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351 Old Sib Road

Ridgefield, Connecticut 06877

ACTIVE$2,295,000
Beds
5
Baths
4 | 2
SqFt
5,725
Acres
4.39
Year Built
1977
Matt Caiola

Matt Caiola

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Wine CellarPool2-Car Garage1 Fireplace

About This Home

Nestled amid 4.39 acres of beautifully landscaped, wooded grounds, The Retreat is an exceptional Ridgefield estate where refined living, privacy, and resort-inspired amenities come together. Designed for both grand entertaining and effortless everyday living, the property unfolds through lush gardens, impressive stonework, expansive terraces and patios, and a spectacular gunite pool, creating a serene setting reminiscent of a private luxury resort. The beautifully appointed main residence features a first-floor primary suite, two private offices, three additional bedrooms, a striking brick fireplace, and an elegant kitchen with butler's pantry and laundry. An expansive wraparound deck creates a seamless connection between the interior and surrounding landscape, offering an extraordinary backdrop for entertaining or quiet relaxation. The finished walk-out lower level is an entertainer's dreamscape, complete with a sophisticated full bar, wine cellar, cigar room with dedicated smoke-extraction HVAC, spacious family room, and a luxurious spa bath with steam room and wall jets. A separate cottage adds a legal studio apartment with a private entrance and outdoor sitting area, plus an additional bonus room and half bath above-ideal for guests, extended stays, or a private retreat. A dedicated indoor wellness spa with a hot tub, sauna, and massage area further elevates the experience. Secluded and tranquil, yet moments from Ridgefield's celebrated Main Street

Key Facts

City/Town
Ridgefield
Neighborhood
N/A
Property / Style
Single Family · Contemporary
Year Built
1977
Days on Market
16 days
Beds
5
Baths
4 full · 2 half
Living Area
5,725 sq ft
Lot Size
4.39 acres
Garage / Parking
2 garage
Property Taxes
$21,092 / Annually

Market Snapshot

The Ridgefield Market

Single Family · trailing 12 months

Median Days on Market

52

47 active listings

Median $ / Sq Ft

$423

47 active listings

Sale-to-List Ratio

101.7%

244 sales

How this home compares

List Price

$2.29M

vs $1.30M median

76.5% above median

Price / Sq Ft

$401

vs $423 median

5.2% below median

Days on Market

16 days

vs 52 days median

36 days fresher than median

Based on 47 active and 244 closed sales (trailing 12 mo) of single family in Ridgefield. Source: SmartMLS · As of September 25, 2026.

Location

351 Old Sib Road, Ridgefield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$14,775

per month

  • Principal & Interest$12,252
  • Property Taxes$1,758
  • Insurance$765
  • HOA$0

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

Location

City/Town
Ridgefield
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Contemporary
Year Built
1977
New Construction
No/Resale
Living Area
5,725 sq ft

Schools

Elementary
Barlow Mountain
High
Ridgefield

Interior

Heating
Zoned
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Laundry Location
Off of Kitchen. Mudroom/Butler pantry
Appliances
Gas CooktopGas RangeOven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullHeatedFully FinishedCooledFull With Walk-Out
In-Law Apartment
YesDetachedSeparate Entry
Additional Rooms
FoyerMud RoomWine Cellar

Exterior & Lot

Lot Size
4.39 acres
Zoning
RAA
Garage / Parking
2 garage spacesAttached GarageDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Pool
GuniteHeatedIn Ground Pool
Construction
Vertical SidingWood
Roof
Asphalt Shingle
Foundation
Concrete
Lot Description
N/A

Listing & Financials

Property Taxes
$21,092 / Annually
Days on Market
16
MLS #
24205321
MLS Status
Active

Similar Properties

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Listed By

Debra Tricarico

(914) 592-3444

Houlihan Lawrence

(203) 746-6565

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

The IDX display contains information sourced from SmartMLS, Inc. as of 9/25/2026. 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 9/25/2026 at 7:05 PM UTC.