287 Bear Hill Road - Chaplin, CT

$789,000

Beds

3.00

Baths

2,900

SqFt

3.39

Acres

Pricing Insight: Originally listed for $853,500, the price was last adjusted to $789,000 on February 6, 2026, a –$64,500 (7.6%) change, approximately 0 days ago. This property has been on the market for approximately 162 days.

287 Bear Hill Road, Chaplin, CT is a 4-bed, 3-bath, 2,900 square foot home built in 1997 , featuring colonial architecture.

This home is within the Chaplin school district. Local, with nearby schools including Chaplin.

MLS #: 24121168

Offered Price: $789,000

Residence Type: Single Family

Architectural Style: Colonial

Living Area: 2,900 Sq. Ft.

Lot Size: 3.39 Acres

Neighborhood: South Chaplin

County: Windham

Year Built: 1997

Design & Construction: Frame

Heating: Baseboard,Hot Water

Cooling: None

Garage Spaces: 0

Price per Sq Ft as listed: $272

Estimated Tax: $10,180

Days on Market: 162

$229,000

2 Beds · 1 Baths · 928 Sq Ft

22 Linkkila Lane, Chaplin

Home Automation: Not specified

Energy Features: Generator, Thermopane Windows

Solar Contract: Not specified

Heating Fuel: Electric, Oil, Wood

Fuel Type: Baseboard, Hot Water

Fuel Tank Location: In Basement

Cooling System: None

Hot Water System: Other, Oil, Domestic

Air Radon Mitigation: Not specified

Water Radon Mitigation: Not specified

Price per square foot: $272 / Sq. Ft.

Tax assessed value: $324,400

Estimated Tax: $10,180

Architectural Style: Colonial

Design & Construction: Frame

Residence Type: Single Family

Year Constructed: 1997

Living Area: 2,900 Sq. Ft.

Lot Size: 3.39 Acres

Fuel: Electric,Oil,Wood

Loading automated valuation...

AUTOMATED VALUATION ESTIMATE

Note: Computer-generated estimate, not an appraisal.

Request CMA Schedule Tour

Understanding This Valuation

The RPR AVM considers:

Recent sales of comparable properties
Property characteristics and location
Market trends in Chaplin
Statistical modeling algorithms

Local Market Context

Active Listings: 7

Average Price: $460,271

Average DOM: 162 days

Complimentary CMAs, no obligation

If you are looking for everything this is the home for you. Home sits on 3.39 acres of beautiful land with a 36x48 Morton barn that has 2 stalls but could be 6, or if you want a kennel it is set up with 5 doggy doors into barn has water and electric and can be heated if you want. Nice areas for pasture and also a chicken coop with water and electric. The home has been completely renovated in the last 2 years and offers front porch with Mahogany entry, Brazilian Walnut floors (IPE) in entry, office, living room and kitchen. Livingroom with vaulted ceilings,fireplace,opens into dining area in kitchen with doors to back deck, kitchen is perfect for the person who loves to cook. Soap stone counters, all new cabinetry, new stainless-steel Bosch appliances with Induction stove. Off kitchen is the laundry room with energy star GE washer and dryer. Office with those wonderful Walnut floors and the primary bedroom on main level with vaulted ceilings 2 step in closets and private full bath all new with porcelain tile in walk in shower and floor, granite vanity. Sunroom is beautiful with vaulted ceilings, skylights and slider to back deck, lots of natural sun light and a solid marble floor. Extra room on main level has own entry and could be perfect for in-law, home business. Home is heated with Central wood boiler or oil heat very easy to switch back and forth,Kubota Diesel whole house generator, underground utilities. If you are looking for a place to start a small farm and homestead

Continue reading ▾

Flood Risk Assessment Water Body Detected Nearby

Water Proximity Detected: This property exhibits indicators suggesting nearby or referenced water features

Location Analysis:

Water features noted

Water Proximity:

Near water body

Topography:

Standard terrain • 3.4 acres

Water Indicators Found:

Water-related features referenced in listing details

Recommendations:

Professional flood assessment advised
Based on identified water-related indicators, flood insurance may warrant consideration
Consult FEMA Flood Maps for zone verification
Evaluate drainage systems
Review local flood history

Risk Level: Moderate

Property near water bodies. Consider flood insurance.

Walkability Score: calculating…
Motif Lifestyle Score: calculating…

Amenity Access Summary

Dining & Café Access: Low to Moderate
Daily Services: Limited
Recreational Space: Limited Nearby

How These Scores Are Calculated

These scores reflect the proximity and concentration of nearby amenities, measured against a typical town-center environment.

Walkability emphasizes access to daily necessities such as groceries, pharmacies, banking, and routine services.
Motif Lifestyle emphasizes dining, cafés, parks, and leisure destinations that contribute to neighborhood character and quality of life.

All scores are normalized on a 0–100 scale to allow consistent comparison across different locations.

7

Homes For Sale

$460,271

Average List Price

Mechanicals & Utilities: Baseboard,Hot Water • Electric,Oil,Wood • None • Private Well water • 1 fireplaces

Exterior Features

Exterior Construction: Wood

Roof Type: Asphalt Shingle

Foundation: Concrete

Patio/Deck: Underground Utilities,Porch,Barn,Deck,Garden Area,Stable,Kennel

Utilities: Water: Private Well

Outbuildings: Underground Utilities,Porch,Barn,Deck,Garden Area,Stable,Kennel

Only motif connects you to a certified
"Local Market Expert"

George Antonopoulos

Real Estate Advisor

Chaplin • Connecticut Shoreline

Licensed Real Estate Agent – Connecticut

Verified Motif Advisor

(800) 555-0001

george@appzentric.com

Good evening George, I'm interested in
287 Bear Hill Road, Chaplin, Connecticut

By proceeding, you consent to receive calls and texts at the number you provided, and artificial voice, and email, from motif about your inquiry and similar properties. Your personal information will never be sold or given to a 3rd party.

motif, the motif logo, and other various trademarks, logos, designs, and slogans are the registered and unregistered trademarks of motif, LLC. dba Motif Luxe International Realty in the U.S. and/or other countries. Corporate Responsibility, Privacy & Legal Notices: motif is a licensed real estate broker, licensed to do business as Motif LLC. No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property conditions), such should be independently verified, and Motif expressly disclaims any liability in connection therewith. No financial or legal advice provided. Equal Housing Opportunity.

The data relating to real estate for sale on this website appears in part through the SmartMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SmartMLS through a licensing agreement. Listing information is from various brokers who participate in the SmartMLS 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 SmartMLS, Inc. MLS

. Designed by Appzentric for motif

Good evening. Welcome to 287 Bear Hill Road, Chaplin, CT