28 Deep Hollow Road
Chester, CT 06412
$559,000
This beautifully maintained 1890 Farm House in coveted Deep Hollow Road is a rare opportunity and has been a labor of love over the time that the sellers have lived here. This 1.04 acre property on "The Hollow" consists of a house, an oversized 24' x 24' garage/shop, antique "pony" barn with authentic outhouse and custom built service barn suited for a man cave, cigar lounge or whatever else you can envision. Walking into the front door, expect an open floor plan with beautiful knotty alder doors, custom moldings, newly refinished arctic maple flooring, 2 tongue & groove cedar ceilings (1 w/rattan ceiling fans). New Kitchen Aid appliances in a kitchen just waiting for your vision & a spacious walk-in pantry w/ample storage. Gorgeous powder room tucked away features pedestal sink and a 100+ yr old antique cabinet. 2nd floor features 3 bedrooms, 2 which have cathedral ceilings w/remotely operated skylights w/rain sensors to automatically close at first sign of precipitation. Master bedroom has been plugged & wired for stackable washer/dryer. A stand up attic includes a whole house attic fan which creates an impressive amount of air flow. Second floor is on 4 zones of radiant heat; first floor is 1 zone. Basement is walk out and 400 sq ft of newly refreshed space. New carpet, great lighting and wonderful space for a playroom for children, man cave or home office/small business as utilized by the previous owners. Half ...
+ Read More| Listing Id: | 24199280 |
|---|---|
| List Price: | $559,000 |
| Property Type: | Single Family |
| Status: | Under Contract Cont. to Show |
| Bank Owned Property: | No |
| Beds Total: | 3 |
| Baths Full: | 1 |
| Baths Half: | 2 |
| Living Area Sqft Per Public Record: | 1,740 |
| Property Tax: | $5,079 |
| Acres: | 1.03 |
| Style: | Colonial |
| Direct Waterfront Yn: | No |
| City: | Chester |
| County: | Middlesex |
| Postal Code: | 06412 |
| Year Built: | 1890 |
| Acres Source: | Public Records |
| Agent Owner Yn: | No |
| Appliances Included: | Oven/Range, Refrigerator, Dishwasher |
| Assessed Value: | $182,840 |
| Attic Description: | Unfinished, Floored, Pull-Down Stairs |
| Attic Yn: | Yes |
| Basement Description: | Yes |
| Basement Description: | Full,Partially Finished,Full With Walk-Out |
| Baths Total: | 3 |
| Color: | tan |
| Comp Only Manual Yn: | No |
| Cooling System: | Window Unit |
| Current Price: | $559,000.00 |
| Date Cont To Show: | 2026-09-24T04:00:00 |
| Directions: | Use GPS |
| Display Fair Market Value Yn: | No |
| Elementary School: | Chester |
| Exterior Features: | Barn, Deck, French Doors |
| Exterior Siding: | Cedar |
| Flood Zone Yn: | No |
| Foundation Type: | Stone |
| Fuel Tank Location: | In Basement |
| Garage & Parking: | Detached Garage |
| Garages Number: | 2 |
| Heat Fuel Type: | Oil |
| Heat Type: | Radiant |
| High School: | Valley |
| Home Owner's Assocation: | No |
| Home Warranty Offered Yn: | No |
| Hot Water Description: | Oil, Domestic |
| In Law Apartment: | No |
| Laundry Room Info: | Lower Level |
| Laundry Room Location: | basement |
| Listing Contract Date: | 2026-09-14 |
| Lot Description: | Fence - Wood, Fence - Partial, Fence - Privacy, Borders Open Space |
| Mil Rate Total: | $27.78 |
| Status: | Under Contract - Continue to Show |
| Nearby Amenities: | Shopping/Mall |
| New Construction Type: | No/Resale |
| Occupied By: | Vacant |
| Original List Price: | $559,000 |
| Parcel Number: | 941507 |
| Parking Total Spaces: | 2 |
| Possession Availability: | Negotiable |
| Potential Short Sale: | No |
| Preferred Phone: | (860) 883-9001 |
| Price: | $559,000 |
| Radon Mitigation Air Ynu: | Unknown |
| Radon Mitigation Water Ynu: | Unknown |
| Remarks Public Addendum: | Last, but not least, living on "The Hollow" is all about living on a most beautiful dead end road that affords you access to hiking, fishing, the ability to walk into town and enjoy its old town charm or short bike ride to the Chester Hadlyme Ferry to enjoy a day of wandering the grounds of Gilette Castle. Whether you are looking for a forever home to raise your family, retiring to peaceful surrounds this home is worth a visit! |
| Roof Information: | Shingle |
| Sewage System: | Septic |
| Sign Yn: | No |
| Sq Ft Est Heated Above Grade: | 1,740 |
| Sq Ft Total: | 1,740 |
| Swimming Pool Yn: | No |
| Tax Year: | July 2026-June 2027 |
| Total Rooms: | 6 |
| Under Agreement Yn: | No |
| Waterfront Description: | Not Applicable |
| Water Source: | Private Well |
| Year Built Source: | Public Records |
| Zoning: | R-2 |
Listing Courtesy of: Property Shoppe, LLC
Listing Agent: Tom Pentalow
(860) 883-9001
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Smart MLS Inc. data last updated on October 08, 2026 06:45 PM - ET
Property Last Updated: October 08, 2026 06:45 PM - ET