Recently Sold Homes in 21620

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  /23

  $312,000 Sold Jun 20, 2025

  • 1,188 Sq Ft
  • $263/SF
  • 21 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1989

  104 Dutchess Rd, Chestertown, MD 21620

  This home is a must see! Join the Chester Harbor Community.A charming home in a lovely neighborhood on Maryland's Eastern Shore. Welcome to Chester Harbor, Queen Anne's County. Only minutes from historic Chestertown, this three bedroom, two bath home offers one-level living and an appealing owner's suite. The expansive, fully fenced backyard is easily accessed from the private deck off of the

  Helen J Butler Taylor Properties

  104 Dutchess Rd, Chestertown, MD 21620
• 

  

  

  /61

  $525,000 Sold Jun 13, 2025

  • 4,086 Sq Ft
  • $128/SF
  • 7 Days On Market

  • 4 Beds
  • 2.5 Baths
  • Built 2011

  325 Devon Dr, Chestertown, MD 21620

  Welcome to this expansive, move-in-ready colonial in the sought-after Coventry Farms II community. Built in 2011 with all available square footage upgrades, this home offers over 4,300 sq ft of thoughtfully designed living space across three levels. This beautiful Colonial offers 4 bedrooms and 2.5 bathrooms Main Level Highlights: Open-concept floor plan with hardwood flooringFormal living and

  Lisa Gambino Berkshire Hathaway HomeServices PenFed Realty

  325 Devon Dr, Chestertown, MD 21620
• 

  

  

  /42

  $312,000 Sold Jun 13, 2025

  • 1,404 Sq Ft
  • $222/SF
  • 55 Days On Market

  • 4 Beds
  • 2 Baths
  • Built 1959

  306 Cedar St, Chestertown, MD 21620

  Lovely 4 bedroom, 2 bath Cape Cod located in College Heights. The house has been freshly painted inside and out and has a new roof. Mostly wood floors throughout the house. Living room has a fireplace but the fireplace is not in working order. The kitchen/dining combo has parquet wood floors. There is a full unimproved basement that was waterproofed sometime in the past and has both inside

  Doug Ashley Doug Ashley Realtors, LLC

  306 Cedar St, Chestertown, MD 21620
• 

  

  

  /32

  $360,000 Sold Jun 12, 2025

  • 1,724 Sq Ft
  • $209/SF
  • 16 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2022

  216 Silver Heel Rd, Chestertown, MD 21620

  Welcome to this move-in ready home, situated on a premium corner lot in The Village at Chestertown! This charming 1,742 square foot, two-story home offers the perfect blend of comfort and style. The inviting front porch is an ideal spot to unwind with your morning coffee, enjoy the view of the open fields, and watch the clouds drift by.Inside, the well-designed layout begins with a foyer and

  Cynthia Gardner CENTURY 21 New Millennium

  216 Silver Heel Rd, Chestertown, MD 21620
• 

  

  

  /8

  $86,000 Sold Jun 09, 2025

  • 973 Sq Ft
  • $88/SF
  • 18 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1974

  1814 Pondtown Rd, Chestertown, MD 21620

  INVESTOR & BUILDER ALERT! 2.69 Acres | No HOA | Unlock the potential of this prime 2.69-acre property in beautiful Queen Anne’s County! A rare opportunity with no HOA and no restrictions, giving you full creative freedom to bring your vision to life. Whether you're a savvy investor, builder, or contractor looking for your next project, this is the blank canvas you've been waiting for.The existing

  Joelle Dolch Cross Street Realtors LLC

  1814 Pondtown Rd, Chestertown, MD 21620
• 

  

  /27

  $280,000 Sold Jun 09, 2025

  • 1,930 Sq Ft
  • $145/SF
  • 164 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2004

  100 Acorn Dr, Chestertown, MD 21620

  Open house! This Saturday, April 19th 11am-1pm. Brand new stainless steel appliances, fresh paint and newly stained deck! Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor.

  Lisa Raffetto Coldwell Banker Chesapeake Real Estate Company

  100 Acorn Dr, Chestertown, MD 21620
• 

  

  /20

  $150,000 Sold Jun 06, 2025

  • 2,240 Sq Ft
  • $67/SF
  • 0 Days On Market

  • 3 Beds
  • 3 Baths
  • Built 1921

  508 Cannon St, Chestertown, MD 21620

  Duplex in the Historic District of Chestertown located near the rails to trails.

  Deborah Dawkins Coldwell Banker Realty

  508 Cannon St, Chestertown, MD 21620
• 

  

  /38

  $575,000 Sold Jun 06, 2025

  • 2,296 Sq Ft
  • $250/SF
  • 19 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 1920

  129 N Queen St, Chestertown, MD 21620

  Welcome to 129 N. Queen Street situated in one of Historic Chestertown's most desirable and sought after locations. Nestled among multiple other restored and renovated residences, this home itself has undergone a tasteful and remarkable transformation. The entire interior has been completely renovated over the past several years utilizing many new modern materials blended with some original

  William Norris Select Land & Homes, LLC

  129 N Queen St, Chestertown, MD 21620
• 

  

  /4

  $15,000 Sold Jun 02, 2025

  • Land
  • 0.48 Acre
  • $31,250 per Acre

  • 4 Days On Market

  22671 Wood Yard Ln, Chestertown, MD 21620

  Almost half acre of recreational property available between Chestertown and Rock Hall! Best use would be hunting since it is surrounded by woods and farms. There is an existing structure that is a tear down of no value. There appears to be electric run to the property but condition is unknown. The county does not have records of the septic and would need to be perc tested to build on. The back of

  Maryn LeClair Chesapeake Real Estate Associates, LLC

  22671 Wood Yard Ln, Chestertown, MD 21620
• 

  

  /43

  $262,500 Sold May 29, 2025

  • 2,106 Sq Ft
  • $125/SF
  • 87 Days On Market

  • 4 Beds
  • 3 Baths
  • Built 1988

  10705 Millbrook Dr, Chestertown, MD 21620

  Welcome to 10705 Millbrook Drive, a charming Cape Cod-style home located in the desirable Chesapeake Landing community. This 3-bedroom, 2-bathroom residence offers comfortable living with modern updates, including bamboo flooring and a high-efficiency water heater. The open floor plan is perfect for entertaining, with a spacious living area and well-appointed kitchen featuring Meganite

  Edward Kowalski EXP Realty, LLC

  10705 Millbrook Dr, Chestertown, MD 21620
• 

  

  /37

  $295,000 Sold May 29, 2025

  • 1,272 Sq Ft
  • $232/SF
  • 120 Days On Market

  • 2 Beds
  • 2 Baths
  • Built 1973

  23315 Sandpiper Rd, Chestertown, MD 21620

  Discover serenity in this charming 2-bedroom, 2-bath oasis with 1,272 sq ft of living space. Nestled in the Chesapeake Landing community, enjoy proximity to Worton Creek's stunning views and easy access to the Chesapeake Bay. This home boasts enchanting features, including a captivating spiral staircase and elegant galvanized tray ceilings that enhance the vibrant, light-filled living area. Relax

  Andrew Meikle Doug Ashley Realtors, LLC

  23315 Sandpiper Rd, Chestertown, MD 21620
• 

  

  /35

  $510,184 Sold May 29, 2025

  • 2,120 Sq Ft
  • $241/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  716 Aldora Dr, Chestertown, MD 21620

  DECORATED MODELS NOW OPEN Luxury 3 Bedroom Villas The layout is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an additional bath for family and

  Terri Hill Builder Solutions Realty

  716 Aldora Dr, Chestertown, MD 21620
• 

  

  /5

  $11,000 Sold May 29, 2025

  • Land
  • 0.34 Acre
  • $32,353 per Acre

  • 371 Days On Market

  0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620

  POST AUCTION: MAKE AN OFFER! Deposit: $5,000. Lot of land located in the Chestertown area of Kent County, MD.JUST MINUTES to the many attractions of the downtown Chestertown area. Easy access to major traffic artery Fairlee Rd. +/- 15,000 SF. Vacant lot of land.

  Adam Shpritz Ashland Auction Group LLC

  0 Sandpiper Rd Unit MDKE2003870, Chestertown, MD 21620
• 

  

  /40

  $750,000 Sold May 22, 2025

  • 1,682 Sq Ft
  • $446/SF
  • 0 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1956

  5594 Langford Bay Rd, Chestertown, MD 21620

  Discover the perfect blend of vintage charm and modern updates with this beautifully maintained 1950s craftsman, peacefully tucked along the scenic Chester River. Whether you're searching for a quiet second home getaway or a prime income-producing investment, this property offers the waterfront lifestyle so many dream about—boating, fishing, and relaxing right from your own private dock.The heart

  Liddy Campbell TTR Sotheby's International Realty

  5594 Langford Bay Rd, Chestertown, MD 21620
• 

  

  /27

  $250,000 Sold May 22, 2025

  • 1,248 Sq Ft
  • $200/SF
  • 16 Days On Market

  • 3 Beds
  • 1.5 Baths
  • Built 1973

  1106 Round Top Rd, Chestertown, MD 21620

  Opportunity knocks! This 3-bedroom, 1.5-bath rancher sits on a spacious 2-acre lot in Queen Anne’s County. Enjoy the convenience of high-speed internet while taking in the peaceful surroundings. The home features an unfinished basement, offering potential for extra storage or future living space. With some vision and TLC, this property could shine—whether you're looking to renovate or start

  Clint Evans Cross Street Realtors LLC

  1106 Round Top Rd, Chestertown, MD 21620
• 

  

  /22

  $490,000 Sold May 21, 2025

  • 1,476 Sq Ft
  • $332/SF
  • 14 Days On Market

  • 2 Beds
  • 2.5 Baths
  • Built 1900

  101 S Mill St, Chestertown, MD 21620

  Historic charm with a modern floor plan. Live just around the corner walking to the shops, galleries, and restaurants of downtown Chestertown in this beautifully updated Victorian on quiet Mill Street. High end appliances such as Miele and Bosch adorn the kitchen and laundry. Easily converted back into a 3 bedroom. The backyard is well landscaped, has a covered outdoor living space, and a

  Murphy ONeill Coldwell Banker Chesapeake Real Estate Company

  101 S Mill St, Chestertown, MD 21620
• 

  

  /40

  $600,000 Sold May 16, 2025

  • 2,536 Sq Ft
  • $237/SF

  • 5 Beds
  • 2.5 Baths
  • Built 1920

  108 N Queen St, Chestertown, MD 21620

  Queen Street Gem! Located in the historic section of Chestertown, walk to the restaurants, shops, theater, farmer's market, and waterfront. Beautiful woodwork and pocket doors. Spacious rooms, hardwood flooring, solid wood doors, thick moldings, and ample closet space. Featuring 5 bedrooms and 2.5 baths, with 3 bedrooms on the second floor and 2 additional bedrooms on the 3rd floor. Bathrooms

  Peter Heller Coldwell Banker Chesapeake Real Estate Company

  108 N Queen St, Chestertown, MD 21620
• 

  

  /8

  $50,000 Sold May 16, 2025

  • Land
  • 2.20 Acres
  • $22,727 per Acre

  • 159 Days On Market

  0 Fairlee Rd, Chestertown, MD 21620

  Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land

  William Norris Select Land & Homes, LLC

  0 Fairlee Rd, Chestertown, MD 21620
• 

  

  /32

  $782,500 Sold May 09, 2025

  • 2,204 Sq Ft
  • $355/SF
  • 10 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2017

  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

  John Burke Gunther-McClary Real Estate

  308 Landing Ln, Chestertown, MD 21620
• 

  

  /51

  $370,000 Sold May 08, 2025

  • 1,296 Sq Ft
  • $285/SF
  • 10 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1968

  8605 Camp Rd, Chestertown, MD 21620

  Your home sweet home retreat - a gorgeous 3 Bedroom 2 Full Bathroom Rancher with attached carport and unfinished basement is available to tour! Major renovations in 2020 and maintained to pristine condition. If you are looking for a place to come home and relax - this is the one! Sit on the front porch and enjoy the afternoon sun, calm surroundings or listen to the birds actively chirping. Head

  Crystal Smith RE/MAX Executive

  8605 Camp Rd, Chestertown, MD 21620
• 

  

  /37

  $290,000 Sold May 08, 2025

  • 1,252 Sq Ft
  • $232/SF
  • 104 Days On Market

  • 3 Beds
  • 1 Bath
  • Built 1966

  202 Glen St, Chestertown, MD 21620

  Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer. Underground oil tank has been removed and the crawlspace is encapsulated.

  Debbie Meikle Doug Ashley Realtors, LLC

  202 Glen St, Chestertown, MD 21620
• 

  

  /38

  $289,500 Sold May 05, 2025

  • 1,867 Sq Ft
  • $155/SF
  • 13 Days On Market

  • 2 Beds
  • 4 Baths
  • Built 2004

  116 Oak Leaf Dr, Chestertown, MD 21620

  Charming & Move-In ReadyDiscover this beautifully maintained end-unit townhome just minutes from downtown Chestertown! This home has been loved and cared for by the original owners. Offering updated hardwood flooring, carpeting on stairs, fresh paint in the primary living space, a new roof, this ensuring peace of mind for years to come.The spacious master suite features vaulted ceilings, a stall

  Grace Crockett Doug Ashley Realtors, LLC

  116 Oak Leaf Dr, Chestertown, MD 21620
• 

  

  /34

  $265,000 Sold May 02, 2025

  • 1,114 Sq Ft
  • $238/SF
  • 120 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1965

  118 Char Nor Manor Blvd, Chestertown, MD 21620

  An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your

  Rylie Patrick Chesapeake Real Estate Associates, LLC

  118 Char Nor Manor Blvd, 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
• 

  

  /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
• 

  

  /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
• 

  

  /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
• 

  /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
• 

  

  /35

  $479,495 Sold Apr 25, 2025

  • 2,120 Sq Ft
  • $226/SF
  • 0 Days On Market

  • 4 Beds
  • 3.5 Baths
  • Built 2025

  720 Aldora Dr Unit 109, Chestertown, MD 21620

  DECORATED MODELS NOW OPEN Luxury 3 Bedroom Villas The layout is welcoming and very functional. Featuring a huge family room, dining area and stunning kitchen. The second floor boasts 3 bedrooms with an owner's suite that includes 2 walk-in closets and private bath which boasts ceramic tile, a double bowl sink, private water closet and seated shower., and an additional bath for family and

  Terri Hill Builder Solutions Realty

  720 Aldora Dr Unit 109, 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, INC.

  3650 Gratitude Way, 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
• 

  

  /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
• 

  

  /36

  $424,900 Sold Apr 18, 2025

  • 1,680 Sq Ft
  • $253/SF
  • 3 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 2025

  206 Springbrook Ln, Millington, MD 21651

  The new construction home you have been waiting for featuring all the builder upgrades! Don't miss out on this opportunity to buy brand new on a 1 plus acre lot for under 425k in QA County, situated on 1.035 private wooded acres this home features an amazing open floor plan with 3 bedrooms and 2 full baths. This home provides ample storage and closest space, including a walk-in pantry, custom

  Samantha Grimes Chesapeake Real Estate Associates, LLC

  206 Springbrook Ln, Millington, MD 21651
• 

  

  /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 in the

  Retha Arrabal Doug Ashley Realtors, LLC

  25740 Collins Ave, 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
• 

  

  /25

  $385,000 Sold Apr 11, 2025

  • 1,811 Sq Ft
  • $213/SF
  • 19 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1982

  149 Longfellow Dr, Chestertown, MD 21620

  Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living.Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living space—ideal for a family room, home office, or play area.The

  Isaac Bahary KW Empower

  149 Longfellow Dr, 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
• 

  

  /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
• 

  

  /41

  $385,000 Sold Apr 04, 2025

  • 1,560 Sq Ft
  • $247/SF
  • 69 Days On Market

  • 3 Beds
  • 2 Baths
  • Built 1977

  109 Secor Rd, Chestertown, MD 21620

  Charming Home in Chester Harbor with Water Access!Welcome to 109 Secor Rd, Chestertown, MD 21620, nestled on a peaceful cul-de-sac in the desirable water-access community of Chester Harbor on the Queen Anne’s side of the Chester River. This home offers a perfect blend of comfort, charm, and recent updates, making it an exceptional choice for your next chapter.Key

  Amy Larrauri Chesapeake Real Estate Associates, LLC

  109 Secor Rd, Chestertown, MD 21620
• 

  

  /46

  $474,000 Sold Apr 03, 2025

  • 1,900 Sq Ft
  • $249/SF
  • 84 Days On Market

  • 3 Beds
  • 2.5 Baths
  • Built 2024

  220 Blakefield Dr, Chestertown, MD 21620

  Brand New Gorgeous Custom Home completed & ready for a family to start their next adventure. Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island & granite counters, cathedral ceilings, huge family room, 1st floor laundry, front porch, sky-basement on 2nd floor for storage, 2 large bedrooms and full bath on second floor. This great floor plan is hard

  Brenda Fornos Taylor Properties

  220 Blakefield Dr, Chestertown, MD 21620

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