552 Breakneck Hill Road

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Sitting room attached to primary suite with access to 2 private covered porches
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den/study off of bedroom 3 with access to covered porch
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Active
$950,000
5 beds4,114 sqft
552 Breakneck Hill Rd, Middlebury, CT 06762
Est: $6,139/moGet pre-approved
Single FamilyProperty Type
3.21 acresLot Size
1855Year Built
$231/sq ftPrice per sq ft
2 carsParking Spaces

Description

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...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.
43 days on Market
  • Listed by: Rebecca L Doh 860.601.4406 rebecca.doh@raveis.com • W. Raveis Lifestyles Realty
  • Listed by: Jackson McCard 860.868.0511 jackson.mccard@raveis.com • W. Raveis Lifestyles Realty
Last updated: 08/31/2026 12:00 AM • Source: SMARTMLS, MLS#: 24198521

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Listing Courtesy of W. Raveis Lifestyles Realty, Rebecca L Doh; W. Raveis Lifestyles Realty, Jackson McCard
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$6,139 per month

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Property Taxes

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Property Information for 552 Breakneck Hill Road

Property Details
  • Taxes: $12,810 / year
  • MLS Type: Residential
  • County: New Haven County
  • Basement Description: Full, Unfinished, Storage, Interior Access, Walk-out, Concrete Floor
  • Direct Waterfront: No
  • Garages Number: 2
  • Style: Colonial
  • Garage Parking Info: Detached Garage
  • Swimming Pool: No
Building Information
  • Year Built: 1855
  • Lot Size: 3.21 AC / 139,827 SF
Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Corner of Breakneck Hill Rd and Mirey Dam Rd. Middlebury, CT
  • Elementary School: Per Board of Ed
  • High School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • Latitude: 41.547623
  • Longitude: -73.126398
  • Middle Jr High School: Per Board of Ed
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $12,810
Interior and Exterior Features
Exterior Features
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer
  • Attic Description: Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Laundry Room Info: Main Level
  • Rooms Total: 11
Room 1
  • Room Entry Order: 1
  • Room Features: Bay/Bow Window,Book Shelves,Built-Ins,Gas Log Fireplace,Hardwood Floor,Wide Board Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 2
  • Room Features: Fireplace,Patio/Terrace,Wide Board Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 3
  • Room Entry Order: 3
  • Room Features: Full Bath,Stall Shower,Interior Balcony
  • Room Level: Upper
  • Room Type: Primary Bedroom
Room 4
  • Room Entry Order: 4
  • Room Level: Upper
  • Room Type: Bedroom
Room 5
  • Listing Key: 58CB839E973D61BEE063E201100A3107
  • Room Entry Order: 5
  • Room Level: Upper
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 6
  • Room Level: Upper
  • Room Type: Bedroom
Room 7
  • Room Entry Order: 7
  • Room Level: Upper
  • Room Type: Bedroom
Room 8
  • Room Entry Order: 8
  • Room Features: Fireplace,Half Bath,Interior Balcony,Hardwood Floor,Wide Board Floor
  • Room Level: Main
  • Room Type: Sun Room
Room 9
  • Listing Key: 58CB839E973D61BEE063E201100A3107
  • Room Entry Order: 9
  • Room Features: Interior Balcony
  • Room Level: Upper
  • Room Type: Study
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vinyl Siding
  • Foundation Type: Stone
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle, Other
  • Year Built: 1855
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 4114
Lot Information
  • Lot Description: Corner Lot, Lightly Wooded, Professionally Landscaped, Rolling, Open Lot
  • Parcel Number: 1194380
  • Sq Ft Est Heated Above Grade: 4114.0
  • Sq Ft Total: 4114.0
  • Zoning: R80
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Electric, Upright Tank
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 552 Breakneck Hill Road

DateEvent & SourcePriceAppreciation
Jul 31, 2019

Closed (Public Record)

Public Record #650446721

$475,000

-1.8% / yr

May 31, 2002

Closed (Public Record)

Public Record #101561795

$653,000

+12.9% / yr

Jul 31, 1995

Closed (Public Record)

Public Record #92288518

$285,000—
DateEvent & SourcePrice
07/31/2019

Closed (Public Record)

Public Record #650446721

$475,000

-1.8% / yr

05/31/2002

Closed (Public Record)

Public Record #101561795

$653,000

+12.9% / yr

07/31/1995

Closed (Public Record)

Public Record #92288518

$285,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 552 Breakneck Hill Road

Taxable ValueLand$112,900Additions$281,000Total$393,900
Tax Record2025$12,810 ($1,068 / month)
Home Facts
Beds5Baths3.5Total Finished SqFt4,114 SqFtAbove Grade Finished SqFt4,114 SqFtUnfinished Basement SqFt2,039 SqFtStories2Lot Size139,828 SqFtStyleSingle Family ResidenceYear Built1855Year Renovated1855ZoningR80CountyNAUGATUCK VALLEYAPNMDBY M:6-10 L:069

Schools near 552 Breakneck Hill Road

This home is within Regional School District 15.
Rating
School
Type
Grades
Distance
Long Meadow Elementary School
Public - PK to 5
Memorial Middle School
Public - 6 to 8
Pomperaug Regional High School
Public - 9 to 12
Rating
School
Distance
Long Meadow Elementary School
PublicPK to 5

Memorial Middle School
Public6 to 8

Pomperaug Regional High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 552 Breakneck Hill Road, Middlebury, CT 06762

552 Breakneck Hill Road is a single family home for sale in Middlebury, CT 06762. This property was listed for sale on August 12, 2026 by W. Raveis Lifestyles Realty, it's currently listed at $950,000. It has been on the market for a total of 43 days and was last sold on July 31, 2019. This listing's school district is Regional School District 15. Nearby schools include Long Meadow Elementary School, Memorial Middle School and Pomperaug Regional High School. 552 Breakneck Hill Road is a 5-bed, 4-bath, 4,114 sqft single family home built in 1855.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of W. Raveis Lifestyles Realty, Rebecca L Doh; W. Raveis Lifestyles Realty, Jackson McCard

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.