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Chester, MD Homes for Sale

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  • 117 Redstart Dr, Chester, MD 21619
    117 Redstart Dr, Chester, MD 21619
    117 Redstart Dr, Chester, MD 21619
    /8

    $879,900 New Construction

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

    117 Redstart Dr, Chester, MD 21619

    Charming kitchen featuring Brellin White cabinets & Statuary Classique quartz countertops. Connected great room & dining area featuring striking vault with painted ceiling beams. Cozy fireplace adds warmth & character to main living spaces. Tranquil primary suite featuring generous walk-in closet. Polished primary bath with dual vanities & matte black finishes. Versatile screened patio for

    K. Hovnanian Homes Builder
    117 Redstart Dr, Chester, MD 21619
  • 519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    519 Warbler Way, Chester, MD 21619
    /20

    $879,900 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
  • 527 Warbler Way, Chester, MD 21619
    527 Warbler Way, Chester, MD 21619
    527 Warbler Way, Chester, MD 21619
    /25

    $869,900 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
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    /4

    $659,000

    • 2 Beds
    • 3.5 Baths
    • 2,400 Sq Ft

    132 Claiborne St, Chester, MD 21619

    Discover exceptional living on an oversized fenced lot in the sought-after community of Gibson’s Grant on Kent Island. This beautifully maintained home offers a rare combination of space, versatility, and thoughtful upgrades—inside and out. A welcoming front porch overlooks a peaceful community green space, setting the tone for the charm found throughout. Step inside to hardwood floors spanning

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 490-0332

    132 Claiborne St, Chester, MD 21619
  • 1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    1916 Stevens Dr, Chester, MD 21619
    /41

    $495,000

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

    1916 Stevens Dr, Chester, MD 21619

    Discover this beautifully updated 3-bedroom, 2.5-bath 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, engineered hardwood floors on the main level and cathedral ceiling with skylights. Relax in the spacious lower-level family

    Kimberly O'Connor Coldwell Banker Realty

    1916 Stevens 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
  • 2907 Cox Neck Rd E, Chester, MD 21619
    2907 Cox Neck Rd E, Chester, MD 21619
    2907 Cox Neck Rd E, Chester, MD 21619
    /43

    $1,899,000

    • 4 Beds
    • 6 Baths
    • 3,460 Sq Ft

    2907 Cox Neck Rd E, Chester, MD 21619

    Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside

    Brad Kappel TTR Sotheby's International Realty

    2907 Cox Neck Rd E, Chester, MD 21619
  • 112 Chessie Ct, Chester, MD 21619
    112 Chessie Ct, Chester, MD 21619
    112 Chessie Ct, Chester, MD 21619
    /47

    $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...right in your own neighborhood! This " Home Sweet Home" in Chester, Queen Anne's County, MD has been thoughtfully improved throughout,

    Carol Delayo Chaney Homes, LLC

    112 Chessie Ct, Chester, MD 21619
  • 302 Teal Ct, Chester, MD 21619
    302 Teal Ct, Chester, MD 21619
    302 Teal Ct, Chester, MD 21619
    /29

    $305,000

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

    302 Teal Ct, Chester, MD 21619

    Beautifully maintained first-floor condominium offering an open, inviting floor plan.This residence features two spacious bedrooms and one and a half bathrooms. The light-filled living and dining areas provide direct access to a patio, with storage closet. All kitchen appliances, stainless steel, only 1 year old, and counter tops updated. Both bathrooms remodeled in 2021. Washer & dryer brand

    Cindy Jacobs Maryland Residential Management Co

    302 Teal Ct, Chester, MD 21619
  • 203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    /68

    $1,099,900 New Construction

    • 5 Beds
    • 3.5 Baths
    • 3,036 Sq Ft

    203 Riverside Dr, Chester, MD 21619

    To-be-built 5BR, 3.5BA waterfront home by Laine Street Homes — now under construction and perfectly positioned to capture breathtaking sunrises over the waterfront of Crab Alley Creek. Thoughtfully designed for modern coastal living, this home will offer panoramic water views from the main level and the primary suite, filling the interior with natural light and scenic beauty. The bright layout

    Chrissy Schultz Long & Foster Real Estate, Inc.

    203 Riverside Dr, Chester, MD 21619
  • 202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    202 Mchenny Ct, Chester, MD 21619
    /63

    $875,000 Open Sat 2PM - 4PM

    • 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
  • 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

    $654,900 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
  • 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

    $654,900 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
  • 54H Queen Caroline Ct, Chester, MD 21619
    54H Queen Caroline Ct, Chester, MD 21619
    /2

    $349,000 Coming Soon

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

    54H Queen Caroline Ct, Chester, MD 21619

    Mary Stevens Long & Foster Real Estate, Inc.

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

    $530,000

    • 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
  • 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

    $654,900 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

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2232, Chester, MD 21619
  • 630 Warbler Way Unit 2233, Chester, MD 21619
    630 Warbler Way Unit 2233, Chester, MD 21619
    630 Warbler Way Unit 2233, Chester, MD 21619
    /48

    $654,900 New Construction

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

    630 Warbler Way Unit 2233, 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

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2233, Chester, MD 21619
  • 3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    3000 Herons Nest Way Unit 11, Chester, MD 21619
    /66

    $555,900

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

    3000 Herons Nest Way Unit 11, Chester, MD 21619

    Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown

    John Freeman Coldwell Banker Realty

    3000 Herons Nest Way Unit 11, Chester, MD 21619
  • 630 Warbler Way Unit 22, Chester, MD 21619
    630 Warbler Way Unit 22, Chester, MD 21619
    630 Warbler Way Unit 22, Chester, MD 21619
    /21

    $574,900 New Construction

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

    630 Warbler Way Unit 22, Chester, MD 21619

    Functional home office with elegant French doors. Beautiful gourmet kitchen with pendant lighting. Spacious dining area and great room with electric fireplace. Palatial owner's suite with triple windows & balcony access. Glamorous owner's spa bath featuring split vanities. Beautiful balcony for outdoor enjoyment.

    K. Hovnanian Homes Builder
    630 Warbler Way Unit 22, 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

    $724,900 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
  • 1870 Harbor Dr, Chester, MD 21619
    1870 Harbor Dr, Chester, MD 21619
    1870 Harbor Dr, Chester, MD 21619
    /34

    $324,900

    • 2 Beds
    • 1 Bath
    • 832 Sq Ft

    1870 Harbor Dr, Chester, MD 21619

    Discover this charming 2-bedroom, 1-bath home in Harbor View featuring beautiful wood floors, a brand-new roof, updated windows, and a spacious rear deck overlooking a large fenced backyard—perfect for relaxing or entertaining while enjoying the Island lifestyle. Ideally located near restaurants, shopping, and easy access to Route 50 for commuting. Come See!

    Rick Parreco RE/MAX Executive

    1870 Harbor Dr, Chester, MD 21619
  • 1221 Cox Neck Rd, Chester, MD 21619
    1221 Cox Neck Rd, Chester, MD 21619
    1221 Cox Neck Rd, Chester, MD 21619
    /35

    $524,900 Open Sat 11AM - 1PM

    • 4 Beds
    • 2.5 Baths
    • 1,482 Sq Ft

    1221 Cox Neck Rd, Chester, MD 21619

    Be the first to see this beautiful two-story house that has been tastefully renovated & upgraded. You will love open concept of living and dining area with a modern & charming electric fireplace; lots of natural lights, vaulted ceiling, beautifully refinished and stained wood floor, maintenance free deck with a lounge area and a firepit, private backyard with a spacious and comfortable lounge

    Jorge Zea Jorge A. Zea

    1221 Cox Neck Rd, Chester, MD 21619
  • 132 Wheelhouse Way, Chester, MD 21619
    132 Wheelhouse Way, Chester, MD 21619
    132 Wheelhouse Way, Chester, MD 21619
    /68

    $1,350,000 New Construction

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

    132 Wheelhouse Way, Chester, MD 21619

    This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly.Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric

    Mary Anne Kowalewski KOVO Realty

    132 Wheelhouse Way, Chester, MD 21619
  • 527 Warbler Way, Stevensville, MD 21666
    527 Warbler Way, Stevensville, MD 21666
    527 Warbler Way, Stevensville, MD 21666
    /45

    $869,900 Open Fri 11AM - 4PM

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

    527 Warbler Way, Stevensville, MD 21666

    This stunning Kerr home offers an inviting open floor plan designed for both comfort and functionality. Featuring 3 bedrooms, 3 baths, and a spacious 3-car garage, this home perfectly blends everyday ease with elevated style. Highlights include a dedicated home office, a cozy screened patio for outdoor relaxation, and a dramatic 2-story stone fireplace that serves as the heart of the great room.

    Mary Anne Kowalewski KOVO Realty

    527 Warbler Way, Stevensville, MD 21666
  • 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

    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, and stainless steel appliances. Brand new Living

    Dori Savani Douglas Realty, LLC

    30 C Queen Mary Ct, Chester, MD 21619
  • 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
  • 201 Golden Eye Ct, Chester, MD 21619
    201 Golden Eye Ct, Chester, MD 21619
    201 Golden Eye Ct, Chester, MD 21619
    /50

    $285,000

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

    201 Golden Eye Ct, Chester, MD 21619

    Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in

    Melissa Tippett TTR Sotheby's International Realty

    201 Golden Eye Ct, Chester, MD 21619
  • 630 Warbler Way Unit 2224, Chester, MD 21619
    630 Warbler Way Unit 2224, Chester, MD 21619
    630 Warbler Way Unit 2224, Chester, MD 21619
    /62

    $724,900 New Construction

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

    630 Warbler Way Unit 2224, Chester, MD 21619

    Introducing the Severn Lot 2224, projected to settle in May 2026. This thoughtfully designed home offers 3 bedrooms, 2.5 baths, and a 1-car garage. Interior highlights include a dry bar, electric fireplace, a spacious owner’s suite with a sitting room, and large walk-in closets. The kitchen is beautifully appointed with a single oven, microwave, gas cooktop, range hood, dishwasher,

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2224, Chester, MD 21619
  • 1839 Harbor Dr, Chester, MD 21619
    1839 Harbor Dr, Chester, MD 21619
    1839 Harbor Dr, Chester, MD 21619
    /23

    $384,999

    • 4 Beds
    • 2 Baths
    • 2,035 Sq Ft

    1839 Harbor Dr, Chester, MD 21619

    REDUCED! Opportunity KnocksWelcome to Harbor View on Kent Island - Just 7 minutes from the Bay BridgeThis oversized ranch style home boasts 4 Bedrooms and 2 Full baths and is located just one block from Cox Creek. The open concept floor plan features a formal living room, large main level bedroom, hardwood flooring throughout, a modern kitchen with ample cabinetry, center island, extra

    Greg Koch Taylor Properties

    1839 Harbor Dr, 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
  • 2865 Cox Neck Rd, Chester, MD 21619
    2865 Cox Neck Rd, Chester, MD 21619
    2865 Cox Neck Rd, Chester, MD 21619
    /38

    $2,259,000

    • 4 Beds
    • 3.5 Baths
    • 5,122 Sq Ft

    2865 Cox Neck Rd, Chester, MD 21619

    An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasting an enchanting open space floorplan. A first floor Ensuite BR has a walk-in closet plus a separate jacuzzi and shower in the updated full bath. The sumptuous approximately 39'X26' Primary Suite with a large sitting room area offers front and rear balconies specifically designed by

    Michele Sinclair Long & Foster Real Estate, Inc.

    2865 Cox Neck Rd, Chester, MD 21619
  • 600 Old Point Rd, Chester, MD 21619
    600 Old Point Rd, Chester, MD 21619
    600 Old Point Rd, Chester, MD 21619
    /8

    $349,900

    • Land
    • 1.5 Acres
    • $233,267 per Acre

    600 Old Point Rd, Chester, MD 21619

    Absolutely Stunning Water View Lot in Sought After Cox Creek Acres on Corner of Old Point Rd and Cox Ct. Huge 1.5 Acres!! Build the House of Your Dreams and even have a basement, in this Quiet Tucked Away Waterfront Neighborhood of Only 14 Homes. A Boat Slip on the Community Pier with Perpetual Lease is included (2nd from the end on the right) at the Community Pier. Lot has approved perc (for 4

    Donna Reichert Keller Williams Flagship

    600 Old Point 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 2026This 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

    Mary Anne Kowalewski KOVO Realty

    630 Warbler Way Unit 2222, Chester, MD 21619
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $995,000

    • 4 Beds
    • 3.5 Baths
    • 3,634 Sq Ft

    132 Kestrel Ln, Chester, MD 21619

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

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • 312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    312 Teal Ct Unit F, Chester, MD 21619
    /40

    $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
  • 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
  • 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
  • 1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    1757 Harbor Dr, Chester, MD 21619
    /18

    $1,125,000 Open Sun 11AM - 1:30PM

    • 4 Beds
    • 3.5 Baths

    1757 Harbor Dr, Chester, MD 21619

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

    George Bailey Keller Williams Flagship

    1757 Harbor Dr, Chester, MD 21619
  • 9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    9B Queen Victoria Way, Chester, MD 21619
    /48

    $399,000

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

    9B Queen Victoria Way, Chester, MD 21619

    This 1680 sq ft , 2 1/2 story townhome & this community have it all! It features many updates within the last year, and it shows beautifully! All It is "move-in ready",!.. The updates include a new main-level half bath & a new full bathroom on the top level, both have new flooring, ADA-compliant toilets, new vanity/sink & faucets, and paint. Interior doors are 6 panel colonial replaced in

    Melanie Mcknight RE/MAX Professionals

    9B Queen Victoria Way, Chester, MD 21619

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Maryland Queen Annes County Chester

Real Estate & Homes for Sale in Chester, MD

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $608,568.
How many homes have sold over the last 12 months in Chester, MD?
181 homes have sold in Chester, MD over the last 12 months.
Is Chester, MD a safe city?
In general, the safest neighborhood in Chester, MD with lower crime scores is Kent Narrows.
What are the most popular zip codes in Chester, MD?
The most popular zip codes in Chester, MD include 21619, 21666, 21638, 21658 and 21409.
What are the most popular neighborhoods in Chester, MD?
The most popular neighborhood in Chester, MD with the most homes for sale is Kent Narrows.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $617,450. If you put a 20% down payment of $123,500 and had a 30-year fixed mortgage with an interest rate of 6.24%, your estimated principal and interest payment would be $3,040 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $130K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, MD?
Chester, MD has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Bayside Elementary School, Matapeake Middle School and Kent Island Elementary School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 42 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 $595,000, up 2% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$595,000
Median Single Family Sale Price
$639,900
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$539,950
Median 1 Bedroom Sale Price
$320,000
Average Price Per Sq Ft
$294
Number of Homes for Sale
59
Last 12 months Home Sales
181
Months of Supply
3.90
Median List Price
$617,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
2%
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