552 Breakneck Hill Road
Middlebury, Connecticut 06762
Reduced from $950,000
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 4,114
- Acres
- 3.21
- Year Built
- 1855
- 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
Exceptional 1855 Greek Revival set in a prestigious Middlebury neighborhood, surrounded by the natural beauty of Flanders Preserve and Middlebury Land Trust land. This 5-bedroom, 31/2-bath architectural stunner is sited on 3.21 beautifully landscaped acres with mature trees, stone walls, perennial gardens and rolling open lawn, offering privacy and a feeling of escape and tranquility. The home includes wide-board floors, three fireplaces and a remarkable series of covered porches and "piazzas" capturing the romance of 19th-century country living. There is effortless flow from the gorgeous sunroom, with walls of windows, into the formal living room, dining room and large entertaining kitchen. A main-floor laundry room, enormous utility room, pantry and powder room add convenience. The primary suite offers a private retreat, with an en-suite bath and adjoining sitting room or study, flanked by two covered porches. Outside, a charming secluded wading pool with fountain provides a wonderfully relaxed setting for summer gatherings, cocktails and afternoons spent enjoying the gardens. A detached 2-car garage with bonus unfinished loft space invites a future artist studio. An exceptional opportunity to bring this distinctive home to the next level. 2 hrs to NYC. Subject to Probate.
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1855
- Days on Market
- 84 days
- Beds
- 5
- Baths
- 3 full · 1 half
- Living Area
- 4,114 sq ft
- Lot Size
- 3.21 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $14,313 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
27
14 under contract
Median List Price
$699,900
27 active listings
Median Closed Price
$557,450
86 sales
Median Days on Market
58
27 active listings
Median $ / Sq Ft
$262
27 active listings
Sale-to-List Ratio
100.0%
86 sales
How this home compares
List Price
$899,000
vs $699,900 median
28.4% above median
Price / Sq Ft
$219
vs $262 median
16.4% below median
Days on Market
84 days
vs 58 days median
26 days longer than median
Based on 27 active and 86 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of November 5, 2026.
Location
552 Breakneck Hill Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$4,901
- Property Taxes$1,193
- Insurance$300
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlebury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1855
- New Construction
- No/Resale
- Living Area
- 4,114 sq ft
Schools
- Elementary
- Per Board of Ed
- Middle
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 3
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveSubzeroDishwasherWasherDryer
- Basement
- FullUnfinishedStorageInterior AccessWalk-outConcrete Floor
Exterior & Lot
- Lot Size
- 3.21 acres
- Zoning
- R80
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Roof
- Asphalt ShingleOther
- Foundation
- Stone
- Lot Description
- Corner LotLightly WoodedProfessionally LandscapedRollingOpen Lot
Listing & Financials
- Property Taxes
- $14,313 / Annually
- Days on Market
- 84
- MLS #
- 24198521
- MLS Status
- Active
Similar Properties
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Co-Listed By
Jackson McCard
W. Raveis Lifestyles Realty
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/5/2026. 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 11/5/2026 at 8:40 PM UTC.