201 Rolling Rd
Chestertown, MD 21620
4 Beds
2 Baths
2,652 sqft (on 0.45 acres)
4 Beds
2 Baths
2,652 sqft
(on 0.45 acres)
Local Information
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Description
Great home located in College Heights. Newer roof, new pool liner and new A/C unit. Parquetand wood floors on main level. Kitchen has center island and combines with a dining area. The family room is huge! There is also a den/office! Skylights provide natural light. Propane gas heat with a tankless water heater. Nicely landscaped with a fenced in-ground pool. Property backs to park-like setting!
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.
Home Highlights
Parking
No Info
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 201 Rolling Rd
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Heating & Cooling Heating: Forced AirAir ConditioningCooling System: CentralHeating Fuel: Forced Air |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details AtticCeiling Fan |
Appliances & Utilities DishwasherDryerRefrigeratorWasher |
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Exterior Home Features Roof: OtherExterior: Brick |
Pool Pool |
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Year Built Year Built: 1975 |
Property Type / Style Property Type: Single Family HomeArchitecture: Conventional |
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Units in Building: 1 |
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Lot Area: 0.45 acres |
Price History for 201 Rolling Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 01/31/2022 | $299,000 | Sold | Bright MLS #MDKE2000754 |
| 12/06/2021 | $299,000 | Pending | Bright MLS #MDKE2000754 |
| 12/01/2021 | $299,000 | Listed For Sale | Bright MLS #MDKE2000754 |
| 11/23/2015 | $210,000 | Sold | N/A |
| 09/24/2015 | $230,000 | Pending | Agent Provided |
| 07/21/2015 | $230,000 | Listed For Sale | Agent Provided |
| 09/12/2013 | $216,000 | ListingRemoved | Agent Provided |
| 05/10/2013 | $216,000 | PriceChange | Agent Provided |
| 04/30/2013 | $216,900 | PriceChange | Agent Provided |
| 09/15/2012 | $239,900 | Listed For Sale | Agent Provided |
| 07/05/2002 | $145,000 | Sold | N/A |
| 02/27/1996 | $37,500 | Sold | N/A |
Market trends in Chestertown
Last updated April 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
60 11MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $9,008 |
| Assessment | $287,400 |
Home facts updated by county records
Homeowner tools
Estimated monthly rent$3,062/mo
Homes for rent near 201 Rolling Rd
See what comparable homes in the neighborhood are renting for.Comparable Sales for 201 Rolling Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.04 | Single-Family Home | $340,000 | 03/19/26 | 3 | 2 | 2,296 | |
0.26 | Single-Family Home | $312,000 | 06/13/25 | 4 | 2 | 1,404 | |
0.20 | Single-Family Home | $325,000 | 01/30/26 | 3 | 2.5 | 2,577 | |
0.16 | Single-Family Home | $455,000 | 10/21/25 | 3 | 2 | 1,886 | |
0.27 | Single-Family Home | $296,337 | 09/30/25 | 3 | 1.5 | 2,212 | |
0.27 | Single-Family Home | $250,000 | 07/31/25 | 4 | 2 | 1,325 | |
0.24 | Single-Family Home | $590,000 | 01/12/26 | 4 | 2 | 2,869 | |
0.10 | Single-Family Home | $415,000 | 01/07/26 | 3 | 2.5 | 1,676 | |
0.27 | Single-Family Home | $495,000 | 04/17/26 | 4 | 3 | 3,984 | |
0.37 | Single-Family Home | $475,000 | 12/11/25 | 3 | 2 | 1,961 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
SOLDMAR 19, 2026Coldwell Banker Chesapeake Real Estate Company
SOLDJAN 7, 2026Coldwell Banker Chesapeake Real Estate Company
OFF MARKETDoug Ashley Realtors, LLC
OFF MARKETDoug Ashley Realtors, LLC
OFF MARKETDoug Ashley Realtors, LLC
SOLDOCT 21, 2025Cross Street Realtors LLC
SOLDJAN 30, 2026Select Land & Homes, LLC
OFF MARKETKeller Williams Select Realtors of Annapolis
OFF MARKETDoug Ashley Realtors, LLC
OFF MARKETDoug Ashley Realtors, LLC
OFF MARKETTTR Sotheby's International Realty
Assigned Schools
These are the assigned schools for 201 Rolling Rd.
- H. H. Garnett Elementary School
- PK-5
- Public
- 347 Students
7/10GreatSchools RatingParent Rating AverageA great school with dedicated teachers and staff and a warm, friendly feel. Principal Rose is engaged and knows all of her students, and Miss Kiki at the front desk is great for answering questions and getting things done. I've had three older kids go through the school and they still reminisce about it, and my youngest is in first grade and loves going to school every day. He is sometimes even disappointed when school is closed for holidays! I could not ask for more in a positive and engaging early experience with learning. This is a great little school that gets a bad rap for test scores, but the truth is our student population has a high level of need that our teachers and staff have to go above and beyond to meet. My only complaint is that they don't get paid enough for all they do for their kids and there aren't enough of them to keep them from being completely overworked all the time. They are real heroes.Parent Review2y ago - Kent County Middle School
- 6-8
- Public
- 399 Students
2/10GreatSchools RatingParent Rating Average
No reviews available for this school. - Kent County High School
- 9-12
- Public
- 531 Students
5/10GreatSchools RatingParent Rating AverageThe school offers STEM academy, Dual enrollment & Career Pathways. It’s a great school, you just have to do a bit of research for the programs offered.Parent Review1y ago 
Check out schools near 201 Rolling Rd.
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.
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Homes for sale near 201 Rolling Rd
Long & Foster Real Estate, Inc.
Long & Foster Real Estate, Inc.
Coldwell Banker Chesapeake Real Estate Company
See more homes for sale inChestertown
Off Market Homes Near 201 Rolling Rd
SOLDJUN 8, 2026Chesapeake Real Estate Associates, LLC
SOLDJUN 5, 2026RE/MAX Executive
SOLDJUN 4, 2026Chesapeake Real Estate Associates, LLC
SOLDMAY 29, 2026Coldwell Banker Chesapeake Real Estate Company
SOLDMAY 27, 2026Cross Street Realtors LLC
SOLDMAY 26, 2026Coldwell Banker Chesapeake Real Estate Company
SOLDMAY 22, 2026Doug Ashley Realtors, LLC- See more homes for sale inChestertown
201 Rolling Rd, Chestertown, MD 21620 is a 4 bedroom, 2 bathroom, 2,652 sqft single-family home built in 1975. This property is not currently available for sale. 201 Rolling Rd was last sold on Jan 31, 2022 for $299,000. The current Trulia Estimate for 201 Rolling Rd is $402,900.