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$1,100,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,136 Sq. Ft.
  • 2 Car Garage
  • Updated 14 hours ago
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Impeccably maintained home in desirable Southern Sherman on 3.8 private, flat acres, right along the CT/ NY border. Welcome to 2 Hollow Brook Road! A rare find where every major mechanical, structural and cosmetic update has already been expertly handled. Truly turn-key and ready for its next chapter. This meticulously updated home blends smart infrastructure with a resort-style backyard. Inside find fresh paint, new interior doors and a stunning chef's kitchen with premium GE Cafe appliances. The primary suite is a true sanctuary with new hardwood floors, a completely remodeled spa-like bath with a walk-in glass shower, spacious walk-in closet and a large office that could also be used as a dressing room. Upstairs features new carpets while the finished basement boasts a private 5th bedroom with full bath - 600 SF of space that could also function as an in-law suite, gym or playroom. Outside is an entertainer's dream: a bluestone patio with a built-in grill, heated salt water pool with new LED lighting and a Sundance hot tub, all framed by professional landscaping & irrigation. Mechanicals are top-tier: 2-year-old roof & solar system, 5 new ductless mini-splits, Nest-controlled heating, epoxy-floor garage, constant-pressure well pump, UV water system and a whole-home alarm. There is nothing left to do but move in and enjoy your private country oasis! Sherman boasts a town beach on Candlewood Lake with boat slips. Easy commutes: 45 min to White Plains, 60 miles to NYC.

Full Property Details for 2 Hollow Brook Rd

General

  • Price: $1,100,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24183159
  • Updated: Today (6/16/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 8
  • Interior Features: Security System
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Wall Oven, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom, 21 x 21, Upper
  • Bedroom 1: Bedroom, 32 x 12, Lower
  • Bedroom 2: Bedroom, 10 x 13, Upper
  • Bedroom 3: Bedroom, 11 x 10, Upper
  • Bedroom 4: Bedroom, 13 x 10, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, 11 x 13, Main
  • Dining Room: Dining Room, 11 x 11, Main
  • Office: Office, 15 x 11, Upper
  • Laundry: Main Level
  • Other Room 1: Other, 8 x 10, Upper

Additional Information

  • Pool: Yes
  • Pool Description: Heated, Salt Water, In Ground Pool

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 4
  • Parking: Attached Garage, Driveway

Location

  • County: Fairfield
  • Subdivision: Southern Sherman
  • Driving Directions: Route 37 To Chapel Hill To Hollow Brook On Left

School Information

  • Elementary School: Sherman
  • High School: Per Board of Ed

Heating & Cooling

  • Cooling Type: Ductless, Split System
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Vinyl Siding
  • Basement Desc.: Full, Heated, Sump Pump, Storage, Partially Finished, Walk-out, Liveable Space
  • Roof: Asphalt Shingle
  • Square Feet: 3,136
  • Above Ground: 2,536 Sq. Ft.
  • Below Ground: 600 Sq. Ft.
  • Year Built: 1998

Lot Features

  • Lot Size (Acres): 3.8
  • Driveway/Sidewalk: Private, Gravel
  • Zoning: Residential
  • Lot Description: Secluded, Level Lot, Professionally Landscaped

Financial Considerations

  • Assessment Amount: $338,500
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 308785

Listed by Compass Connecticut, LLC, Donna Kennedy

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Listing agent

— 2 Hollow Brook Rd —

  • Donna Kennedy

    Compass Connecticut, LLC

Agent Contact: (917) 669-2642 Office Contact: (203) 290-2477

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2 Hollow Brook Rd

School District:Sherman School District
NameGradesDistance
Sherman School, Sherman, CT
2 Route 37 East, Sherman, CT 06784
PK-83.1 mi
New Fairfield High School
54 Gillotti Road, New Fairfield, CT 06812
9-125.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2 Hollow Brook Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/16/2026
Listed
$1,100,000
118.91%
MLS
8/09/2005
Sold
$502,500
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2 Hollow Brook Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$5,643
2%
$338,500
—
2023
$5,538
-8%
$338,500
—
2023
$6,032
-2%
$338,500
—
2022
$6,154
-2%
$338,500
—
2021
$6,310
-2%
$338,500
—
2020
$6,469
-4%
$338,500
—
2019
$6,706
-4%
$338,500
-2%
2018
$6,996
13%
$344,100
13%
2017
$6,205
-1%
$305,200
-1%
2016
$6,272
1%
$308,490
—
2015
$6,182
1%
$308,490
—
2014
$6,120
9%
$308,490
-7%
2011
$5,612
—
$333,270
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 2 Hollow Brook Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by Compass Connecticut, LLC, Donna Kennedy

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2 Hollow Brook Road, Sherman, CT 06784 (MLS# 24183159) is a Single Family property with 5 bedrooms, 3 full bathrooms and 1 partial bathroom. 2 Hollow Brook Road is currently listed for $1,100,000 and was received on June 16, 2026. Want to learn more about 2 Hollow Brook Road? Do you have questions about finding other Single Family real estate for sale in Sherman? You can browse all Sherman real estate or contact a Coldwell Banker agent to request more information.

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