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 bedrooms, 4 full baths, and 1 half bath over 3 levels, including a legal accessory apartment. A dramatic two-story foyer sets the tone, showcasing a split staircase with sleek stainless-steel cabling and an open balcony above. The main level 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 with premium stainless-steel appliances, a waterfall island, and a 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 with a tray ceiling provides an ideal setting for a home office or formal dining space. The first-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 and an expansive mudroom with custom cabinetry connect effortlessly to the attached two-car garage, crowned with a classic cupola. Upstairs, the second level continues to impress with a well-balanced layout. Bedroom #2 enjoys an ensuite bath, while bedrooms #3 and #4 share a full hall bath. A versatile workspace or recreation area with custom cabinetry adds further flexibility, complemented by a dedicated laundry room, storage room, and a charming cupola that draws in sunlight from all directions. The walk-out basement features 10-foot ceilings with both finished and unfinished space. In 2023, a beautifully designed 750 SF legal accessory apartment was added, offering its own private entrance and parking area. This self-contained space includes a living room, full kitchen, bedroom #5, full bath, dual closets, and additional storage. Designed with efficiency and sustainability in mind, the home is equipped with top-tier mechanical systems, a full-house generator, and discreet solar panels that significantly reduce energy costs. Outdoors, a gentle stream borders the western edge, while surrounding conservation land enhances privacy and preserves the natural setting. Seasonal mountain views and stunning western sunsets provide a picturesque backdrop. Bluestone patios and walkways create inviting outdoor living spaces, complemented by a designated pool site and a fenced raised-bed garden with irrigation. The landscaping, thoughtfully designed by GardenLarge, embraces a naturalistic landscaping approach, replacing invasive species without the use of chemicals, with hundreds of native plantings that support local wildlife and pollination. Upland Pastures Farm is a small country subdivision of custom homes on large lots with no further subdivision. Access to 2 additional protected properties of Open Space (pasture & woodlands) totaling over 77 acres (Northwest Connecticut Land Conservancy - CT's largest Land Trust) abuts miles of walking, riding, hiking trails. A short walk to the White Silo Farm, a small specialty winery that produces fresh fruit and grapes, with wines made from the fruit grown at the farm. Wine tastings and old dairy barn showcasing local artists. 1 minute to quaint Town Center, community tennis & pickle ball courts, basketball court, ball field and short walk to town pavilion, beach, boat slips and canoe/kayak racks on Candlewood Lake. 6 minutes to the Audubon Society Land Trust (835 acre bird sanctuary). 7 minutes to the River Oaks Golf Club. 20 minutes to Metro North Train Station. Just 5 minutes to the NY line and 90 minutes to NYC. Potential for Guest House. Room for barn/horses/tennis/cited for pool.
Single-familyProperty Type
2022Year Built
12.77 acresLot Size
$471Price/Sq.Ft.
2 garage spacesParking
Listed by Claudia Jiskra• McGrath Realty Inc
Contact: 845-855-5550
Bought with Non Non Member-MLS• Buyer Representation Office
Est. $4,316 per month, based on comparable rentals
Sale and tax history for 5 Upland Pastures Rd
Sale History
Tax History
Date
Event
Price
OneKey® MLS as Distributed by MLS Grid #977923
Jun 15, 2026
Sold
$2,000,000
$471/sq ft
May 2, 2026
Pending
—
Mar 30, 2026
Listed
$1,999,000
$470/sq ft
Smart MLS #24153961
Jun 15, 2026
Sold
$2,000,000
$471/sq ft
May 1, 2026
Pending
—
Apr 22, 2026
Contingent
—
Mar 30, 2026
Listed
$1,999,000
$470/sq ft
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.
A versatile workspace or recreation area w/custom cabinetry adds further flexibility, complemented by a dedicated laundry room, storage room, and a charming cupola that draws in sunlight from all directions. The walk-out basement features 10-foot ceilings with both finished and unfinished space. In 2023, a beautifully designed 750 SF legal accessory apartment was added, offering its own private entrance and parking area. This self-contained space includes a living room, full kitchen, BDRM #5, full bath, dual closets & ample additional storage. Designed with efficiency and sustainability in mind, the home is equipped with top-tier mechanical systems, a full-house generator, and discreet solar panels that significantly reduce energy costs. Outdoors, a gentle stream borders the western edge, while surrounding conservation land enhances privacy and preserves the natural setting. Seasonal mountain views and stunning western sunsets provide a picturesque backdrop. Bluestone patios and walkways create inviting outdoor living spaces, complemented by a designated pool site and a fenced raised-bed garden with irrigation. The landscaping, thoughtfully designed by GardenLarge, embraces a naturalistic landscaping approach, replacing invasive species without the use of chemicals, with hundreds of native plantings that support local wildlife and pollination. UPLAND PASTURES FARM - a small country subdivision of custom homes w/large lots that cannot be further subdivided. Access to 2 additional protected properties of Open Space (pasture & woodlands) totaling over 77 ACRES (Northwest Connecticut Land Conservancy - CT's largest Land Trust) abuts miles of walking, riding, hiking trails. A short walk to the White Silo Farm, a small specialty winery that produces fresh fruit & grapes, wines made from fruit grown at the farm. Wine tastings, old dairy barn showcasing local artists. 1M to quaint Town Center, community tennis & pickle ball courts, basketball court, ball field & short walk to town pavilion, BEACH, Boat slips & Canoe/Kayak Racks on CANDLEWOOD LAKE. 6M to Audubon Society Land Trust (835 Acres Bird Sanctuary). 7M to River Oaks Golf Club. 20M to Metro North Train Station. Just 5M to NY Line and 90M to NYC. Potential for Guest House. Room for Barn/Horses/Tennis/Cited for Pool.
Public Records
Jan 4, 2022
Sold
$1,500,000
$353/sq ft
Smart MLS #170401235
Dec 31, 2021
Sold
$1,600,000
$376/sq ft
Sep 14, 2021
Contingent
—
May 18, 2021
Listed
$1,500,000
$353/sq ft
NEW CONSTRUCTION - Completion Date - 10/21. Small Country Subdivision of Custom Homes w/large lots that cannot be further subdivided. Easy living Contemporary Country Barn/Style Home w/flexible and open floor plan. Huge pictures windows overlook private back to nature setting w/Western VIEWS. 2-Story soaring entry foyer (15 x 13). ML Master Suite. Vaulted & 9' Ceilings w/reclaimed Wood Beams/Marvin Integrity Windows/Flooring 3/4" x 8 Solid Live White Oak 4-10'/Kingswood Cabinets/Dacor Stainless Steel Appliances/ Mud Room(9.5x11.5) Add 1800 sq ft on walk out LL w/10'Ceilings (plumbed for bath).Efficient propane heat/closed cell spray foam insulation. Easy to Show. Plans & Specs available for qualified buyers. UPLAND PASTURES FARM - Access to 2 open, protected properties of Open Space (pasture & woodlands) totally over 77 ACRES (Northwest Connecticut Land Conservancy-CT's largest Land Trust)-w/miles of walking, riding, hiking trails.A short walk to the White Silo Farm)Small specialty winery produces fresh fruit & grapes wines made from fruit grown at the farm. Wine tastings, old dairy barn showcasing local artists. 1M to quaint Town Center, community tennis, basketball court, ball field & walk to pavilion, BEACH, Boat slips & Canoe/Kayak Racks on CANDLEWOOD LAKE. 2M to Audubon Society Land Trust. 20M to Metro North Train Station. Just 90 M to New York. POTENTIAL for Guest House, Barn/Horse Property. Pool has been sited. PLEASE NOTE THAT BUILDER HAS MAINTAINED PRICE!
Smart MLS #170265498
Jul 31, 2020
Sold
$300,000
$71/sq ft
Jun 28, 2020
Contingent
—
Jan 22, 2020
Listed
$312,500
$74/sq ft
Smart MLS #170034402
Jan 20, 2020
Listing Removed
—
Nov 25, 2017
Listed
$350,000
$82/sq ft
Smart MLS #98481255
Oct 24, 2012
Listing Removed
—
Oct 24, 2010
Listed
$399,000
$94/sq ft
Smart MLS #98404110
Jun 22, 2010
Listing Removed
—
Dec 22, 2008
Listed
$479,900
$113/sq ft
Smart MLS #F981730
May 12, 2009
Listing Removed
—
Nov 12, 2008
Listed
$479,000
$113/sq ft
Smart MLS #98356173
Dec 3, 2008
Listing Removed
—
Nov 3, 2007
Listed
$479,900
$113/sq ft
Smart MLS #98304990
Oct 8, 2007
Listing Removed
—
Oct 8, 2006
Listed
$479,000
$113/sq ft
Public Records
May 24, 2007
Sold
$465,000
$109/sq ft
Smart MLS #98251479
Aug 29, 2006
Listing Removed
—
Sep 6, 2005
Listed
$509,000
$120/sq ft
Public Records
Jul 1, 2005
Sold
$450,000
$106/sq ft
Smart MLS #98227140
Apr 6, 2005
Listing Removed
—
Feb 28, 2005
Listed
$1,600,000
$376/sq ft
Smart MLS #98219283
Nov 29, 2004
Listed
$473,000
$111/sq ft
Smart MLS #98186199
Jul 1, 2004
Listing Removed
—
Jan 30, 2004
Listed
$389,000
$92/sq ft
Smart MLS #98171427
Dec 31, 2003
Listing Removed
—
Jul 31, 2003
Listed
$389,900
$92/sq ft
Smart MLS #98127183
Apr 10, 2002
Listed
$275,000
$65/sq ft
Smart MLS #98044647
May 23, 1999
Listed
$209,000
$49/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$10,364 (−2.0%)
$112,900 + $468,700
$581,600
2022
$10,573 (+402.8%)
$112,900 + $468,700
$581,600
2021
$2,103 (+7.6%)
$112,800
2020
$1,955 (−3.6%)
$102,300
2019
$2,027 (−2.5%)
$102,300
2018
$2,080
$102,300
2017
$2,080
$102,300
Public record
Beds
4
Baths
3.5
Stories
2
Lot width
—
Lot depth
—
Lot size
12.77 Acres
Year renovated
—
Sq. Ft.
4,194
Year built
2021
Style
Single Family Residential
County
Fairfield County
APN
309207
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 12, 2023.
Property details
Parking
Parking Information
Carport YN: No
Parking Total: 10
Parking Features: Attached, Driveway, Garage
Garage Information
Garage Spaces: 2
Has Garage
Interior
Fireplace Information
Has Fireplace
Fireplaces Total: 1
Fireplace Features: Family Room, Wood Burning
Heating & Cooling
Cooling: Central Air
Heating: Forced Air, Propane
Interior Features
Interior Features: First Floor Bedroom,First Floor Full Bath,Beamed Ceilings,Built-in Features,Ceiling Fan(s),Chandelier,Chefs Kitchen,Eat-in Kitchen,Entrance Foyer,Formal Dining,High Ceilings,High Speed Internet,His and Hers Closets,In-Law Floorplan,Kitchen Island,Natural Woodwork,Open Floorplan,Open Kitchen,Pantry,Primary Bathroom,Quartz/Quartzite Counters,Recessed Lighting,Soaking Tub,Speakers,Storage,Tray Ceiling(s),Walk-In Closet(s),Wet Bar
Window Features: Oversized Windows
Laundry Features: In Basement, Laundry Room, Multiple Locations
Appliances: Dishwasher, Dryer, Electric Oven, Exhaust Fan, Gas Oven, Microwave, Refrigerator, Stainless Steel Appliance(s), Washer, Gas Water Heater
Flooring: Hardwood, Tile, Vinyl
Levels: Three Or More
Patio And Porch Features: Covered, Patio
Room Information
Basement YN: Yes
Attic: Pull Stairs,Unfinished
Rooms Total: 16
Basement: Full, Partially Finished, See Remarks, Storage Space, Walk-Out Access
Directions: Route 37 to Upland Pastures Road, across from the White Silo Farm & Winery. Take the private road until you see the large metal #5 sign.
County Or Parish: Out of Area
Public facts
Beds: 4
Baths: 3.5
Sq. Ft.: 4,194
Stories: 2.0
Lot Size: 12.77 acres
Style: Single Family Residential
Year Built: 2021
Year Renovated: —
County: Fairfield County
APN: 309207
Home facts updated by county records on Jul 12, 2023
Around this home
Schools
Sherman School
Public PreK-8 • Assigned • 1.1mi
9/10
New Milford High School
Public 9-12 • Assigned • 5.3mi
6/10
Provided by GreatSchools
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
3/10 Heat Factor
7 days above 96° expected this year, 14 days in 30 years
4/10 Wind Factor
18% chance of strong winds in next 30 years
2/10 Air Factor
2 unhealthy days expected this year, 2 days in 30 years
Provided by First Street
Historical weather
Sherman, CT • 06784
Average low and high temperatures (°F)
33
20
36
22
53
33
62
42
69
51
80
61
85
67
80
60
75
56
65
46
52
37
38
24
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
91/ 100
Exceptional sunlight
Sunscore
This home ranks in the top 7% for direct sun exposure in Sherman. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
9.8 hrs
6 hrs
JuneDecember
Provided by Shadowmap
Estimated sale price
$1.88M – $2.27M
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