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22 Pent Road

Weston, Connecticut 06883

ACTIVE$2,995,000

Reduced from $3,595,000

Beds
4
Baths
5 | 1
SqFt
5,448
Acres
3.67
Year Built
1959
Matt Caiola

Matt Caiola

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About This Home

Extraordinary riverfront modern retreat set against a breathtaking backdrop of waterfall, woodland, and sweeping water views in one of Weston's most remarkable settings. Surrounded by preserved land and trails of Devil's Den Preserve, this extensively renovated residence offers a rare connection to nature paired with sophisticated design and luxury amenities. Walls of glass, soaring ceilings, and thoughtfully reimagined interiors create a seamless relationship between indoors and out. The stunning chef's kitchen was completely redesigned. A dramatic four-season sunroom with floor-to-ceiling window systems opens at the touch of a button to create an unparalleled indoor-outdoor living experience. The primary suite is a serene riverfront retreat featuring expansive views and a spa-inspired bath with heated floors, steam shower, soaking tub, glass-front sauna overlooking the water, and custom closets. Three additional ensuite bedrooms are on the second level. Additional highlights include a spectacular media room, billiard room, office/gym space, stone terraces, and a beautifully positioned pool overlooking the river. An exceptional offering combining architectural sophistication and an immersive, private natural setting.

Key Facts

City/Town
Weston
Neighborhood
Devil'S Den
Property / Style
Single Family · Contemporary
Year Built
1959
Days on Market
69 days
Beds
4
Baths
5 full · 1 half
Living Area
5,448 sq ft
Lot Size
3.67 acres
Garage / Parking
2 garage
Property Taxes
$31,697 / Annually

Market Snapshot

The Weston Market

Single Family · trailing 12 months

Median Days on Market

48

30 active listings

Median $ / Sq Ft

$382

30 active listings

Sale-to-List Ratio

100.1%

129 sales

How this home compares

List Price

$3.00M

vs $1.50M median

99.7% above median

Price / Sq Ft

$550

vs $382 median

44.0% above median

Days on Market

69 days

vs 48 days median

21 days longer than median

Based on 30 active and 129 closed sales (trailing 12 mo) of single family in Weston. Source: SmartMLS · As of July 29, 2026.

Location

22 Pent Road, Weston, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$18,910

per month

  • Principal & Interest$15,271
  • Property Taxes$2,641
  • Insurance$998
  • HOA$0

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

Location

City/Town
Weston
Neighborhood
Devil'S Den
County
Fairfield

Residence

Property Type
Single Family
Style
Contemporary
Year Built
1959
New Construction
No/Resale
Living Area
5,448 sq ft

Schools

Elementary
Hurlbutt
Middle
Weston
High
Weston

Interior

Heating
Hot AirRadiant
Heat Fuel
OilPropane
Cooling
Central AirSplit SystemZoned
Fireplaces
2
Laundry
Lower LevelMain Level
Laundry Location
2 laundry rooms
Appliances
Wall OvenRefrigeratorFreezerDishwasherWasherDryer
Basement
FullHeatedCooledPartially FinishedFull With Walk-Out
Interior Features
Audio SystemAuto Garage Door OpenerOpen Floor PlanSaunaSecurity System
Additional Rooms
Exercise RoomFoyerLaundry RoomMud RoomMusic RoomSteam/SaunaSolarium

Exterior & Lot

Lot Size
3.67 acres
Zoning
R
Garage / Parking
2 garage spacesAttached Garage
Waterfront
Direct waterfront
Waterfront Details
River
Water Source
Private Well
Sewer
Septic
Pool
HeatedSafety FenceIn Ground Pool
Construction
Shingle
Color
Gray
Roof
Asphalt Shingle
Foundation
ConcreteMasonry
Exterior Features
DeckGuttersLightingStone WallUnderground SprinklerPatio
Lot Description
SecludedTreedOn Cul-De-SacProfessionally LandscapedWater View

Listing & Financials

Property Taxes
$31,697 / Annually
Days on Market
69
MLS #
24176936
MLS Status
Active

Similar Properties

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

Listed By

Jennifer Twombly

(203) 505-4329

Compass Connecticut, LLC

(203) 293-9715

Co-Listed By

Jennifer Leahy

Compass Connecticut, LLC

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 11:05 AM UTC.