For sale

$749,900

Est. $4,725/mo —

•

2,674

sq ft

77 Crest Rd, Middlebury, CT 06762

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 and pool vacuum 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.

Single-familyProperty Type

1935Year Built

1.5 acresLot Size

$280Price/Sq.Ft.

2 garage spacesParking

Listed by Michael Vartolone • William Raveis Real Estate

Contact: Agent Attribution Contact: (203) 733-1104 | Office Attribution Contact: (203) 794-9494

Source:Smart MLS #24193938

Payment calculator

$4,725 per month

Principal and interest$3,743

Property taxes

$695

HOA dues

Home insurance

$287

Utilities

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Affordability tools

See this home in person

This home is unavailable to tour on this day.

Next available date: Wednesday, August 26

Open houses

No upcoming open houses.

Nearby open houses (10)

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3 beds2 baths1,408 sq ft
179 High St, Naugatuck, CT 06770
OPEN SAT, 11AM TO 3PM
$545,000
4 beds2.5 baths1,969 sq ft
6 Paugussett Rd, Sandy Hook, CT 06482
OPEN SAT, 1PM TO 3PM
$580,000
7 beds3 baths3,515 sq ft
125 Clematis Ave, Waterbury, CT 06708
OPEN SUN, 11AM TO 2PM
$235,000
2 beds2 baths1,071 sq ft
857 Heritage Vlg Unit A, Southbury, CT 06488
OPEN SUN, 11AM TO 1PM
$875,000
5 beds3.5 baths4,180 sq ft
132 Good Hill Rd, Woodbury, CT 06798
OPEN SUN, 12PM TO 2PM
$424,900
2 beds2 baths1,432 sq ft
397 Heritage Vlg Unit B, Southbury, CT 06488
OPEN SUN, 12PM TO 1:30PM
$589,990
3 beds3 baths1,248 sq ft
21 Carriage Ln, Roxbury, CT 06783
OPEN SUN, 12:30PM TO 2:30PM
$314,900
2 beds2 baths1,032 sq ft
502 Heritage Vlg Unit A, Southbury, CT 06488
OPEN SUN, 1PM TO 3PM
$199,000
2 beds1.5 baths1,039 sq ft
200 Yale St Unit 27B, Waterbury, CT 06704
OPEN SUN, 1PM TO 4PM
$829,000
4 beds2.5 baths2,774 sq ft
5 Stone Gate Dr, Sandy Hook, CT 06482

Around this home

Schools

K - 12
Preschool & daycare

Middlebury Elementary School

Public PreK-5 • Assigned • 1.0mi

5/10

Memorial Middle School

Public 6-8 • Assigned • 1.7mi

8/10

Pomperaug Regional High School

Public 9-12 • Assigned • 2.9mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Offer insights

77 Crest Rd · $749,900

Strong offer

$785K and above

75% chance or better to win

Why $785K+ is a strong offer

DAYS ON MARKET

The average home goes pending in 42 days.

SALE-TO-LIST

Most homes are selling 3% above list price.

About offer insights

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Built-in audio system
Security system
Thermostats (programmable)

Bedrooms
4 bedrooms

Bathrooms
3 full bathrooms
1 half bathroom

Kitchen
Gas range
Wall oven
Microwave
Range hood
Refrigerator
Dishwasher

Laundry & utility
Washer and dryer included
Laundry located in the basement / lower level

Flooring
Concrete floor in partial basement

Heating & cooling
Hot water heat (oil-fired)
Central air conditioning
Fireplace insert

Sale and tax history for 77 Crest Rd

Sale History
Tax History

Date

Event

Price

Smart MLS #24193938

Aug 10, 2026

Listed

$749,900

$280/sq ft

SMARTMLS #24103854

Jul 12, 2025

Rental Removed

$4,500

$2/sq ft

Jun 14, 2025

Listed for Rent

$4,500

$2/sq ft

Smart MLS #24101291

Jul 12, 2025

Listing Removed

—

Jun 5, 2025

Listed

$799,000

$299/sq ft

Jun 4, 2025

Coming Soon

Smart MLS #W10220655

Aug 18, 2017

Sold

$435,000

$163/sq ft

May 27, 2017

Listed

$449,000

$168/sq ft

Welcome home to this charming multi-level property in a much sought after area. This home is across the street from the Middlebury Library, walking distance to the Shepardson/Senior Center, close to the Greenway, Middlebury Consignment Shop & restaurants! Immediately you are warmly greeted as you enter into the foyer with beautiful hardwood flooring that spills into the over sized FLR with a wood-burning FP & a picture window over looking the front yard. Gain access to the patio by simply adding french doors to the living room! Pass the conveniently located half bath to get to the FR for more entertaining space! Prefer to host a dinner party in the FDR? The FDR right off of the tastefully updated kitchen with access to the over sized wrap around patio! Wish there was patio access from the kitchen? There is, just walk through the classic dutch door to the patio! Enjoy the peaceful privacy of this 1.5 acre lot with a heated Gunite pool! Follow your heart back inside this home to the private MB suite with a generous walk in closet & FBA! Three additional BR's, one w/FB. An additional FB is located in the hallway just steps from the bedrooms. As if this home could not be any more charming just a few more steps and you walk into a fabulous bonus room! Could be a craft room, play room, office you name it! Crown molding, built-ins, hardwood flooring, custom plantation shutters, creative use of space, & workshop. You must see this! Come call this one of a kind property your HOME!

Smart MLS #99060555

Sep 23, 2014

Listing Removed

—

May 14, 2014

Listed

$693,250

$259/sq ft

Smart MLS #W1075929

Sep 23, 2014

Listing Removed

—

Apr 3, 2014

Listed

$693,250

$259/sq ft

Public Records

Mar 20, 1997

Sold

$263,000

$98/sq ft

Year

Property tax

Land + Additions

Assessment*

2022

$8,012 (−6.7%)

$92,400 + $163,900

$256,300

2021

$8,586 (−0.8%)

$103,700 + $142,800

$246,500

2020

$8,652 (+5.1%)

$103,700 + $142,800

$246,500

2019

$8,233 (+2.7%)

$103,700 + $142,800

$246,500

2018

$8,014 (+3.7%)

$103,700 + $142,800

$246,500

2017

$7,731 (−2.6%)

$103,700 + $141,800

$245,500

2016

$7,939 (+5.7%)

$121,800 + $134,200

$256,000

2014

$7,511 (+1.7%)

$121,800 + $134,200

$256,000

2011

$7,388

$121,800 + $134,200

$256,000

Public record

Beds

Baths

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.5 Acres

Year renovated

—

Finished Sq. Ft.

2,674

Unfinished Sq. Ft.

—

Total Sq. Ft.

2,674

Year built

1935

Style

Single Family Residential

County

New Haven County

APN

1194838

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 97° expected this year, 15 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

3/10 Air Factor

2 unhealthy days expected this year, 4 days in 30 years

Provided by First Street

Historical weather

Middlebury, CT • 06762

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

90/ 100

Exceptional sunlight

Sunscore

There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

10.3 hrs

6.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 77 Crest Rd

We cannot show automated home-value estimates for this home.

Nearby homes have recently sold between $475,000 and $815,000.

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $475K to $815K.

SOLD JAN 27, 2026
$645,000 Last sold price
4 beds3.5 baths3,244 sq ft
51 Cross Rd, Middlebury, CT 06762
$81/sq ft
smaller lot
42 years newer
SOLD MAY 22, 2026
$510,000 Last sold price
3 beds2 baths1,780 sq ft
38 E Ridge Dr, Middlebury, CT 06762
$7/sq ft
smaller lot
35 years newer
SOLD MAY 1, 2026
$599,900 Last sold price
2 beds1.5 baths1,749 sq ft
428 Breakneck Hill Rd, Middlebury, CT 06762
$63/sq ft
larger lot
13 years newer
SOLD JUL 31, 2026
$475,000 Last sold price
3 beds2 baths1,575 sq ft
420 Charcoal Ave, Middlebury, CT 06762
$22/sq ft
larger lot
52 years older
SOLD JUL 29, 2026
$815,000 Last sold price
3 beds2.5 baths3,217 sq ft
38 Avalon Dr, Middlebury, CT 06762
$27/sq ft
smaller lot
70 years newer
SOLD MAY 21, 2026
$500,000 Last sold price
3 beds2.5 baths2,208 sq ft
622 Lakeside Blvd W, Waterbury, CT 06708
$54/sq ft
smaller lot
45 years newer

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Make a winning offer with the help of a local agent

Ask a question

(203) 633-8554

Early Access listings

3D WALKTHROUGH

Contact for price

3 beds1.5 baths928 sq ft

188 Cianci Rd, New Britain, CT 06053

EARLY ACCESSCOMPASS COMING SOON

$750,000

4 beds3 baths2,166 sq ft

25 Warren Ave, Fairfield, CT 06825

Nearby similar homes

$1,399,900

4 beds3.5 baths5,237 sq ft

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FOR SALE BY OWNER

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3 beds4 baths3,024 sq ft

25 Juniper Rd, Middlebury, CT 06762

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3D WALKTHROUGH

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New listings for sale in 06762

COMING SOON

$829,900

3 beds2.5 baths2,796 sq ft

29 Cambridge Ct, Middlebury, CT 06762

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4 beds3.5 baths5,237 sq ft

67 Abbott Farms Rd, Middlebury, CT 06762

COMING SOON

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Details provided by Smart MLS and may not match the public record. Learn more.

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About this home

Payment calculator

Affordability tools

See this home in person

Nearby open houses (10)

Around this home

Schools

Lifestyle

Offer insights

Property details

Sale and tax history for 77 Crest Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 77 Crest Rd

Early Access listings

Nearby similar homes

New listings for sale in 06762

More real estate resources