80 Pine Hollow Drive
Middlebury, Connecticut 06762
Reduced from $749,900
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 2,806
- Acres
- 1.65
- Year Built
- 1979
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
- 171 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
Active Listings
27
27 under contract
Median List Price
$600,000
27 active listings
Median Closed Price
$522,500
70 sales
Median Days on Market
44
27 active listings
Median $ / Sq Ft
$272
27 active listings
Sale-to-List Ratio
100.0%
70 sales
How this home compares
List Price
$724,900
vs $600,000 median
20.8% above median
Price / Sq Ft
$258
vs $272 median
5.1% below median
Days on Market
171 days
vs 44 days median
127 days longer than median
Based on 27 active and 70 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of September 12, 2026.
Location
80 Pine Hollow Drive, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$3,765
- Property Taxes$979
- Insurance$242
- 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
- 171
- MLS #
- 24161366
- MLS Status
- Under Contract - Continue to Show
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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 9/12/2026. 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 9/12/2026 at 11:40 PM UTC.