Step back in time with this quintessential 1940s Connecticut estate, where classic elegance meets modern luxury. Set on 3.3 acres of professionally landscaped, park-like grounds with specimen trees & gardens, this one-of-a-kind home showcases extraordinary architectural craftsmanship and intricate millwork throughout. A grand front-to-back foyer sets the tone for the timeless sophistication found in every room. Designed for effortless entertaining, the spacious, well-appointed living areas flow seamlessly to multiple terraces adorned with vibrant perennial gardens. The renovated gourmet kitchen, breakfast room, and family room serve as the heart of the home-a perfect gathering spot for friends and family. Host memorable dinners in the Thanksgiving-sized dining room, which opens to lush gardens and patios, or unwind in the expansive living room that leads to a private conservatory-solarium. The 2nd floor offers a luxurious primary suite featuring six rooms, including dual baths, custom walk-in closets, a sitting area, and office space. Additional bedrooms are generously sized &ensuite, providing comfort and privacy for everyone. Fitness enthusiasts will appreciate the state-of-the-art gym w/ a full bath and sauna, while wine connoisseurs will love the 1,500-bottle wine cellar & tasting room. Newly installed windows bathe the home in natural light, highlighting serene garden views. Outdoors, no detail was overlooked in the construction of the pool & pool/guest house. The property includes a one-bedroom pool house, featuring a full indoor kitchen, laundry, bathroom plus outdoor Viking kitchen & dining area-creating the ultimate summer oasis for gatherings & relaxation (adding an additional 750+ square feet). With mature trees, ambient night lighting, and professionally landscaped grounds, this property represents a rare opportunity to own a peaceful, gracious retreat in Fairfield County, combining timeless design with modern comfort.
Sold for $4,250,000
$4,250,000
36 Chestnut Hill Road, Wilton, CT 06897
7beds
11,451sqft
Single Family Residence
Built in 1940
3.3 Acres Lot
$4,248,700 Zestimate®
$371/sqft
$6,433 Estimated rent
Home value
$4,248,700
$3.78M - $4.76M
$6,433/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
HANNELORE KAPLAN TEAM,
Hannelore Kaplan 914-450-3880,
William Raveis Real Estate 203-966-3555,
Co-Listing Agent: Sarah Fair 203-858-6301,
William Raveis Real Estate
Bought with:
Laura Davis, RES.0827179
Brown Harris Stevens
Source: Smart MLS,MLS#: 24068237
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 7
- Bathrooms: 12
- Full bathrooms: 9
- 1/2 bathrooms: 3
Rooms
- Room types: Breezeway, Exercise Room, Laundry, Sitting Room, Solarium, Staff Quarters
Primary bedroom
- Level: Upper
- Area: 309.55 Square Feet
- Dimensions: 20.5 x 15.1
Bedroom
- Level: Other
Bedroom
- Level: Upper
- Area: 218.68 Square Feet
- Dimensions: 15.4 x 14.2
Bedroom
- Level: Upper
- Area: 248.4 Square Feet
- Dimensions: 18.4 x 13.5
Bedroom
- Level: Upper
- Area: 228.62 Square Feet
- Dimensions: 16.1 x 14.2
Bedroom
- Level: Upper
- Area: 239.89 Square Feet
- Dimensions: 16.1 x 14.9
Bedroom
- Level: Upper
- Area: 298.2 Square Feet
- Dimensions: 21.3 x 14
Dining room
- Level: Main
- Area: 378.4 Square Feet
- Dimensions: 21.5 x 17.6
Family room
- Level: Main
- Area: 350.26 Square Feet
- Dimensions: 21.1 x 16.6
Kitchen
- Level: Main
- Area: 601.65 Square Feet
- Dimensions: 19.1 x 31.5
Library
- Level: Main
- Area: 288.41 Square Feet
- Dimensions: 15.1 x 19.1
Living room
- Level: Main
- Area: 661.5 Square Feet
- Dimensions: 21 x 31.5
Media room
- Level: Upper
- Area: 411.28 Square Feet
- Dimensions: 21.2 x 19.4
Office
- Level: Upper
- Area: 250.8 Square Feet
- Dimensions: 13.2 x 19
Sun room
- Level: Main
- Area: 681.6 Square Feet
- Dimensions: 21.3 x 32
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Gas Range, Oven/Range, Microwave, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Lower Level, Upper Level, Mud Room
Features
- Entrance Foyer
- Doors: French Doors
- Basement: Full
- Attic: Walk-up
- Number of fireplaces: 4
Interior area
- Total structure area: 11,451
- Total interior livable area: 11,451 sqft
- Finished area above ground: 10,685
- Finished area below ground: 766
Property
Parking
- Total spaces: 5
- Parking features: Attached
- Attached garage spaces: 5
Features
- Patio & porch: Porch, Patio
- Exterior features: Garden, Stone Wall, Underground Sprinkler
- Has private pool: Yes
- Pool features: Heated, In Ground
Lot
- Size: 3.3 Acres
- Features: Level, Landscaped
Details
- Additional structures: Cabana, Guest House, Pool House
- Parcel number: 1923495
- Zoning: R-2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Shake
Condition
- New construction: No
- Year built: 1940
Utilities & green energy
- Sewer: Septic Tank
- Water: Public, Well
Community & HOA
Community
- Features: Basketball Court, Golf, Health Club, Library, Medical Facilities, Park, Playground, Near Public Transport
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Wilton
Financial & listing details
- Price per square foot: $371/sqft
- Tax assessed value: $2,230,900
- Annual tax amount: $53,408
- Date on market: 1/13/2025
Price history
| Date | Event | Price |
|---|---|---|
| 3/28/2025 | Sold | $4,250,000+6.3%$371/sqft |
Source:  Smart MLS #24068237 Report a problem | ||
| 3/10/2025 | Pending sale | $3,999,999$349/sqft |
Source: Smart MLS #24068237 Report a problem | ||
| 3/10/2025 | Listed for sale | $3,999,999$349/sqft |
Source:  William Raveis Real Estate, Mortgage & Insurance #24068237 Report a problem | ||
| 1/30/2025 | Pending sale | $3,999,999$349/sqft |
Source: William Raveis Real Estate, Mortgage & Insurance #24068237 Report a problem | ||
| 1/13/2025 | Listed for sale | $3,999,999-20%$349/sqft |
Source: Smart MLS #24068237 Report a problem | ||
| 12/6/2024 | Listing removed | $4,999,000$437/sqft |
Source: William Raveis Real Estate, Mortgage & Insurance #24045609 Report a problem | ||
| 10/8/2024 | Price change | $4,999,000-20%$437/sqft |
Source: Smart MLS #24045609 Report a problem | ||
| 9/22/2024 | Listed for sale | $6,250,000+204.1%$546/sqft |
Source: Smart MLS #24045609 Report a problem | ||
| 5/21/1997 | Sold | $2,055,000+448%$179/sqft |
Source: Smart MLS #96037699 Report a problem | ||
| 7/20/1988 | Sold | $375,000$33/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $54,456 +2% | $2,230,900 |
| 2024 | $53,408 -4.2% | $2,230,900 +17% |
| 2023 | $55,770 +3.6% | $1,906,030 |
| 2022 | $53,807 +1.3% | $1,906,030 |
| 2021 | $53,121 +1.5% | $1,906,030 |
| 2020 | $52,340 -3.8% | $1,906,030 |
| 2019 | $54,398 -8.7% | $1,906,030 -9.8% |
| 2018 | $59,602 +1.5% | $2,114,280 |
| 2017 | $58,714 +1.6% | $2,114,280 |
| 2016 | $57,804 +1.9% | $2,114,280 |
| 2015 | $56,726 +1.2% | $2,114,280 |
| 2014 | $56,050 +2% | $2,114,280 |
| 2013 | $54,950 +2.3% | $2,114,280 -17.1% |
| 2012 | $53,711 +1% | $2,551,570 |
| 2011 | $53,200 +3.4% | $2,551,570 |
| 2010 | $51,440 +3% | $2,551,570 |
| 2009 | $49,960 +7.8% | $2,551,570 +6.3% |
| 2008 | $46,365 -17.5% | $2,401,070 +3.5% |
| 2007 | $56,229 +3.3% | $2,320,640 -0.3% |
| 2006 | $54,434 +3.7% | $2,327,220 |
| 2005 | $52,479 +5% | $2,327,220 |
| 2004 | $49,989 +6.9% | $2,327,220 |
| 2003 | $46,777 +18.7% | $2,327,220 +66% |
| 2001 | $39,399 +16.6% | $1,401,600 +7.4% |
| 2000 | $33,798 +13.1% | $1,304,450 +5.1% |
| 1999 | $29,877 | $1,240,750 |
Find assessor info on the county website
Neighborhood: 06897
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Nearby schools
GreatSchools rating
- NAMiller-Driscoll SchoolGrades: PK-2Distance: 2.2 mi
- 10/10Middlebrook SchoolGrades: 6-8Distance: 3.1 mi
- 10/10Wilton High SchoolGrades: 9-12Distance: 3.4 mi
Schools provided by the listing agent
- Elementary: Miller-Driscoll
- Middle: Middlebrook
- High: Wilton
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Wilton
- 06897
- 36 Chestnut Hill Road
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