Step into a rare offering that 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 half an acre, this gracious home offers more than 6,100 sqft of character, elegance, and modern comfort. A stunning formal living room with a soaring 12-foot ceiling is among the home's most impressive features, highlighted by a beautiful bow window and opening to the veranda and sun-filled garden room with heated slate floors. This extraordinary space creates an unforgettable first impression and is even more impressive in person than photos can capture. Rich hardwood flooring, natural wood beams, intricate moldings, and three fireplaces showcase timeless craftsmanship rarely found today. Designed for both comfortable living and elegant entertaining, the home also features a formal dining room and an inviting family room. The gourmet kitchen is thoughtfully appointed with a large center island, six-burner gas range, Sub-Zero refrigeration, warming drawer, wet bar, and a convenient back staircase to the second level. Two potential primary suites provide exceptional flexibility, each offering spa-like baths and peaceful retreats. Updates include central air, a newer boiler, natural gas conversion, and integrated sound throughout the main living areas, primary suite, and veranda. Multiple outdoor spaces, along with FRONT AND REAR DRIVEWAYS, complete this exceptional offering. Close to train and Holmes school.
For sale
$3,495,000
5 Middlesex Road, Darien, CT 06820
5beds
6,195sqft
Est.:
Single Family Residence
Built in 1880
0.69 Acres Lot
$3,550,100 Zestimate®
$564/sqft
$-- HOA
What's special
- 5 days |
- 4,127 |
- 105 |
Zillow last checked: 7 hours ago
Listing updated: 8 hours ago
Listed by:
Team AFA at William Raveis Real Estate,
Allison Santopietro (203)216-2462,
William Raveis Real Estate 203-255-6841
Source: Smart MLS,MLS#: 24157558
Tour with a local agent
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 5
- Full bathrooms: 4
- 1/2 bathrooms: 1
Primary bedroom
- Features: Balcony/Deck, Beamed Ceilings, Gas Log Fireplace, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Beamed Ceilings, Full Bath, Wide Board Floor
- Level: Upper
Bedroom
- Features: Bay/Bow Window, Wide Board Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Den
- Features: Hardwood Floor
- Level: Third,Upper
Dining room
- Features: Bay/Bow Window, Hardwood Floor
- Level: Main
Family room
- Features: Built-in Features, Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Balcony/Deck, Breakfast Bar, Wet Bar, Eating Space, Kitchen Island, Hardwood Floor
- Level: Main
Library
- Features: Bookcases, Hardwood Floor
- Level: Main
Living room
- Features: Bay/Bow Window, High Ceilings, Fireplace, Patio/Terrace, Hardwood Floor
- Level: Main
Other
- Features: Hardwood Floor
- Level: Third,Upper
Other
- Features: Full Bath, Hardwood Floor
- Level: Third,Upper
Sun room
- Features: Wet Bar, Slate Floor
- Level: Main
Heating
- Forced Air, Zoned, Natural Gas
Cooling
- Central Air, Zoned
Appliances
- Included: Gas Range, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Upper Level
Features
- Sound System
- Basement: Partial,Unfinished
- Attic: Access Via Hatch
- Number of fireplaces: 3
Interior area
- Total structure area: 6,195
- Total interior livable area: 6,195 sqft
- Finished area above ground: 6,195
Property
Parking
- Total spaces: 6
- Parking features: Attached, Paved, Driveway, Garage Door Opener, Private
- Attached garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Terrace, Deck, Patio
- Exterior features: Rain Gutters, Garden, Lighting, Stone Wall, Underground Sprinkler
- Fencing: Partial
Lot
- Size: 0.69 Acres
- Features: Wooded, Level, Landscaped
Details
- Parcel number: 105522
- Zoning: R13
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Stone
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1880
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & HOA
Community
- Security: Security System
HOA
- Has HOA: No
Location
- Region: Darien
Financial & listing details
- Price per square foot: $564/sqft
- Tax assessed value: $1,487,640
- Annual tax amount: $23,029
- Date on market: 3/30/2026
Estimated market value
$3,550,100
$3.27M - $3.94M
$7,698/mo
Price history
Price history
| Date | Event | Price |
|---|---|---|
| 4/2/2026 | Listed for sale | $3,495,000+33.7%$564/sqft |
Source:  Smart MLS #24157558 Report a problem | ||
| 5/2/2022 | Sold | $2,615,000+5%$422/sqft |
Source: Smart MLS #170468463 Report a problem | ||
| 3/5/2022 | Contingent | $2,490,000$402/sqft |
Source: Smart MLS #170468463 Report a problem | ||
| 2/24/2022 | Listed for sale | $2,490,000+63.3%$402/sqft |
Source: Smart MLS #170468463 Report a problem | ||
| 11/16/2009 | Sold | $1,525,000+1.6%$246/sqft |
Source: Public Record Report a problem | ||
| 5/27/2004 | Sold | $1,501,000+93.7%$242/sqft |
Source: Smart MLS #98192386 Report a problem | ||
| 12/16/1998 | Sold | $775,000+66.7%$125/sqft |
Source: Public Record Report a problem | ||
| 2/21/1996 | Sold | $465,000$75/sqft |
Source: Public Record Report a problem | ||
Public tax history
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $23,029 +5.4% | $1,487,640 |
| 2024 | $21,853 +5.1% | $1,487,640 +26% |
| 2023 | $20,798 +2.2% | $1,181,040 |
| 2022 | $20,349 +2.3% | $1,181,040 |
| 2021 | $19,889 +3.1% | $1,181,040 |
| 2020 | $19,286 -0.9% | $1,181,040 |
| 2019 | $19,452 +0.4% | $1,181,040 -1.9% |
| 2018 | $19,366 -0.5% | $1,204,350 |
| 2017 | $19,462 +2.5% | $1,204,350 |
| 2016 | $18,993 +2.7% | $1,204,350 |
| 2015 | $18,487 +2.3% | $1,204,350 |
| 2014 | $18,077 +20.7% | $1,204,350 +5.9% |
| 2013 | $14,983 +3.9% | $1,137,640 |
| 2012 | $14,425 +3.9% | $1,137,640 |
| 2011 | $13,879 +3.9% | $1,137,640 |
| 2010 | $13,356 +3.3% | $1,137,640 |
| 2009 | $12,935 +1.2% | $1,137,640 +29.5% |
| 2008 | $12,784 +5.5% | $878,640 +0.6% |
| 2007 | $12,118 +3.5% | $873,670 |
| 2006 | $11,707 -28% | $873,670 -30% |
| 2005 | $16,250 +55.7% | $1,248,100 +42.9% |
| 2004 | $10,440 +26.1% | $873,670 +37.8% |
| 2003 | $8,282 -6.8% | $634,130 |
| 2001 | $8,891 +7.4% | $634,130 -30% |
| 2000 | $8,282 +5.5% | $905,900 +104.5% |
| 1999 | $7,848 | $442,880 |
Find assessor info on the county website
BuyAbility℠ payment
Est. payment
$22,672/mo
Principal & interest
$17750
Property taxes
$4922
More affordability tools
Climate risks
Neighborhood: 06820
Nearby schools
GreatSchools rating
- 8/10Holmes Elementary SchoolGrades: PK-5Distance: 0.2 mi
- 9/10Middlesex Middle SchoolGrades: 6-8Distance: 0.9 mi
- 10/10Darien High SchoolGrades: 9-12Distance: 1.4 mi
Schools provided by the listing agent
- Elementary: Holmes
- Middle: Middlesex
- High: Darien
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
Local experts in 06820
- Connecticut
- Fairfield County
- Darien
- 06820
- 5 Middlesex Road
Nearby cities
Nearby neighborhoods
Nearby zip codes
Other Darien Topics
