305 Pine Tree Rd, Chestertown, MD 21620
Property image
Property image
OFF MARKET

$271,900

Trulia Estimate
  • 2 Beds
  • 1 Bath
  • 826 sqft (on 0.81 acres)

305 Pine Tree Rd, Chestertown, MD 21620

Est. Refi. Payment $1,701/mo*
Refinance Your Home
Currently Off Market - Sold Feb 6, 2025 for $260,000

Home Value

Trulia Estimate
$272K
Since last month
Decreased$5K (-1.8%)
Since last year
Increased$3K (+1%)
Since last sale
Increased$10K (+3.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +230% in the last 10 years
MonthEstimated value
2026
September 2026$270K
August 2026$272K
July 2026$275K
June 2026$272K
May 2026$277K
April 2026$274K
March 2026$268K
February 2026$260K
January 2026$261K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
108 Springbrook Ln, Millington, MD
0.23
Single-Family Home
$475,900
04/17/26
3
2
1,677
2032 Pondtown Rd, Chestertown, MD
0.70
Single-Family Home
$365,000
05/29/26
3
2
1,120
105 Pearl Creek Ln, Chestertown, MD
0.38
Single-Family Home
$459,000
03/27/26
3
2.5
1,961
1904 Pondtown Rd, Chestertown, MD
0.71
Single-Family Home
$247,500
08/10/26
3
1
1,967
101 Pine Tree Rd, Chestertown, MD
0.53
Single-Family Home
$480,000
05/04/26
4
2
1,848
2101 Dudley Corners Rd, Crumpton, MD
1.27
Single-Family Home
$250,000
10/30/25
2
1
1,200
2010 McGinnes Rd, Chestertown, MD
1.40
Single-Family Home
$354,900
11/10/25
3
1
1,253
102 Pine St, Crumpton, MD
1.41
Single-Family Home
$339,900
08/17/26
3
2
1,250
321 Front St, Crumpton, MD
1.47
Single-Family Home
$385,000
06/12/26
3
2.5
1,484
1517 Dudley Corners Rd, Millington, MD
0.77
Single-Family Home
$220,000
05/18/26
6
3
2,948

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
200 Ashley Ln, Chestertown, MD 21620
0.20
$476,900
3
1.5
1,656
Off Market
206 Springbrook Ln, Millington, MD 21651
0.19
$451,700
3
2
1,680
Off Market
108 Springbrook Ln, Millington, MD 21651
0.23
$475,900
3
2
1,677
Recently Sold
136 Pearl Creek Ln, Chestertown, MD 21620
0.33
-
3
2.5
1,460
Off Market
105 Pearl Creek Ln, Chestertown, MD 21620
0.38
$459,000
3
2.5
1,961
Recently Sold
204 Spring Rd, Millington, MD 21651
0.33
$189,100
Studio
1
759
Off Market
Par 113 Spring Rd, Millington, MD 21651
0.35
-
-
-
-
Off Market
224 Spring Rd, Millington, MD 21651
0.45
-
-
-
-
Off Market
112 Pine Tree Rd, Chestertown, MD 21620
0.49
-
-
-
-
Off Market
1814 Pondtown Rd, Chestertown, MD 21620
0.59
$91,000
3
1
973
Off Market
101 Pine Tree Rd, Chestertown, MD 21620
0.53
$480,000
4
2
1,848
Recently Sold

Local Information

  • Map ViewExplore the area around 305 Pine Tree Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1961
0.81 acre lot
826 sqft
$329/sqft
Open Parking

About this House

BRING ALL OFFERS! Welcome to this newly renovated home with stunning upgrades throughout! This charming, easy-living home, in Chestertown, MD has all new LVP flooring, paint and drywall, a brand-new kitchen featuring sleek grey cabinets, stainless steel appliances, a deep sink, backsplash, and quarts countertops. The bathroom boasts a beautifully tiled shower. New washer and dryer on the main floor, and beautiful windows to let in an abundance of natural light. Enjoy almost an acre of land with plenty of room to enjoy the quiet outdoors. This home is located in Queen Anne’s County, close to rt 301, making for a short commute 25 minutes to Middletown, DE, 35 minutes to the Chesapeake Bay Bridge, and lots of local amenities near by.
305 Pine Tree Rd, Chestertown, MD 21620 is a 2 bedroom, 1 bathroom, 826 sqft single-family home built in 1961. It last sold for $260,000 on Feb 6, 2025 (2% above the $255,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $271,900, with a rent estimate of $1,666/month.
Last check for updates: about 3 hours ago
Listed by Kaitlyn Collins, (410) 490-9157
Benson & Mangold, LLC
Listing Team: Chesapeake Bay Properties Team Of Benson & Mangold
Bought with: Roxana TAPIA, (410) 980-4665, Long & Foster Real Estate, Inc.
Source: Bright MLS, MLS#MDQA2007694

Home Details for 305 Pine Tree Rd

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 1Types of Rooms: Basement
Beds & Baths
Number of Bedrooms: 2Main Level Bedrooms: 2Number of Bathrooms: 1Number of Bathrooms (full): 1Number of Bathrooms (main level): 1
Dimensions and Layout
Living Area: 826 Square Feet
Appliances & Utilities
Appliances: Electric Water HeaterLaundry: Main Level
Heating & Cooling
Heating: Central,OilHas CoolingAir Conditioning: Central Air,ElectricHas HeatingHeating Fuel: Central
Fireplace & Spa
No Fireplace
Levels, Entrance, & Accessibility
Stories: 1Levels: OneAccessibility: None
View
No View

Exterior Features

Exterior Home Features
Other Structures: Above Grade, Below GradeFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
No CarportNo GarageNo Attached GarageHas Open ParkingParking: Gravel,Driveway,Off Street
Pool
Pool: None
Frontage
Not on Waterfront
Water & Sewer
Sewer: Private Sewer
Finished Area
Finished Area (above surface): 826 Square Feet

Property Information

Year Built
Year Built: 1961
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceStructure Type: DetachedArchitecture: Ranch/Rambler
Building
Construction Materials: MixedNot a New ConstructionHas Additional Parcels
Property Information
Parcel Number: 1807001142

Price & Status

Price
List Price: $255,000
Status Change & Dates
Off Market Date: Mon Sep 16 2024Possession 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 District: Queen Anne's County Public Schools

Building

Building Area
Building Area: 826 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.81 acres

Listing Info

Special Conditions: Standard

Offer

Contingencies: Home InspectionListing Agreement Type: Exclusive Right To SellListing Terms: Cash, Conventional, FHA, USDA Loan, VA Loan

Business

Business Information
Ownership: Fee Simple

Miscellaneous

BasementMls Number: MDQA2007694Above Grade Unfinished Area: 826

Price and Tax history

DateEventPrice
Feb 6, 2025
Source: N/A
Sold
$260,000
Sep 13, 2024
Source: Bright MLS #MDQA2007694
Sold
$260,000
Jul 18, 2024
Source: Bright MLS #MDQA2007694
Pending
$255,000
Jul 7, 2024
Source: Bright MLS #MDQA2007694
PendingToActive
$255,000
Jun 6, 2024
Source: Bright MLS #MDQA2007694
Pending
$255,000

Market trends in Chestertown

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
64
5MoM

Around this home

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

LGBTQ Local Legal Protections

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

Frequently asked questions about 305 Pine Tree Rd

  • What is 305 Pine Tree Rd estimated to be worth?
    Trulia's estimated value for 305 Pine Tree Rd in Chestertown, MD is $271,900.
  • What is the price history for 305 Pine Tree Rd?
    305 Pine Tree Rd in Chestertown, MD last sold for $260,000 in February 2025.
  • Is Chestertown a buyer's or seller's market?
    Chestertown is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Chestertown?
    Residents describe Chestertown, MD as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See recently sold homes in Chestertown, MD.
  • Does 305 Pine Tree Rd have air conditioning?
    Yes, 305 Pine Tree Rd in Chestertown, MD has air conditioning.
  • Does 305 Pine Tree Rd have laundry facilities?
    Yes, 305 Pine Tree Rd in Chestertown, MD has laundry facilities.

Explore by feature - Pet Friendly

Explore by feature - Air Conditioning

6 rentals with air conditioning in Chestertown, MD

Explore by feature - Washer/dryer

Apartments for Rent

Skip to last item
  • Results are loading
Skip to first item

Off Market Homes Near 305 Pine Tree Rd

Skip to last item
Skip to first item

Homes for sale near 305 Pine Tree Rd

Skip to last item
Skip to first item
Skip to last item
  • Results are loading
Skip to first item