4 Sypher Road
Chester, CT 06412
3 Beds
2.5 Baths
2,272 sqft (on 2.02 acres)
3 Beds
2.5 Baths
2,272 sqft
(on 2.02 acres)
Local Information
- Map ViewExplore the area around 4 Sypher Road.
- Schools1 Preschool School1 Elementary School1 Middle School1 High School
- Shop & Eat
-- mins to
Description
Discover a rare gem in the picturesque town of Chester, Connecticut, with this charming 3-bedroom, 2.5-bath colonial home. Nestled on a private 2-acre lot, this property is a dream come true for horse lovers, featuring a barn that offers ample space for your equestrian needs and a chicken coop. Enjoy direct access to nearby state forest trails for riding or exploring. As you step inside, you will be welcomed by a spacious living room featuring a cozy fireplace, perfect for those relaxing evenings. The home also boasts a large family room that opens to a beautiful wood deck, providing a wonderful space for entertaining and enjoying serene views of your expansive property. Upstairs, you will find a spacious primary suite complete with a walk-in closet and a full bath, offering the privacy and comfort you deserve. Chester is known for its delightful eateries, unique galleries, and quaint shops, creating a vibrant community atmosphere. Additionally, the scenic Connecticut River is just a stone's throw away, providing excellent opportunities for boating and fishing, ideal for any outdoor enthusiast. With its convenient location, you are only 2.5 hours from both New York City and Boston. This is a unique opportunity to own a beautiful home in a storybook setting. Embrace the lifestyle you've always dreamed of in this enchanting property!
4 Sypher Road, Chester, CT 06412 is a 3 bedroom, 3 bathroom, 2,272 sqft single-family home built in 1969. It last sold for $525,000 on Jul 25, 2025 (5% above the $499,000 asking price). It is currently off market. The Trulia Estimate is $557,500, with a rent estimate of $3,509/month.
Home Highlights
Parking
2 Car Garage
Outdoor
Deck
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 4 Sypher Road
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Interior Details Basement: Full,Partially FinishedNumber of Rooms: 7Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Living Room |
Beds & Baths Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 2272 Square Feet |
Appliances & Utilities Appliances: Oven/Range, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main LevelMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Hot Water,OilHas CoolingAir Conditioning: Window Unit(s)Has HeatingHeating Fuel: Hot Water |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
Windows, Doors, Floors & Walls Window: Thermopane Windows |
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Exterior Home Features Roof: AsphaltPatio / Porch: DeckOther Structures: Barn(s), Stable(s)Exterior: Garden, Stone WallFoundation: Concrete PerimeterGardenNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Farm & Range Allowed to Raise Horses |
Finished Area Finished Area (above surface): 2272 Square Feet |
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Year Built Year Built: 1969 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Aluminum SidingNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 940103 |
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Price List Price: $499,000 |
Status Change & Dates Off Market Date: Wed Jun 11 2025Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: Chester |
School Information Elementary School: ChesterJr High / Middle School: Region 4High School: Valley |
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Building Area Building Area: 2272 Square Feet |
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Community Features: Health Club, Lake, Library, Medical Facilities, Park, Playground, Shopping/Mall, Stables/Riding |
Other Playground |
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No HOA |
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Lot Area: 2.02 Acres |
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Energy Efficiency Features: Windows |
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BasementMls Number: 24100784Attic: Access Via HatchAbove Grade Unfinished Area: 2272 |
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Health ClubLakeLibraryMedical FacilitiesParkPlaygroundShopping/MallStables/Riding |
Last check for updates: about 3 hours ago
Listed by Kelly Puorro, (860) 575-8666
Puorro Realty Group, (860) 558-9740
Brandon Puorro, (860) 575-8799
Puorro Realty Group, (860) 558-9740
Bought with: Craig Milton, (860) 391-3811, Re/Max Valley Shore, (860) 388-1228
Source: Smart MLS, MLS#24100784
Price History for 4 Sypher Road
| Date | Price | Event | Source |
|---|---|---|---|
| 07/25/2025 | $525,000 | Sold | Smart MLS #24100784 |
| 07/05/2025 | $499,000 | Pending | Smart MLS #24100784 |
| 06/06/2025 | $499,000 | Listed For Sale | Smart MLS #24100784 |
| 12/31/2018 | $296,000 | Sold | Smart MLS #170137978 |
| 11/30/2018 | $299,900 | Pending | Agent Provided |
| 11/15/2018 | $299,900 | PriceChange | Agent Provided |
| 10/24/2018 | $325,000 | Listed For Sale | Agent Provided |
| 05/22/1996 | $180,000 | Sold | N/A |
Market trends in Chester
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
8
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $7,518 |
| Assessment | $277,620 |
Home facts updated by county records
Comparable Sales for 4 Sypher Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.05 | Single-Family Home | $495,000 | 06/05/26 | 4 | 2 | 1,906 | |
0.32 | Single-Family Home | $715,000 | 03/06/26 | 3 | 2.5 | 2,139 | |
0.47 | Single-Family Home | $610,000 | 12/01/25 | 3 | 2.5 | 2,324 | |
0.78 | Single-Family Home | $737,000 | 05/29/26 | 3 | 2 | 2,349 | |
0.72 | Single-Family Home | $733,000 | 11/07/25 | 3 | 2.5 | 1,927 | |
1.02 | Single-Family Home | $518,000 | 06/26/26 | 3 | 2 | 1,842 | |
0.70 | Single-Family Home | $700,000 | 12/16/25 | 4 | 3 | 3,864 | |
0.98 | Single-Family Home | $436,000 | 07/31/25 | 3 | 2 | 1,270 | |
1.23 | Single-Family Home | $635,000 | 10/24/25 | 3 | 3 | 1,989 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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Assigned Schools
These are the assigned schools for 4 Sypher Road.
- John Winthrop Middle School
- 7-8
- Public
- 197 Students
4/10GreatSchools RatingParent Rating AverageI think bullying was the worst problem that happened during my time at JWMS. The adult authorities at the school had a difficult time understanding situations and that often made it worse. I'm also not stating that it was just the kids at the school who would bully but it was also teachers. I remember my 8th grade science teacher would verbally bully girls and pick on them, and it was always girls he was picking on. I was one of them. It didn't help that I had a counselor who couldn't care less if one of there students just jumped off a bridge. They could care less of there students well being, and the same goes with the principles. I honestly would recommend going to a different school, I mean unless you want your child to become depressed.Other Review8y ago - Valley Regional High School
- 9-12
- Public
- 429 Students
7/10GreatSchools RatingParent Rating AverageI enjoyed going to Valley. It is different as a parent I see things differently. However compared to other schools I would say Valley is above the rest.Parent Review7y ago - Chester Elementary School
- PK-6
- Public
- 198 Students
7/10GreatSchools RatingParent Rating AverageCES has a lot of potential with the proper leadership, which it lacks.Other Review6y ago 
Check out schools near 4 Sypher Road.
What Locals Say about Chester
At least 14 Trulia users voted on each feature.
95 % Say car is needed
94 % Say it's dog friendly
93 % Say there's holiday spirit
93 % Say yards are well-kept
84 % Say people would walk alone at night
79 % Say parking is easy
78 % Say they plan to stay for at least 5 years
74 % Say it's walkable to restaurants
74 % Say there's wildlife
69 % Say it's quiet
63 % Say neighbors are friendly
59 % Say there are sidewalks
52 % Say kids play outside
44 % Say streets are well-lit
37 % Say there are community events
18 % Say it's walkable to grocery stores
Sourced by Trulia users. Learn more about our methodology.
LGBTQ Local Legal Protections
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Apartments for Rent
Homes for sale near 4 Sypher Road
2.4 ACRESWilliam Pitt Sotheby's Int'l
2.8 ACRESWilliam Raveis Real Estate
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2.3 ACRESWilliam Pitt Sotheby's Int'l
OPEN SUN, 10-12PM6.4 ACRESColdwell Banker Realty
OPEN SUN, 12-2PM4.4 ACRESWilliam Raveis Real Estate
See more homes for sale inChester
Off Market Homes Near 4 Sypher Road
SOLDJUL 2, 2026William Pitt Sotheby's Int'l
SOLDJUN 29, 2026William Raveis Real Estate
SOLDJUN 26, 2026Coldwell Banker Realty
SOLDJUN 22, 2026William Pitt Sotheby's Int'l
SOLDJUN 17, 2026William Raveis Real Estate
SOLDJUN 11, 2026William Pitt Sotheby's Int'l
SOLDJUN 10, 2026Coldwell Banker Realty
SOLDJUN 1, 2026William Pitt Sotheby's Int'l- See more homes for sale inChester
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