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$4,022,500

  • Sold
  • Closed
  • Single Family
  • 5 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 4,932 Sq. Ft.
  • 2 Car Garage
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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.

Full Property Details for 39 Deepwood Rd

General

  • Sold For: $4,022,500
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24095468
  • Added to Site: 283 day(s) ago

Interior

  • Number of Rooms: 11
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Oven/Range, Refrigerator, Freezer, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Fireplace, Full Bath, Walk-In Closet, Hardwood Floor, 17 x 13, Upper
  • Bedroom 1: Bedroom, 14 x 13, Upper
  • Bedroom 2: Bedroom, 15 x 12, Upper
  • Bedroom 3: Bedroom, 16 x 12, Upper
  • Bedroom 4: Bedroom, 19 x 19, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 25 x 17, Main
  • Family Room: Family Room - Beams, Fireplace, 26 x 17, Main
  • Kitchen: Kitchen - Remodeled, Island, Pantry, Hardwood Floor, Main
  • Dining Room: Dining Room - Fireplace, French Doors, Hardwood Floor, 17 x 15, Main
  • Study: 12 x 11, Main

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, In Ground Pool

Exterior

  • Color: white

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Driving Directions: hollow tree to deepwood

School Information

  • Elementary School: Holmes
  • High School: Darien

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Domestic

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Crawl Space, Interior Access
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 4,932
  • Above Ground: 4,932 Sq. Ft.
  • Year Built: 1940

Lot Features

  • Lot Size (Acres): 0.77
  • Zoning: R-1
  • Lot Description: Dry, Level Lot, Professionally Landscaped

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $1,664,040
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 105576

Listed by Houlihan Lawrence, Amanda Spatola and Compass Connecticut, LLC, Christopher Gugelmann
Sold by Sotheby's International Realty, Susheila Starr

Listing agents

— 39 Deepwood Rd —

  • Amanda Spatola

    Houlihan Lawrence

  • Christopher Gugelmann

    Compass Connecticut, LLC

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 39 Deepwood Rd

School District:Darien School District
NameGradesDistance
Holmes Elementary School, Darien, CT
18 Hoyt Street, Darien, CT 06820
K-50.7 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-80.4 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-120.6 mi
Disclaimer: School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 39 Deepwood Rd

Date
Details
Price
Change
Source
8/01/2025
Sold
$4,022,500
-4.11%
MLS
5/16/2025
Listed
$4,195,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Listed by Houlihan Lawrence, Amanda Spatola and Compass Connecticut, LLC, Christopher Gugelmann
Sold by Sotheby's International Realty, Susheila Starr

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39 Deepwood Road, Darien, CT 06820 (MLS# 24095468) is a Single Family property that was sold at $4,022,500 on August 01, 2025. Want to learn more about 39 Deepwood Road? Do you have questions about finding other Single Family real estate for sale in Darien? You can browse all Darien real estate or contact a Coldwell Banker agent to request more information.