55

Studio to 3 Bedroom Homes for Sale in Chester, MD

Section Image Section Image Section Image
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $814,900

    • 3 Beds
    • 3 Baths
    • 2,399 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

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 295-8334

    135 Nauset Ln, 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

    $489,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /26

    $818,900 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
  • 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

    $668,900 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $858,900 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
  • 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

    $751,900 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    312 Blenny Ln, Chester, MD 21619
    /39

    $479,000

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

    312 Blenny Ln, Chester, MD 21619

    You do not want to miss this opportunity to enjoy island living in this maintenance free, WATER 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

    Judith Brown Samson Properties

    312 Blenny Ln, 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

    $489,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
  • 30 C Queen Mary Ct, Chester, MD 21619
    30 C Queen Mary Ct, Chester, MD 21619
    30 C Queen Mary Ct, Chester, MD 21619
    /60

    $339,900

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

    30 C Queen Mary Ct, Chester, MD 21619

    Settlement possible for the Holidays & New Year! Enjoy low-maintenance living in the desirable waterfront community of Queen’s Landing, offering scenic views and direct access to the Chester River via Northeast Bay. This beautifully updated home features expansive pond and fountain views the moment you walk in, along with a brand new kitchen showcasing shaker-style cabinetry, quartz countertops,

    Dori Savani Douglas Realty, LLC

    30 C Queen Mary Ct, Chester, MD 21619
  • 132 Wheelhouse Way Unit 43, Chester, MD 21619
    132 Wheelhouse Way Unit 43, Chester, MD 21619
    132 Wheelhouse Way Unit 43, Chester, MD 21619
    /30

    $1,350,000 New Construction

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

    132 Wheelhouse Way Unit 43, Chester, MD 21619

    Stunning kitchen with wall oven & spacious central island. Dry bar in the dining area adds a stylish touch. Great room features an electric fireplace for cozy evenings. Sliding doors open to a private balcony off the great room. Owner’s suite with direct balcony access for fresh air. Dual vanities in the spa-inspired owner’s bath. Elegant double doors lead you to private home

    K. Hovnanian Homes Builder
    132 Wheelhouse Way Unit 43, Chester, MD 21619
  • 0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    0 Harbor Dr, Chester, MD 21619
    /12

    $499,900 New Construction

    • 3 Beds
    • 2 Baths
    • 1,250 Sq Ft

    0 Harbor Dr, Chester, MD 21619

    New home being built! Act now and pick all your colors! Finished models can be seen! Call agent for details.

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • 630 Warbler Way Unit 33, Chester, MD 21619
    630 Warbler Way Unit 33, Chester, MD 21619
    630 Warbler Way Unit 33, Chester, MD 21619
    /30

    $644,990 New Construction

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

    630 Warbler Way Unit 33, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinetry & wall oven. Open concept living spaces with electric fireplace & dry bar. Private owner's suite for rest & relaxation. Refreshing primary bath featuring split vanities. Functional home office featuring double doors for added privacy. Lovely balcony for spending time with friends.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 33, Chester, MD 21619
  • 112 Chessie Ct, Chester, MD 21619
    112 Chessie Ct, Chester, MD 21619
    112 Chessie Ct, Chester, MD 21619
    /37

    $519,900

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    112 Chessie Ct, Chester, MD 21619

    Step inside and see this meticulously cared for home!This home features a first floor primary bedroom with an ensuite full bath.Just 5 minutes from the Chesapeake Bay Bridge and all the beaches, parks, boat ramps, and waterfront venues you love to visit...all within a few minutes drive.This single detached home has been thoughtfully improved throughout, with luxury vinyl plank floors,

    Carol Delayo Chaney Homes, LLC

    112 Chessie Ct, Chester, MD 21619
  • 630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    630 Warbler Way Unit 12, Chester, MD 21619
    /8

    $499,990 New Construction

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

    630 Warbler Way Unit 12, Chester, MD 21619

    Charming gourmet kitchen featuring center island & ample counter space. Electric fireplace adds warmth to spacious great room. Refined dining area with dry bar. Functional home office for studying or reading. Private owner's suite & spa bath with walk-in closet. Versatile covered patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 12, 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
  • 630 Warbler Way Unit 2222, Chester, MD 21619
    630 Warbler Way Unit 2222, Chester, MD 21619
    630 Warbler Way Unit 2222, Chester, MD 21619
    /48

    $574,900 New Construction

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

    630 Warbler Way Unit 2222, Chester, MD 21619

    Chester|| Available May 2026 This home offers 2 bedrooms, 2.5 baths, and a 1-car garage. Standout features include a dry bar, an electric fireplace, and a dedicated home office with lited French doors. The kitchen is thoughtfully designed with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lights, and a tile backsplash, all accented by quartz countertops. The flooring

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2222, Chester, MD 21619
  • 630 Warbler Way Unit 2232, Chester, MD 21619
    630 Warbler Way Unit 2232, Chester, MD 21619
    630 Warbler Way Unit 2232, Chester, MD 21619
    /48

    $644,990 New Construction

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

    630 Warbler Way Unit 2232, Chester, MD 21619

    The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2232, Chester, MD 21619
  • 1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    1401 Calvert Rd, Chester, MD 21619
    /33

    $454,900

    • 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 baths, 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
  • 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
    /79

    $499,000

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

    170 Harrier Way Unit 22, Chester, MD 21619

    Leaves are falling—and so is the price of this stunning condo in the fun, vibrant, and highly sought-after Four Seasons at Kent Island community. Act fast! This is the most breathtaking time of year to make this home yours. As the trees shift from summer green to the rich colors of fall, Mother Nature puts on her finest show. And once the leaves drop, the Chester River opens up before you—right

    Vic Pascoe Keller Williams Select Realtors of Annapolis

    170 Harrier Way Unit 22, Chester, MD 21619
  • 170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    170 Harrier Way Unit 34, Chester, MD 21619
    /81

    $710,000

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

    170 Harrier Way Unit 34, Chester, MD 21619

    Just reduced by $30,000 to $710,000 with immediate availability. This is one of only two 3-bedroom condos on the market in Four Seasons with the immediate availability. Welcome to luxury condo living at Four Seasons at Kent Island, an active 55+ community packed with amenities. No need to wait for a new condo to be built – you can move in now to 170 Harrier Way #34. This third floor Severn model

    Barry Davis Long & Foster Real Estate, Inc.

    170 Harrier Way Unit 34, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, 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
  • 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
    /28

    $499,000

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

    1000 Herons Nest Way Unit 32, Chester, MD 21619

    Move in this May and enjoy low-maintenance living in the sought-after 55+ community of Four Seasons on Kent Island. This 2-bedroom, 2-bath home offers spacious one-level living with an open layout, freshly painted interiors, and a stylish kitchen featuring a modern glass subway tile backsplash—perfect for entertaining or relaxing. A 1-car garage with additional storage units keeps everything

    Jennifer Thomas RE/MAX Executive

    1000 Herons Nest Way Unit 32, Chester, MD 21619
  • 141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    /61

    $684,950

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

    141 Switchgrass Way Unit 34, Chester, MD 21619

    **** NICE VIEWS OF THE CHESTER RIVER**** ***** LOWEST PRICED SEVERN MODEL****K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, Chester, MD 21619
  • 630 Warbler Way Unit 24, Chester, MD 21619
    630 Warbler Way Unit 24, Chester, MD 21619
    630 Warbler Way Unit 24, Chester, MD 21619
    /19

    $714,990 New Construction

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

    630 Warbler Way Unit 24, Chester, MD 21619

    Gourmet kitchen with central island for prep & dining. Dining area enhanced by a built-in dry bar. Great room warmed by an electric fireplace. Owner’s suite with private sitting room retreat. Balcony accessible from both great room & sitting room. Owner’s suite includes dual walk-in closets. Spa-inspired owner’s bath with dual vanities.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 24, 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***Price Reduced! Better than New! Custom Window Treatments! Oversized Garage w/Custom Floor!Why Wait Months-and Spend Thousands More-You Can Move into This Home in 30 Days. ****** Owner is also offering a Home Warranty with acceptable offer******The Donegal model is a spacious and airy 2 bedroom, 2 bath home boasting an

    Ralph Kennedy RE/MAX Executive

    154 Harrier Way, Chester, MD 21619
  • 54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    /3

    $349,000

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

    54H Queen Caroline Ct, Chester, MD 21619

    Professional pictures coming! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and will be getting new carpet throughout, as well as new flooring in the kitchen. A propane fireplace highlights the great room for cozy chilly nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of

    Mary Stevens Long & Foster Real Estate, Inc.

    54H Queen Caroline Ct, Chester, MD 21619
  • 1704 Bayside Dr, Chester, MD 21619
    1704 Bayside Dr, Chester, MD 21619
    1704 Bayside Dr, 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
  • 906 Auckland Way, Chester, MD 21619
    906 Auckland Way, Chester, MD 21619
    906 Auckland Way, Chester, MD 21619
    /36

    $520,000

    • 3 Beds
    • 3.5 Baths
    • 2,076 Sq Ft

    906 Auckland Way, Chester, MD 21619

    This beautifully maintained 3-bedroom, 3.5-bath marina-front townhouse with a 1-car garage offers the perfect blend of comfort, convenience, and Chesapeake lifestyle. Ideally located in the heart of Kent Island, you’ll enjoy stunning marina and Chester River views from multiple levels. The main floor features new luxury vinyl plank flooring, an open-concept kitchen, dining, and family room, and a

    Courtney Chipouras TTR Sotheby's International Realty

    906 Auckland Way, Chester, MD 21619
  • 519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    /20

    $849,990 New Construction

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

    519 Warbler Way, Chester, MD 21619

    Convenient Extra Suite for guests to stay overnight. Functional home office off foyer for working from home. Breathtaking kitchen with Winstead Maple Flagstone cabinetry. Beautiful Calacatta Abezzo quartz countertops & island. Refined great room & equisite fireplace. Intimate dining area for hosting dinner parties. Private primary suite & spa-like bath with dual vanities. Stunning screened patio

    K. Hovnanian Homes Builder
    519 Warbler Way, Chester, MD 21619
  • 127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    127 Flycatcher Way, Chester, MD 21619
    /49

    $1,100,000 New Construction

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

    127 Flycatcher Way, Chester, MD 21619

    The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a

    Mary Anne Kowalewski KOVO Realty

    127 Flycatcher Way, Chester, MD 21619
  • 200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    200 Harrier Way Unit 21, Chester, MD 21619
    /44

    $679,900

    • 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
  • 527 Warbler Way, Chester, MD 21619
    527 Warbler Way, Chester, MD 21619
    527 Warbler Way, Chester, MD 21619
    /25

    $799,990 New Construction

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

    527 Warbler Way, Chester, MD 21619

    Polished kitchen featuring Brellin White cabinets & Statuary Clasique quartz countertops. Spacious great room with stylish ceiling treatment & warm fireplace. Private Extra Suite for overnight guests. Functional home office for working remotely. Lavish primary suite & bath featuring generous walk-in closet. Inviting screened patio for outdoor enjoyment. Attached 3-car garage provides ample

    K. Hovnanian Homes Builder
    527 Warbler Way, Chester, MD 21619
  • 630 Warbler Way Unit 32, Chester, MD 21619
    630 Warbler Way Unit 32, Chester, MD 21619
    630 Warbler Way Unit 32, Chester, MD 21619
    /30

    $644,990 New Construction

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

    630 Warbler Way Unit 32, Chester, MD 21619

    Efficient gourmet kitchen featuring designer cabinetry & center island. Spacious great room with electric fireplace. Charming dining area featuring dry bar. Lavish owner's suite & spa bath with walk-in closet. Productive home office featuring double doors. Versatile balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 32, Chester, MD 21619
  • 1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    1340 Queen Anne Dr, Chester, MD 21619
    /27

    $459,900

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

    1340 Queen Anne Dr, Chester, MD 21619

    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 accented with stylish

    Darlene Winegardner RE/MAX Executive

    1340 Queen Anne Dr, Chester, MD 21619
  • 1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    1906 Harbor Dr, Chester, MD 21619
    /3

    $499,900 Coming Soon

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

    1906 Harbor Dr, Chester, MD 21619

    Beautifully renovated/remodeled 3 bedroom, 2 full bath home in Chester, MD. Expected date to go active on the market is January 1st, 2026.

    Gregory Bennett Jr. Five Star Real Estate

    1906 Harbor Dr, 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
  • 306 Teal Ct, Chester, MD 21619
    306 Teal Ct, Chester, MD 21619
    306 Teal Ct, Chester, MD 21619
    /24

    $295,000

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

    306 Teal Ct, Chester, MD 21619

    Beautifully maintained first-floor condominium offering serene lake views and an open, inviting floor plan.This residence features two spacious bedrooms and two full bathrooms. The light-filled living and dining areas provide direct access to a private patio overlooking the lake, perfect for enjoying peaceful mornings.Located in a highly desirable community of Bayside, offering

    Cindy Jacobs Maryland Residential Management Co

    306 Teal Ct, Chester, MD 21619
  • 202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    /63

    $825,000

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

    202 Mchenny Ct, Chester, MD 21619

    Beautiful Home in Gibson’s Grant with Elevator, Open Floor Plan & Two-Car GarageWelcome to this beautifully appointed home in the sought-after waterfront community of Gibson’s Grant on Kent Island. This residence offers a perfect blend of comfort, style, and convenience — featuring a spacious open floor plan and an attached two-car garage.No need to worry about stairs — a full elevator

    Dee Dee McCracken Coldwell Banker Realty

    202 Mchenny Ct, Chester, MD 21619
  • 1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    /40

    $495,000

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

    1916 Stevens Dr, Chester, MD 21619

    Discover 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

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Annes County Chester

Studio to 3 Bedroom Homes for Sale in Chester, MD

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 101 days on the market compared to the national average of 53 days. The median sale price for homes in Chester, MD over the last 12 months is $634,950, up 10% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$634,950
Median Single Family Sale Price
$649,000
Median Townhouse Sale Price
$395,000
Median 2 Bedroom Sale Price
$540,656
Median 1 Bedroom Sale Price
$320,000
Average Price Per Sq Ft
$293
Number of Homes for Sale
63
Last 12 months Home Sales
188
Months of Supply
4.00
Median List Price
$642,445
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
10%
How to Buy a Home How to Finance a Home How to Sell a 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.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2025 CoStar Group