14 Old Redding Rd
Weston, CT 06883
5 Beds
3.5 Baths
3,777 sqft (on 2 acres)
5 Beds
3.5 Baths
3,777 sqft
(on 2 acres)
Local Information
- Map ViewExplore the area around 14 Old Redding Rd.
- Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Premier opportunity to enjoy Connecticut history melding with transitional design. Finely updated and improved classic home with all the modern amenities. Peace and tranquility on manicured two acres yet within a quick drive to both Weston and Westport town centers, beach, and shopping and restaurants. Wide plank chestnut hardwood floors, exposed beams, original hardware, four amazing fireplaces, 4/5 generously sized bedrooms and even plenty of storage. Unique to this well maintained home, the current owners built an incredible post and beam barn with private office. Downstairs there is room for four cars, while upstairs is perfect as party barn, art studio, gym or man/woman cave.
14 Old Redding Rd, Weston, CT 06883 is a 5 bedroom, 4 bathroom, 3,777 sqft single-family home built in 1786. It last sold for $760,000 on Aug 15, 2019. It is currently off market. The Trulia Estimate is $1,668,200, with a rent estimate of $7,842/month.
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 14 Old Redding Rd
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Interior Details BasementAtticNumber of Rooms: 12 |
Heating & Cooling Heating: Baseboard, GasAir ConditioningCooling System: CentralHeating Fuel: Baseboard |
Appliances & Utilities DishwasherDryerRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: Shake ShingleExterior: Shingle Not Wood, WoodPatio |
Parking & Garage GarageParking Spaces: 4Parking: Garage Detached |
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Year Built Year Built: 1786Year Updated: 1994 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 2.00 acres |
Price History for 14 Old Redding Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 08/15/2019 | $760,000 | Sold | Smart MLS #170183451 |
| 02/16/2019 | $799,000 | PriceChange | Agent Provided |
| 12/03/2018 | $849,000 | Listed For Sale | Agent Provided |
| 10/02/2018 | $875,000 | ListingRemoved | Agent Provided |
| 06/14/2018 | $875,000 | PriceChange | Agent Provided |
| 04/23/2018 | $899,000 | Listed For Sale | Agent Provided |
| 03/09/2018 | $960,000 | ListingRemoved | Agent Provided |
| 10/30/2017 | $960,000 | PriceChange | Agent Provided |
| 07/06/2017 | $969,000 | PriceChange | Agent Provided |
| 03/10/2017 | $989,000 | Listed For Sale | Agent Provided |
| 12/08/2016 | $1,149,000 | ListingRemoved | Agent Provided |
| 07/25/2016 | $1,149,000 | PriceChange | Agent Provided |
| 06/22/2016 | $1,199,000 | PriceChange | Agent Provided |
| 05/18/2016 | $1,250,000 | PriceChange | Agent Provided |
| 05/03/2016 | $1,199,000 | PriceChange | Agent Provided |
| 12/07/2015 | $1,250,000 | Listed For Sale | Agent Provided |
| 09/02/2012 | $1,199,000 | ListingRemoved | Agent Provided |
| 02/14/2012 | $1,199,000 | Listed For Sale | Agent Provided |
| 04/03/1987 | $557,500 | Sold | N/A |
Market trends in Weston
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
44
6MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $19,315 |
| Assessment | $808,150 |
Home facts updated by county records
Comparable Sales for 14 Old Redding Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.48 | Single-Family Home | $760,000 | 04/28/26 | 5 | 3.5 | 3,226 | |
0.16 | Single-Family Home | $2,100,000 | 02/25/26 | 6 | 6 | 6,342 | |
0.49 | Single-Family Home | $2,577,000 | 10/15/25 | 5 | 3 | 4,170 | |
0.50 | Single-Family Home | $1,501,000 | 04/15/26 | 3 | 3.5 | 3,452 | |
0.59 | Single-Family Home | $1,390,000 | 11/10/25 | 4 | 3 | 3,025 | |
0.85 | Single-Family Home | $736,000 | 06/30/26 | 4 | 3 | 2,427 | |
0.90 | Single-Family Home | $915,000 | 10/03/25 | 5 | 2.5 | 2,756 | |
0.56 | Single-Family Home | $952,500 | 12/30/25 | 4 | 3 | 1,686 | |
0.53 | Single-Family Home | $1,317,500 | 12/29/25 | 4 | 3 | 1,686 | |
0.77 | Single-Family Home | $2,170,000 | 11/10/25 | 5 | 3.5 | 5,750 |
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Assigned Schools
These are the assigned schools for 14 Old Redding Rd.
- Hurlbutt Elementary School
- PK-2
- Public
- 443 Students
NAGreatSchools RatingParent Rating AverageOur child has attended PK-2 - is now in her final year at the school. The change in her has been dramatic - she entered with fairly signficant social, vocabulary and motor challenges, and will leave a well adjusted, generally happy kid at or above grade level in basically everything. Sure, we played some part in. The absolutely outstanding, beyond any belief level of support she got in school was a bigger part than we were, even - the level of structure and careful adjustment of the program to adjust to new information helped us help her as well.We moved here for the schools and really haven't been disappointed.Other Review4y ago - Weston High School
- 9-12
- Public
- 691 Students
10/10GreatSchools RatingParent Rating AverageThis school is nice, but they focus too much on sports instead of other afterschool programs such as the theater department. This school was also effective in swiftly evacuating us from school when there was an unsubstantiated bomb threat on our school. I’ve met great friends at this school and have built strong relationships with them. Some people in the school are very cliquey, but most are nice and welcoming. The school is very competitive and most teachers are amazing, but there are some who are down right horrible. Recently, there has been little to no school spirit and a lot of judgement of others takes place. Despite this, I think that overall, this school would be worth going to. I’d recommend it. Just work hard and do well in school.Student Review1y ago - Weston Middle School
- 6-8
- Public
- 474 Students
9/10GreatSchools RatingParent Rating AverageIt is a great school all around but it was some flus like under or overcooked food and they usually have a great policy on, trying not to bully people, but sometimes they’ll look at the really small things and not the bigger things that could pose a bigger problemStudent Review2y ago - Weston Intermediate School
- 3-5
- Public
- 478 Students
10/10GreatSchools RatingParent Rating AverageMy twins are currently attending this school. The facility is lovely and very clean.Parent Review3y ago 
Check out schools near 14 Old Redding Rd.
What Locals Say about Weston
At least 40 Trulia users voted on each feature.
98 % Say car is needed
96 % Say yards are well-kept
95 % Say parking is easy
95 % Say it's quiet
85 % Say there's wildlife
80 % Say it's dog friendly
73 % Say there's holiday spirit
62 % Say neighbors are friendly
62 % Say people would walk alone at night
56 % Say kids play outside
52 % Say they plan to stay for at least 5 years
47 % Say there are community events
Sourced by Trulia users. Learn more about our methodology.
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