321 Oenoke Ridge
New Canaan, Connecticut 06840
Reduced from $3,300,000
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 3,040
- Acres
- 1.25
- Year Built
- 1958
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
An elegant Regency-style residence with dramatic architectural presence is positioned in a premier location just moments from the village. Inside, ten-foot ceilings and Palladian windows flood the home with natural light. From the barrel-vaulted living room-a true Grand Salon-to the striking onyx-floored dining room, the interior spaces flow effortlessly to an expansive terrace, creating an unforgettable setting for both grand entertaining and quiet family relaxation. Offering a rare opportunity for luxurious, SINGLE-LEVEL living, the home seamlessly pairs grand scale with absolute privacy. The thoughtfully designed floor plan features a chef's kitchen, a sun-drenched breakfast room, a recreation/playroom, three en-suite bedrooms, and an elegant powder room. Outside, 1.25 acres of sweeping private lawns surround an impressively sized swimming pool, offering a private oasis. This exceptional residence is located in New Canaan, widely considered the most beautifully preserved New England town within one hour of New York City. Renowned for its unique design, the town's vibrant boutiques, fine dining, outstanding schools, and services are clustered in one charming, walkable center, with the residential community radiating outward in quiet, leafy tranquility.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Single Family · Ranch
- Year Built
- 1958
- Days on Market
- 45 days
- Beds
- 3
- Baths
- 3 full · 1 half
- Living Area
- 3,040 sq ft
- Lot Size
- 1.25 acres
- Garage / Parking
- 2 garage · 7 total
- Property Taxes
- $20,628 / Annually
Market Snapshot
The New Canaan Market
Single Family · trailing 12 months
Active Listings
33
25 under contract
Median List Price
$3.69M
33 active listings
Median Closed Price
$2.81M
210 sales
Median Days on Market
62
33 active listings
Median $ / Sq Ft
$673
33 active listings
Sale-to-List Ratio
102.4%
210 sales
How this home compares
List Price
$2.98M
vs $3.69M median
19.5% below median
Price / Sq Ft
$979
vs $673 median
45.5% above median
Days on Market
45 days
vs 62 days median
17 days fresher than median
Based on 33 active and 210 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of November 9, 2026.
Location
321 Oenoke Ridge, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$16,123
- Property Taxes$1,719
- Insurance$992
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Canaan
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Ranch
- Year Built
- 1958
- New Construction
- No/Resale
- Living Area
- 3,040 sq ft
- Below Grade
- 280 sq ft
Schools
- Elementary
- West
- High
- NCHS
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Cook TopWall OvenMicrowaveRefrigeratorFreezerDishwasherWasherDryer
- Basement
- Full
- Interior Features
- Auto Garage Door OpenerCable - AvailableOpen Floor PlanSecurity System
- Additional Rooms
- Foyer
Exterior & Lot
- Lot Size
- 1.25 acres
- Zoning
- 1AC
- Garage / Parking
- 2 garage spaces7 total parking spacesAttached GaragePaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- HeatedSafety FenceIn Ground Pool
- Construction
- Stucco
- Color
- Cream & White
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- TerraceShedAwningsGuttersGarden AreaLightingFrench DoorsUnderground Sprinkler
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $20,628 / Annually
- Days on Market
- 45
- MLS #
- 24208523
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/9/2026. 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 11/9/2026 at 8:20 PM UTC.