8 Bayberry Hill
Roxbury, Connecticut 06783
Reduced from $4,500,000
- Beds
- 5
- Baths
- 4 | 2
- SqFt
- 5,940
- Acres
- 31.77
- Year Built
- 1986
- 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
Privately Sited on a Hill in the Midst of 31+ acres, this Elegantly Renovated 5,000+ sq ft Colonial Offers Panoramic Sunset Views and Exceptional Privacy. Graciously Proportioned Rooms Populate the Main Level & Include: a Vaulted-Ceiling Living Room with Fireplace, Paneled Library, Inviting Family Room, and a Spacious Eat-in Kitchen with Top-tier Appliances. The Refined Primary Suite Features a Fireplace, ModernLuxury Bath, and Dressing Room. A Separate 1-Bedroom Guest Suite Adds Versatility. Outdoors, Discover A Heated Gunite Pool Surrounded by Mature Award-Winning Gardens. Large Stone Terraces & a Meandering Garden Path Add a Texture to this Layered Property. 3-Car Over-sized Attached Garage. Only Minutes from Roxbury, Washington Depot, and Historic Woodbury CT. First Time on the Market in Over 35 Years
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1986
- Days on Market
- 469 days
- Beds
- 5
- Baths
- 4 full · 2 half
- Living Area
- 5,940 sq ft
- Lot Size
- 31.77 acres
- Garage / Parking
- 3 garage · 8 total
- Property Taxes
- $27,497 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
30
8 under contract
Median List Price
$1.30M
30 active listings
Median Closed Price
$1.40M
29 sales
Median Days on Market
87
30 active listings
Median $ / Sq Ft
$506
30 active listings
Sale-to-List Ratio
96.1%
29 sales
How this home compares
List Price
$3.65M
vs $1.30M median
2.8× the median
Price / Sq Ft
$614
vs $506 median
21.3% above median
Days on Market
469 days
vs 87 days median
382 days longer than median
Based on 30 active and 29 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of July 27, 2026.
Location
8 Bayberry Hill, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$18,610
- Property Taxes$2,291
- Insurance$1,217
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Roxbury
- Neighborhood
- N/A
- County
- Litchfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 5,940 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 3
- Appliances
- Gas CooktopWall OvenRange HoodSubzeroIcemakerDishwasherWasherDryer
- Basement
- FullUnfinishedInterior Access
- In-Law Apartment
- YesSecond FloorOver Garage
- Additional Rooms
- Bonus RoomFoyer
Exterior & Lot
- Lot Size
- 31.77 acres
- Zoning
- C
- Garage / Parking
- 3 garage spaces8 total parking spacesAttached GaragePavedDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedIn Ground Pool
- Construction
- Clapboard
- Roof
- Shake
- Foundation
- Concrete
- Exterior Features
- TerraceFruit TreesGarden AreaFrench Doors
- Lot Description
- Lightly WoodedClearedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $27,497 / Annually
- Days on Market
- 469
- MLS #
- 24088086
- MLS Status
- Under Contract - Continue to Show
Similar Properties
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Co-Listed By
Carolyn Klemm
Klemm Real Estate Inc
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. 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 7/27/2026 at 7:20 PM UTC.