15 Hickory Hill Drive
Chester, Connecticut 06412
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 3,233
- Acres
- 1.21
- Year Built
- 1988
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
A truly special Chester Village treasure! Beautifully nestled in a private, peaceful neighborhood on a desirable cul-de-sac with no through traffic. This pristine home offers an exceptional blend of timeless character, refined comfort, and an enviable location less than a half-mile stroll to Historic Downtown Chester. From the moment you enter, the warmth and elegance are unmistakable. The gracious living room features a stunning paneled wall, gorgeous fireplace, and beautiful wide board hardwood floors. The elegant formal dining room is perfect for intimate dinners or festive gatherings. The inviting kitchen is a true focal point, offering a generous island with granite countertops and its own fireplace. Three bedrooms and two full baths are privately located on the second floor, while convenient main-level laundry adds to the ease of everyday living. The newly finished lower level provides versatile living space-ideal for a family room, media room, office, gym, or private retreat. Outside, the beautifully landscaped grounds create a private oasis with a charming gazebo, patio, and handsome stone walls. A wonderful setting for summer entertaining, cozy autumn evenings, or simply enjoying the tranquility of your own backyard. Come discover this exceptional home and experience the good life in Historic Chester Village. Professional photos will be added soon.
Key Facts
- City/Town
- Chester
- Neighborhood
- N/A
- Property / Style
- Single Family · Saltbox
- Year Built
- 1988
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 3,233 sq ft
- Lot Size
- 1.21 acres
- Garage / Parking
- 2 garage · 4 total
- Property Taxes
- $10,065 / Annually
Market Snapshot
The Chester Market
Single Family · trailing 12 months
Active Listings
7
7 under contract
Median List Price
$764,900
7 active listings
Median Closed Price
$550,000
37 sales
Median Days on Market
35
7 active listings
Median $ / Sq Ft
$292
7 active listings
Sale-to-List Ratio
100.0%
37 sales
How this home compares
List Price
$875,000
vs $764,900 median
14.4% above median
Price / Sq Ft
$271
vs $292 median
7.2% below median
Days on Market
0 days
vs 35 days median
35 days fresher than median
Based on 7 active and 37 closed sales (trailing 12 mo) of single family in Chester. Source: SmartMLS · As of September 30, 2026.
Location
15 Hickory Hill Drive, Chester, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 24, 2026per month
- Principal & Interest$4,671
- Property Taxes$839
- Insurance$292
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Chester
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Single Family
- Style
- Saltbox
- Year Built
- 1988
- New Construction
- No/Resale
- Living Area
- 3,233 sq ft
- Below Grade
- 800 sq ft
Schools
- Elementary
- Chester
- High
- Region 4
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Whole House Fan
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullPartially Finished
- Interior Features
- Auto Garage Door Opener
Exterior & Lot
- Lot Size
- 1.21 acres
- Zoning
- R-1
- Garage / Parking
- 2 garage spaces4 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPaved
- Waterfront Details
- Beach RightsWater Community
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Yellow
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesGuttersStone WallPatio
- Lot Description
- In Subdivision
Listing & Financials
- Property Taxes
- $10,065 / Annually
- Days on Market
- 0
- MLS #
- 24210144
- MLS Status
- Coming Soon
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/30/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/30/2026 at 3:15 PM UTC.
