248 Turtle Back Road, New Canaan, CT 06840
Property image
Property image
FOR SALE
3.41 ACRES

$4,000,000

  • 5 Beds
  • 5.5 Baths
  • 5,291 sqft (on 3.41 acres)

248 Turtle Back Road, New Canaan, CT 06840

Est. Mortgage $26,740/mo*
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Home Highlights

Single-Family Home
Built in 1963
3.41 acre lot
$756/sqft
5 Car Garage

Local Information

  • Map ViewExplore the area around 248 Turtle Back Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

What's unique:En-suite guest roomBeautifully proportioned interiorsSubstantial character-filled interiorsVaulted beamed ceilingSunroom with wet barGenerous cabinetry
Classic New England architecture, beautifully proportioned interiors and exceptional privacy come together at 248 Turtle Back Road, a distinguished five-bedroom Colonial offering 5,291 square feet of living space in one of New Canaan's most desirable settings. Inside, the home is filled with warmth, character and natural light. The impressive great room features a vaulted beamed ceiling, creating a dramatic yet inviting space for everyday living and entertaining. An eat-in kitchen with center island, generous cabinetry and French doors is complemented by a dining room overlooking the gorgeous backyard, family room and den, providing both open gathering spaces and quieter places to retreat. Upstairs, the primary suite offers a private dressing room and en-suite bath, joined by three additional bedrooms, including an en-suite guest room. The fully finished walk-out lower level significantly expands the home's versatility with an additional bedroom and full bath, sunroom with wet bar, recreation room, office and exercise space. Outside, the home is set on 3.41 beautifully landscaped acres, where specimen plantings, mature trees, stone walls and terraces create a remarkable sense of privacy and established beauty. A circular drive, greenhouse and garage parking for 5 complete the property. Set just minutes from the heart of New Canaan, 248 Turtle Back Road pairs substantial, character-filled interiors with the privacy and scale that are rare to find this close to town.
Last check for updates: about 6 hours ago
Listing courtesy of John E. Dunn, (203) 388-5353
Compass Connecticut, LLC, (203) 388-5353
Source: Smart MLS, MLS#24178727
Also Listed on Smart MLS.

Home Details for 248 Turtle Back Road

Interior Features

Interior Details
Basement: Full,Heated,Finished,Cooled,Liveable SpaceNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Den, Dining Room, Family Room, Great Room, Kitchen, Loft, Office, Other, Rec Play Room, Sun Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 6Number of Bathrooms (full): 5Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 5291 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Oven/Range, Refrigerator, Subzero, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Oil,PropaneHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace

Exterior Features

Exterior Home Features
Roof: MetalFencing: PartialOther Structures: GreenhouseFoundation: Concrete PerimeterNo Private Pool
Parking & Garage
Number of Garage Spaces: 5Number of Covered Spaces: 5No CarportHas a GarageHas an Attached GarageParking Spaces: 5Parking: Attached,Detached
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 4191 Square FeetFinished Area (below surface): 1100 Square Feet

Days on Market

Days on Market: 14

Property Information

Year Built
Year Built: 1963
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Clapboard, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 184797

Price & Status

Price
List Price: $4,000,000Price Per Sqft: $756
Status Change & Dates
Possession Timing: Negotiable

Active Status

MLS Status: Active

Location

Direction & Address
City: New Canaan
School Information
Elementary School: WestJr High / Middle School: Saxe MiddleHigh School: New Canaan

Agent Information

Listing Agent
Listing ID: 24178727

Building

Building Area
Building Area: 5291 Square Feet

HOA

No HOA

Lot Information

Lot Area: 3.41 Acres

Miscellaneous

BasementMls Number: 24178727Attic: Pull Down StairsAttribution Contact: (203) 388-5353Above Grade Unfinished Area: 4191Activation Date: Thu Sep 10 2026

Around this home

What Locals Say about New Canaan

At least 102 Trulia users voted on each feature.

  • 87 % Say car is needed

  • 84 % Say it's dog friendly

  • 83 % Say it's quiet

  • 82 % Say there's holiday spirit

  • 79 % Say yards are well-kept

  • 79 % Say parking is easy

  • 76 % Say people would walk alone at night

  • 74 % Say they plan to stay for at least 5 years

  • 70 % Say there's wildlife

  • 69 % Say kids play outside

  • 60 % Say neighbors are friendly

  • 48 % Say streets are well-lit

  • 44 % Say it's walkable to restaurants

  • 44 % Say there are community events

  • 41 % Say there are sidewalks

  • 32 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Marisa_abdoo
    "Dogs are a welcome staple in town. Some shop keepers have treats! There are also a lot of walking trails."
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  • Marisa_abdoo
    "There is a train station that originates in New Canaan, which is helpful! Final destination is Grand Central terminal in NYC."
    0
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  • Marisa_abdoo
    "A lot of dogs in town! Some shops have treats. Parks are great too for dogs… a lot of space to run and great trails."
    0
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  • Kerry.carebear
    "Commute is long. Do not recommend commuting. Traffic to and from is not ideal either. However most of Fairfield county experiences this."
    0
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  • Michelle
    "There are great parks for the dogs to walk in and there’s even specifically a dog park that they can go to within the larger Waveny park complex ."
    2
    Flag
  • Wroot
    "Wonderful community. Top public schools. Beautiful downtown shopping district. Kids are happy & healthy. Parks are amazing and well used by the community. Doesn’t get better. "
    1
    Flag
  • Trulia User
    "It’s neighborly but also spaced out and peaceful. There is a lot of privacy and people respect one another. "
    1
    Flag
  • Scott.c.towbin
    "Amazing Schools, super friendly town where it's easy to make friends and keep friends. great downtiwn with restaurant and shops. Easy train commute into NYC; train is waiting for you in AM..it starts in New Canaan!"
    8
    Flag
  • Ashley D. W.
    "Safe and lovely town that although close to nyc feels like it’s worlds away. A place to move where life feels like it can be really lived..."
    2
    Flag
  • Scott.c.towbin
    "Amazing schools, check out the new comers club, the best town center in Fairfield county...a great place to make friends and raise a family"
    2
    Flag
  • Liza O.
    "This is an idyllic place to raise a family with great parks and restaurants. There are also many great neighboring towns"
    2
    Flag
  • Liza O.
    "Our neighborhood is a community. The people here are kind caring and considerate. It’s great for children and its inclusive."
    1
    Flag
  • Uniquefasgion1
    "The best its very safe, quality school’s, strong community, the best downtown, great restaurant and retail stores "
    2
    Flag
  • Amy F.
    "The commute is great and honestly could not be any better! It is a 5 minute walk into town and an 8 minute walk to the Metro North Train Station. "
    4
    Flag
  • Lauren C.
    "Halloween trick or treating in town is amazing. There are events throughout the year - Santa visiting downtown and an Easter egg hunt, etc."
    3
    Flag
  • Mtehrani99
    "Good neighborhoods and great neighbors. Beautiful town and lots of open space and great schools. Lots of parks and easy access to metro north."
    1
    Flag
  • Andreatonello76
    "easy commute to NYC, abundance of parks, sense of safety wherever you go: this is the ideal place to raise your children"
    0
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  • Lauren C.
    "There are lots of parks and paths to walk dogs and all of the downtown businesses are dog friendly. You can walk your dog on a leash anywhere."
    0
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  • Amber
    "Lots of special events down the Main Street called “elm.” Great support for local businesses. Outstanding newcomers club with weekly connection points."
    0
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  • Kathrynquirk445
    "People walk their dogs all the time in this neighborhood. There is a dog park nearby at Waveny. Up and down are dogs and their walkers up and down South Avenue all day long."
    0
    Flag
  • Jmc791
    "Sidewalks are available in and around town. Lots of parks to take your dog to and even if there aren’t sidewalks where you live there are beautiful roads. "
    1
    Flag
  • Lauren C.
    "The houses have large backyards and there are plenty of dog parks nearby for dogs to run and play. I recommend it for dog owners."
    0
    Flag
  • Jmc791
    "Very family oriented town. Downtown is wonderful and plenty of parks and public spaces. School system is very good as well "
    0
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  • John O.
    "Great schools and great community and activities for families, adults and children. Beautiful setting."
    0
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  • Andreatonello76
    "I have lived in this neighborhood for four month. It’s quiet and never feels crowded. Parks are everywhere. Perfect balance between urban and country living"
    0
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  • bonbon
    "I love it it’s the best town to Raise your kids the best schools the best community around quiet very clean a lot of parks and train is on the town I recommend it everybody was looking nice and quiet or healthy family"
    0
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  • Scanlonceciliaa
    "I just moved here about a year ago. People are nice and really go the extra mile to take care of their houses and lawns. Which makes the area look nice"
    1
    Flag
  • Tamara C.
    "Neighborhood potlucks. Memorial Day parade, Fourth of July at Waveny, Christmas Caroling at God’s Acre."
    1
    Flag
  • Lori
    "Memorial Day parade. Sidewalk sale days, dog park, Fourth of July events, local church events, football Friday’s, "
    0
    Flag
  • Scanlonceciliaa
    "Really great schools. I mean top notch. Very family friendly town with lots of child activities. That’s why we moved here."
    0
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  • Al T
    "Awesome schools, programs for every interest, sports, town spirit. reasonable NYC commute. Better than Darien."
    0
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  • Lauren C.
    "New Canaan is one of the nicest towns in the New York metro area of Connecticut. It has a wonderful little town with shops and restaurants, lots of wonderful public amenities and an amazing school district. It has options for private school and a newly renovated country club. "
    1
    Flag
  • Anthony R.
    "Nice area the rise a family great location and school small town setting and very safe high income area . Schools "
    0
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  • Scanlonceciliaa
    "Very safe town with exceptional schools. Cute town with family friendly dining options. That’s why we moved here."
    0
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  • Scanlonceciliaa
    "Love living here. It’s beautiful in Silvermine by the river and people are friendly and take care of their homes"
    0
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Market trends in New Canaan

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$2.36M
$202KMoM
Sale-to-List Price
105.2%
1.1%MoM
Price per sq ft
$629
$0MoM
Available listings
46
23MoM

Home Value

Trulia Estimate
$3.91M
Since last month
Increased$1M (+44.2%)
Since last year
Increased$1M (+56.2%)
Since last sale
Increased$3M (+272.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +98% in the last 10 years
MonthEstimated value
2026
September 2026$3.91M
August 2026$2.71M
July 2026$2.67M
June 2026$2.72M
May 2026$2.74M
April 2026$2.64M
March 2026$2.6M
February 2026$2.48M
January 2026$2.41M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
340 Turtle Back Road, New Canaan, CT
0.15
Single-Family Home
$4,510,000
10/01/25
6
6
7,361
54 Saint George Lane, New Canaan, CT
0.52
Single-Family Home
$3,053,000
06/25/26
4
4
5,244
1191 Oenoke Ridge, New Canaan, CT
0.59
Single-Family Home
$4,700,000
08/04/26
5
5.5
6,557
108 Logan Road, New Canaan, CT
0.48
Single-Family Home
$3,325,000
08/26/26
6
7
6,069
176 Logan Road, New Canaan, CT
0.69
Single-Family Home
$2,678,671
03/31/26
5
3.5
4,428
1541 Oenoke Ridge, New Canaan, CT
0.79
Single-Family Home
$3,200,000
06/22/26
5
5.5
5,687
148 West Hills Road, New Canaan, CT
0.77
Single-Family Home
$3,100,000
02/19/26
5
4.5
5,731
1038 West Road, New Canaan, CT
0.75
Single-Family Home
$2,500,000
05/01/26
4
3
4,562
584 West Road, New Canaan, CT
0.43
Single-Family Home
$6,785,000
04/29/26
7
8
9,114

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
253 Turtle Back Road, New Canaan, CT 06840
0.08
$3,659,900
4
4.5
5,754
Off Market
216 Turtle Back Road, New Canaan, CT 06840
0.07
$3,729,200
5
4.5
5,236
Off Market
340 Turtle Back Road, New Canaan, CT 06840
0.15
$4,847,700
6
6
7,361
Off Market
17 Turtle Back Lane West, New Canaan, CT 06840
0.17
$4,114,900
5
5
4,821
Off Market
77 Turtle Back Lane East, New Canaan, CT 06840
0.24
$2,845,800
4
3.5
4,200
Off Market
36 Apple Tree Lane, New Canaan, CT 06840
0.20
$2,731,200
5
3
3,280
Off Market
1052 Oenoke Ridge, New Canaan, CT 06840
0.28
$3,057,200
4
3
3,624
Off Market
106 Logan Road, New Canaan, CT 06840
0.34
$2,631,700
4
3.5
4,273
Off Market
930 Oenoke Ridge, New Canaan, CT 06840
0.29
$7,041,400
7
6.5
7,358
Off Market
110 Turtle Back Road, New Canaan, CT 06840
0.30
$4,742,200
5
4.5
4,853
Off Market
871 West Road, New Canaan, CT 06840
0.38
$3,328,400
5
3.5
5,368
Off Market

Price and Tax history

DateEventPrice
Sep 10, 2026
Source: Smart MLS #24178727
Listed For Sale
$4,000,000
Jul 29, 1994
Source: N/A
Sold
$1,049,000

LGBTQ Local Legal Protections

John E. Dunn, Compass Connecticut, LLC, (203) 388-5353
Agent Phone: (203) 388-5353
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 248 Turtle Back Road

  • What is the estimated monthly payment for 248 Turtle Back Road?
    Based on a $4,000,000 list price with 20% down at today's rates, the estimated monthly payment for 248 Turtle Back Road in New Canaan, CT is approximately $27,423 (about $21,715 principal & interest, $5,633 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 248 Turtle Back Road compare to homes in New Canaan?
    248 Turtle Back Road in New Canaan, CT is listed at $4,000,000, about 69% above the $2.36M median sale price in New Canaan.
  • What do residents say about New Canaan?
    Residents describe New Canaan, CT as dog-friendly, quiet, and well-kept. Most residents say you need a car. See homes for sale in New Canaan, CT.
  • What are the closest schools to 248 Turtle Back Road?
    The closest schools to 248 Turtle Back Road in New Canaan, CT are New Canaan High School (rated 10/10), Saxe Middle School (Elementary, rated 10/10), West School (Pre-K/Elementary, rated 10/10).
  • Does 248 Turtle Back Road have air conditioning?
    Yes, 248 Turtle Back Road in New Canaan, CT has air conditioning.
  • Does 248 Turtle Back Road have laundry facilities?
    Yes, 248 Turtle Back Road in New Canaan, CT has in-unit laundry.
248 Turtle Back Road, New Canaan, CT 06840 is a 5 bedroom, 6 bathroom, 5,291 sqft single-family home built in 1963. This property is currently available for sale and was listed by Smart MLS on Sep 8, 2026. The MLS # for this home is MLS# 24178727.