds
    • 2 Baths
    • 1,444 Sq Ft

    1401 Calvert Rd, Chester, MD 21619

    Kent Island - Marling Farms - Brick Rancher - Waterviews of Crab Alley Bay - PRICE REDUCED - All on one level - Beautifully landscaped 3/4 acre lot that backs to trees - fenced patio area - 2 bedrooms with lots of windows and large closets - 2 full beths, one with a tub, one with a walkin shower - fabulous sunroom addition - quiet office area - updated kitchen with granite counters, newer

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, Chester, MD 21619
  • 224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    224 Bayberry Dr, Chester, MD 21619
    /51

    $624,900

    • 2 Beds
    • 2 Baths
    • 1,913 Sq Ft

    224 Bayberry Dr, Chester, MD 21619

    Welcome to Easy Living on the Eastern Shore! ***Discover the perfect blend of comfort, style, and resort-style living in this impeccably maintained, one-owner home — tucked into the highly sought-after, water-privileged 55+ community of Four Seasons at Kent Island.From the moment you walk in, you’ll notice the difference. The open-concept floor plan is thoughtfully designed and

    Petra Quinn Realty Navigator

    224 Bayberry Dr, Chester, MD 21619
  • 1405 Little Creek Rd, Chester, MD 21619
    1405 Little Creek Rd, Chester, MD 21619
    /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.Please note that

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • 49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    49 Queen Guinivere Way, Chester, MD 21619
    /79

    $529,250

    • 2 Beds
    • 2.5 Baths
    • 1,600 Sq Ft

    49 Queen Guinivere Way, Chester, MD 21619

    Welcome to Queens Landing, where resort-style living meets the comfort of home. This beautifully updated townhome offers 1,440 square feet of thoughtfully designed living space plus an open sunroom, adding approximately 160 additional square feet, creating a seamless and spacious floor plan ideal for everyday living and entertaining.Enjoy panoramic water views from every room - lake and

    Julia Stevens Realty Navigator

    49 Queen Guinivere Way, Chester, MD 21619
  • 15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    15 Queen Anne Way Unit E, Chester, MD 21619
    /68

    $499,000

    • 2 Beds
    • 2.5 Baths
    • 1,680 Sq Ft

    15 Queen Anne Way Unit E, Chester, MD 21619

    The BIGGEST price drop yet!! Wake up to shimmering Chester River views and let every day feel like a getaway!This beautifully maintained 2.5-level townhome offers 1,680 square feet of stylish and functional living space in the sought-after waterfront community of Queens Landing. The main level features a cozy living area with a gas fireplace, luxury vinyl plank flooring, and access to a

    Julia Stevens Realty Navigator

    15 Queen Anne Way Unit E, Chester, MD 21619
  • 1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    1000 Herons Nest Way Unit 22, Chester, MD 21619
    /59

    $488,000

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

    1000 Herons Nest Way Unit 22, Chester, MD 21619

    Welcome to 1000 Heron's Nest Way. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. With 1900 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet

    Ralph Kennedy RE/MAX Executive

    1000 Herons Nest Way Unit 22, Chester, MD 21619
  • 154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    154 Harrier Way, Chester, MD 21619
    /45

    $639,500

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

    154 Harrier Way, Chester, MD 21619

    *** WELCOME to 154 HARRIER WAY and FOUR SEASONS at KENT ISLAND***The Donegal model is a spacious and airy 2 bedroom, 2 bath home boasting an expansive open floor plan with nearly 2000 square feet of luxurious living space on one level. This home features a lavish gourmet kitchen and dining area, a spacious and airy great room with gas fireplace, plus office or den. You decide! The

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • 121 Wheelhouse Way Unit 32, Chester, MD 21619
    121 Wheelhouse Way Unit 32, Chester, MD 21619
    121 Wheelhouse Way Unit 32, Chester, MD 21619
    /26

    $679,900 New Construction

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

    121 Wheelhouse 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

    Builder Photo

    K. Hovnanian Homes

    Builder

    121 Wheelhouse Way Unit 32, Chester, MD 21619
  • 121 Wheelhouse Way Unit 42, Chester, MD 21619
    121 Wheelhouse Way Unit 42, Chester, MD 21619
    121 Wheelhouse Way Unit 42, Chester, MD 21619
    /32

    $779,900 New Construction

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

    121 Wheelhouse Way Unit 42, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinets & center island.Connected dining area & great room for seamless flow.Convenient dry bar & electric firepelace in main living spaces.Peaceful owner's suite & bath with walk-in closet.Organized home office for leisure activities.Versatile balcony for outdoor enjoyment.

    Builder Photo

    K. Hovnanian Homes

    Builder

    121 Wheelhouse Way Unit 42, Chester, MD 21619
  • 131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    131 Flycatcher Way Unit 36492116, Chester, MD 21619
    /12

    $628,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,690 Sq Ft

    Bernstein II Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, Chester, MD 21619

    Elegant foyer welcoming guests to your home. Convenient single-story living. Kitchen with spacious pantry and oversized island. Open-concept great room and dining area adjacent to kitchen. Private primary suite with large walk-in closet and spa bath. Laundry room and HovHall with plenty of space to store and organize.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36492116, Chester, MD 21619
  • 131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    131 Flycatcher Way Unit 36471203, Chester, MD 21619
    /11

    $764,900 New Construction

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

    Kelly Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36471203, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
    /33

    $474,990 New Construction

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

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

    Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owner’s suite with spa bath and access to balcony. Large secondary bedroom with access to balcony. Pricing is inclusive of an average location premium.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493320, Chester, MD 21619
Maryland Queen Annes County Chester

2-Bedroom Homes for Sale in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 42 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MD over the last 12 months is $597,450, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$597,450
Median Single Family Sale Price
$637,900
Median Townhouse Sale Price
$437,500
Median 2 Bedroom Sale Price
$499,000
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$294
Number of Homes for Sale
59
Last 12 months Home Sales
170
Months of Supply
4.20
Median List Price
$595,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
How to Buy a Home How to Finance a Home How to Sell a Home

In Chester, there are currently 24 2-bedroom homes for sale. Offering versatile living spaces ideal for small families, roommates, or those in need of extra space for a home office or guest room, these properties strike a balance between affordability and functionality. Whether you're in search of a cozy townhouse, a spacious condo, or a charming single-family home, there are options to suit your preferences. Explore the selection of 2-bedroom homes for sale in Chester, MD and find the perfect place to call home.

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

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