77 Crest Road, Middlebury, Connecticut

$749,900

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4

Beds

4

Baths

2,674

Square feet

1.50

Acres

About 77 Crest Road

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.

Features of 77 Crest Road

MLS® # 24193938
Price $749,900
Bedrooms 4
Bathrooms 4.00
Full Baths 3
Half Baths 1
Square Footage 2,674
Acres 1.50
Type Single Family For Sale
Style Contemporary
Status Active

Community Information

Address 77 Crest Road
Area N/A
City Middlebury
County New Haven
State Connecticut
Zip Code 06762

Amenities

Features Extra Insulation, Fireplace Insert, Programmable Thermostat, Storm Doors, Storm Windows
Parking Spaces 8
Parking Tandem, Detached Garage, Paved, Driveway
# of Garages 2
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Gunite, Heated, Safety Fence, Salt Water, In Ground Pool

Interior

Interior Features Audio System, Security System
Appliances Gas Range, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher, Washer, Dryer
Heating Hot Water, Oil
Cooling Central Air
Fireplace Yes
# of Fireplaces 1
Has Basement Yes
Basement Partial, Sump Pump, Concrete Floor

Exterior

Exterior Vinyl Siding
Exterior Features Grill, Porch, Gutters, Stone Wall, French Doors, Patio
Lot Description Fence - Partial, Lightly Wooded, Borders Open Space, Level Lot, Cleared, Professionally Landscaped
Roof Asphalt Shingle
Foundation Block

School Information

Elementary Long Meadow
Middle Memorial
High Pomperaug

Additional Information

Date Listed August 10th, 2026
Days on Market 30
Zoning R80
RE / Bank Owned No

Listing Details

OfficeWilliam Raveis Real Estate

Listing Map

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Listing information last updated on September 10th, 2026 at 3:10am EDT.