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2 Hollow Brook Road

Sherman, Connecticut 06784

PENDING$1,100,000
Beds
5
Baths
3 | 1
SqFt
3,136
Acres
3.80
Year Built
1998
Matt Caiola

Matt Caiola

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Pool2-Car Garage1 Fireplace

About This Home

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.

Key Facts

City/Town
Sherman
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1998
Days on Market
43 days
Beds
5
Baths
3 full · 1 half
Living Area
3,136 sq ft
Lot Size
3.80 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$6,538 / Annually

Market Snapshot

The Sherman Market

Single Family · trailing 12 months

Median Days on Market

62

28 active listings

Median $ / Sq Ft

$333

28 active listings

Sale-to-List Ratio

96.7%

42 sales

How this home compares

List Price

$1.10M

vs $1.05M median

In line with median

Price / Sq Ft

$351

vs $333 median

5.4% above median

Days on Market

43 days

vs 62 days median

19 days fresher than median

Based on 28 active and 42 closed sales (trailing 12 mo) of single family in Sherman. Source: SmartMLS · As of July 29, 2026.

Location

2 Hollow Brook Road, Sherman, Connecticut

Property + 4 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,521

per month

  • Principal & Interest$5,609
  • Property Taxes$545
  • Insurance$367
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Sherman
Neighborhood
N/A
County
Fairfield
Subdivision
Southern Sherman

Residence

Property Type
Single Family
Style
Colonial
Year Built
1998
New Construction
No/Resale
Living Area
3,136 sq ft
Below Grade
600 sq ft

Schools

Elementary
Sherman
High
Per Board of Ed

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
DuctlessSplit System
Fireplaces
1
Laundry
Main Level
Laundry Location
off mud room
Appliances
Gas CooktopWall OvenMicrowaveRefrigeratorFreezerDishwasherWasherDryer
Basement
FullHeatedSump PumpStoragePartially FinishedWalk-outLiveable Space
In-Law Apartment
PossibleSeparate Entry
Interior Features
Security System

Exterior & Lot

Lot Size
3.80 acres
Zoning
Residential
Garage / Parking
2 garage spaces4 total parking spacesAttached GarageDrivewayPrivateGravel
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
HeatedSalt WaterIn Ground Pool
Construction
Vinyl Siding
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
SecludedLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$6,538 / Annually
Days on Market
43
MLS #
24183159
MLS Status
Under Contract - Continue to Show

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Donna Kennedy

(917) 669-2642

Compass Connecticut, LLC

(203) 290-2477

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information 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 or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/29/2026 at 10:10 AM UTC.