2 Hollow Brook Road, Sherman, CT 06784 - Photo 1

1/1

$925,000

Sold
Closed
Single Family
5 Beds
3 Full Baths
1 Partial Bath
3,136 Sq. Ft.
2 Car Garage

1/1

Property Description

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

Full Property Details for 2 Hollow Brook Rd

General

Sold For: $925,000
Taxes: (July 2025-June 2026)
Status: Closed
Type: Single Family
Source: SMARTMLS
MLS ID: 24183159
Added to Site: 115 day(s) ago

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 and Sold 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

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Schools

Schools serving 2 Hollow Brook Rd

School District:Sherman School District

Name	Grades	Distance
Sherman School, Sherman, CT 2 Route 37 East, Sherman, CT 06784	PK-8	3.1 mi
New Fairfield High School 54 Gillotti Road, New Fairfield, CT 06812	9-12	5.4 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

Date

Details

Price

Change

Source

9/22/2026

Sold

$925,000

-15.91%

MLS

6/16/2026

Listed

$1,100,000

—

MLS

Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

64 Connelly Rd, New Milford, CT 06776 - Photo 1

Just Listed

$389,000

Open House

64 Connelly Rd New Milford, CT 06776

Single Family
Active
Updated 23 hours ago

3
Beds
3
Total Baths
1,812
Sq. Ft.

Listed by Chris LaCava (860) 354-4111 x39

435 Long Mountain Rd, New Milford, CT 06776 - Photo 1

Just Listed

$950,000

435 Long Mountain Rd New Milford, CT 06776

Single Family
Active
Updated 16 hours ago

3
Beds
3
Total Baths
2,308
Sq. Ft.

Listed by Larry Corrow (203) 770-0166 and Lori Campbell (860) 354-4111

41 McNulty Dr, New Milford, CT 06776 - Photo 1

Just Listed

$765,000

41 McNulty Dr New Milford, CT 06776

Single Family
Active
Updated 1 day ago

4
Beds
5
Total Baths
4,794
Sq. Ft.

Listed by Joseph Chemero (860) 354-4111

16 Ironwood Ln, New Milford, CT 06776 - Photo 1

Just Listed

$399,900

16 Ironwood Ln New Milford, CT 06776

Single Family
Active
Updated 15 hours ago

3
Beds
1
Total Bath
1,644
Sq. Ft.

Listed by Todd P Sargent (860) 354-4111

40 Valley View Ln, New Milford, CT 06776 - Photo 1

Price Reduced

-$15,000 (-3.41%)

$425,000

40 Valley View Ln New Milford, CT 06776

Single Family
Active
Updated 1 day ago

3
Beds
2
Total Baths
1,359
Sq. Ft.

Listed by McHenry Cooney Team (203) 948-0477

121 Litchfield Rd, New Milford, CT 06776 - Photo 1

Price Reduced

-$10,000 (-1.83%)

$535,000

121 Litchfield Rd New Milford, CT 06776

Single Family
Active
Updated 6 days ago

4
Beds
3
Total Baths
2,030
Sq. Ft.

Listed by Joseph Chemero (860) 354-4111 and Christina Reza (949) 280-0124

Price Reduced

-$10,000 (-1.83%)

$535,000

121 Litchfield Rd New Milford, CT 06776

Commercial
Active

Listed by Joseph Chemero (860) 354-4111 and Christina Reza (949) 280-0124

12 Mountain View Ave, New Milford, CT 06776 - Photo 1

12 Mountain View Ave New Milford, CT 06776

Single Family
Active
Updated 1 day ago

3
Beds
2
Total Baths
2,018
Sq. Ft.

Listed by Joseph Chemero (860) 354-4111

45 Big Trail, Sherman, CT 06784 - Photo 1

Sold

$915,000

45 Big Trail Sherman, CT 06784

Single Family
Closed

2
Beds
3
Total Baths
2,140
Sq. Ft.

Listed and Sold by William Pitt Sotheby's Int'l

12 Mauweehoo Hill, Sherman, CT 06784 - Photo 1

Sold

$850,000

12 Mauweehoo Hill Sherman, CT 06784

Single Family
Closed

4
Beds
3
Total Baths
4,089
Sq. Ft.

Listed by William Pitt Sotheby's Int'l
Sold by W. Raveis Lifestyles Realty

7 Glenview Dr, Sherman, CT 06784 - Photo 1

Sold

$830,000

7 Glenview Dr Sherman, CT 06784

Single Family
Closed

4
Beds
3
Total Baths
5,342
Sq. Ft.

Listed by Marinablue Realty
Sold by William Raveis Real Estate

3 Handol Ln, New Fairfield, CT 06812 - Photo 1

Sold

$879,500

3 Handol Ln New Fairfield, CT 06812

Single Family
Closed

4
Beds
3
Total Baths
3,068
Sq. Ft.

Listed by Houlihan Lawrence
Sold by Dream House Realty

2 Hollow Brook Road, Sherman, CT 06784 (MLS# 24183159) is a Single Family property that was sold at $925,000 on September 22, 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.

2 Hollow Brook Rd Sherman, CT 06784