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80 Pine Hollow Drive

Middlebury, Connecticut 06762

ACTIVE$749,900
Beds
4
Baths
3 | 1
SqFt
2,806
Acres
1.65
Year Built
1979
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool2-Car Garage2 Fireplaces

About This Home

Discover your tranquil retreat at 80 Pine Hollow Drive! This unique and spacious home offers the perfect blend of comfortable living, exceptional entertaining space, and flexible floor plans to meet any need. The heart of the home is the large, eat-in kitchen, perfect for casual meals and morning coffee. This seamlessly opens to a spacious dining room, creating an effortless flow for hosting dinner parties. The entertaining continues into a well-lit living room and a separate, cozy family room-offering plenty of space for everyone to relax. Upstairs, you'll find the home's private sleeping quarters, featuring three bedrooms and two full bathrooms. Need more room? Then travel downstairs to a highly versatile area that can function as additional bedrooms, a dedicated office space, or even a perfect in-law suite thanks to an additional full bathroom. The partially finished basement is an entertainer's dream, complete with a dedicated media room and storage galore. The unfinished portion offers even more practicality, serving as a workshop for tools and crafts, along with abundant extra storage. Step outside to your private yard, a true outdoor oasis! The landscaped pool area is an entertainer's delight, offering the perfect backdrop for summer barbecues and weekend relaxation. With plenty of parking, hosting friends and family is always a breeze. This distinctive property truly is a must-see!

Key Facts

City/Town
Middlebury
Neighborhood
N/A
Property / Style
Single Family · Split Level
Year Built
1979
Days on Market
126 days
Beds
4
Baths
3 full · 1 half
Living Area
2,806 sq ft
Lot Size
1.65 acres
Garage / Parking
2 garage
Property Taxes
$11,749 / Annually

Market Snapshot

The Middlebury Market

Single Family · trailing 12 months

Median Days on Market

44

20 active listings

Median $ / Sq Ft

$277

20 active listings

Sale-to-List Ratio

99.8%

74 sales

How this home compares

List Price

$749,900

vs $672,000 median

11.6% above median

Price / Sq Ft

$267

vs $277 median

In line with median

Days on Market

126 days

vs 44 days median

82 days longer than median

Based on 20 active and 74 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of July 29, 2026.

Location

80 Pine Hollow Drive, Middlebury, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,053

per month

  • Principal & Interest$3,824
  • Property Taxes$979
  • 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
Split Level
Year Built
1979
New Construction
No/Resale
Living Area
2,806 sq ft

Schools

Elementary
Middlebury
High
Pomperaug

Interior

Heating
Hydro Air
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
2
Laundry
Lower Level
Appliances
Electric RangeMicrowaveRefrigeratorFreezerDishwasherDisposalWasherElectric Dryer
Basement
FullPartially Finished
In-Law Apartment
PossibleSeparate Entry
Interior Features
Auto Garage Door OpenerCable - Available

Exterior & Lot

Lot Size
1.65 acres
Zoning
R40
Garage / Parking
2 garage spacesUnder House Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Pool
GuniteHeatedAuto CleanerVinylSalt WaterIn Ground Pool
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedGuttersPatio
Lot Description
Lightly WoodedOn Cul-De-Sac

Listing & Financials

Property Taxes
$11,749 / Annually
Days on Market
126
MLS #
24161366
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Gina Farra

(703) 314-4872

Keller Williams Realty

(203) 438-9494

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. 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 7/29/2026 at 11:01 AM UTC.