414 Pine Tree Rd, Chestertown, MD 21620
OFF MARKET

414 Pine Tree Rd
Chestertown, MD 21620

  • 4 Beds
  • 2 Baths
  • 1,688 sqft (on 0.98 acres)

$383,400

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $2,230/mo*
Refinance Your Home

$383,400

Trulia Estimate
as of Jun 4, 2026
Est. Refi. Payment $2,230/mo*
Refinance Your Home
4 Beds
2 Baths
1,688 sqft
(on 0.98 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Reduced for a quick sale! Don’t miss out! Country living at its best! Just under 1 acre, this 4 bedroom home boasts an open floorplan, separate level laundry/mudroom with skylight, and a spacious basement for storage or drywall finish for extra living space. The main level includes all bedrooms, eat-in kitchen with bright white cabinets, separate dining room, living room, and a additional family room or office. Within the last 2 years a 500 square foot addition has been added, the roof replaced, new siding, new gutters, new windows, and a brand new septic system installed. There is also the possibility to expand for even more home square footage! Head outdoors to enjoy the sizeable fenced yard with plenty of room for chickens, growing vegetables, landscaping, entertaining on the deck, or simply relaxing by the firepit. Eastern Shore living is calling! This property is located in Queen Anne's County, just minutes to Rt. 301. BONUE: Seller is including a 1 year Home Warranty with the house sale!!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from June 27, 2023

Home Highlights

Parking
Open Parking
Outdoor
Porch, Patio, Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago

Home Details for 414 Pine Tree Rd

Interior Features

Interior Details
Basement: Connecting Stairway,ConcreteNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 4Main Level Bedrooms: 4Number of Bathrooms: 2Number of Bathrooms (full): 2Number of Bathrooms (main level): 2
Dimensions and Layout
Living Area: 1688 Square Feet
Appliances & Utilities
Appliances: Electric Water HeaterLaundry: Lower Level,Laundry Room
Heating & Cooling
Heating: Central,Heat Pump,ElectricHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa
No FireplaceNo Spa
Windows, Doors, Floors & Walls
Flooring: Hardwood
Levels, Entrance, & Accessibility
Stories: 2.5Levels: Multi/Split, Two and One HalfAccessibility: NoneFloors: Hardwood
View
No View

Exterior Features

Exterior Home Features
Roof: Architectural ShinglePatio / Porch: Deck, Patio, PorchFencing: Privacy, Partial, Panel, WoodOther Structures: Above Grade, Below GradeExterior: Play AreaFoundation: SlabNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Driveway
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Private Septic Tank
Finished Area
Finished Area (above surface): 1688 Square Feet

Property Information

Year Built
Year Built: 1968
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Raised Ranch/Rambler
Building
Construction Materials: FrameNot a New ConstructionNo Additional Parcels
Property Information
Condition: Very GoodIncluded in Sale: ShedParcel Number: 1807014325

Price & Status

Price
List Price: $349,900
Status Change & Dates
Off Market Date: Tue Jun 27 2023Possession Timing: Close Of Escrow

Active Status

MLS Status: CLOSED

Location

Direction & Address
City: CHESTERTOWNCommunity: None Available
School Information
Elementary School District: Queen Anne's County Public SchoolsJr High / Middle School District: Queen Anne's County Public SchoolsHigh School: Queen Anne's CountyHigh School District: Queen Anne's County Public Schools

Building

Building Area
Building Area: 2332 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.98 acres

Listing Info

Special Conditions: Standard

Offer

Listing Agreement Type: Exclusive AgencyListing Terms: Conventional, Cash, FHA, USDA Loan, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDQA2006134Above Grade Unfinished Area: 1688
Last check for updates: about 11 hours ago
Listed by Kimberly A Raeder, (410) 320-9630
Keller Williams Select Realtors of Annapolis
Bought with: Kate Meckley, (484) 716-6758, Foraker Realty Co.
Source: Bright MLS, MLS#MDQA2006134

Price History for 414 Pine Tree Rd

DatePriceEventSource
06/27/2023$350,000Sold
Bright MLS #MDQA2006134
05/25/2023$349,900PendingBright MLS #MDQA2006134
05/24/2023$349,900PriceChange
Bright MLS #MDQA2006134
04/16/2023$360,500PriceChange
Bright MLS #MDQA2006134
04/08/2023$375,000Listed For SaleBright MLS #MDQA2006134
06/30/2021$260,000Sold
Bright MLS #MDQA146966
12/06/2012$31,493Sold
N/A
10/24/2012$55,250Listed For SaleAgent Provided
08/17/2012$59,900ListingRemovedAgent Provided
08/10/2012$59,900PriceChange
Agent Provided
08/02/2012$77,006PriceChange
Agent Provided
07/03/2012$87,507PriceChange
Agent Provided
06/02/2012$99,440PriceChange
Agent Provided
04/22/2012$113,000Listed For SaleAgent Provided
05/18/2011$173,655Sold
N/A

Market trends in Chestertown

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
60
11MoM
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Property Tax and Assessment

Year2025
Tax$2,378
Assessment$246,100
Home facts updated by county records

Comparable Sales for 414 Pine Tree Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
105 Pearl Creek Ln, Chestertown, MD
0.05
Single-Family Home
$459,000
03/27/26
3
2.5
1,961
2032 Pondtown Rd, Chestertown, MD
0.58
Single-Family Home
$365,000
05/29/26
3
2
1,120
108 Springbrook Ln, Millington, MD
0.55
Single-Family Home
$475,900
04/17/26
3
2
1,677
101 Pine Tree Rd, Chestertown, MD
0.85
Single-Family Home
$480,000
05/04/26
4
2
1,848
1814 Pondtown Rd, Chestertown, MD
0.30
Single-Family Home
$86,000
06/09/25
3
1
973
1520 Dudley Corners Rd, Millington, MD
0.94
Single-Family Home
$297,500
08/20/25
3
2.5
1,912
1517 Dudley Corners Rd, Millington, MD
0.80
Single-Family Home
$220,000
05/18/26
6
3
2,948
2010 McGinnes Rd, Chestertown, MD
1.40
Single-Family Home
$354,900
11/10/25
3
1
1,253
122 3rd St, Crumpton, MD
1.86
Single-Family Home
$389,000
07/01/25
3
2
1,344
2101 Dudley Corners Rd, Crumpton, MD
1.57
Single-Family Home
$250,000
10/30/25
2
1
1,200

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Assigned Schools

These are the assigned schools for 414 Pine Tree Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Chestertown

At least 34 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 84 % Say there's holiday spirit

  • 83 % Say it's dog friendly

  • 77 % Say people would walk alone at night

  • 77 % Say parking is easy

  • 76 % Say yards are well-kept

  • 74 % Say it's quiet

  • 61 % Say neighbors are friendly

  • 57 % Say there's wildlife

  • 56 % Say it's walkable to restaurants

  • 54 % Say there are sidewalks

  • 49 % Say kids play outside

  • 46 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

  • 41 % Say there are community events

  • 38 % Say they plan to stay for at least 5 years

Sourced by Trulia users. Learn more about our methodology.
  • Trulia User
    "Washington park is a great, safe and family oriented are!! I’ve never live there permanently but by mom is from that are and my grandparents still live there!! I live always visiting! And hope to have a hoke there myself one day!!!"
    1
    Flag
  • Trulia User
    "Short and very accessible. Everything is within 10 minutes and waterfront on the Chester river is spectacular"
    1
    Flag
  • Trulia User
    "I lived in this neighborhood for tens you’d and the community is very friendly. Community clean up after their dog and they watch over one another "
    0
    Flag
  • Kesha C.
    "Chestertown is okay area to live in. Its what you make it honestly. Nothing major or minimal happening."
    0
    Flag
  • Tracy W.
    "The schools are better in Queen Anne's County. The town is well-maintained, and houses and businesses in town have to meet the strict guidelines of the historical society. Restaurants are generally mediocre in quality and high in price. "
    0
    Flag
  • Rancraw
    "This is just a great place to live. I am from Dallas, TX, I have lived in six countries, DC, and Miami. This is my favorite place to live. ONLY down side is getting to an airport under an hour."
    9
    Flag
  • Acaldwell1297
    "I am basically on the main road.... pretty easy to get in and out. I don’t live far from work! So pretty easy for me "
    1
    Flag
  • Guillermo A.
    "Good Community, friendly people, good services. "
    0
    Flag
  • Nancy M.
    "People do not come to Chestertown because it is quite like everywhere else . . but because it is exceptionally itself."
    5
    Flag
  • asso
    "Quiet - not for night owls. Nice farmer's market, good library. Easy acess for weekends in DC, Baltimore, Philly, & Ocean Beaches. College town, Chester River"
    0
    Flag
  • Dafoster
    "Historic town along the Chester River and home to Washington College. Convenient to shops, restaurants, farmers market, waterfront, Garfield Center for the Arts and College Activities. A walker's paradise and a favorite for bikers and boaters."
    5
    Flag

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Homes for sale near 414 Pine Tree Rd

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Off Market Homes Near 414 Pine Tree Rd

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. Click here for more information

Homes for rent near 414 Pine Tree Rd

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414 Pine Tree Rd, Chestertown, MD 21620 is a 4 bedroom, 2 bathroom, 1,688 sqft single-family home built in 1968. This property is not currently available for sale. 414 Pine Tree Rd was last sold on Jun 27, 2023 for $350,000 (0% higher than the asking price of $349,900). The current Trulia Estimate for 414 Pine Tree Rd is $383,400.