This home's estimate is 41.2% higher than the average sale price ($494K) of 5 comparable homes.
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- Sale & tax history
- Property details
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11 Deep Hollow Rd, Chester, CT 06412
About this home
Want to get away? Come visit this idyllic mini compound situated beside a flowing, clear water pond and waterfall. The classic red barn with upstairs studio combines with a charming “hobbit” style potting shed and gated gardens.Take it all in from the huge wraparound rear deck or sit back in your Adirondacks and listen to the waterfall. The open interior offers kitchen, living room, family room and/or dining room options. Two main floor bedrooms include upgraded full baths and laundry. Follow the circular stair to access the third bedroom/loft/study area. Located a short walk from the charming destination village of Chester, this food lovers paradise includes award winning restaurants, a downtown Sunday farmers market, local arts and craft shops and lots of outdoor dining.
Redfin Estimate
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Market trends in 06412, CT
Last updated September 2026
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Sale history for 11 Deep Hollow Rd
$296/sq ft
$280/sq ft
$249/sq ft
$254/sq ft

Tastefully restored waterfront property sits aside a mill pond, just a short walk to historic chester village. New barn and artist's studio add to the character and utility of this charming compound. Home to a local designer, interior appointments abound.
$189/sq ft
$189/sq ft
Tax history for 11 Deep Hollow Rd
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.
Public record
Property details
Parking
- Garage Information
- Garage & Parking: Barn
- Garages Number: 1
Interior
- Virtual Tour Information
- Has Virtual Tour
- Interior Information
- Total Rooms: 8
- Laundry Room Location: In guest bath
- Laundry Room Info: Main Level
- Interior Features: Cable - Available, Open Floor Plan
- In-Law Apartment: No
- Thermostat(s)
- Fireplaces Total: 1
- Cooling System: Ceiling Fans, Central Air
- Appliances Included: Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Electric Dryer
- Bathroom Information
- # of Baths (Full): 2
- Bedroom Information
- Beds Total: 2
- Room Information
- Room Count: 6
- Basement Description: Full, Unfinished
Exterior
- Exterior Features
- Roof Information: Asphalt Shingle
- Exterior Siding: Clapboard
- Exterior Features: Barn, Deck, Fruit Trees, Garden Area, Shed, Wrap Around Deck
- Lot Information
- Lot Description: Level Lot, Lightly Wooded
- Building Information
- Foundation Type: Block
- Construction Description: Frame
- Property Information
- Waterfront Description: Frontage, Pond, View
- Radon Mitigation Air
- Property Type: Single Family For Sale
- Driveway Type: Asphalt, Crushed Stone
Financial
- Assessments Information
- Assessed Value: $239,440
Utilities
- Utility Information
- Water Source: Private Well
- Sewage System: Septic
- Hot Water Description: Oil
- Heat Type: Baseboard, Hot Air
- Heat Fuel Type: Oil
- Fuel Tank Location: In Basement
Location
- School Information
- Middle Jr High School: Winthrop
- Intermediate School: Per Board of Ed
- High School: Valley
- Elementary School: Chester
- Location Information
- State: Connecticut
- Flood Zone
- Directions: GPS Friendly
- Direct Waterfront
- County: Middlesex
Public facts
- Beds: —
- Baths: —
- Sq. Ft.: —
- Stories: —
- Lot Size: 0.5 acres
- Style: Other
- Year Built: —
- Year Renovated: —
- County: Middlesex County
- APN: 941584
Other
- Documents & Disclosures
- Supplement Count Public: 1
Around this home
Schools
Public PreK-6 • Assigned • 0.4mi
Public 7-8 • Assigned • 3.0mi
Public 9-12 • Assigned • 2.7mi
Lifestyle
Provided by Walk Score and Local Logic
Climate risks
Estimated 19-29% chance of a flood reaching the building in the next 30 years
Unlikely to be in a wildfire in next 30 years
7 days above 96° expected this year, 16 days in 30 years
77% chance of strong winds in next 30 years
3 unhealthy days expected this year, 5 days in 30 years
Sun exposure
Try the sun simulator tool to see how light moves across the property at different times of day and year.
Nearby similar homes
New listings for sale in 06412
Home values near 11 Deep Hollow Rd
| Address | Redfin Estimate |
|---|---|
3 Beds | 1 Baths | 912 Sq. Ft. | $337,309 |
3 Beds | 2 Baths | 1471 Sq. Ft. | $358,966 |
| Address | Redfin Estimate |
|---|---|
3 Beds | 4.5 Baths | 2910 Sq. Ft. | $1,008,308 |
4 Beds | 1 Baths | 1180 Sq. Ft. | $365,082 |
| Address | Redfin Estimate |
|---|---|
4 Beds | 1.5 Baths | 2066 Sq. Ft. | $655,867 |
2 Beds | 1 Baths | 1087 Sq. Ft. | $346,992 |
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