$306,300
3 Beds
1.5 Baths
1,196 sqft (on 0.34 acres)
308 Longfellow Dr, Chestertown, MD 21620
Est. Refi. Payment $1,930/mo*
Refinance Your HomeCurrently Off Market - Sold Sep 2, 2021 for $220,000
Home Value
Trulia Estimate
$306KSince last month
Increased$300 (+0.1%)Since last year
Increased$2K (+0.7%)Since last sale
Increased$86K (+39.2%)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 +97% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $306K |
| August 2026 | $306K |
| July 2026 | $310K |
| June 2026 | $313K |
| May 2026 | $314K |
| April 2026 | $311K |
| March 2026 | $308K |
| February 2026 | $305K |
| January 2026 | $300K |
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 |
|---|---|---|---|---|---|---|---|
0.12 | Single-Family Home | $300,000 | 05/27/26 | 3 | 1 | 1,408 | |
0.25 | Single-Family Home | $170,000 | 08/24/26 | 3 | 2 | 1,232 | |
0.08 | Single-Family Home | $379,000 | 01/30/26 | 3 | 2 | 1,700 | |
0.25 | Single-Family Home | $317,000 | 03/09/26 | 3 | 2 | 1,232 | |
0.34 | Single-Family Home | $289,000 | 08/21/26 | 3 | 1 | 1,248 | |
0.40 | Single-Family Home | $330,000 | 03/31/26 | 3 | 2 | 1,170 | |
0.43 | Single-Family Home | $322,000 | 11/14/25 | 3 | 2 | 1,232 | |
0.34 | Single-Family Home | $220,000 | 04/14/26 | 4 | 1 | 1,248 | |
0.27 | Single-Family Home | $349,000 | 09/22/26 | 3 | 2 | 1,792 | |
0.47 | Single-Family Home | $228,000 | 07/13/26 | 3 | 1.5 | 2,260 |
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 |
|---|---|---|---|---|---|---|
0.02 | $347,500 | 3 | 2 | 1,560 | Off Market | |
0.08 | $334,000 | 3 | 2 | 1,360 | Off Market | |
0.08 | $379,000 | 3 | 2 | 1,700 | Recently Sold | |
0.12 | $300,000 | 3 | 1 | 1,408 | Recently Sold | |
0.14 | $296,500 | 3 | 1 | 1,056 | Off Market | |
0.16 | $408,100 | 3 | 2 | 1,811 | Off Market | |
0.18 | $246,000 | 3 | 1 | 1,056 | Off Market | |
0.25 | $317,000 | 3 | 2 | 1,232 | Recently Sold | |
0.22 | $408,400 | 3 | 2 | 1,560 | Off Market | |
0.27 | $324,200 | 3 | 1 | 1,104 | Off Market | |
0.29 | $354,200 | 3 | 2 | 1,200 | Off Market | |
0.29 | $294,500 | 3 | 1 | 1,120 | Off Market |
Local Information
- Map ViewExplore the area around 308 Longfellow Dr.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Home Highlights
Single-Family Home
Built in 1977
0.34 acre lot
1,196 sqft
$256/sqft
Garage
About this House
Spectacular Ranch style home on sizable semi-private lot is situated in the popular water accessible community of Chester Harbor. Newly painted bedrooms and Jack & Jill bathroom accessible from living room, kitchen and bedroom. With only a few minor upgrades, this affordable Queen Anne's County gem could be that forever home you've been looking for. Newer HVAC as of 10/2016!
308 Longfellow Dr, Chestertown, MD 21620 is a 3 bedroom, 2 bathroom, 1,196 sqft single-family home built in 1977. It last sold for $220,000 on Sep 2, 2021. More recently, it was listed as a rental in July 2017 with an asking price of $1,100 per month. That rental listing was removed on July 7, 2017. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $306,300, with a rent estimate of $2,303/month.
Home Details for 308 Longfellow Dr
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Heating & Cooling Heating: BaseboardAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Levels, Entrance, & Accessibility Stories: 1Floors: Hardwood |
Appliances & Utilities DryerRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: Shake ShingleExterior: Metal |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1977 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Units in Building: 1 |
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Lot Area: 0.34 acres |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Sep 2, 2021 Source: Bright MLS #MDQA2000324 | Sold | $220,000 |
Jul 19, 2021 Source: Bright MLS #MDQA2000324 | Contingent | $199,000 |
Jul 14, 2021 Source: Bright MLS #MDQA2000324 | Listed For Sale | $199,000 |
Jun 7, 2018 Source: Agent Provided | ListingRemoved | $169,900 |
Nov 29, 2017 Source: Agent Provided | PriceChange | $169,900 Price increased by 15,345% |
Jul 7, 2017 Source: Agent Provided | ListingRemoved | $1,100 |
Jul 4, 2017 Source: Agent Provided | Listed For Rent | $1,100 |
Jul 3, 2017 Source: Agent Provided | Listed For Sale | $179,900 |
Dec 1, 2006 Source: N/A | Sold | $218,000 |
Jul 25, 2000 Source: N/A | Sold | $90,000 |
Aug 18, 1999 Source: N/A | Sold | $60,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $2,061 | $212,400 |
Home facts updated by county records
Market trends in Chestertown
Last updated August 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections
Frequently asked questions about 308 Longfellow Dr
- What is 308 Longfellow Dr estimated to be worth?Trulia's estimated value for 308 Longfellow Dr in Chestertown, MD is $306,300.
- What is the price history for 308 Longfellow Dr?308 Longfellow Dr in Chestertown, MD last sold for $220,000 in September 2021.
- 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 308 Longfellow Dr have air conditioning?Yes, 308 Longfellow Dr in Chestertown, MD has air conditioning.
- Does 308 Longfellow Dr have laundry facilities?Yes, 308 Longfellow Dr in Chestertown, MD has in-unit laundry.
Apartments for Rent
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Off Market Homes Near 308 Longfellow Dr
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SOLDSEP 8, 2026Coldwell Banker Chesapeake Real Estate Company
SOLDSEP 1, 2026Long & Foster Real Estate, Inc.- SOLDAUG 24, 2026
SOLDAUG 21, 2026Keller Williams Flagship
SOLDAUG 18, 2026CENTURY 21 New Millennium
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