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$899,000

Active

552 Breakneck Hill Road

Middlebury, Connecticut, 06762 · New Haven County

5

Beds

4

Baths

4,114

Sq Ft

1855

Built

MLS # 24198521

Price / Sq Ft

$219

Property Type

Single Family For Sale

Lot Size

3.21

Class

Property

About This Property

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.

Property Details

552 Breakneck Hill Road, Middlebury Connecticut 06762 — Single Family For Sale listed at $899,000.

At a Glance

5

Bedrooms

4

Bathrooms

4,114

Sq Ft

3.21

Lot Size

--

Garage

1855

Year Built

The Details

Property TypeSingle Family For Sale
NeighborhoodNew Haven
Address552 Breakneck Hill Road
MLS Number24198521
Year Built1855
Square Footage4,114
Lot Size3.21
Bedrooms5
Bathrooms4
Water SourcePrivate Well

Property Details

Other Details

Appliances IncludedOven/Range,Microwave,Subzero,Dishwasher,Washer,Dryer
Lockbox LocationBack Porch Table
Parcel Number1194380
ZoningR80

Financial

Assessed Value393900
Mil Rate Total32.52
Property Tax12810
Tax YearJuly 2025-June 2026

Property Features

Attic DescriptionWalk-up
Attic YN1
Basement DescriptionFull,Unfinished,Storage,Interior Access,Walk-out,Concrete Floor
Cooling SystemCentral Air
Exterior SidingVinyl Siding
Fireplaces Total3
Foundation TypeStone
Fuel Tank LocationIn Basement
Garage ParkingDetached Garage
Garages Number2
Heat Fuel TypeOil
Heat TypeHot Air
Hot Water DescriptionElectric,Upright Tank
Laundry Room InfoMain Level
Roof InformationAsphalt Shingle,Other

All Photos (38)

Contact Rebecca Doh

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Affordability Calculator

$899,000

Down Payment$179,800
Loan Amount$719,200
Principal & Interest$4,546/mo
Property Tax$899/mo
Insurance$100/mo
Est. Monthly$5,545/mo

Listing Agent

R

Rebecca Doh

W. Raveis Lifestyles Realty

Quick Facts

StatusActive
TypeSingle Family For Sale
ClassProperty
MLS #24198521
Last Updated2026-10-11