168 Upper Grassy Hill Road

Woodbury, CT
$ 1,999,900 Beds 4 Baths 3 Sq 3,354 Virtual Tour
Monthly Estimate* How much can I afford?

Fly in for the weekend! Gorgeous cape home abutting a local AIRSTRIP offering the possibility of flying home with the appropriate permission. Recently built with security in mind, you will love this pristine cape with all the measures taken for security and living off the grid. Nestled up against the Roxbury/Woodbury line this home abuts the old Roxbury airport, a 38x60 clear-span heated barn for all your toys, and is an incredibly efficient home with state-of-the-art heating, electrical, and engineering. Some of these mechanical upgrades include a 45 KW diesel generator plumbed to the oil tank, a solar array that makes more power than the property can use including heating and AC, electric gates with automatic watering systems on the walls and plantings, a casino grade security camera system, a 400 amp split service to operate the generator and solar in synchrony, and extensive underground and outdoor lighting to light up every inch of the 7 plus acres. Let's not forget the house, which has a welcoming open floor plan with lots of light, a gorgeous kitchen/great room with a cathedral ceiling, the main level master bedroom, and plenty of room for expansion. Built to last this contemporary cape provides all foam insulation, a 60-year roof, copper gutters, cedar shake siding with azek trim, and garage space for 16 or more vehicles. There is plenty of outdoor space including a ground-level deck with retractable awning, and a glass solarium with electricity and cable.

Single Family

  • Price
  • $ 1,999,900
  • City
  • Woodbury
  • Bedrooms
  • 4
  • Full Bathrooms
  • 3
  • County
  • Half Bathrooms
  • 0
  • Area
  • Lot Size
  • 7.08 Acres
  • Zip
  • 06798
  • Sqr Footage
  • 3,354
  • Year Built
  • 2011
  • Taxes
  • $ 16448
  • Style
  • Cape Cod,Contemporary
  • MLS#
  • 170480181
Listed By: Timothy Drakeley with Drakeley Real Estate, Inc.
Data Source: Smart MLS



Acres 7.0800
Association Amenities None
Elementary School Mitchell
Energy Features Active Solar, Extra Insulation, Generator, Thermopane Windows
High School Nonnewaug
In Law Apartment YNP Possible
Middle School/High School Woodbury
Nearby Amenities Golf Course, Lake, Library, Park, Private School(s), Tennis Courts
Neighborhood West Side
New Construction Type No/Resale
Property Type Single Family For Sale
Status Active
Style Cape Cod, Contemporary
Tax Year July 2022-June 2023
Virtual Tour https://www.zillow.com/view-3d-home/964eddfe-f902-4ca1-b231-218453be2430/?utm_source=captureapp
Virtual Tour Yn Yes
Waterfront Description Not Applicable
Year Built 2011
Year Built Source Public Records
Zoning OS80

Interior Features

Appliances Included Electric Range, Wall Oven, Microwave, Refrigerator, Dishwasher, Washer, Dryer
Attic Description Walk-up, Floored, Storage Space
Basement Description Full, Full With Walk-Out, Unfinished, Interior Access, Garage Access, Walk-out
Beds Total 4
Cooling System Attic Fan, Central Air, Whole House Fan
Fireplaces Total 1
Fuel Tank Location In Basement
Full Baths 3
Heat Fuel Type Oil
Heat Type Hydro Air
Hot Water Description Propane
Interior Features Auto Garage Door Opener, Central Vacuum, Open Floor Plan, Security System
Laundry Room Room with sink and cabinets
Laundry Room Info Main Level
Room Count 8
Rooms Additional Bonus Room, Foyer, Laundry Room, Workshop
Sq Ft Est Heated Above Grade 3354
Sq Ft Total 3354
Total Baths 3.00
Total Rooms 8

Exterior Features

Driveway Type Private, Circular, Crushed Stone
Exterior Features Awnings, Barn, Deck, French Doors, Garden Area, Lighting, Porch, Sidewalk, Underground Utilities
Foundation Concrete
Garage Parking Info Attached Garage, Under House Garage, Barn
Garages Number 16
Lot Description Open Lot, Cleared, Secluded, Level Lot
Pool Description In Ground Pool, Gunite
Roof Information Fiberglass Shingle
Sewage System Septic
Siding Shake, Cedar, Wood
Swimming Pool Yn Yes
Water Source Private Well


  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator


Per Month

Based on the average sale price from the Wallingford, CT office

  • Monthly Principal & interest $2,268
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
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Default based on a 30-year fixed rate of 5.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA, or jumbo loans.


Elementary School Mitchell Elementary School
Middle School Woodbury Middle School
High School Nonnewaug High School

Price History

4/8/2022 Listed $2,200,000
6/13/2022 10% - $1,999,900

Property vs Zip Code Average in 06798

AVG $690K
AVG $8,685
AVG 14
Year Built
AVG 1950


Areas That We Cover

168 Upper Grassy Hill Road Woodbury, CT is a Single Family Home for sale at $1999900 with 3354 sqft and a lot size of 7.08 Acres Acre(s). 168 Upper Grassy Hill Road Woodbury has 4 bedrooms, 3 baths and was built in 2011. The property's zip code is 06798 which is in Woodbury, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 5.49% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site 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.