70 Pine Hollow Drive
Middlebury, Connecticut 06762
Reduced from $669,000
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 3,174
- Acres
- 1.22
- Year Built
- 1978
- 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
MOTIVATED SELLERS! MAKE OFFER! Nestled on 1.22 acres of park-like grounds, a large custom designed home offering privacy & serenity and maintained by its original owners. Step inside and be greeted by a sunken, front-to-back living room anchored by a fireplace, setting the tone for the thoughtful design found throughout. Entertain in style in the formal dining room with elegant French doors or gather in the huge family room- another fireplace and generous proportions make it the heart of the home. The eat-in kitchen features a breakfast bar, perfect for casual mornings. Three bedrooms, 2.5 baths, and 3 fireplaces offer the comfort and warmth your family deserves. And, when you want to escape, a finished mancave with wet bar is all yours. Outside, a 54-foot deck provides the ultimate backdrop for outdoor entertaining, overlooking your own private retreat. Three oversized garages and newly paved driveway add convenience and curb appeal alike. Oh, and by the way, please do not forget to walk up a couple of steps behind the deck to a beautiful level lot adjacent to a tree lined area. Perfect for incorporating your very own fire pit or gazebo, for further relaxation and enjoyment. Recent updates including a new whole-house generator (1 yr), deck (3 yrs), electric hot water heater (3 yrs), paved driveway (2 yr), and a 15-year roof. Located in the New England town of Middlebury, known for its small-town character and top-rated schools. MOTIVATED SELLERS! MAKE OFFER!
Key Facts
- City/Town
- Middlebury
- Neighborhood
- N/A
- Property / Style
- Single Family · Contemporary
- Year Built
- 1978
- Days on Market
- 115 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 3,174 sq ft
- Lot Size
- 1.22 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $8,123 / Annually
Market Snapshot
The Middlebury Market
Single Family · trailing 12 months
Active Listings
25
21 under contract
Median List Price
$670,000
25 active listings
Median Closed Price
$540,000
79 sales
Median Days on Market
46
25 active listings
Median $ / Sq Ft
$280
25 active listings
Sale-to-List Ratio
100.0%
79 sales
How this home compares
List Price
$649,900
vs $670,000 median
In line with median
Price / Sq Ft
$205
vs $280 median
26.8% below median
Days on Market
115 days
vs 46 days median
69 days longer than median
Based on 25 active and 79 closed sales (trailing 12 mo) of single family in Middlebury. Source: SmartMLS · As of October 13, 2026.
Location
70 Pine Hollow Drive, Middlebury, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 8, 2026per month
- Principal & Interest$3,600
- Property Taxes$677
- Insurance$217
- 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
- Contemporary
- Year Built
- 1978
- New Construction
- No/Resale
- Living Area
- 3,174 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Ceiling FansSplit System
- Fireplaces
- 3
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedStorageInterior Access
Exterior & Lot
- Lot Size
- 1.22 acres
- Zoning
- R40
- Garage / Parking
- 3 garage spacesAttached GarageDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Vinyl Siding
- Color
- Tan
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- SidewalkShedDeckGutters
- Lot Description
- SecludedLightly WoodedOn Cul-De-Sac
Listing & Financials
- Property Taxes
- $8,123 / Annually
- Days on Market
- 115
- MLS #
- 24185515
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 10/13/2026. 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 10/13/2026 at 6:50 PM UTC.