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. BBQ included in the sale. 2 hours to NYC, walking distance to bars and restaurants, and an easily converted in-law apt if desired, 77 Crest Rd has everything one could possibly want for a personal retreat or family home. Come live the life of updated, meticulous serenity. Agents, a Full List of renovations and updates is in the Documents Tab.

Facts and features

Schools

• Middlebury Elementary School

  elementary · K-5 · 1.0 mi

  5

• Memorial Middle School

  middle · 6-8 · 1.7 mi

  8

• Pomperaug Regional High School

  high · 9-12 · 2.9 mi

  8

• Westover School

  high · 9-12 · 0.3 mi

• Long Meadow Elementary School

  elementary · K-5 · 2.5 mi

  5

• Holy Cross High School

  high · 9-12 · 2.8 mi

Price history

• Nov 2, 2026 · Price Changed$699,900
• Aug 10, 2026 · Listed$749,900
• Jul 18, 2025 · Listing Removed$4,500
• Jul 13, 2025 · Listing Removed—
• Jun 13, 2025 · Listed For Rent$4,500
• Jun 4, 2025 · Listed$799,000
• Aug 18, 2017 · Sold$435,000
• Aug 15, 2017 · Listing Removed$449,000

Tax history

• 2025$8,335 tax · $256,300 assessed
• 2023$8,268 tax · $256,300 assessed
• 2022$8,012 tax · $256,300 assessed
• 2021$8,586 tax · $246,500 assessed
• 2020$8,652 tax · $246,500 assessed
• 2019$8,233 tax · $246,500 assessed
• 2018$8,014 tax · $246,500 assessed
• 2017$7,731 tax · $245,500 assessed

Home value

$739,925

• Quantarium$739,925
• Collateral Analytics$742,000
• Cotality$735,300

Where it is