41-B Whippoorwill Road
Old Lyme, Connecticut 06371
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,694
- Acres
- 12.78
- Year Built
- 2026
- Neighborhood
- Whippoorwill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
22
21 under contract
Median List Price
$799,000
22 active listings
Median Closed Price
$673,000
90 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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 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.