Welcome to 492 Pear Tree Point Road: an exceptional Chester River waterfront home with unique upriver views. Spacious rooms, gorgeous cherry hardwoods, a back deck to die for, private setting, and with space to add; this home has it all! Good water depth for a dock and center console. Nearly an acre of elevated land - out of the flood zone - that backs to picturesque horse pasture. The main floor features a huge open-concept kitchen and living/dining room space which naturally flows onto the unmatched second-story wrap-around deck; perfect for crab feasts, bbq, and watching summer sunsets. Perched on the second floor is the primary suite with private Romeo and Juliet style balcony high above. Ensuite bath is unfinished but is plumbed and ready for tile and final fixtures. Walk down the sunroom to the oversized two-car garage with workshop behind and the massive unfinished loft above. With electric and insulation already in place, this space is a blank canvas ready to be turned into a fantastic rec room or 4th bedroom. Finishing the loft and primary bath would make the home over 3,000 square feet of finished space and 3/4 bedrooms and 3 fun baths. Add the final touches to make this space your own. Walkout basement has tons of storage for outdoor equipment and has a bedroom and full bath. Open House Saturday October 18, 10:00 - 2:00. Come join us.
Under contract
Price cut: $45K (11/6)
$875,000
492 Pear Tree Point Rd, Chestertown, MD 21620
3beds
3,720sqft
Est.:
Single Family Residence
Built in 2001
0.91 Acres Lot
$849,600 Zestimate®
$235/sqft
$-- HOA
What's special
Chester river waterfront homeBack deckWalkout basementTons of storageSpacious roomsSecond-story wrap-around deckPrimary suite
- 61 days |
- 135 |
- 2 |
Likely to sell faster than
Zillow last checked: 8 hours ago
Listing updated: November 14, 2025 at 04:43pm
Listed by:
Joseph Ciganek 410-708-3924,
Coldwell Banker Chesapeake Real Estate Company 410-778-0330
Source: Bright MLS,MLS#: MDQA2015126
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
- Main level bathrooms: 1
- Main level bedrooms: 1
Basement
- Area: 1270
Heating
- Heat Pump, Electric
Cooling
- Heat Pump, Central Air, Electric
Appliances
- Included: Microwave, Dishwasher, Washer, Dryer, Oven/Range - Electric, Refrigerator, Stainless Steel Appliance(s), Water Heater
- Laundry: In Basement
Features
- Entry Level Bedroom, Bathroom - Tub Shower, Breakfast Area, Combination Kitchen/Living, Open Floorplan, Family Room Off Kitchen, Kitchen - Gourmet, Recessed Lighting, 9'+ Ceilings
- Flooring: Hardwood, Luxury Vinyl, Wood
- Doors: Insulated, Sliding Glass
- Basement: Connecting Stairway,Full,Improved,Interior Entry,Exterior Entry,Walk-Out Access,Windows
- Number of fireplaces: 1
Interior area
- Total structure area: 4,770
- Total interior livable area: 3,720 sqft
- Finished area above ground: 2,600
- Finished area below ground: 1,120
Property
Parking
- Total spaces: 2
- Parking features: Garage Faces Front, Storage, Oversized, Attached
- Attached garage spaces: 2
Accessibility
- Accessibility features: None
Features
- Levels: Three
- Stories: 3
- Patio & porch: Deck, Wrap Around
- Exterior features: Extensive Hardscape, Lighting, Storage
- Pool features: None
- Has view: Yes
- View description: River, Scenic Vista, Trees/Woods, Pasture
- Has water view: Yes
- Water view: River
- Waterfront features: River
- Body of water: Chester
- Frontage length: Water Frontage Ft: 150
Lot
- Size: 0.91 Acres
- Features: Front Yard, Landscaped, Level, Not In Development, Wooded, Private, Rear Yard, Rural, Secluded, SideYard(s)
Details
- Additional structures: Above Grade, Below Grade
- Parcel number: 1807003919
- Zoning: NC-20
- Special conditions: Standard
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Coastal,Traditional
- Property subtype: Single Family Residence
Materials
- Stick Built
- Foundation: Block
- Roof: Architectural Shingle
Condition
- Very Good
- New construction: No
- Year built: 2001
Utilities & green energy
- Sewer: On Site Septic, Private Septic Tank
- Water: Well
Community & HOA
Community
- Subdivision: Pear Tree Point
HOA
- Has HOA: No
Location
- Region: Chestertown
Financial & listing details
- Price per square foot: $235/sqft
- Tax assessed value: $699,600
- Annual tax amount: $6,142
- Date on market: 10/17/2025
- Listing agreement: Exclusive Agency
- Listing terms: Cash,Conventional,FHA,VA Loan,USDA Loan,Other
- Ownership: Fee Simple
Estimated market value
$849,600
$807,000 - $892,000
$3,403/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 11/14/2025 | Contingent | $875,000$235/sqft |
Source:  Bright MLS #MDQA2015126 Report a problem | ||
| 11/6/2025 | Price change | $875,000-4.9%$235/sqft |
Source: Bright MLS #MDQA2015126 Report a problem | ||
| 10/17/2025 | Listed for sale | $920,000-3.1%$247/sqft |
Source: Bright MLS #MDQA2015126 Report a problem | ||
| 9/2/2025 | Listing removed | $949,900$255/sqft |
Source: Bright MLS #MDQA2013108 Report a problem | ||
| 8/30/2025 | Price change | $949,900-13.6%$255/sqft |
Source: Bright MLS #MDQA2013108 Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $6,650 +8.3% | $699,600 +7.3% |
| 2024 | $6,142 +7.9% | $652,000 +7.9% |
| 2023 | $5,693 +8.5% | $604,400 +8.5% |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$5,061/mo
Principal & interest
$4179
Property taxes
$576
Home insurance
$306
Climate risks
Neighborhood: 21620
Nearby schools
GreatSchools rating
- 4/10Church Hill Elementary SchoolGrades: PK-4Distance: 5.8 mi
- 5/10Sudlersville Middle SchoolGrades: 5-8Distance: 9.7 mi
- 4/10Queen Anne's County High SchoolGrades: 9-12Distance: 12.6 mi
Schools provided by the listing agent
- District: Queen Anne's County Public Schools
Source: Bright MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
- Loading
