77 Crest Road
Middlebury, Connecticut 06762
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,674
- Acres
- 1.50
- Year Built
- 1935
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About This Home
Privacy, charm, and timeless craftsmanship define this exceptional Contemporary Craftsman on 1.5 acres in Middlebury's Historic District. Bordering the 9+ acre Crest Preserve, this 2,600+ sq. ft. home offers 4 bedrooms, 3.5 baths, a spacious living room, and a large family room with a flexible floor plan. Character abounds with original hand-carved staircases, hardwood floors, colonial shutters, reading nooks, and a finished attic, while thoughtful updates include a recently painted interior, updated baths, upgraded electrical, central air, gas fireplace insert, and a chef's kitchen with quartz countertops, double ovens, and stainless-steel appliances. Picture windows overlook the private backyard oasis featuring two Bluestone patios, a Belgian block patio, and a renovated Gunite saltwater pool with waterfall, newer mechanicals, and fencing. Exterior improvements include newer siding, roof, chimney, barn-style lighting, and professional landscaping. Surrounded by protected woodlands and the sounds of nearby church bells, this one-of-a-kind home offers the perfect blend of historic character, modern updates, and peaceful New England living.
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Contemporary
- Year Built
- 1935
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 2,674 sq ft
- Lot Size
- 1.50 acres
- Garage / Parking
- 2 garage · 8 total
- Property Taxes
- $8,335 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
25
19 under contract
Median List Price
$575,000
25 active listings
Median Closed Price
$520,000
73 sales
Median Days on Market
33
25 active listings
Median $ / Sq Ft
$264
25 active listings
Sale-to-List Ratio
100.0%
73 sales
How this home compares
List Price
$749,900
vs $575,000 median
30.4% above median
Price / Sq Ft
$280
vs $264 median
6.1% above median
Days on Market
0 days
vs 33 days median
33 days fresher than median
Based on 25 active and 73 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of August 10, 2026.
Location
77 Crest Road, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 6, 2026per month
- Principal & Interest$3,867
- Property Taxes$695
- Insurance$250
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Middlebury
- Neighborhood
- N/A
- County
- New Haven
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1935
- New Construction
- No/Resale
- Living Area
- 2,674 sq ft
Schools
- Elementary
- Long Meadow
- Middle
- Per Board of Ed
- High
- Pomperaug
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Lower Level
- Laundry Location
- Basement
- Appliances
- Gas RangeWall OvenMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- PartialSump PumpConcrete Floor
- In-Law Apartment
- PossibleFirst FloorSeparate Entry
- Interior Features
- Audio SystemSecurity System
Exterior & Lot
- Lot Size
- 1.50 acres
- Zoning
- R80
- Garage / Parking
- 2 garage spaces8 total parking spacesTandemDetached GaragePavedDrivewayPrivatePaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedSafety FenceSalt WaterIn Ground Pool
- Construction
- Vinyl Siding
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- GrillPorchGuttersStone WallFrench DoorsPatio
- Lot Description
- Fence - PartialLightly WoodedBorders Open SpaceLevel LotClearedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $8,335 / Annually
- Days on Market
- 0
- MLS #
- 24193938
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 8/10/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 8/10/2026 at 9:10 PM UTC.