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Chester, MD Homes for Sale

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  • 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
  • 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
  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /40

    $836,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

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

    Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36476268, 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

    $740,900 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
  • 131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $872,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

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

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36477689, 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
  • 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

    $844,900 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36451844, 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

    $659,900 New Construction

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

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - Single Family, 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 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /26

    $807,900 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 444 Macum Creek Dr, Chester, MD 21619
    444 Macum Creek Dr, Chester, MD 21619
    444 Macum Creek Dr, Chester, MD 21619
    /75

    $850,000

    • 3 Beds
    • 2.5 Baths
    • 2,771 Sq Ft

    444 Macum Creek Dr, Chester, MD 21619

    **PLEASE CLICK ON VIRTUAL TOUR ICON FOR INTERACTIVE FLOOR PLAN****Welcome to 444 Macum Creek Drive**Enjoy the Water Views from the Main Level Porch, Upper-Level Porch and Primary Suite**Formal Dining Room leads into the Stunning Living Area w/Upgraded Kitchen Cabinets and New Appliances**Main Level Office w/Waterview**Freshly Painted throughout in 2023**Main Level w/Hardwood Flooring**3

    Deborah Savoie Long & Foster Real Estate, Inc.

    444 Macum Creek Dr, Chester, MD 21619
  • 132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    132 Kestrel Ln, Chester, MD 21619
    /45

    $1,049,000 Open Sat 12PM - 2PM

    • 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

    Brad Kappel TTR Sotheby's International Realty

    132 Kestrel Ln, Chester, MD 21619
  • 108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    108 Bodys Neck Rd, Chester, MD 21619
    /10

    $499,900 Open Sat 1PM - 3PM

    • 3 Beds
    • 2.5 Baths
    • 1,791 Sq Ft

    108 Bodys Neck Rd, Chester, MD 21619

    Coming Soon in Bayside on Kent Island – Resort-Style Island Living with Unmatched Water Views!Discover the perfect blend of coastal charm and modern luxury in this rarely available, oversized end-unit townhome Perfectly positioned to capture water views and marina, this meticulously updated 3-bedroom, 2.5-bath home offers a true resort-style experience in one of the Eastern Shore’s most

    Bill Longest Realty Navigator

    108 Bodys Neck Rd, Chester, MD 21619
  • 245 Peregrine Dr, Chester, MD 21619
    245 Peregrine Dr, Chester, MD 21619
    245 Peregrine Dr, Chester, MD 21619
    /34

    $700,000

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft

    245 Peregrine Dr, Chester, MD 21619

    Professional photos coming soon-This spacious 4-bedroom, 3-bathroom home offers the perfect balance of comfort, style, and functionality. Nestled in a tranquil and highly sought-after neighborhood, this home boasts an open-concept layout, ideal for entertaining guests with the screen in back porch. The inviting living room flows seamlessly into the luxury kitchen, featuring modern appliances,

    Brandi Bradshaw Keller Williams Select Realtors of Annapolis

    245 Peregrine Dr, Chester, MD 21619
  • 124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    124 Nauset Ln, Chester, MD 21619
    /45

    $847,500

    • 3 Beds
    • 3 Baths
    • 2,583 Sq Ft

    124 Nauset Ln, Chester, MD 21619

    NEW UPDATED PHOTOS!! Take another look!Turnkey Luxury with Over $175K in Upgrades – Four Seasons at Kent IslandThis beautifully enhanced Killarney with Loft model in Phase I offers the ultimate in resort-style living, featuring over $100K in builder upgrades and $75K in custom renovations.The gourmet kitchen impresses with a 10’ white quartz island, dry bar, SMART stainless

    Jennifer Thomas RE/MAX Executive

    124 Nauset Ln, Chester, MD 21619
  • 104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    104 Woods Rd, Chester, MD 21619
    /38

    $800,000

    • 5 Beds
    • 3.5 Baths
    • 3,065 Sq Ft

    104 Woods Rd, Chester, MD 21619

    PERFECT MULTI GENERATIONAL HOME!!!! LIST PRICE ADJUSTED !!FANTASTIC HOME! THE COMPLETE PACKAGE AND THEN MORE! INGROUND POOL! TWO PRIMARY BEDROOM/BATH SUITES! BOTH WITH GIANT WALK IN CLOSETS! EACH PRIMARY BATH HAS A STEP IN SHOWER, DOUBLE STONE VANITY PLUS SOAKING TUB! THIS HOME HAS A TOTAL OF 5 BEDROOMS PLUS 3 AND ONE HALF BATHS! PLENTY OF SPACE FOR THE HOME OFFICE! THE OPEN KITCHEN IS FULLY

    Temple Peirce Cummings & Co. Realtors

    104 Woods Rd, Chester, MD 21619
  • 314 Thomas White Blvd, Chester, MD 21619
    314 Thomas White Blvd, Chester, MD 21619
    314 Thomas White Blvd, Chester, MD 21619
    /73

    $769,000

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

    314 Thomas White Blvd, Chester, MD 21619

    WOW! this is your opportunity to get into this sought after community for UNDER $800k! Welcome to 314 Thomas White Blvd. Nestled in the sought-after waterfront community of Gibson’s Grant, this 4-bedroom, 3.5-bath home offers the perfect blend of refined living and relaxed coastal comfort. You will fall in love with the inviting front porch to the detached garage with the 4th bedroom and 3rd full

    Kathleen Higginbotham Keller Williams Flagship

    314 Thomas White Blvd, 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
  • 162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    /37

    $1,195,000

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft

    162 Kirwans Landing Ln, Chester, MD 21619

    Welcome to 162 Kirwans Landing Lane—a beautifully updated residence located in the sought-after, water-privileged community of Kirwans Landing. Set on 1.4 private acres, this 4-bedroom, 2.5-bath home offers a seamless blend of refined comfort and exceptional outdoor living.Inside, you’ll find hardwood floors throughout both levels, a renovated kitchen with granite countertops, custom

    Brad Kappel TTR Sotheby's International Realty

    162 Kirwans Landing Ln, 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

    Judith Brown Samson Properties

    312 Blenny Ln, 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
  • 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
  • 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
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    /77

    $725,000

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

    132 Claiborne St, Chester, MD 21619

    Sitting pretty on one of the largest, level lots in the prestigious Gibson's Grant Community, w/ beautiful landscaping, flowers now blooming, and a lawn irrigation system. The lot is enhanced with landscape lighting and a wood fence. This front porch Chatham model is inviting w/sidewalk extension and has a good view of the peaceful pond and natural surroundings. The foyer and main level have

    Melanie Mcknight RE/MAX Professionals

    132 Claiborne St, Chester, MD 21619
  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /34

    $482,090

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

    807 Auckland Way, Chester, MD 21619

    PRICE REDUCED! Waterside Living on Kent Island! Discover the perfect blend of comfort and convenience in this spacious 3-bedroom, 3.5-bathroom condo located on Kent Island, in the Bayside Condominiums waterside community. This 3-level condo offers a wonderful combination of space, style, and serene coastal living.The open-concept main floor features a freshly painted, inviting living

    Andrew Spagnolo Samson Properties

    807 Auckland Way, 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
  • 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

    $574,852 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.

    Builder Photo

    K. Hovnanian Homes

    Builder

    630 Warbler Way Unit 12, Chester, MD 21619
  • 629 Warbler Way, Chester, MD 21619
    629 Warbler Way, Chester, MD 21619
    629 Warbler Way, Chester, MD 21619
    /11

    $709,900 New Construction

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

    629 Warbler Way, Chester, MD 21619

    Open kitchen, dining area, and great room. Kitchen with Statuary Classique quartz central island. Great room with fireplace for cozy gatherings. Screened patio off great room extends living space. Primary suite with elegant ceiling treatment. Primary bath with dual freestanding vanities. Private home office tucked away from main living areas.

    Builder Photo

    K. Hovnanian Homes

    Builder

    629 Warbler Way, Chester, MD 21619
  • 121 Wheelhouse Way Unit 11, Chester, MD 21619
    121 Wheelhouse Way Unit 11, Chester, MD 21619
    121 Wheelhouse Way Unit 11, Chester, MD 21619
    /10

    $539,900 New Construction

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

    121 Wheelhouse Way Unit 11, Chester, MD 21619

    Home office with double doors near entry.Gourmet kitchen with central island for prep & dining.Dining area includes built-in dry bar.Great room features a sleek electric fireplace.Multi-slide glass doors open to rear patio.Owner’s suite with walk-in closet for storage.Spa-inspired owner’s bath with dual sinks.

    Builder Photo

    K. Hovnanian Homes

    Builder

    121 Wheelhouse Way Unit 11, Chester, MD 21619
  • 121 Wheelhouse Way Unit 2111, Chester, MD 21619
    121 Wheelhouse Way Unit 2111, Chester, MD 21619
    121 Wheelhouse Way Unit 2111, Chester, MD 21619
    /73

    $539,900 New Construction

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

    121 Wheelhouse Way Unit 2111, Chester, MD 21619

    This Magothy condo offers low-maintenance luxury with a smart layout and designer features. With 2 bedrooms, 2.5 bathrooms, a 1-car garage, and a dedicated home office with French doors, it’s the perfect mix of comfort and versatility. Enjoy cozy evenings by the electric fireplace or entertaining at the built-in dry bar.The kitchen includes quartz countertops, a gas cooktop, range hood,

    Mary Anne Kowalewski KOVO Realty

    121 Wheelhouse Way Unit 2111, Chester, MD 21619
  • 131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    131 Flycatcher Way Unit 36464519, Chester, MD 21619
    /13

    $691,900 New Construction

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

    Simone Plan at K. Hovnanian’s® Four Seasons at Kent Island - Single Family, Chester, MD 21619

    Private bedroom 2 located off foyer for overnight guests. Striking kitchen with large island and plenty of counter space. Open and airy great room with slider to covered patio. Convenient covered patio with screened patio option. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with split vanities. Versatile loft on second floor with 2 secondary bedrooms and full

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36464519, Chester, MD 21619
  • 0 Newtown Rd, Chester, MD 21619
    0 Newtown Rd, Chester, MD 21619
    0 Newtown Rd, Chester, MD 21619
    /7

    $346,000

    • Land
    • 1.68 Acres
    • $205,952 per Acre

    0 Newtown Rd, Chester, MD 21619

    Looking for peace and serenity, look no further! You won't find a better opportunity on the eastern shore, total of 1.68 acres (per the tax record)! This is a total of 3 parcels of land with 3 tax ID numbers being sold as a package. Buyer to verify sewer and water source and specific lot lines and land survey. The tax ID's are as follows: Lot #1 -1804063945, Lot #2 - 1804105664, Lot #3 -

    Rob Carter Douglas Realty, LLC

    0 Newtown Rd, 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
  • 204 Dominion Ln, Chester, MD 21619
    204 Dominion Ln, Chester, MD 21619
    204 Dominion Ln, Chester, MD 21619
    /38

    $395,000

    • 4 Beds
    • 1 Bath
    • 1,492 Sq Ft

    204 Dominion Ln, Chester, MD 21619

    Just steps from the scenic Crab Alley Creek and a short drive to Crab Alley Marina. This charming four-bedroom, one-bath rancher offers both comfort and convenience in a prime location on a peaceful dead-end street just minutes away from shopping, restaurants and the Bay Bridge. Perfectly situated on a premium, level .44-acre lot, the home provides 1,492 square feet of living space all on one

    James Real Estate Group EXP Realty, LLC

    204 Dominion Ln, 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

    $709,900

    • 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

    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
    /34

    $485,000

    • 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 - 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 cabinetry, beverage

    Suzanne Hitt Coldwell Banker Waterman Realty

    1401 Calvert Rd, 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

    $425,000

    • 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. 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 2024! The main level features new

    Melanie Mcknight RE/MAX Professionals

    9B Queen Victoria Way, Chester, MD 21619
  • 203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    /53

    $475,000

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft

    203 Barren Ridge Rd, Chester, MD 21619

    Priced to Sell- VERY motivated sellers!!! Nestled in the tranquil community of Chester, Maryland, 203 Barren Ridge Road offers a unique blend of coastal charm and suburban comfort. This inviting Colonial-style home, situated on a 0.31-acre lot, features three bedrooms on the second floor with an oversized full bath that can easily be reconfigured to meet your needs! The main level provides ample

    Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 2

Maryland Queen Annes County Chester

Real Estate & Homes for Sale in Chester, MD

Why Live in Chester

Chester, MD, located on Kent Island between the Chester River and Chesapeake Bay, offers a blend of coastal charm and modern convenience. The area is known for its maritime atmosphere, with numerous marinas and waterfront views. Chester is 17 miles from Annapolis, home to the United States Naval Academy. Outdoor enthusiasts can enjoy Terrapin Nature Park's walking paths and tidal marshes, or the Cross Island Trail for hiking and cycling. Castle Marina provides opportunities for boating and fishing. Indoor fitness options include Club One Fitness and Aerobics. Housing in Chester ranges from ranch-style homes and colonials to New Traditional builds, with properties south of Highway 50 dating back to the mid-20th century and newer developments in the north. The area features a mix of single-family homes, condos, and townhouses, with some waterfront estates requiring additional flood insurance. Annual events like the Kent Island Crab Feast and the Annapolis Baygrass Music Festival foster community spirit. Shopping and dining are centered around Highway 50, with big-box stores like Safeway and Target, and bayside dining options in nearby Kent Narrows, including The Jetty and Bridges. Chester's schools are highly rated, with Bayside Elementary, Stevensville Middle, and Kent Island High all receiving commendable scores. Highway 50 is the main transportation route, connecting Chester to Annapolis, Baltimore, and Washington, D.C., while BWI International Airport is about 30 miles away.

Learn more about living in Chester

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $600,652.
How many homes have sold over the last 12 months in Chester, MD?
171 homes have sold in Chester, MD over the last 12 months.
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 $575,000. If you put a 20% down payment of $115,000 and had a 30-year fixed mortgage with an interest rate of 6.56%, your estimated principal and interest payment would be $2,930 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $126K a year to afford the median home price in Chester.
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 Stevensville Middle 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 44 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 $595,000, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$595,000
Median Single Family Sale Price
$633,900
Median Townhouse Sale Price
$459,000
Median 2 Bedroom Sale Price
$510,000
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$293
Number of Homes for Sale
64
Last 12 months Home Sales
171
Months of Supply
4.50
Median List Price
$575,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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