28 Deep Hollow Road, Chester, CT 06412
$559,000
3 BedroomBedrooms
3 BathroomBathrooms
1 Full BathroomFull Bathrooms
2 Half BathroomHalf Bathrooms
1,740 Sqft

28 Deep Hollow Road, Chester, CT 06412

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$559,000

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3 BedroomBedrooms
3 BathroomBathrooms
1,740 Sqft
Single Family
Contract Signed
MLS/ID# 24199280

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28 Deep Hollow Road, Chester, CT 06412: 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 bath in basement as well.

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!

Property Information for 28 Deep Hollow Road, Chester, CT 06412

Days on Market: 23

Last Updated: Tuesday, September 29, 2026 12:03 PM

Listing Courtesy of Property Shoppe, LLC , (860) 883-9001

MLS ID24199280
Zip Code06412
TypeSingle Family
StyleColonial
Bedrooms3
Bathrooms3
Full Bathrooms1
Half Bathrooms2
Total Rooms6
Sq. Ft.1, 740
Fireplaces0
BasementFull, Partially Finished, Full With Walk-Out
AtticUFIN, Floored, Pull-Down Stairs
Exterior FeaturesBarn, Deck, French Doors
Parking Detached Garage
Pets Allowed0
Garage Space2
HeatingRadiant
CoolingWindow Unit
WaterPrivate Well
SewerSeptic
Year Built1890
Acreage1.03
High SchoolValley
Assessment$182,840

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Cell860-358-0880
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35 Thorpe Avenue Suite 201 Wallingford CT 06492

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Listing courtesy of: Tom Pentalow, Property Shoppe, LLC

This information is assembled from a variety of different sources with varying degrees of reliability and is not guaranteed accurate. Information important to your buying decisions needs to be independently verified.