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552 Breakneck Hill Road

Middlebury, Connecticut 06762

ACTIVE - NEW$950,000
Beds
5
Baths
3 | 1
SqFt
4,114
Acres
3.21
Year Built
1855
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage3 Fireplaces

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.

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1855
Days on Market
0 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
$12,810 / Annually

Market Snapshot

The Middlebury Market

Single Family · trailing 12 months

Median Days on Market

36

25 active listings

Median $ / Sq Ft

$264

25 active listings

Sale-to-List Ratio

100.0%

72 sales

How this home compares

List Price

$950,000

vs $585,000 median

62.4% above median

Price / Sq Ft

$231

vs $264 median

12.5% below median

Days on Market

0 days

vs 36 days median

36 days fresher than median

Based on 25 active and 72 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of August 13, 2026.

Location

552 Breakneck Hill Road, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,274

per month

  • Principal & Interest$4,889
  • Property Taxes$1,068
  • Insurance$317
  • 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
$12,810 / Annually
Days on Market
0
MLS #
24198521
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Rebecca Doh

(860) 601-4406

W. Raveis Lifestyles Realty

(860) 868-0511

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 8/13/2026. 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 8/13/2026 at 9:50 PM UTC.