552 Breakneck Hill Road, Middlebury, Connecticut

$950,000

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5

Beds

4

Baths

4,114

Square feet

3.21

Acres

About 552 Breakneck Hill Road

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.

Features of 552 Breakneck Hill Road

MLS® # 24198521
Price $950,000
Bedrooms 5
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 4,114
Acres 3.21
Type Single Family For Sale
Style Colonial
Status Active

Community Information

Address 552 Breakneck Hill Road
Area N/A
City Middlebury
County New Haven
State Connecticut
Zip Code 06762

Amenities

Parking Detached Garage
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool No

Interior

Appliances Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer
Heating Hot Air, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 3
Has Basement Yes
Basement Full, Unfinished, Storage, Interior Access, Walk-out, Concrete Floor

Exterior

Exterior Vinyl Siding
Lot Description Corner Lot, Lightly Wooded, Professionally Landscaped, Rolling, Open Lot
Roof Asphalt Shingle, Other
Foundation Stone

School Information

Elementary Per Board of Ed
Middle Per Board of Ed
High Per Board of Ed

Additional Information

Date Listed August 13th, 2026
Days on Market 29
Zoning R80
RE / Bank Owned No

Listing Details

OfficeW. Raveis Lifestyles Realty

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Listing information last updated on September 11th, 2026 at 1:40am EDT.