Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$3,495,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 5 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 6,195 Sq. Ft.
  • 2 Car Garage
  • Updated 1 hour ago

Next open house:

Open House: 12:00 PM - 3:00 PM

Saturday 4/4 12:00 PM - 3:00 PM

5 Middlesex Road,Darien, CT 06820

5 Middlesex RoadDarienCT06820

Get directions
See This Home
Save This Home
See This Home
Save This Home
Step into a rare offering that beautifully captures the essence of classic New England living-a stately 1880s residence set in one of the Gold Coast's most desirable towns. South-facing and beautifully sited on over 1/2 acre, this gracious home offers more than 6,100 sqft of character, elegance, and modern comfort. From the grand living room with its soaring ceiling to the warmth of 3 fireplaces and hardwood flooring throughout, the home is rich with architectural detail. Bow windows, natural wood beams, and intricate moldings create a timeless sense of craftsmanship that is rarely found today. Every room tells a story while offering spaces designed for both everyday living and memorable entertaining. Host elegant gatherings in the formal dining room, relax in the sun-filled garden room with heated slate floors, or unwind in the inviting family room. The home's warmth and charm are felt throughout, yet thoughtful updates ensure modern comfort, including newer central air, boiler, natural gas conversion, and integrated sound throughout the main living areas, primary suite, and veranda. The gourmet kitchen is thoughtfully designed, featuring a large center island, 6 burner gas range, Sub-Zero refrigeration, warming drawer & a wet bar. A back staircase provides convenient access to the upper level. Outdoor living is equally inviting, with multiple spaces for quiet or lively gatherings. Front and back driveways. This home is a true blend of heritage, elegance and modern luxury.

Full Property Details for 5 Middlesex Rd

General

  • Price: $3,495,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24157558
  • Updated: 4/2/2026
  • Added to Site: 3 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: Audio System, Auto Garage Door Opener, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Gas Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 5
  • Primary Bedroom: Primary Bedroom - Balcony/Deck, Beams, Gas Log Fireplace, Full Bath, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 1: Bedroom - Beams, Full Bath, Wide Board Floor, Upper
  • Bedroom 2: Bedroom - Bay/Bow Window, Wide Board Floor, Upper
  • Bedroom 3: Bedroom - Hardwood Floor, Upper
  • Bedroom 4: Bedroom - Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Bay/Bow Window, 9 ft+ Ceilings, Fireplace, Patio/Terrace, Hardwood Floor, Main
  • Family Room: Family Room - Built-Ins, Fireplace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Balcony/Deck, Breakfast Bar, Wet Bar, Eating Space, Island, Har, Main
  • Dining Room: Dining Room - Bay/Bow Window, Hardwood Floor, Main
  • Den: Den - Hardwood Floor, On 3rd Floor, Upper
  • Library: Library - Book Shelves, Hardwood Floor, Main
  • Laundry: Upper Level
  • Other Room 1: Other - Full Bath, Hardwood Floor, On 3rd Floor, Upper
  • Other Room 2: Other - Hardwood Floor, On 3rd Floor, Upper

Exterior

  • Exterior Features: Terrace, Deck, Gutters, Garden Area, Lighting, Stone Wall, Underground Sprinkler, Patio
  • Color: White

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking: Attached Garage, Paved, Driveway

Location

  • County: Fairfield
  • Driving Directions: Middlesex to #5. Please use front driveway. Enter thru stone pillars

School Information

  • Elementary School: Holmes
  • Middle School: Middlesex
  • High School: Darien

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Zoned, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Other

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Partial, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 6,195
  • Above Ground: 6,195 Sq. Ft.
  • Year Built: 1880

Lot Features

  • Lot Size (Acres): 0.69
  • Driveway/Sidewalk: Private, Paved, Crushed Stone
  • Zoning: R13
  • Lot Description: Fence - Partial, Treed, Level Lot, Professionally Landscaped

Financial Considerations

  • Assessment Amount: $1,487,640
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 105522

Listed by William Raveis Real Estate, Team AFA at William Raveis Real Estate, Allison Santopietro

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Listing agent

— 5 Middlesex Rd —

  • Allison Santopietro

    William Raveis Real Estate

Agent Contact: (203) 216-2462 Office Contact: (203) 255-6841

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 5 Middlesex Rd

School District:Darien School District
NameGradesDistance
Holmes Elementary School, Darien, CT
18 Hoyt Street, Darien, CT 06820
K-50.2 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-80.9 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-121.4 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 5 Middlesex Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/02/2026
Listed
$3,495,000
33.65%
MLS
5/02/2022
Sold
$2,615,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 5 Middlesex Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$23,029
5%
$1,487,640
—
2023
$21,853
5%
$1,487,640
26%
2023
$20,798
2%
$1,181,040
—
2022
$20,349
2%
$1,181,040
—
2021
$19,889
3%
$1,181,040
—
2020
$19,286
-1%
$1,181,040
—
2019
$19,452
—
$1,181,040
-2%
2018
$19,366
—
$1,204,350
—
2017
$19,462
2%
$1,204,350
—
2016
$18,993
3%
$1,204,350
—
2015
$18,487
2%
$1,204,350
—
2014
$18,077
21%
$1,204,350
6%
2012
$14,983
—
$1,137,640
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 5 Middlesex Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Listed by William Raveis Real Estate, Team AFA at William Raveis Real Estate, Allison Santopietro

Similar Properties near 5 Middlesex Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

128 5 Mile River Rd, Darien, CT 06820 - Photo 1
$3,300,000

128 5 Mile River Rd  Darien, CT 06820

  • Single Family
  • Active
  • Updated 9 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 2,478
    Sq. Ft.
Listed by Houlihan Lawrence
399 Stanwich Rd, Greenwich, CT 06830 - Photo 1
$3,499,000
Open House

399 Stanwich Rd  Greenwich, CT 06830

  • Single Family
  • Active
  • Updated 6 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 5,389
    Sq. Ft.
Listed by Sotheby's International Realty
41 Londonderry Dr, Greenwich, CT 06830 - Photo 1
$3,495,000

41 Londonderry Dr  Greenwich, CT 06830

  • Single Family
  • Active
  • Updated 6 days ago
  • 5
    Beds
  • 5
    Total Baths
  • 6,330
    Sq. Ft.
Listed by Sotheby's International Realty
21A South Brook Dr, Stamford, CT 06903 - Photo 1
$3,389,000

21A South Brook Dr  Stamford, CT 06903

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 6,103
    Sq. Ft.
Listed by Elaine Voss (914) 774-5459 and Compass Connecticut, LLC

Just Listed near 5 Middlesex Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

107 Strawberry Hill Ave, Norwalk, CT 06851 - Photo 1 Just Listed
$699,000

107 Strawberry Hill Ave  Norwalk, CT 06851

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,691
    Sq. Ft.
Listed by Fowler Sakey Team at Coldwell Banker Realty (475) 888-9713
970 Hope St, Stamford, CT 06907 - Photo 1 Just Listed
$345,000

970 Hope St  #5E  Stamford, CT 06907

  • Condo
  • Active
  • Updated 5 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 860
    Sq. Ft.
Listed by Xanthi Ananiadis (203) 524-1825
50 Glenbrook Rd, Stamford, CT 06902 - Photo 1 Just Listed
$375,000

50 Glenbrook Rd  #5G  Stamford, CT 06902

  • Condo
  • Active
  • Updated 4 days ago
  • 1
    Bed
  • 2
    Total Baths
  • 1,071
    Sq. Ft.
Listed by Jim Cullinan (203) 554-6432
3 Shorehaven Rd, Norwalk, CT 06855 - Photo 1 Just Listed
$3,795,000
Open House

3 Shorehaven Rd  Norwalk, CT 06855

  • Single Family
  • Active
  • Updated 14 hours ago
  • 5
    Beds
  • 6
    Total Baths
  • 5,481
    Sq. Ft.
Listed by Darlene Letersky (203) 227-8787

Price Reduced near 5 Middlesex Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

206 Sunrise Hill Rd, Norwalk, CT 06851 - Photo 1 Price Reduced
-$5,000 (-1.02%)
$485,000

206 Sunrise Hill Rd  #206  Norwalk, CT 06851

  • Townhouse
  • Active
  • Updated 6 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,202
    Sq. Ft.
Listed by Gigi Fryer (203) 508-2550
154 Cold Spring Rd, Stamford, CT 06905 - Photo 1 Price Reduced
-$4,005 (-1%)
$394,995

154 Cold Spring Rd  #APT 18  Stamford, CT 06905

  • Condo
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,160
    Sq. Ft.
Listed by Diana Gould (203) 249-6656
22 Ensign Rd, Norwalk, CT 06853 - Photo 1 Price Reduced
-$50,000 (-0.87%)
$5,700,000

22 Ensign Rd  Norwalk, CT 06853

  • Single Family
  • Active
  • Updated 5 days ago
  • 5
    Beds
  • 4
    Total Baths
  • 4,147
    Sq. Ft.
Listed by Compass Connecticut, LLC
71a Osborne Ave, Norwalk, CT 06855 - Photo 1 Price Reduced
-$39,000 (-8.69%)
$410,000

71a Osborne Ave  #APT A4  Norwalk, CT 06855

  • Condo
  • Active
  • Updated 7 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,227
    Sq. Ft.
Listed by Derek Greene

Recent Sales near 5 Middlesex Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

19 Georgian Ln, Darien, CT 06820 - Photo 1 Sold
$3,250,000

19 Georgian Ln  Darien, CT 06820

  • Single Family
  • Closed
  • 6
    Beds
  • 6
    Total Baths
  • 6,407
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by William Raveis Real Estate
311 Noroton Ave, Darien, CT 06820 - Photo 1 Sold
$3,550,000

311 Noroton Ave  Darien, CT 06820

  • Single Family
  • Closed
  • 5
    Beds
  • 6
    Total Baths
  • 5,356
    Sq. Ft.
Listed by Compass Connecticut, LLC
Sold by Compass Connecticut, LLC
20 Seagate Rd, Darien, CT 06820 - Photo 1 Sold
$3,350,000

20 Seagate Rd  Darien, CT 06820

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,851
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by Houlihan Lawrence
35 Outlook Dr, Darien, CT 06820 - Photo 1 Sold
$3,510,000

35 Outlook Dr  Darien, CT 06820

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,294
    Sq. Ft.
Listed by Compass Connecticut, LLC
Sold by Compass Connecticut, LLC

5 Middlesex Road, Darien, CT 06820 (MLS# 24157558) is a Single Family property with 5 bedrooms, 4 full bathrooms and 1 partial bathroom. 5 Middlesex Road is currently listed for $3,495,000 and was received on March 30, 2026. Want to learn more about 5 Middlesex 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.

Tour this property