Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,999,000

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,411 Sq. Ft.
  • Updated 7 days ago
See This Home
Save This Home
See This Home
Save This Home
In the heart of Darien, where history lingers and owls whisper through the trees, stands a timeless 1800s home at 561 Middlesex Road - a place where memory breathes and dreams take root. Set upon 2.6 serene and level acres, yet close to all amenities, this enchanting farmhouse rests within a world of quiet beauty, where a secret garden path winds softly beneath the shade, inviting you to wander, reflect and simply be. Rich with the echo of generations, this home opens its doors to warmth and welcome with its wide plank floors, worn smooth by countless footsteps, that guide you through rooms that glow with quiet charm - from the parlor's embrace to the dining room's gentle light. At its heart lies a light-filled, open-plan kitchen, where aromas mingle with laughter and recipes become the language of love and memory, all while uniting you with the outdoors. A great room, crowned with exposed beams and centered by a wood-burning hearth, promises long evenings of conversation, storytelling and shared delight. A cozy den invites quiet moments with a favorite book, while a cheerful playroom offers a world of imagination for the young at heart. With four inviting bedrooms and 3.5 baths, this home offers space for family and friends alike. Here, every corner whispers of possibility - a sanctuary waiting for its next chapter, for new hands to shape its story, for new hearts to call it home. Within its walls, time softens, and life unfolds like poetry written in sunlight and laughter

Full Property Details for 561 Middlesex Rd

General

  • Price: $2,999,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24130400
  • Updated: 1/8/2026
  • Added to Site: 71 day(s) ago

Interior

  • Number of Rooms: 11
  • Fireplace: Yes
  • Number of Fireplaces: 4
  • Appliances: Oven/Range, Refrigerator, Washer, Dryer

Rooms

Bathrooms

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

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Full Bath, Walk-In Closet, 20 x 15, Upper
  • Bedroom 1: Bedroom, 11 x 12, Upper
  • Bedroom 2: Bedroom, 11 x 19, Upper
  • Bedroom 3: Bedroom, 9 x 13, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, 10 x 13, Main
  • Great Room: Great Room - Fireplace, 20 x 19, Main
  • Family Room: Family Room - Fireplace, 16 x 19, Main
  • Eat In Kitchen: Eat-In Kitchen - Laundry Hookup, Pantry, 24 x 12, Main
  • Dining Room: Dining Room, 11 x 13, Main
  • Den: Den, 10 x 14, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Fireplace, 18 x 19, Main
  • Rec Room: Fireplace, 18 x 19, Main
  • Laundry: Upper Level

Exterior

  • Exterior Features: Shed, Porch, Barn, Garden Area
  • Color: White

Parking

  • Total Spaces: 6
  • Parking: Paved

Location

  • County: Fairfield
  • Driving Directions: Mansfield or Ox Ridge Lane to Middlesex Road.

School Information

  • Elementary School: Ox Ridge
  • Middle School: Middlesex
  • High School: Darien

Heating & Cooling

  • Cooling Type: None
  • Heating Type: Hot Water, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Tank Size Unknown

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Antique, Farm House
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Partial, Partial With Hatchway
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,411
  • Above Ground: 3,411 Sq. Ft.
  • Year Built: 1856

Lot Features

  • Lot Size (Acres): 2.64
  • Zoning: R2
  • Lot Description: Level Lot

Water Features

  • Water Front Desc.: Beach Rights

Financial Considerations

  • Assessment Amount: $1,095,500
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 102682

Listed by Brown Harris Stevens, Serena Richards

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

— 561 Middlesex Rd —

  • Serena Richards

    Brown Harris Stevens

Agent Contact: (203) 273-2073 Office Contact: (203) 655-1418

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 561 Middlesex Rd

School District:Darien School District
NameGradesDistance
Ox Ridge Elementary School
395 Mansfield Avenue, Darien, CT 06820
K-50.2 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-81.9 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-121.1 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 561 Middlesex Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
11/05/2025
Listed
$2,999,000
566.59%
MLS
4/06/1992
Sold
$449,900
—
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 561 Middlesex Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$16,958
5%
$1,095,500
—
2023
$16,093
-12%
$1,095,500
6%
2023
$18,198
2%
$1,033,410
—
2022
$17,806
2%
$1,033,410
—
2021
$17,403
3%
$1,033,410
—
2020
$16,846
-1%
$1,031,590
—
2019
$16,990
-23%
$1,031,590
-25%
2018
$22,078
—
$1,372,980
—
2017
$22,187
2%
$1,372,980
—
2016
$21,652
3%
$1,372,980
—
2015
$21,075
2%
$1,372,980
—
2014
$20,608
-8%
$1,372,980
-19%
2012
$22,440
—
$1,703,870
—
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 561 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 Brown Harris Stevens, Serena Richards

Similar Properties near 561 Middlesex Rd

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

39 Running Brook Ln, New Canaan, CT 06840 - Photo 1
$3,195,000
Open House

39 Running Brook Ln  New Canaan, CT 06840

  • Single Family
  • Active
  • Updated 2 days ago
  • 5
    Beds
  • 6
    Total Baths
  • 9,170
    Sq. Ft.
Listed by Houlihan Lawrence
120 West Ln, Stamford, CT 06905 - Photo 1 Just Listed
$2,895,000

120 West Ln  Stamford, CT 06905

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 5
    Total Baths
  • 5,000
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
48 Brookwood Ln, New Canaan, CT 06840 - Photo 1
$2,950,000

48 Brookwood Ln  New Canaan, CT 06840

  • Single Family
  • Active
  • 3
    Beds
  • 2
    Total Baths
  • 1,483
    Sq. Ft.
Listed by Houlihan Lawrence
64 Ocean Dr E, Stamford, CT 06902 - Photo 1
$2,950,000

64 Ocean Dr E  Stamford, CT 06902

  • Single Family
  • Active
  • Updated 10 days ago
  • 4
    Beds
  • 4
    Total Baths
  • 3,132
    Sq. Ft.
Listed by Compass Connecticut, LLC

Just Listed near 561 Middlesex Rd

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

850 E Main St, Stamford, CT 06902 - Photo 1 Just Listed
$560,000
Open House

850 E Main St  #APT 518  Stamford, CT 06902

  • Condo
  • Active
  • Updated 2 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,335
    Sq. Ft.
Listed by THE REID TEAM AT COLDWELL BANKER REALTY (203) 400-0841
206 Sunrise Hill Rd, Norwalk, CT 06851 - Photo 1 Just Listed
$490,000

206 Sunrise Hill Rd  #206  Norwalk, CT 06851

  • Townhouse
  • Active
  • Updated 3 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,202
    Sq. Ft.
Listed by Gigi Fryer (203) 508-2550
Calf Pasture Island, Norwalk, CT 06854 - Photo 1 Just Listed
$3,500,000

Calf Pasture Island  Norwalk, CT 06854

  • Single Family
  • Active
  • Updated 2 days ago
  • 3
    Beds
  • 4
    Total Baths
  • 1,299
    Sq. Ft.
Listed by Brown Harris Stevens
281 Greenwich Ave, Stamford, CT 06902 - Photo 1 Just Listed
$2,499,000

281 Greenwich Ave  Stamford, CT 06902

  • Multi-Family
  • Active
  • Updated 3 days ago
  • 15
    Total Beds
Listed by BHGRE Shore & Country

Price Reduced near 561 Middlesex Rd

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

33 N Water St, Norwalk, CT 06854 - Photo 1 Price Reduced
-$35,000 (-4.79%)
$695,000

33 N Water St  #505  Norwalk, CT 06854

  • Condo
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,395
    Sq. Ft.
Listed by Compass Connecticut, LLC
104 Strawberry Hill Ave, Stamford, CT 06902 - Photo 1 Price Reduced
-$10,000 (-4.17%)
$230,000

104 Strawberry Hill Ave  #2  Stamford, CT 06902

  • Co-op
  • Active
  • Updated 1 day ago
  • 2
    Beds
  • 1
    Total Bath
  • 900
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
48 Fair St, Norwalk, CT 06851 - Photo 1 Price Reduced
-$12,000 (-2.02%)
$581,000

48 Fair St  Norwalk, CT 06851

  • Single Family
  • Active
  • Updated 5 days ago
  • 3
    Beds
  • 2
    Total Baths
  • 1,643
    Sq. Ft.
Listed by Acorn Action LLC
5 Tower Dr, Norwalk, CT 06850 - Photo 1 Price Reduced
-$10,100 (-1.55%)
$639,900

5 Tower Dr  Norwalk, CT 06850

  • Single Family
  • Active
  • Updated 3 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 1,260
    Sq. Ft.
Listed by Rodney J. Baptiste Broker

Recent Sales near 561 Middlesex Rd

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

23 Maplewood Dr, Darien, CT 06820 - Photo 1 Sold
$2,710,000

23 Maplewood Dr  Darien, CT 06820

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 3,506
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by Brown Harris Stevens
37 Salisbury Rd, Darien, CT 06820 - Photo 1 Sold
$2,795,000

37 Salisbury Rd  Darien, CT 06820

  • Single Family
  • Closed
  • 4
    Beds
  • 4
    Total Baths
  • 3,261
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by William Raveis Real Estate
202 Mansfield Ave, Darien, CT 06820 - Photo 1 Sold
$2,795,000

202 Mansfield Ave  Darien, CT 06820

  • Single Family
  • Closed
  • 6
    Beds
  • 7
    Total Baths
  • 6,058
    Sq. Ft.
Listed by Compass Connecticut, LLC
Sold by Foreign Listing
4 Rabbit Ln, Darien, CT 06820 - Photo 1 Sold
$2,675,000

4 Rabbit Ln  Darien, CT 06820

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 3,690
    Sq. Ft.
Listed and Sold by Brown Harris Stevens

561 Middlesex Road, Darien, CT 06820 (MLS# 24130400) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 561 Middlesex Road is currently listed for $2,999,000 and was received on November 05, 2025. Want to learn more about 561 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