35 Raven Rock Road
Roxbury, Connecticut 06783
- Beds
- 5
- Baths
- 5 | 3
- SqFt
- 13,619
- Acres
- 114.34
- Year Built
- 2002
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Privately set at the crest of a hill beyond a gated drive, 35 Raven Rock Road commands breathtaking views across miles of bucolic Litchfield County countryside and the Shepaug River Valley. Spanning over 114 acres, this exceptional country compound offers extraordinary privacy, with 20+ acres of cultivated lawns, extensive gardens, sculptures, pond and specimen trees creating a remarkable estate setting. Built in 2002, the approximately 13,600 SF stone and slate residence pairs gracious proportions with exquisite finishes, superb custom millwork, marble floors, and 8 fireplaces. A marble entry hall leads to an elegant living room opening onto an expansive stone terrace overlooking the grounds and countryside. A formal dining room, paneled library and inviting family room adjoining a heated porch provide beautiful settings for entertaining and everyday living. The chef's kitchen features a professional range, Traulsen refrigeration and a separate cooking room with charbroilers and a stone pizza oven. The main-level primary suite offers a fireplace, dual walk-in closets, separate water closets and a marble bath. Four additional bedrooms feature en suite baths, complemented by an upstairs media/rec room. The finished lower level includes a gym, steam room, cedar closets and wine cellar. A heated pool, pool house, Har-Tru tennis court, 4-car garage with guest quarters and heated barn enrich the estate. Major infrastructure upgrade includes newly installed additional well system.
Key Facts
- City/Town
- Roxbury
- Neighborhood
- N/A
- Property / Style
- Single Family · Georgian Colonial
- Year Built
- 2002
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 5 full · 3 half
- Living Area
- 13,619 sq ft
- Lot Size
- 114.34 acres
- Garage / Parking
- 4 garage · 6 total
- Property Taxes
- $75,159 / Annually
Market Snapshot
The Roxbury Market
Single Family · trailing 12 months
Active Listings
25
1 under contract
Median List Price
$1.29M
25 active listings
Median Closed Price
$960,000
31 sales
Median Days on Market
95
25 active listings
Median $ / Sq Ft
$485
25 active listings
Sale-to-List Ratio
96.8%
31 sales
How this home compares
List Price
$12.99M
vs $1.29M median
10.0× the median
Price / Sq Ft
$954
vs $485 median
96.7% above median
Days on Market
0 days
vs 95 days median
95 days fresher than median
Based on 25 active and 31 closed sales (trailing 12 mo) of single family in Roxbury. Source: SmartMLS · As of October 23, 2026.
Location
35 Raven Rock Road, Roxbury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$71,413
- Property Taxes$6,263
- Insurance$4,332
- 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
- Georgian Colonial
- Year Built
- 2002
- New Construction
- No/Resale
- Living Area
- 13,619 sq ft
- Below Grade
- 3,519 sq ft
Schools
- Elementary
- Booth Free
- High
- Shepaug
Interior
- Heating
- Zoned
- Cooling
- Central Air
- Fireplaces
- 8
- Laundry
- Lower Level
- Appliances
- Oven/RangeRefrigeratorFreezerDishwasherWasherDryer
- Basement
- FullFully Finished
- Additional Rooms
- Exercise RoomGymLaundry RoomWine Cellar
Exterior & Lot
- Lot Size
- 114.34 acres
- Zoning
- Residence C
- Garage / Parking
- 4 garage spaces6 total parking spacesDetached GarageDrivewayPrivate
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- HeatedPool HouseIn Ground Pool
- Construction
- Stone
- Roof
- Slate
- Foundation
- Concrete
- Exterior Features
- GrillTerraceShedTennis CourtPorchBarnCabanaPatio
- Lot Description
- Rolling
Listing & Financials
- Property Taxes
- $75,159 / Annually
- Days on Market
- 0
- MLS #
- 24216276
- MLS Status
- Active
Similar Properties
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Co-Listed By
Amanda Thornton
Corcoran Centric Realty
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/23/2026. 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 10/23/2026 at 11:15 PM UTC.