552 Breakneck Hill Road, Middlebury, CT 06762

• 5 beds |
• 4 baths |
• 4,114 sqft

Property 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 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.

Listing Status:

Active

Date Added:

August 13, 2026

Data Last Updated:

October 5, 2026 at 12:50PM

Listing Office:

W. Raveis Lifestyles Realty : (860) 868-0511

Listing Agent:

Rebecca Doh : (860) 601-4406

MLS ID:

24198521

Interior

• Appliances: Oven/RangeMicrowaveSubzeroDishwasherWasherDryer
• Laundry: Main Level
• Basement: FullUnfinishedStorageInterior AccessWalk-outConcrete Floor
• A/C: Central Air
• Heating: Hot AirOil
• Fireplace: Fireplaces: 3

Exterior

• Style: Colonial

Construction

• Roofing: Asphalt ShingleOther

Location

• County: New Haven

Lot

• Zoning: R801194380

Utilities

• Water: Private Well
• Sewer: Septic