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41-B Whippoorwill Road

Old Lyme, Connecticut 06371

ACTIVE$2,299,000
Beds
5
Baths
4 | 1
SqFt
4,694
Acres
12.78
Year Built
2026
Matt Caiola

Matt Caiola

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3-Car Garage2 FireplacesNew Construction

About This Home

Set on more than 12 private acres in one of Old Lyme's most desirable locations, this exceptional new construction residence offers a rare combination of luxury, flexibility, and space to grow. Thoughtfully designed for today's lifestyle, the home features four bedrooms, including a spacious primary suite on the main level, and a beautifully appointed guest suite ideal for extended family, visiting guests, or a private home office. Inside, vaulted ceilings, custom millwork, rich hardwood floors, and a striking fireplace create an atmosphere of timeless elegance and warmth. The open concept design seamlessly blends sophisticated living with everyday comfort, while expansive windows invite natural light and frame picturesque views of the surrounding landscape. The property's expansive grounds are enhanced by stunning natural rock formations and thoughtfully designed outdoor living spaces, including a welcoming front paver patio and a large rear paver patio ideal for entertaining, dining al fresco, or simply enjoying the peaceful setting. With ample room for a pool, pool house, gardens, or additional recreational amenities, the possibilities are endless. Surrounded by natural beauty yet just minutes from the historic village of Old Lyme, beaches, marinas, and major commuting routes, this is a rare opportunity to enjoy the privacy of a country estate with the convenience of shoreline living. A truly exceptional property where luxury, craftsmanship, and nature come together.

Key Facts

City/Town
Old Lyme
Neighborhood
Whippoorwill
Property / Style
Single Family · Ranch,Farm House
Year Built
2026
Days on Market
32 days
Beds
5
Baths
4 full · 1 half
Living Area
4,694 sq ft
Lot Size
12.78 acres
Garage / Parking
3 garage · 6 total
Property Taxes
$2,391 / Annually
HOA Fee
$100 / Monthly

Market Snapshot

The Old Lyme Market

Single Family · trailing 12 months

Median Days on Market

48

22 active listings

Median $ / Sq Ft

$517

22 active listings

Sale-to-List Ratio

99.2%

90 sales

How this home compares

List Price

$2.30M

vs $799,000 median

2.9× the median

Price / Sq Ft

$490

vs $517 median

5.2% below median

Days on Market

32 days

vs 48 days median

16 days fresher than median

Based on 22 active and 90 closed sales (trailing 12 mo) of single family in Old Lyme. Source: SmartMLS · As of July 28, 2026.

Location

41-B Whippoorwill Road, Old Lyme, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$12,787

per month

  • Principal & Interest$11,722
  • Property Taxes$199
  • Insurance$766
  • HOA$100

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

Location

City/Town
Old Lyme
Neighborhood
Whippoorwill
County
New London
Subdivision
The Woods At Whippoorwill

Residence

Property Type
Single Family
Style
Ranch,Farm House
Year Built
2026
New Construction
Under Construction
Living Area
4,694 sq ft

Schools

Elementary
Per Board of Ed
High
Lyme-Old Lyme

Interior

Heating
Hydro AirZoned
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
2
Laundry
Main Level
Laundry Location
main level
Appliances
Allowance
Basement
FullUnfinishedConcrete Floor
In-Law Apartment
YesFirst FloorSeparate Entry
Interior Features
Auto Garage Door OpenerOpen Floor PlanSecurity System
Additional Rooms
Exercise RoomLaundry RoomMud Room

Exterior & Lot

Lot Size
12.78 acres
Zoning
RU-80
Garage / Parking
3 garage spaces6 total parking spacesAttached GarageDrivewayPrivateCircularCrushed Stone
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Hardie Board
Color
Gray
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
Underground UtilitiesFrench DoorsPatio
Lot Description
In SubdivisionLightly WoodedBorders Open Space

HOA / Association

Fee
$100 / Monthly

Listing & Financials

Property Taxes
$2,391 / Annually
Days on Market
32
MLS #
24183457
MLS Status
Active

Similar Properties

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

Listed By

Tammy Tinnerello

(860) 867-6120

William Pitt Sotheby's Int'l

(860) 434-2400

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

The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. 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 7/28/2026 at 6:10 AM UTC.