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
| Office | W. Raveis Lifestyles Realty |
|---|
