315 Middlesex Rd, Darien, CT 06820
OFF MARKET

315 Middlesex Rd
Darien, CT 06820

  • 5 Beds
  • 2.5 Baths
  • 4,232 sqft (on 1 acre)

$2,614,300

Trulia Estimate
as of Jun 1, 2026
Est. Refi. Payment $16,798/mo*
Refinance Your Home

$2,614,300

Trulia Estimate
as of Jun 1, 2026
Est. Refi. Payment $16,798/mo*
Refinance Your Home
5 Beds
2.5 Baths
4,232 sqft
(on 1 acre)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

The John Stevens House - Character and charm abound in this 1853 Colonial Farmhouse. Tastefully renovated and expanded for today's active lifestyle, this beautifully landscaped one-acre property boasts 2 home offices, a full gym, and is a short walk to Town, Train, High School, Middle School, and a short drive to Ox Ridge Elementary. The first-floor circular flow is an entertainer's dream! The updated kitchen opens to a breakfast room and spacious family room, with adjoining sunroom that flows naturally onto an oversize stone-walled patio. The formal living and dinning rooms offer an elegant blend of period details with modern sophistication. A large open bonus room above the 2-car garage is currently used as a full gym, but could be a 5th bedroom, playroom or office. Building experts remark on the sound construction, and old-home specialists characterize it as "a pristine, solid and charming home". This home is move-in ready, and checks all the boxes! Come fall in love with this quintessential New England home and all it has to offer!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 315 Middlesex Rd

Interior Features

Interior Details
BasementIn-law unitNumber of Rooms: 20
Heating & Cooling
Heating: Forced Air, OilAir ConditioningCooling System: CentralHeating Fuel: Forced Air
Levels, Entrance, & Accessibility
Stories: 2Floors: Hardwood
Appliances & Utilities
DishwasherDisposalDryerMicrowaveRefrigeratorWasher
Fireplace & Spa
Fireplace
Security
Security System

Property Information

Year Built
Year Built: 1853Year Updated: 2004
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Exterior Features

Exterior Home Features
Exterior: WoodPatioSprinkler System
Parking & Garage
GarageParking Spaces: 2Parking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 1 acre

Price History for 315 Middlesex Rd

DatePriceEventSource
01/29/2021$1,375,000Sold
Smart MLS #170354642
11/13/2020$1,375,000Listed For SaleAgent Provided
06/04/2010$1,499,000ListingRemovedAgent Provided
07/05/2009$1,499,000PriceChange
Agent Provided
04/11/2009$1,649,000Listed For SaleAgent Provided
10/08/1999$640,000Sold
Smart MLS #98014670
01/20/1989$430,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax$16,431
Assessment$1,061,410
Home facts updated by county records

Comparable Sales for 315 Middlesex Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
26 Holly Lane, Darien, CT
0.18
Single-Family Home
$2,500,000
05/08/26
4
3.5
4,260
25 Libby Lane, Darien, CT
0.21
Single-Family Home
$4,325,000
07/29/25
5
6
5,545
3 Revere Road, Darien, CT
0.40
Single-Family Home
$2,350,000
05/01/26
5
3
3,395
162 Leroy Avenue, Darien, CT
0.52
Single-Family Home
$3,825,000
07/15/25
5
5
4,295
6 Priscilla Lane, Darien, CT
0.43
Single-Family Home
$4,800,000
12/18/25
5
4.5
6,192
54 Stony Brook Rd, Darien, CT
0.26
Single-Family Home
$4,425,000
08/04/25
6
6
6,446
109 West Avenue, Darien, CT
0.48
Single-Family Home
$2,050,000
09/05/25
5
4.5
3,591
29 Stony Brook Road, Darien, CT
0.33
Single-Family Home
$4,200,000
07/14/25
4
4.5
5,308
39 Deepwood Road, Darien, CT
0.68
Single-Family Home
$4,022,500
08/01/25
5
3.5
4,932
76 Deepwood Road, Darien, CT
0.95
Single-Family Home
$2,287,500
02/27/26
5
4
3,897

Nearby homes

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Assigned Schools

These are the assigned schools for 315 Middlesex Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Darien

At least 147 Trulia users voted on each feature.

  • 92 % Say it's dog friendly

  • 89 % Say yards are well-kept

  • 88 % Say parking is easy

  • 87 % Say car is needed

  • 84 % Say there's holiday spirit

  • 81 % Say people would walk alone at night

  • 80 % Say kids play outside

  • 73 % Say there's wildlife

  • 71 % Say it's quiet

  • 70 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are community events

  • 58 % Say there are sidewalks

  • 55 % Say it's walkable to restaurants

  • 48 % Say it's walkable to grocery stores

  • 44 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Kimrichardnyc
    "Happy, safe and friendly place to live and raise children. Need more diversification like in wesport CT though. "
    0
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  • Trulia User
    "This is the best town to raise kids and build friendships. The beaches, parks, restaurants, nature and proximity to NYC also makes a great place to live. We have found the people generally friendly and welcoming. "
    0
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  • Trulia User
    "great place to raise kids, we have lived here for about a decade. fantastic schools, great neighbors"
    0
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  • Jessica_hatch7
    "NA commute to the city is an easy 65 minute train ride. We have two stations in Darien, both easily accessible. "
    3
    Flag
  • Peter S.
    "Holidays and school events. Dining and activities such as sports, the arts and many many social events"
    0
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  • Mzengo8
    "My neighborhood plays kid lacrosse/ basketball or football games. And we have parties on almost every holiday. Which is very fun for all of the kids on the block "
    0
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  • Bill T.
    "Dead end but on a hill and has a loop so kids can run around, play and explore. Lots of trees and woods surround the neighborhood."
    3
    Flag
  • Tad
    "My commute is five minutes to the train station, five minute walk from parking lot to the tracks, then an hour on the train to grand central each work day. "
    1
    Flag
  • Allison w.
    "They would love it, such a friendly area. Dogs are everywhere and appreciated. I have 2 dogs and I am so glad there are a ton of dogs around. "
    0
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  • Chad W.
    "Darien is as family friendly as it gets. There is a lot of money here. Some are kind, but many are snobby. It's a bit of a bubble, which is why many families move here."
    0
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  • Jessica_hatch7
    "The people are amazing and the schools are fantastic. We are only 60 minutes from the city and the trains run very frequently. "
    2
    Flag
  • Victoria_belluscio
    "Great place to raise children- excellent schools- everything is 5-10 min away so good for busy schedules! 2 train stations for easy commuting, beaches, parks and more!"
    0
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  • Kathrynquirk445
    "Beautiful area. Gorgeous homes. Lovely neighbors. Lived here many years and love it. Great privacy and incredibly convenient."
    0
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  • Bill T.
    "Big circle where no cars or trucks visit unless they live here or have business in the neighborhood... great place for kids"
    1
    Flag
  • dwenger
    "Spectacular location: Walk to beaches, shops, Train to NYC, convenient to I-95 and more "
    0
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315 Middlesex Rd, Darien, CT 06820 is a 5 bedroom, 3 bathroom, 4,232 sqft single-family home built in 1853. This property is not currently available for sale. 315 Middlesex Rd was last sold on Jan 29, 2021 for $1,375,000. The current Trulia Estimate for 315 Middlesex Rd is $2,614,300.