Set in one of Darien's most desirable neighborhoods, this impeccably renovated home blends timeless charm with modern luxury- all within walking distance to schools, the train station, and the shops and restaurants of Noroton Commons. The location simply can't be beat. Sitting on nearly one flat acre, the stunning and ultra-private backyard feels like your own secluded retreat. Mature landscaping offers complete privacy, while two elegant bluestone patios and a gunite pool make this outdoor space perfect for entertaining or relaxing in style. Inside, every room has been thoughtfully updated, preserving the classic architecture while enhancing functionality and design. The spacious, sunlit kitchen features a walk-in pantry and high-end finishes, seamlessly connecting to the rest of the home. The first floor is made for entertaining, with a formal living room with a wood-burning fireplace, a vaulted-ceiling family room with direct backyard access, a striking dining room (with its own fireplace), and a cozy library - each space as inviting as the next. Upstairs, the primary suite is a true sanctuary, complete with a newly renovated bathroom and walk-in closet. Four additional bedrooms and two full baths complete the second floor, offering the perfect layout for family and guests. This is a rare opportunity to own a turnkey, magazine-worthy home in a truly unbeatable location. Classic charm, thoughtful updates, and exceptional indoor/outdoor living- this one has it all.
Single-familyProperty Type
1940Year Built
0.77 acresLot Size
$917Est. Price/Sq.Ft.
2 car garageParking
Listed by Amanda Spatola• Houlihan Lawrence
Listed by Christopher Gugelmann• Compass Connecticut, LLC
Bought with Susheila Starr• Sotheby's International Realty
Source:Smart MLS #24095468
Redfin Estimate
$4,522,618
$500K since sold in August 2025$4,000 since August
Recently sold homes
Estimate history
Homes for sale
This home's estimate is 50.8% higher than the average sale price ($3.00M) of 6 comparable homes.
This absolutely wonderful 6BR, 4BTH home on a tree lined street offers the best of everything! Centrally located & close to schools, train, shops & restaurants it offers the unique combination of privacy & convenience. The oversized living, family & dining rooms are perfect for entertaining. Beamed ceilings & 4 wood burning fpls add charm & warmth. The spacious remodeled KIT boasts granite counter tops, a large eat-in area & office nook. The attached 2-car garage enters into the mudroom w/built in storage. Upstairs bedrooms are all generously sized & there are two options for use as the master. Outside is equally impressive with 2 flagstone patios & a large level backyard. Freshly painted inside & out, this home is ready to move right in!
Smart MLS #99040491
Jan 17, 2014
Listing Removed
—
Sep 9, 2013
Listed
$1,895,000
$384/sq ft
Public Records
Jun 19, 1992
Sold
$646,500
$131/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$22,053 (+2.2%)
$609,350 + $642,950
$1,252,300
2022
$21,577 (+2.3%)
$609,350 + $642,950
$1,252,300
2021
$21,089 (+3.1%)
$609,350 + $642,950
$1,252,300
2020
$20,450 (−0.8%)
$609,350 + $642,950
$1,252,300
2019
$20,625 (+2.1%)
$609,350 + $642,950
$1,252,300
2018
$20,194 (−0.5%)
$612,920 + $642,950
$1,255,870
2017
$20,295 (+2.5%)
$612,920 + $642,950
$1,255,870
2016
$19,805 (+17.9%)
$612,920 + $642,950
$1,255,870
2014
$16,792
$612,920 + $505,820
$1,118,740
Tax history for 39 Deepwood Rd
Year
Property tax
Land + Additions
Assessment*
2023
$22,053 (+2.2%)
$609,350 + $642,950
$1,252,300
2022
$21,577 (+2.3%)
$609,350 + $642,950
$1,252,300
2021
$21,089 (+3.1%)
$609,350 + $642,950
$1,252,300
2020
$20,450 (−0.8%)
$609,350 + $642,950
$1,252,300
2019
$20,625 (+2.1%)
$609,350 + $642,950
$1,252,300
2018
$20,194 (−0.5%)
$612,920 + $642,950
$1,255,870
2017
$20,295 (+2.5%)
$612,920 + $642,950
$1,255,870
2016
$19,805 (+17.9%)
$612,920 + $642,950
$1,255,870
2014
$16,792
$612,920 + $505,820
$1,118,740
*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.