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Explore Similar Homes Within 25 Miles of Chestertown, MD

  • /15

    $376,000

    • 2 Beds
    • 2 Baths
    • 1,061 Sq Ft

    40 Oak Ct, Annapolis, MD 21401

    Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring

    Gregory Golding ExecuHome Realty

    40 Oak Ct, Annapolis, MD 21401
  • /37

    $380,000

    • 3 Beds
    • 2 Baths
    • 2,925 Sq Ft

    105 Simmons Rd, Severna Park, MD 21146

    This is a Fannie Mae Reverse Mortgage Foreclosure. Please assure your Realtor shares all documents. This is set up at 2 units. The Upper Level unit has an entrance on each side of the house. The main level entrance is through the front porch. The basement is full and unfinished with two at level entrances. The lot is extensive. The location is wonderful!

    Michele Michael CENTURY 21 New Millennium

    105 Simmons Rd, Severna Park, MD 21146
  • /28

    $299,900

    • 3 Beds
    • 1.5 Baths
    • 1,989 Sq Ft

    3519 Royston Ave, Baltimore, MD 21206

    Beautifully Renovated 3-Bedroom, 2-Bath HomeStep into modern comfort with this beautifully renovated 3-bedroom, 2-bath home that blends style and functionality. Inside, you’ll find brand-new luxury vinyl plank (LVP) flooring, plush new carpeting in the upper bedroom, and fresh recessed lighting that brightens every space.The heart of the home features a stunning kitchen with new

    Mark Smith RE/MAX Realty Group

    3519 Royston Ave, Baltimore, MD 21206
  • /6

    $302,000

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

    1012 Peters Corner Rd, Sudlersville, MD 21668

    Cozy rancher on 6.77 wooded acres, plenty of privacy! Home features a split floor plan with two primary bedrooms. Open floor plan, real wood burning stove in the living room, and wood floors throughout the home. Large rear deck and fenced yard for pets. This one deserves a look around. Call Today!

    John Carroll Village Real Estate Company LLC

    1012 Peters Corner Rd, Sudlersville, MD 21668
  • /67

    $419,900

    • 4 Beds
    • 2.5 Baths
    • 2,492 Sq Ft

    1612 Cattail Commons Way, Denton, MD 21629

    Discover this charming home in the desirable Cattail Commons neighborhood. Lots of recent upgrades completed and ready for you to move-in. As you arrive, you will immediately notice the brand new white fence which is ideal for privacy and the cozy front porch for those days you wish to unwind. Open the door and you are greeted with an expansive and open floorplan with fresh paint throughout. To

    Daniel Register Northrop Realty

    1612 Cattail Commons Way, Denton, MD 21629
  • /2

    $251,600

    • 4 Beds
    • 1.5 Baths
    • 1,456 Sq Ft

    5944 Clayton Ave, Baltimore, MD 21206

    Great Opportunity to own this single-family home built in 1932 featuring 4 bedrooms and 1.1 bathrooms. ***SPECIAL NOTES: (1) This is a CASH ONLY transaction. (2) Seller to pay Taxes, HOA, and Municipal/Utility Liens. (3) Please read the Auction disclaimers carefully before placing a bid or submitting an offer. *** No showings, No access provided. Drive by only. Property is lender-owned, being

    Val Laborevitch RealHome Services and Solutions, Inc.

    5944 Clayton Ave, Baltimore, MD 21206
  • /21

    $245,000

    • 3 Beds
    • 1 Bath
    • 1,343 Sq Ft

    8105 Candle Ln, Rosedale, MD 21237

    Brick Front Rancher in the Rosedale Community! As you pull into the drive, you are welcomed by the sun porch & large bow window. Enter the living room to a great floor plan for entertaining. The living room is open to the dining room with lots of natural light. The kitchen has table space adjacent to large window overlooking the rear yard. Down the hall are 3 spacious bedrooms & 1 bath. The lower

    Frederick Golding RE/MAX Advantage Realty

    8105 Candle Ln, Rosedale, MD 21237
  • /23

    $397,000

    • 3 Beds
    • 1 Bath
    • 1,196 Sq Ft

    9910 Forge Park Rd, Perry Hall, MD 21128

    Welcome to Gunpowder Estates! This charming 3-bedroom, 1-bathroom home offers both comfort and character in the heart of Perry Hall. The bright living room is anchored by a cozy wood-burning fireplace and a beautiful bay window that fills the space with natural light. Enjoy meals in the separate dining room, and extend your living space to the screened sunroom, perfect for relaxing or

    Mackenzie Hoffer CENTURY 21 New Millennium

    9910 Forge Park Rd, Perry Hall, MD 21128
  • /32

    $283,000

    • 2 Beds
    • 1 Bath
    • 1,268 Sq Ft

    1814 Division Rd, Pasadena, MD 21122

    This is a Fannie Mae Reverse Mortgage Foreclosure. This home offers extensive parking in the driveway and fencing. The main level has two bedrooms, bath, kitchen and living room. There is a side porch with basement access. The enclosed front porch has an access ramp. The lower level has interior stairs, a large rec room, storage, additional possible third bedroom and utility area. The lot

    Michele Michael CENTURY 21 New Millennium

    1814 Division Rd, Pasadena, MD 21122
  • /26

    $289,900

    • 3 Beds
    • 1 Bath
    • 1,568 Sq Ft

    1915 Arundel Rd, Pasadena, MD 21122

    FINAL AND BEST OFFERS DUE 10/3 AT 10AM!This Freddie Mac Foreclosure features a Charming ranch-style home tucked away in this water-oriented community of Venice-on-the-Bay. This 3-bedroom, 1-bath residence offers the ease of single-level living across a spacious floor plan, set on an expansive 0.6-acre lot that provides privacy, room to expand, and endless outdoor enjoyment.Inside,

    Mackenzie Hoffer CENTURY 21 New Millennium

    1915 Arundel Rd, Pasadena, MD 21122
  • /26

    $366,500

    • 3 Beds
    • 2 Baths
    • 1,140 Sq Ft

    434 Salisbury Rd, Edgewater, MD 21037

    Welcome to Edgewater – a vibrant, water-accessible community where every day feels like a getaway! This well-maintained Rambler offers 3 bedrooms, 2 beautifully updated bathrooms, and an open living/dining area with easy-care vinyl tile flooring. Step outside to enjoy a spacious yard complete with a deck and storage shed, perfect for entertaining or relaxing outdoors.The location is hard to

    LaTosha French Coast To Coast Home Consultants INC

    434 Salisbury Rd, Edgewater, MD 21037
  • /51

    $314,900

    • 5 Beds
    • 2.5 Baths
    • 2,250 Sq Ft

    5416 Parkside Place, Baltimore, MD 21206

    Welcome to this colonial home in the community of Frankford. Enjoy the open layout of the main level with luxury vinyl plank flooring that flows from the living to the dining rooms. The family room with fireplace opens to the updated kitchen with stainless steel appliances and cherry wood cabinets. Venturing to the upper level, you will find four bedrooms, each unique with its own, and a full

    Gina Gargeu Century 21 Downtown

    5416 Parkside Place, Baltimore, MD 21206
  • /44

    $260,000

    • 2 Beds
    • 2 Baths
    • 1,200 Sq Ft

    7656 Old Battle Grove Rd, Dundalk, MD 21222

    Affordable waterfront living opportunity. Water front rancher with oversize garage, dock and pier, and more. Tons of potential. The water footage is an estimate.Rancher style home in need of repairs. Oversized garage with separate electric panel, shed and outbuilding with pier.BANK OWNED PROPERTY SOLD STRICTLY AS IS. SELLER WILL MAKE NO REPAIRS.

    Barbara Perdue Real Estate Professionals, Inc.

    7656 Old Battle Grove Rd, Dundalk, MD 21222
  • /23

    $259,000

    • 3 Beds
    • 1 Bath
    • 1,008 Sq Ft

    18 Terrace Rd, Essex, MD 21221

    Cozy and on the corner. Here we sit pretty in this tight little established community situated just across from Back River in lovely Essex. We have a full fresh rehab that was just completed and this place has great curb appeal and is very welcoming as you enter and notice a full compliment of fine finishes from top to bottom. There’s a full basement, two main floor bedrooms, a brand new fresh

    Jon Leary Cummings & Co. Realtors

    18 Terrace Rd, Essex, MD 21221
  • /39

    $285,000

    • 4 Beds
    • 1 Bath
    • 1,396 Sq Ft

    1813 Weyburn Rd, Rosedale, MD 21237

    Welcome to this brick home nestled in the tranquil neighborhood of Kenwood. This four-bedroom one full-bathroom home combines classic style with modern convenience and offers an ample living space with hardwood floors. The main level is an open concept floor plan with seamless integration of the living, dining, and kitchen areas creating a warm atmosphere. From the kitchen, you can easily access

    Gina Gargeu Century 21 Downtown

    1813 Weyburn Rd, Rosedale, MD 21237
  • /20

    $304,000

    • 3 Beds
    • 2.5 Baths
    • 1,500 Sq Ft

    4908 Aspen St, Shady Side, MD 20764

    Welcome to this 2-story home nestled in the serene Avalon Shores community. This home features 3 bedrooms, 2 full baths, and 1 half bath. Eat in kitchen with additional room for table space. The exterior boasts multi-level decks ideal for outdoor entertaining, a shady yard offering privacy, and spacious 2 car garage. Located in the peaceful Avalon Shores subdivision, this home is close to Anne

    Brenda Sarver Maryland Realty Connection

    4908 Aspen St, Shady Side, MD 20764
  • /2

    $254,300

    • 4 Beds
    • 2.5 Baths
    • 1,904 Sq Ft

    7530 Marks Ave, Nottingham, MD 21236

    Opportunity awaits in this home built in 1923 and features 4 bedrooms and 2.1 bathrooms. Take a drive by and see if this may be your next investment ***SPECIAL NOTES: (1) This is a CASH ONLY transaction. (2) Seller to pay Taxes, HOA, and Municipal/Utility Liens. (3) Please read the Auction disclaimers carefully before placing a bid or submitting an offer at hubzu.com.***

    Dana Rowell RealHome Services and Solutions, Inc.

    7530 Marks Ave, Nottingham, MD 21236
  • /59

    $649,900

    • 4 Beds
    • 3.5 Baths
    • 3,198 Sq Ft

    1502 Brierhill Estates Dr, Bel Air, MD 21015

    Discover your Dream Home at 1502 Brierhill Estates Dr. Don't miss the opportunity to call this stunning property your new home! Located in the highly desirable Brierhill Estates community, this spacious home offers the perfect blend of classic elegance and modern comfort. With 4 bedrooms, 3.5 baths, and a 2-car garage, there's plenty of room for your family to grow. As you enter, you’ll be

    Jean Waters American Premier Realty, LLC

    1502 Brierhill Estates Dr, Bel Air, MD 21015
  • /19

    $598,100

    • 4 Beds
    • 4.5 Baths
    • 3,190 Sq Ft

    3208 Havenwood Ct, Edgewater, MD 21037

    Welcome to 3208 Havenwood Ct, a prime investment auction opportunity nestled in a sought-after community that blends suburban tranquility with urban convenience. This well-designed home features an attached3 car front-entry garage and thoughtful design elements that cater to both comfort and functionality, including 2 story foyer and family room, main level bedroom with sitting room, and second

    Brenda Sarver Maryland Realty Connection

    3208 Havenwood Ct, Edgewater, MD 21037
  • /17

    $105,000

    • 3 Beds
    • 1.5 Baths
    • 1,848 Sq Ft

    406 West St, Clayton, DE 19938

    There are miltiple offers all offers submitted should be highest and best. -Step back in time with this home in downtown Clayton brimming with character and original details waiting to be brought back to life. From the inviting front porch to the warm sunroom overlooking the fenced back yard, this property offers the kind of charm that con't be replicated today. Inside you'll find hardwood

    Steve Schmidt RE/MAX Horizons

    406 West St, Clayton, DE 19938
  • /28

    $175,000

    • 3 Beds
    • 1.5 Baths
    • 1,312 Sq Ft

    3545 Moultree Place, Nottingham, MD 21236

    Buyers come take a look at this spacious 3 bedroom townhome in Belmont South, that has just been painted throughout and has all new appliances! This home features a open living room/dining room combo and spacious kitchen. Lower level has a large family room with a half bath, laundry and bonus room that could be used as a home office space or storage. Sliders lead out to a rear deck and fenced

    Kim Novak Star Realty Inc.

    3545 Moultree Place, Nottingham, MD 21236
  • /18

    $139,000

    • 3 Beds
    • 1 Bath
    • 960 Sq Ft

    105 Downes Dr, Hartly, DE 19953

    We currently have multiple offers. Any offer submitted now MUST be highest and best and MUST be submitted no later than 2:00 PM on Tuesday 9/30/25. NO EXCEPTIONS! NO ESCALATION CLAUSES! INVESTORS ALERT!! This sweet little rancher could be a real charmer with some elbow grease. Open living room/kitchen/dining area. Nice sized lot with a deck on the back located in a cute subdivision west of

    Joseph Larrimore Classic Realty

    105 Downes Dr, Hartly, DE 19953
  • /38

    $235,000

    • 3 Beds
    • 2.5 Baths
    • 1,672 Sq Ft

    629 Nollmeyer Rd, Middle River, MD 21220

    Welcome to this end of the group townhome in the well-established neighborhood of Carrollwood Manor. Step inside and you will find an open floor plan with lots of natural light and carpet flooring. The seamless integration of the living, dining, and kitchen areas creates a warm and inviting atmosphere. The nice sized kitchen has custom-made cabinet, tile flooring and appliances. While the

    Gina Gargeu Century 21 Downtown

    629 Nollmeyer Rd, Middle River, MD 21220
  • /19

    $324,900

    • 4 Beds
    • 2 Baths
    • 960 Sq Ft

    8577 Main Ave, Pasadena, MD 21122

    Experience life on The Riviera. Riviera Beach that is. In grand old Pasadena. Everyone knows it takes a lot of coin to find a home situated around the water but we made it easy for you with this one. That’s a rock bottom price right there and this place has been fully rehabbed top to bottom, inside and out. New flooring, stainless steel appliances, luxury countertops, two full bathrooms, four

    Jon Leary Cummings & Co. Realtors

    8577 Main Ave, Pasadena, MD 21122
  • /10

    $104,000

    • 2 Beds
    • 1 Bath
    • 648 Sq Ft

    115 2nd St, North East, MD 21901

    RED POINT BEACH - Come check out this water oriented bungalow and make it your new vacation hideaway! Affordable price so you can make it your own!This property is now under auction terms. All Bids must be submitted during the auction via the property’s listing page at www.servicelinkauction.com. This sale is subject to a buyer’s premium pursuant to the auction Terms & Conditions. All

    John Carroll Village Real Estate Company LLC

    115 2nd St, North East, MD 21901
  • /8

    $84,900

    • 3 Beds
    • 2 Baths
    • 1,064 Sq Ft

    208 Holly Hill Dr, Smyrna, DE 19977

    Brand Spanking new. Just off the lot. Priced to sell. This bad boy must go. Bring any and all offers. You can't get a deal if you don't make an offer. Come on down and check out your new home. 3 beds 2 baths and plenty of room for entertaining. Updated pictures to come.

    Anthony Lapinsky First Coast Realty LLC

    208 Holly Hill Dr, Smyrna, DE 19977
  • /22

    $114,900

    • 3 Beds
    • 1.5 Baths
    • 1,152 Sq Ft

    5542 Whitby Rd, Baltimore, MD 21206

    ### **Fixer-Upper Opportunity in Prime Cedonia Location!****3 Bed | 1.5 Bath | Rear Parking | Fenced Yard | Partially Finished Basement**Bring your vision and unlock the full potential of this classic **Cedonia rowhouse** in a highly desirable neighborhood! This **3-bedroom, 1.5-bath** home is a diamond in the rough — perfect for investors, rehabbers, or ambitious homeowners ready for a

    Deric Beckett Berkshire Hathaway HomeServices PenFed Realty

    5542 Whitby Rd, Baltimore, MD 21206
  • /75

    $224,900

    • 4 Beds
    • 2.5 Baths
    • 2,403 Sq Ft

    4203 Springwood Ave, Baltimore, MD 21206

    Opportunity awaits at 4203 Springwood Avenue! This 3-bedroom, 1.5-bath home offers a spacious layout with an open living and dining area and a large backyard. The property includes a full basement and off-street parking. Conveniently located near major commuter routes, shopping, schools, and parks. Property is being sold as-is; seller will make no repairs. Great potential for investors or buyers

    Edward Kowalski EXP Realty, LLC

    4203 Springwood Ave, Baltimore, MD 21206
  • /15

    $389,900

    • 2 Beds
    • 2 Baths
    • 1,061 Sq Ft

    40 Oak Ct, Annapolis, MD 21401

    Introducing a distinctive opportunity for visionary entrepreneurs and investors: a commercial/residential property brimming with potential, situated ideally for both business and pleasure. Formerly a boutique dress shop, this structure is primed for a creative transformation, making it a unique investment. The property houses two Bedrooms/Offices, two full bathrooms, and robust hardwood flooring

    Gregory Golding ExecuHome Realty

    40 Oak Ct, Annapolis, MD 21401
  • /16

    $102,000

    • 3 Beds
    • 2 Baths
    • 1,216 Sq Ft

    182 182-B Hemlock Way Unit 276, Smyrna, DE 19977

    Welcome to Holly Hills where the living is easy. This luxurious 3 bed 2 bath is practically brand new. Yes ladies and Gents, its a 2024 model fresh off the line. If you're looking for a Move-in-ready, plop your stuff and live the good life, this house is for you. The master bath comes with a nice soaking tub to cleanse the day's stresses away. Between the kitchen and living room, you have the

    Anthony Lapinsky First Coast Realty LLC

    182 182-B Hemlock Way Unit 276, Smyrna, DE 19977
  • /21

    $155,000

    • 3 Beds
    • 2 Baths
    • 1,476 Sq Ft

    404 Liberty Ct, Edgewood, MD 21040

    Welcome to this nice townhome in the vibrant neighborhood of Harford Square. The main level has seamless integration of the living room and kitchen with lots of natural light and laminate flooring. The kitchen-dining combo is spacious and has granite countertops and stainless-steel appliances. From the kitchen, you can easily access the patio and the fenced backyard, which is a great place for

    Gina Gargeu Century 21 Downtown

    404 Liberty Ct, Edgewood, MD 21040
  • /11

    $329,900

    • 3 Beds
    • 2 Baths
    • 1,734 Sq Ft

    7849 Hidden Creek Way Unit 24, Stoney Beach, MD 21226

    2, possibly 3 bedroom (in basement), 2.5 bath Townhome in Stoney Beach.. Kitchen updated within last 5 years or so. New carpet. Shows well but sold as is. This property is eligible under the Freddie Mac First Look Initiative thru 7/9/2025. ONLY OWNER OCCUPANT OFFERS WILL BE ACCEPTED DURING THIS TIME.SOLD AS-IS. SELLER WILL NOT MAKE ANY REPAIRS. GR/HOA/FF fees and financing options

    Heidi Heiderman Samson Properties

    7849 Hidden Creek Way Unit 24, Stoney Beach, MD 21226
  • /23

    $235,000

    • 3 Beds
    • 1.5 Baths
    • 1,482 Sq Ft

    4503 Lasalle Ave, Baltimore, MD 21206

    Discover this charming Cape Cod home with very huge living area and lots of natural lighting coming in from the bay window. The finished basement offers additional living space, while the fireplace adds warmth to the living room. Enjoy the convenience of modern appliances, including a gas oven/range, refrigerator, dishwasher, and microwave. This home also features three spacious bedrooms and 1.5

    Daniel Register Northrop Realty

    4503 Lasalle Ave, Baltimore, MD 21206
  • /25

    $215,000

    • 2 Beds
    • 1 Bath
    • 1,387 Sq Ft

    5416 Pembroke Ave, Baltimore, MD 21206

    Investor Alert... This detached home in Watherson is a great find. 2 bedrooms, 1 huge bathroom that can be reimagined with the right person. Spacious main level offers a great opportunity for the right buyer. 2 large bedrooms upstairs with a very large bathroom. Unfinished basement with tons of potential. Come view this today.

    Jolene Smith JS Realty LLC

    5416 Pembroke Ave, Baltimore, MD 21206
  • /6

    $64,900

    • 3 Beds
    • 2 Baths
    • 1,440 Sq Ft

    5207 Nuth Ave, Baltimore, MD 21206

    Welcome to this cape cod home located a few minutes away from Barbara and Parkwood Park in Baltimore City. This property will be a great addition to any investor's portfolio to renovate and flip. It can also be an amazing investment for homeowners looking for an affordable property to rehabilitate and live. Home is seated in 0.16 acres lot with 7096 of living space, 3 bedrooms and 2 full baths.

    Gina Gargeu Century 21 Downtown

    5207 Nuth Ave, Baltimore, MD 21206
  • /5

    $585,000

    • 4 Beds
    • 2.5 Baths
    • 3,520 Sq Ft

    40 Loder Dr, Smyrna, DE 19977

    Spacious home with over 3500 sq ft of living space with an expansive outdoor entertainment area! Paver patio, inground pool, fenced yard. Property also as a 3 car garage, full basement. Property is being sold As Is and all offers must be entered online on the auction company's website.

    Mark Levering Patterson-Schwartz-Dover

    40 Loder Dr, Smyrna, DE 19977
  • /3

    $219,700

    • 3 Beds
    • 1 Bath
    • 1,400 Sq Ft

    7430 School Ln, Dundalk, MD 21222

    Great Opportunity to own this single-family home oozing with potential. This home was built in 1943 and features 3 bedrooms and 1 bathroom, with plenty of living space. ***SPECIAL NOTES: (1) This is a CASH ONLY transaction. (2) Seller to pay Taxes, HOA, and Municipal/Utility Liens. (3) Please read the Auction disclaimers carefully before placing a bid or submitting an offer. ***

    Sherry Price RealHome Services and Solutions, Inc.

    7430 School Ln, Dundalk, MD 21222
  • /2

    $149,900

    • 3 Beds
    • 2 Baths
    • 834 Sq Ft

    217 S Woodwell Rd, Dundalk, MD 21222

    Bank owned property sold as is. If a ground rent exist seller will not redeem

    Irene Parks Coldwell Banker Realty

    217 S Woodwell Rd, Dundalk, MD 21222

Home Trends in Chestertown, MD

Housing Trends

Median Sale Price
$355,000
Median Single Family Sale Price
$385,000
Median Townhouse Sale Price
$263,750
Median 2 Bedroom Sale Price
$482,000
Median 1 Bedroom Sale Price
$285,000
Average Price Per Sq Ft
$220
Number of Homes for Sale
35
Last 12 months Home Sales
90
Months of Supply
4.70
Median List Price
$367,450
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
5%
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