Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$1,999,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 4,250 Sq. Ft.
  • 2 Car Garage
  • Updated 6 hours ago
See This Home
Save This Home
See This Home
Save This Home
A striking blend of modern design and timeless barn-inspired architecture, this exceptional 4,250 SF home sits privately on 12.77 acres and offers a rare sense of space, light, and tranquility. Built in 2022, the residence still feels brand new, with 5 BD, 4 BA, and 1 half bath over 3 levels, including a legal accessory apartment. A dramatic two-story foyer sets the tone, showcasing a split staircase w/sleek stainless-steel cabling and an open balcony above. The ML is defined by soaring 9-foot ceilings, reclaimed wood beams, wide-plank white oak floors, and expansive windows and doors that invite natural light into every corner. The open-concept design seamlessly connects the great room to a chef's kitchen outfitted w/premium stainless-steel appliances, a waterfall island & bright breakfast area. The adjoining dining room, anchored by a floor-to-ceiling stone fireplace and access to a side patio, offers flexibility as either a formal gathering space or a relaxed family room. A music room w/tray ceiling provides an ideal setting for a home office or formal dining space. 1st floor primary suite is a private retreat, complete with dual walk-in closets and a spa-like bath featuring a soaking tub and walk-in shower. A powder room & expansive mudroom w/custom cabinetry connect effortlessly to the attached two-car garage, crowned w/a classic cupola. The UL continues to impress with a well-balanced layout. BDRM#2 enjoys an ensuite bath, while BDRMS #3 and #4 share a full BA.

Full Property Details for 5 Upland Pastures Rd

General

  • Price: $1,999,000
  • HOA FEE: $133/month
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24153961
  • Updated: Today (3/30/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 16
  • Rooms/Areas: Foyer, Laundry Room, Mud Room, Music Room
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Open Floor Plan
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1
  • Full Bath: 9.5 x 9.5, Lower

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - 9 ft+ Ceilings, Beams, Bedroom Suite, Full Bath, Walk-In Closet, Wide Board Floor, 18 x 15.5, Main
  • Bedroom 1: Bedroom, 14.5 x 18, Lower
  • Bedroom 2: Bedroom - Bedroom Suite, Full Bath, Wide Board Floor, 15 x 11, Upper
  • Bedroom 3: Bedroom - Wide Board Floor, 15 x 15, Upper
  • Bedroom 4: Bedroom - Wide Board Floor, 15 x 15, Upper

Other Rooms

  • Living Room: Living Room, 10.5 x 18.5, Lower
  • Great Room: Great Room - 9 ft+ Ceilings, Beams, Wide Board Floor, 18 x 16, Main
  • Kitchen: Kitchen, 13.5 x 14, Lower
  • 2nd Kitchen: Kitchen - Quartz Counters, Dining Area, Island, Wide Board Floor, 21 x 12, Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Fireplace, Wide Board Floor, 19 x 17.5, Main
  • Office: Office - Wide Board Floor, 12 x 15.5, Main
  • Laundry: Lower Level, Upper Level
  • Other Room 1: Other - 2 Story Window(s), 9 ft+ Ceilings, Half Bath, Wide Board Floor, 18 x 16, Main
  • Other Room 2: Other - Built-Ins, Wide Board Floor, 21 x 8, Main
  • In-Law/Au Pair Suite: Yes

Exterior

  • Exterior Features: Underground Utilities, Garden Area, Lighting, Patio
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 10
  • Parking: Attached Garage, Unpaved

Location

  • County: Fairfield
  • Driving Directions: Route 37 - Upland Pastures Road, #5 on left.

School Information

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

Community

  • Association: Yes
  • Home Owners Assn.: 1
  • Assoc. Fees Include: Road Maintenance

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Zoned, Propane
  • Heating Fuel: Propane
  • Water Heater: Propane, Tankless Hotwater

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Barn, Modern
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Storage, Apartment, Full With Walk-Out
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,250
  • Above Ground: 3,500 Sq. Ft.
  • Below Ground: 750 Sq. Ft.
  • Year Built: 2022

Lot Features

  • Lot Size (Acres): 12.77
  • Zoning: res
  • Lot Description: Secluded, Some Wetlands, Lightly Wooded, Borders Open Space, On Cul-De-Sac

Green Features

  • Energy Features: Active Solar, Generator

Financial Considerations

  • Association Fee: $133
  • Assoc Fee Freq.: Monthly
  • Assessment Amount: $1,035,900
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 309207
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agent

Meet the listing agent
— 5 Upland Pastures Rd —

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 5 Upland Pastures Rd

School District:Sherman School District
NameGradesDistance
Sherman School, Sherman, CT
2 Route 37 East, Sherman, CT 06784
PK-81.1 mi
New Fairfield High School
54 Gillotti Road, New Fairfield, CT 06812
9-129 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 5 Upland Pastures Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
3/30/2026
Listed
$1,999,000
33.27%
MLS
12/29/2021
Sold
$1,500,000
—
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 5 Upland Pastures Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$9,695
2%
$581,600
—
2023
$9,515
-8%
$581,600
—
2023
$10,364
-2%
$581,600
—
2022
$10,573
403%
$581,600
416%
2021
$2,103
8%
$112,800
10%
2020
$1,955
-4%
$102,300
—
2019
$2,027
-3%
$102,300
—
2018
$2,080
—
$102,300
—
2017
$2,080
—
$102,300
—
2016
$2,081
1%
$102,340
—
2015
$2,051
1%
$102,340
—
2014
$2,030
-33%
$102,340
-43%
2011
$3,022
—
$179,480
—
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 5 Upland Pastures Rd

$
Down Payment
%
$
%

$
$
$

*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

Similar Properties near 5 Upland Pastures Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

6 Brinsmade Ln, Sherman, CT 06784 - Photo 1
$1,849,000

6 Brinsmade Ln  Sherman, CT 06784

  • Single Family
  • Active
  • Updated 7 days ago
  • 6
    Beds
  • 5
    Total Baths
  • 5,500
    Sq. Ft.
Listed by William Raveis Real Estate
32 Ferris Estates Rd, New Milford, CT 06776 - Photo 1
$1,790,000

32 Ferris Estates Rd  New Milford, CT 06776

  • Single Family
  • Active
  • 3
    Beds
  • 4
    Total Baths
  • 3,800
    Sq. Ft.
Listed by Compass Connecticut, LLC
54 Indian Trail, Brookfield, CT 06804 - Photo 1
$2,225,000

54 Indian Trail  Brookfield, CT 06804

  • Single Family
  • Active
  • Updated 7 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 3,361
    Sq. Ft.
Listed by Derek Greene
13 Nicoles Ct, Brookfield, CT 06804 - Photo 1
$1,999,999

13 Nicoles Ct  Brookfield, CT 06804

  • Single Family
  • Active
  • 4
    Beds
  • 5
    Total Baths
  • 4,834
    Sq. Ft.
Listed by Lakeshore Realty

Just Listed near 5 Upland Pastures Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

11 Willow Rd, New Milford, CT 06776 - Photo 1 Just Listed
$519,900

11 Willow Rd  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 3
    Total Baths
  • 1,600
    Sq. Ft.
Listed by Lori Campbell (860) 354-4111 and Larry Corrow (203) 770-0166
24 Caldwell Dr, New Milford, CT 06776 - Photo 1 Just Listed
$529,000

24 Caldwell Dr  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 4 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,594
    Sq. Ft.
Listed by Jessica Diaz (860) 605-0018
21 Rolling Glen Dr, New Milford, CT 06776 - Photo 1 Just Listed
$489,000

21 Rolling Glen Dr  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,666
    Sq. Ft.
Listed by Joseph Chemero (860) 354-4111
22 Meadowood Dr, New Milford, CT 06776 - Photo 1 Just Listed
$795,000

22 Meadowood Dr  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 4 hours ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,214
    Sq. Ft.
Listed by Jonathan Meyer (860) 354-4111

Price Reduced near 5 Upland Pastures Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

25 Howland Rd, New Milford, CT 06776 - Photo 1 Price Reduced
-$30,099 (-5.02%)
$569,900

25 Howland Rd  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 12 hours ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,705
    Sq. Ft.
Listed by Brandy Granata (203) 788-0580
4 Main St, New Milford, CT 06776 - Photo 1 Price Reduced
-$150 (-25%)
$450

4 Main St  New Milford, CT 06776

  • Commercial Lease
  • Active
Listed by Brandy Granata (203) 788-0580
297 Long Mountain Rd, New Milford, CT 06776 - Photo 1 Price Reduced
-$15,000 (-1.94%)
$760,000

297 Long Mountain Rd  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,564
    Sq. Ft.
Listed by Chris LaCava (860) 354-4111 x39
8 Pebble Ln, New Milford, CT 06776 - Photo 1 Price Reduced
-$20,000 (-3.08%)
$629,900

8 Pebble Ln  New Milford, CT 06776

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 2,990
    Sq. Ft.
Listed by Todd P Sargent (860) 354-4111

Recent Sales near 5 Upland Pastures Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

5 Stone Wall la, Sherman, CT 06784 - Photo 1 Sold
$1,900,000

5 Stone Wall la  Sherman, CT 06784

  • Single Family
  • Closed
  • 4
    Beds
  • 5
    Total Baths
  • 5,427
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by Dan Reilly
595 Candlewood Lake Rd, Brookfield, CT 06804 - Photo 1 Sold
$1,800,000

595 Candlewood Lake Rd  Brookfield, CT 06804

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 4,301
    Sq. Ft.
Listed by Berkshire Hathaway NE Prop.
Sold by Erin Porter
13 Cove Rd, Brookfield, CT 06804 - Photo 1 Sold
$1,850,000

13 Cove Rd  Brookfield, CT 06804

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 7,014
    Sq. Ft.
Listed and Sold by Howard Hanna Rand Realty

5 Upland Pastures Road, Sherman, CT 06784 (MLS# 24153961) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 5 Upland Pastures Road is currently listed for $1,999,000 and was received on March 30, 2026. This property is listed by Katie Harrison from our New Milford Office.Want to learn more about 5 Upland Pastures 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.

Tour this property