Chestertown MD FSBO Homes (106)

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We have 106 homes for sale by owner in Chestertown, MD. The median list price in Chestertown, MD is $3,008,927.

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Homes For Sale

$549,000

  • 3 Bed
  • 2.0 Bath
  • 1,961 Sqft
  • 18200 Sqft(Lot)
101 Birch Run Road , Chestertown, MD

A sleek, thoughtfully executed renovation with clean lines and a minimalist aesthetic—sure to impress even the... Read More

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Homes For Sale

$599,900

  • 5 Bed
  • 2.5 Bath
  • 2,536 Sqft
  • 3400 Sqft(Lot)
108 N Queen Street , Chestertown, MD

Queen street gem! located in the historic section of chestertown, walk to the restaurants, shops, theater,... Read More

Coming Soon
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Homes For Sale

$525,000

  • 4 Bed
  • 2.5 Bath
  • 4,086 Sqft
  • 11400 Sqft(Lot)
325 Devon Drive , Chestertown, MD

Welcome to this expansive, move-in-ready colonial in the sought-after coventry farms ii community. built in 2011... Read More

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Vacant Land For Sale

$150,000

  • 87,120 Sqft
  • 87120 Sqft(Lot)
Georgetown Road Se SE, Chestertown, MD

Beautiful 2-acre lot – build your dream home! come and experience the charm of this picturesque 2-acre lot,... Read More

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Homes For Sale

$99,900

  • 2 Bed
  • 1.0 Bath
  • 910 Sqft
  • 2400 Sqft(Lot)
132 Prospect Street , Chestertown, MD

Priced to sell fast! renovate & resell or buy & hold, desirable 2 level colonial, spacious kitchen, spacious... Read More

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Homes For Sale

$334,000

  • 3 Bed
  • 1.0 Bath
  • 1,104 Sqft
  • 20000 Sqft(Lot)
24095 Chestertown Road , Chestertown, MD

This gem just outside of chestertown will be active mid-april. new hvac, new roof, new flooring and other... Read More

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Homes For Sale

$865,000

  • 2 Bed
  • 2.0 Bath
  • 1,966 Sqft
  • 399881 Sqft(Lot)
26889 Morgnec Road , Chestertown, MD

This waterfront farmette is a rare find just a few minutes from downtown chestertown and features extensive... Read More

Coming Soon
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Homes For Sale

$575,000

  • 3 Bed
  • 2.5 Bath
  • 2,010 Sqft
  • 84942 Sqft(Lot)
25285 Foxchase Drive , Chestertown, MD

Welcome to your private oasis! this charming home boasts mature landscaping that provides both beauty and... Read More

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Homes For Sale

$725,000

  • 2 Bed
  • 2.5 Bath
  • 3,300 Sqft
100 Little Harbor Way , Chestertown, MD

Welcome to 100 little harbor way, a charming home nestled in the desirable chestertown community of chester... Read More

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Vacant Land For Sale

$15,000

  • 30,056 Sqft
  • 30056.4 Sqft(Lot)
23683 L Road , Chestertown, MD

This wooded property offers a peaceful, rural setting while still being close to local amenities and waterfront... Read More

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Vacant Land For Sale

$120,000

  • 78,408 Sqft
  • 78408 Sqft(Lot)
Georgetown Rd & Cross Road , Chestertown, MD

Live just down the road from fairlee creek! public access is less than a mile away allowing the chesapeake bay... Read More

Coming Soon
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Homes For Sale

$220,000

  • 1 Bed
  • 1.0 Bath
  • 882 Sqft
  • 7600 Sqft(Lot)
619 Cannon Street , Chestertown, MD

Ideally situated in chestertown’s sought-after historic district, this charming 1-bedroom, 1-bathroom cottage... Read More

Active Under Contract
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Homes For Sale

$749,900

  • 5 Bed
  • 3.0 Bath
  • 3,394 Sqft
  • 43560 Sqft(Lot)
7988 Aldan Drive , Chestertown, MD

This is a stunning property! it combines elegance and functionality with its spacious layout, beautiful... Read More

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Vacant Land For Sale

$10,000

  • 32,000 Sqft
  • 32000 Sqft(Lot)
Iowa Avenue , Chestertown, MD

Court ordered sale - all offers subject to third party approval. lot does not have a water/sewer allocation.... Read More

Coming Soon
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Homes For Sale

$459,000

  • 2 Bed
  • 2.0 Bath
  • 1,496 Sqft
  • 36225 Sqft(Lot)
114 Ryan Court , Chestertown, MD

Perched above the peaceful waters of rosin creek, this charming waterfront cottage offers a rare opportunity to... Read More

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Homes For Sale

$649,000

  • 3 Bed
  • 2.5 Bath
  • 2,296 Sqft
  • 2968 Sqft(Lot)
129 N Queen Street N N, Chestertown, MD

Welcome to 129 n. queen street situated in one of historic chestertown's most desirable and sought after... Read More

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Homes For Sale

$579,900

  • 1 Bath
  • 1,148 Sqft
  • 140350 Sqft(Lot)
5179 Quaker Neck Road , Chestertown, MD

A one-of-a-kind historic treasure reimagined for modern living step into history with this extraordinary greek... Read More

Active Under Contract
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Homes For Sale

$795,000

  • 4 Bed
  • 4.0 Bath
  • 4,401 Sqft
  • 22194 Sqft(Lot)
211 David Drive , Chestertown, MD

Big, bold, and beautiful! this wonderfully updated 2 story brick colonial in chestertown is just minutes walking... Read More

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Homes For Sale

$1,200,000

  • 5 Bed
  • 4.5 Bath
  • 3,078 Sqft
  • 83200 Sqft(Lot)
22153 1st Point Road , Chestertown, MD

Experience the waterfront lifestyle like never before in this stunning mid-century modern home, which seamlessly... Read More

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Homes For Sale

$364,900

  • 3 Bed
  • 2.5 Bath
  • 1,724 Sqft
  • 4864 Sqft(Lot)
216 Silver Heel Road , Chestertown, MD

Welcome to this move-in ready home, situated on a premium corner lot in the village at chestertown! this... Read More