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$950,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,114 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago

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Open House: 12:00 PM - 2:00 PM

Saturday 8/15 12:00 PM - 2:00 PM

552 Breakneck Hill Road,Middlebury, CT 06762

552 Breakneck Hill RoadMiddleburyCT06762

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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.

Full Property Details for 552 Breakneck Hill Rd

General

  • Price: $950,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24198521
  • Updated: 8/13/2026
  • Added to Site: 3 day(s) ago

Interior

  • Number of Rooms: 11
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Full Bath, Stall Shower, Interior Balcony, Upper
  • Bedroom 1: Bedroom, Upper
  • Bedroom 2: Bedroom, Upper
  • Bedroom 3: Bedroom, Upper
  • Bedroom 4: Bedroom, Upper

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, Book Shelves, Built-Ins, Gas Log Fireplace, Hardwood Floor, Wide Board Floor, Main
  • Dining Room: Dining Room - Fireplace, Patio/Terrace, Wide Board Floor, Main
  • Study: Interior Balcony, Upper
  • Laundry: Main Level

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Parking: Detached Garage

Location

  • County: New Haven
  • Driving Directions: Corner of Breakneck Hill Rd and Mirey Dam Rd. Middlebury, CT

School Information

  • Elementary School: Per Board of Ed
  • Middle School: Per Board of Ed
  • Intermediate School: Per Board of Ed
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Electric, Upright Tank

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Unfinished, Storage, Interior Access, Walk-out, Concrete Floor
  • Roof: Asphalt Shingle, Other
  • Attic: Yes
  • Square Feet: 4,114
  • Above Ground: 4,114 Sq. Ft.
  • Year Built: 1855

Lot Features

  • Lot Size (Acres): 3.21
  • Zoning: R80
  • Lot Description: Corner Lot, Lightly Wooded, Professionally Landscaped, Rolling, Open Lot

Financial Considerations

  • Assessment Amount: $393,900
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 1194380

Listed by W. Raveis Lifestyles Realty, Rebecca Doh and W. Raveis Lifestyles Realty, Jackson McCard

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Listing agents

— 552 Breakneck Hill Rd —

  • Rebecca Doh

    W. Raveis Lifestyles Realty

  • Jackson McCard

    W. Raveis Lifestyles Realty

Agent Contact: (860) 601-4406 Office Contact: (860) 868-0511

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 552 Breakneck Hill Rd

School District:Regional School District 15
NameGradesDistance
Long Meadow Elementary School
65 North Benson Road, Middlebury, CT 06762
PK-53.3 mi
Memorial Middle School, Middlebury, CT
1 Memorial Drive, Middlebury, CT 06762
6-81.7 mi
Pomperaug Regional High School
234 Judd Road, Southbury, CT 06488
9-123.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 552 Breakneck Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
8/12/2026
Listed
$950,000
45.48%
MLS
5/31/2002
Sold
$653,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 552 Breakneck Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$12,810
—
$393,900
—
2023
$12,841
1%
$393,900
—
2023
$12,707
3%
$393,900
—
2022
$12,313
1%
$393,900
12%
2021
$12,236
-1%
$351,300
—
2020
$12,331
5%
$351,300
—
2019
$11,733
3%
$351,300
—
2018
$11,421
3%
$351,300
-1%
2017
$11,125
4%
$353,300
2%
2016
$10,711
3%
$345,400
—
2015
$10,403
3%
$345,400
—
2014
$10,134
2%
$345,400
—
2011
$9,968
—
$345,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 552 Breakneck Hill Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by W. Raveis Lifestyles Realty, Rebecca Doh and W. Raveis Lifestyles Realty, Jackson McCard

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552 Breakneck Hill Road, Middlebury, CT 06762 (MLS# 24198521) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 552 Breakneck Hill Road is currently listed for $950,000 and was received on August 12, 2026. Want to learn more about 552 Breakneck Hill Road? Do you have questions about finding other Single Family real estate for sale in Middlebury? You can browse all Middlebury real estate or contact a Coldwell Banker agent to request more information.

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