6,883

Chestertown, MD Homes

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  • 117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    117 N Water St Unit 1A, Chestertown, MD 21620
    /28

    $725,000

    • 3 Beds
    • 3 Baths

    117 N Water St Unit 1A, Chestertown, MD 21620

    Completely remodeled, this three-bedroom waterfront home boasts a charming front porch and enormous back porch - your private space overlooking the river - along with an enclosed sunroom featuring gorgeous river views through walls of windows. Enjoy abundant outdoor areas and stunning water views from nearly every room. The dock features 3+ feel MLW, with slips available for purchase. This

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 589-6299

    117 N Water St Unit 1A, Chestertown, MD 21620
  • 425 High St Unit 5, Chestertown, MD 21620
    425 High St Unit 5, Chestertown, MD 21620
    425 High St Unit 5, Chestertown, MD 21620
    /9

    $1,495 per month

    • 2 Beds
    • 1 Bath
    • 900 Sq Ft
    • Condo for Rent

    425 High St Unit 5, Chestertown, MD 21620

    Property Id: 1426365A modern apartment in the heart of Chestertown. Blocks from Fountain Park and Washington College, this third floor, 2 bedroom apartment is in a building that was recently renovated to the studs, with modern windows and HVAC and original features, such as wood floors and exposed beams. In-building laundry and shared yard for tenants' use. Available immediately. Landlord

    425 High St Unit 5, Chestertown, MD 21620
  • 107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    107 Chester Arms Dr, Chestertown, MD 21620
    /19

    $230,000 Sold May 01, 2025

    • 1,140 Sq Ft
    • $202/SF
    • 14 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2022

    107 Chester Arms Dr, Chestertown, MD 21620

    Why rent when you can own for less?!?! Three beds, 2 baths!! This inviting one-level home offers easy one-level living. Featuring luxury vinyl plank flooring , a stylish open kitchen and granite countertops, and a cozy eat-in area that opens to the living room, this home feels very welcoming. The comfortable primary suite features a full bath, while two additional bedrooms provide flexibility

    Casey Scattergood Cross Street Realtors LLC

    107 Chester Arms Dr, Chestertown, MD 21620
    • 103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      103 Trafford Dr, Chestertown, MD 21620
      /31

      Est $322,317 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 1,944 Sq Ft

      103 Trafford Dr, Chestertown, MD 21620

      103 Trafford Dr, Chestertown, MD 21620
  • Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    Lot 9 Prestwick Dr, Chestertown, MD 21620
    /20

    $212,000

    • Land
    • 1.95 Acres
    • $108,718 per Acre

    Lot 9 Prestwick Dr, Chestertown, MD 21620

    Lot 9 overlooks the 5th hole tee box and the picturesque par 3 water hole # 4. Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 806-9518

    Lot 9 Prestwick Dr, Chestertown, MD 21620
  • 128 N Queen St, Chestertown, MD 21620
    128 N Queen St, Chestertown, MD 21620
    128 N Queen St, Chestertown, MD 21620
    /19

    $1,900 per month

    • 2 Beds
    • 1 Bath
    • 1,455 Sq Ft
    • House for Rent

    128 N Queen St, Chestertown, MD 21620

    Welcome to 128 N Queen Street, Unit 2. A beautiful Victorian apartment located downtown Chestertown within walking distance to the Chester River and situated close to the Washington College. Downstairs features a large living area, formal living/dining room that could be used as a 3rd bedroom, open kitchen/dining area with laundry. Tenant would have private access to 2 of the three porches.

    Amanda Morgan Brenton Realty Group

    128 N Queen St, Chestertown, MD 21620
  • 123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    123 Burchard Sawmill Rd, Chestertown, MD 21620
    /53

    $485,000 Sold May 01, 2025

    • 1,648 Sq Ft
    • $294/SF
    • 4 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1918

    123 Burchard Sawmill Rd, Chestertown, MD 21620

    This is it! This is the one you and your horse have been dreaming about! Absolutely darling 4+ acre farmette! Charm charm charm plus function function function. Turnkey and ready for your horses, your ponies or your 4-H projects, or all of the above! Built in 1918, this 3 Bedroom American Folk merges vernacular farmhouse (winder staircase, built-in corner cupboard, beautiful curved plaster wall)

    Crystal Pickett EXP Realty, LLC

    123 Burchard Sawmill Rd, Chestertown, MD 21620
    • 27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      27370 Morgnec Rd, Chestertown, MD 21620
      /23

      Est $290,862 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths
      • 1,008 Sq Ft

      27370 Morgnec Rd, Chestertown, MD 21620

      27370 Morgnec Rd, Chestertown, MD 21620
  • Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    /15

    $150,000

    • Land
    • 1.18 Acres
    • $127,119 per Acre

    Lot 3 Muirfield Dr, Chestertown, MD 21620

    Lot 3 located at the midway point of Fairway #10, a perfect spot to enter the back nine and head to the club house for lunch or dinner (membership required) Prestwick offers the best in eastern shore living with the small town charm of Chestertown Md, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington DC. Join the club and have access to the great golfing, club pool,

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 331-9489

    Lot 3 Muirfield Dr, Chestertown, MD 21620
  • 312 Hilltop Ln, Chestertown, MD 21620
    312 Hilltop Ln, Chestertown, MD 21620
    312 Hilltop Ln, Chestertown, MD 21620
    /29

    $1,900 per month

    • 3 Beds
    • 2.5 Baths
    • 1,200 Sq Ft
    • Townhouse for Rent

    312 Hilltop Ln, Chestertown, MD 21620

    Property Id: 1799413Welcome to this charming 3 bedroom, 2 1/2 bathroom townhome in desirable Chestertown, Maryland. This bright and sunny townhome has new carpeting with neutral paint throughout. The first floor has a kitchen with a large sunny window a microwave oven, stainless steel sink, dishwasher and a combined washer and dryer. There is a large great room with sliding patio

    312 Hilltop Ln, Chestertown, MD 21620
  • 505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    505 N Kent St, Chestertown, MD 21620
    /23

    $352,500 Sold Apr 30, 2025

    • 1,402 Sq Ft
    • $251/SF
    • 9 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1985

    505 N Kent St, Chestertown, MD 21620

    Charming Rancher in Sought-After Byford Development!Nestled in the desirable Byford Development of Chestertown, this 1,402 sq. ft. rancher sits on a spacious 1/3-acre lot offering comfort, convenience, and opportunity! Featuring 3 bedrooms and 2 full baths, this one-level home boasts a primary suite with double sinks and an oversized shower, as well as a bright enclosed Florida room with vaulted

    Sarah Ulrick Rock Hall Properties Real Estate

    505 N Kent St, Chestertown, MD 21620
    • 0 Foxchase Dr, Chestertown, MD 21620
      0 Foxchase Dr, Chestertown, MD 21620
      0 Foxchase Dr, Chestertown, MD 21620
      /29

      Not Listed For Sale

      0 Foxchase Dr, Chestertown, MD 21620

      0 Foxchase Dr, Chestertown, MD 21620
  • 117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    117 N Water St Unit 2A, Chestertown, MD 21620
    /28

    $399,000

    • 2 Beds
    • 1 Bath
    • 787 Sq Ft

    117 N Water St Unit 2A, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. This unit offers a 2 Bed 1 bath has a brand new kitchen, with island and upgraded bathroom along with up and down river views. Enjoy all the amenities of living waterfront--Community

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 824-5609

    117 N Water St Unit 2A, Chestertown, MD 21620
  • 101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    101 Morgnec Rd, Chestertown, MD 21620
    /11

    $1,300 per month

    • 1 Bed
    • 1 Bath
    • 785 Sq Ft
    • Condo for Rent

    101 Morgnec Rd, Chestertown, MD 21620

    One, two and three bedroom apartments located near Washington College, wellness/ rehab center, Churches, shopping and a short walk to downtown Chestertown. Short distance to the Chester River and Chesapeake Bay. Immediate Availability.

    Herschell Claggett Davis Real Estate, Inc.

    101 Morgnec Rd, Chestertown, MD 21620
  • 113 Pine Cove Ln, Chestertown, MD 21620
    113 Pine Cove Ln, Chestertown, MD 21620
    /2

    $57,500 Sold Apr 30, 2025

    • Land
    • 0.45 Acre
    • $127,778 per Acre
    • 185 Days On Market

    113 Pine Cove Ln, Chestertown, MD 21620

    Wonderful opportunity to purchase two established adjoining residential lots within a short walking distance to the Chester River and deep water boat ramp. These two recorded lots were purchased many years ago by a family that vacationed in a home nearby. These lots have not been perc tested but the soil types are conducive to percing and there are homes on the neighboring parcels. Please

    William Norris Select Land & Homes, LLC

    113 Pine Cove Ln, Chestertown, MD 21620
    • 148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      148 Grant Ct, Chestertown, MD 21620
      /30

      Est $455,956 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,664 Sq Ft

      148 Grant Ct, Chestertown, MD 21620

      148 Grant Ct, Chestertown, MD 21620
  • 117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    117 N Water St Unit 3B, Chestertown, MD 21620
    /24

    $299,900

    • 1 Bed
    • 1 Bath
    • 652 Sq Ft

    117 N Water St Unit 3B, Chestertown, MD 21620

    A stately 1800’s waterfront Victorian home, rich in history enters a new chapter in life with 6 new condominium units. Make sure to bring all you water toys or a lounge chair to relax on the banks of Chester River. All the units have been renovated with with upgraded bathrooms and brand new kitchens. Enjoy all the amenities of living waterfront--Community dock, kayak storage, patio, and your own

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 453-1375

    117 N Water St Unit 3B, Chestertown, MD 21620
  • 425 High St Unit 4, Chestertown, MD 21620
    425 High St Unit 4, Chestertown, MD 21620
    425 High St Unit 4, Chestertown, MD 21620
    /14

    $1,000 per month

    • Studio
    • 1 Bath
    • 300 Sq Ft
    • Condo for Rent

    425 High St Unit 4, Chestertown, MD 21620

    Property Id: 1770574Studio apartment in walking distance to Washington College and downtown Chestertown. Second floor studio apartment in recently renovated building. Updated insulation, modern windows and HVAC with original features, such as wood floors. In-building laundry and shared yard for tenants' use. Available early June. Landlord requires a minimum 650 credit score and month

    425 High St Unit 4, Chestertown, MD 21620
  • 3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    3650 Gratitude Way, Chestertown, MD 21620
    /18

    $636,383 Sold Apr 24, 2025

    • 3,599 Sq Ft
    • $177/SF
    • 1 Day On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    3650 Gratitude Way, Chestertown, MD 21620

    TO BE BUILT......Welcome to Ryan Homes at Gilbert Meadows. Offering ranch style & 2-story single family homes with 1st floor primary suites in Harford County, MD. Minutes to Rte. 22 & I-95 - Starting from the low $500's. Our homes are designed to make your life easier with open and modern designs connecting all the spaces you use most! Plus, our homes all offer all the conveniences of main-level

    Tineshia Johnson NVR Services, Inc.

    3650 Gratitude Way, Chestertown, MD 21620
    • 104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      104 Metcalf Rd, Chestertown, MD 21620
      /17

      Est $261,842 Not Listed For Sale

      • 3 Beds
      • 1.5 Baths

      104 Metcalf Rd, Chestertown, MD 21620

      104 Metcalf Rd, Chestertown, MD 21620
  • 308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    308 Landing Ln, Chestertown, MD 21620
    /32

    $789,000 Under Contract

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

    308 Landing Ln, Chestertown, MD 21620

    Exceptional Chester River Landing townhome with elevated views of the Chester River. Enjoy sunrises over the Chester from the balcony and living space. Beautiful views any time of year. A deep water boat slip is included in the sale. The living room offers, cozy gas fireplace, has beautiful water views all year. This condo boast an open floor plan with tons of natural light, ample room for

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (410) 779-9803

    308 Landing Ln, Chestertown, MD 21620
  • 21179 Montgomery Ave, Chestertown, MD 21620
    21179 Montgomery Ave, Chestertown, MD 21620
    21179 Montgomery Ave, Chestertown, MD 21620
    /21

    $1,995 per month

    • 3 Beds
    • 2 Baths
    • 1,400 Sq Ft
    • House for Rent

    21179 Montgomery Ave, Chestertown, MD 21620

    Charming Ranch Home in Tolchester Estates – Walk to the Bay!Welcome to this well-maintained ranch-style home, offering easy one-level living in the heart of Tolchester Estates. Relax on the cozy front porch and enjoy the peaceful surroundings with open space on both sides of the property—perfect for added privacy.This friendly waterfront community features a private beach and boat

    Kathy Hagerty Long & Foster Real Estate, Inc.

    21179 Montgomery Ave, Chestertown, MD 21620
  • 130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    130 Sheaffer Rd, Chestertown, MD 21620
    /25

    $431,000 Sold Apr 22, 2025

    • 1,766 Sq Ft
    • $244/SF
    • 1 Day On Market
    • 4 Beds
    • 2 Baths
    • Built 1999

    130 Sheaffer Rd, Chestertown, MD 21620

    Welcome to The Grove in Chestertown, a picturesque location in Queen Anne's county, located just a short drive from Chesapeake College and historic Chestertown.130 Sheaffer Road offers peaceful living on over an acre of land with highlights such as main level bedrooms, an expansive fenced in backyard, two car garage, large shed for additional storage, and more! As you enter through the front

    Biana Arentz Coldwell Banker Realty

    130 Sheaffer Rd, Chestertown, MD 21620
    • 213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      213 Pine Cove Ln, Chestertown, MD 21620
      /16

      Est $363,233 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,400 Sq Ft

      213 Pine Cove Ln, Chestertown, MD 21620

      213 Pine Cove Ln, Chestertown, MD 21620
  • 10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    10141 Flatland Rd, Chestertown, MD 21620
    /5

    $292,900

    • 2 Beds
    • 1 Bath
    • 2,142 Sq Ft

    10141 Flatland Rd, Chestertown, MD 21620

    Farmhouse located on two acre cleared lot that overlooks farmland. Improvements have been made to the property, including a metal farm/garage/workshop building with electric and three garage doors. There is a shed that improvements have started on, but not complete. Property has two bedrooms and one bath, with a traditional floor plan typical for a farmhouse style home. The kitchen is in

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 618-9426

    10141 Flatland Rd, Chestertown, MD 21620
  • 7938 Radcliffe Rd, Chestertown, MD 21620
    7938 Radcliffe Rd, Chestertown, MD 21620
    7938 Radcliffe Rd, Chestertown, MD 21620
    /44

    $560,000 Sold Apr 21, 2025

    • 2,408 Sq Ft
    • $233/SF
    • 115 Days On Market
    • 5 Beds
    • 3.5 Baths
    • Built 1976

    7938 Radcliffe Rd, Chestertown, MD 21620

    This impeccably maintained home is a true standout and has it ALL! With 5 spacious bedrooms - with both main level & upper level primary suites - and 3.5 baths, including a main level primary suite with a walk-in closet featuring a premium wood built-in system, dual vanity, and a double-headed walk-in tiled shower. This home offers both luxury and convenience. The updated kitchen is an ideal

    Liddy Campbell TTR Sotheby's International Realty

    7938 Radcliffe Rd, Chestertown, MD 21620
    • 7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      7499 Poplar Ave, Chestertown, MD 21620
      /34

      Est $262,486 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      7499 Poplar Ave, Chestertown, MD 21620

      7499 Poplar Ave, Chestertown, MD 21620
  • 21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    21082 Wyoming Ave, Chestertown, MD 21620
    /61

    $1,799,000

    • 3 Beds
    • 3.5 Baths
    • 4,647 Sq Ft

    21082 Wyoming Ave, Chestertown, MD 21620

    Charming Chesapeake Bay Home with Stunning Water Views and Incredible Sunsets! Discover the beauty of waterfront living in this exquisite home featuring panoramic views of the Chesapeake Bay. Having undergone a comprehensive renovation in 2022-2023, this property continues to impress with ongoing enhancements. The large deck overlooking the pool is the latest improvement. Inside the main

    Agent Photo

    Retha Arrabal

    Doug Ashley Realtors, LLC

    (410) 883-5429

    21082 Wyoming Ave, Chestertown, MD 21620
  • 25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    25740 Collins Ave, Chestertown, MD 21620
    /53

    $375,000 Sold Apr 16, 2025

    • 3,389 Sq Ft
    • $111/SF
    • 29 Days On Market
    • 5 Beds
    • 3 Baths
    • Built 1956

    25740 Collins Ave, Chestertown, MD 21620

    Large Home with Private Pool & Separate Apartment!Nestled in a prime location, this solid, well-maintained home offers breathtaking views of the Chester River Yacht and Country Club Golf Course, creating an inviting and peaceful atmosphere. Originally built in 1956, the character and charm of this property shine through, with a cozy wood stove in the large den, and a welcoming fireplace

    Retha Arrabal Doug Ashley Realtors, LLC

    25740 Collins Ave, Chestertown, MD 21620
    • 724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      724 Deep Landing Rd, Chestertown, MD 21620
      /63

      Est $387,489 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,311 Sq Ft

      724 Deep Landing Rd, Chestertown, MD 21620

      724 Deep Landing Rd, Chestertown, MD 21620
  • 24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    24095 Chestertown Rd, Chestertown, MD 21620
    /45

    $334,000

    • 3 Beds
    • 1 Bath
    • 1,104 Sq Ft

    24095 Chestertown Rd, Chestertown, MD 21620

    This gem just outside of Chestertown will be active mid-April. New HVAC, new roof, new flooring and other upgrades! Great living space with a front porch and back patio. Large backyard that overlooks beautiful farm fields. There is a one car detached insulated garage. This home offers close proximity to Rock Hall and all downtown Chestertown amenities, schools, and parks and is only 25 minutes

    Agent Photo

    Lona Todd

    Taylor Properties

    (410) 724-1462

    24095 Chestertown Rd, Chestertown, MD 21620
  • 21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    /16

    $195,000 Sold Apr 11, 2025

    • 1,350 Sq Ft
    • $144/SF
    • 0 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1955

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620

    This property is in great condition, with a nice kitchen, a living/dining room combo on the main level, a utility room and plenty of storage space. The living room has a slider out to the patio, and there is a storage shed there for outdoor storage. This is an end unit in great condition. Upstairs there are three bedrooms and a full bath. Nice light from windows and indoor lighting.

    Retha Arrabal Doug Ashley Realtors, LLC

    21313 Persimmon Dr Unit 24, Chestertown, MD 21620
    • 10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      10570 Cogar Rd, Chestertown, MD 21620
      /56

      Est $357,061 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 2,862 Sq Ft

      10570 Cogar Rd, Chestertown, MD 21620

      10570 Cogar Rd, Chestertown, MD 21620
  • 103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    103 Landing Ln, Chestertown, MD 21620
    /41

    $579,000 Open Sat 11AM - 1:30PM

    • 2 Beds
    • 2.5 Baths
    • 2,100 Sq Ft

    103 Landing Ln, Chestertown, MD 21620

    Step into this nearly new, impeccably maintained two-bedroom townhouse located in the highly desirable Chester River Landing community. Recent upgrades make this home truly turn-key, perfect for those seeking comfort and style. Relax and entertain all summer long on the beautifully designed screened-in porch, ideal for enjoying warm evenings and gentle breezes.On the second floor, the spacious

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 981-2534

    103 Landing Ln, Chestertown, MD 21620
  • 473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    473 Pear Tree Point Rd, Chestertown, MD 21620
    /24

    $359,900 Sold Apr 11, 2025

    • 1,512 Sq Ft
    • $238/SF
    • 67 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2024

    473 Pear Tree Point Rd, Chestertown, MD 21620

    Come By this brand new Cape Cod nestled in charming Pear Tree Point! This 3-bedroom, 3-bathroom haven offers the tranquility of coastal living with the ease of new construction. Step inside and discover the warmth of this open floor plan luxury vinyl plank flooring flowing throughout the main level. Unwind in the light-filled living area, perfect for entertaining, or retreat to the inviting

    David Moore RE/MAX Executive

    473 Pear Tree Point Rd, Chestertown, MD 21620
    • 209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      209 Blakefield Dr, Chestertown, MD 21620
      /9

      Est $451,671 Not Listed For Sale

      • 3 Beds
      • 2 Baths

      209 Blakefield Dr, Chestertown, MD 21620

      209 Blakefield Dr, Chestertown, MD 21620
  • Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    Lot 3 Muirfield Dr, Chestertown, MD 21620
    /8

    $790,000 New Construction

    • 3 Beds
    • 2.5 Baths

    Lot 3 Muirfield Dr, Chestertown, MD 21620

    Spec home located in small 12 home development (to be built). Prestwick offers the best in eastern shore living with the small town charm of Chestertown, MD, yet only 1 to 2 hours from Wilmington, Philadelphia, Baltimore and Washington, DC. Join the club and have access to the great golfing, club pool, marina (with boat slips) and boat ramp or just launch the boat, paddle board or kayak at the

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 966-6341

    Lot 3 Muirfield Dr, Chestertown, MD 21620
  • 234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    234 Blakefield Dr, Chestertown, MD 21620
    /3

    $553,500 Sold Apr 07, 2025

    • 2,400 Sq Ft
    • $231/SF
    • 0 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    234 Blakefield Dr, Chestertown, MD 21620

    3 BEDROOM, 2.5 BTHROOM NEW CONSTRUCTION TO START. FINISHED BONUS ROOM. FULL UNFINISHED BASEMENT. APROX 2400 SF.

    Chris Haddaway Chesapeake Real Estate Associates, LLC

    234 Blakefield Dr, Chestertown, MD 21620
    • 221 Central Dr, Chestertown, MD 21620
      221 Central Dr, Chestertown, MD 21620
      221 Central Dr, Chestertown, MD 21620
      /11

      Est $335,316 Not Listed For Sale

      • 3 Beds
      • 2 Baths
      • 1,232 Sq Ft

      221 Central Dr, Chestertown, MD 21620

      221 Central Dr, Chestertown, MD 21620
  • 228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    228 S Water St, Chestertown, MD 21620
    /24

    $950,000 New Construction

    • 3 Beds
    • 3.5 Baths

    228 S Water St, Chestertown, MD 21620

    Newly constructed 3 Bedroom townhouses with nearly all the desired attributes of town living, with water views and access from the marina on one side and waterfront park on the other. Walk to downtown shops and restaurants, just a few blocks away.

    Agent Photo

    John Burke

    Gunther-McClary Real Estate

    (443) 230-5332

    228 S Water St, Chestertown, MD 21620

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