
28 Hoop Pole Hill Rd Chester, CT 06412
Estimated payment $5,376/month
Highlights
- 2.01 Acre Lot
- Cape Cod Architecture
- Attic
- Valley Regional High School Rated A-
- Deck
- 1 Fireplace
About This Home
Discover the perfect blend of elegance and convenience in this custom Cape Cod home, nestled privately in Chester, CT. Boasting 4 bedrooms and 3.5 baths, this residence is convenient to the vibrant downtown area and easily accessible to the highway, yet set in a quiet woodland sanctuary, directly across from over 100 acres of state forest and trails. With timeless decor that exudes classic charm, the main level is thoughtfully designed with your comfort in mind. It features a primary bedroom suite with a spa-like full bath for ease of living, a cozy living room with built-ins provides a tranquil space to unwind, while the formal dining room is ideal for hosting gatherings. The heart of the home is the kitchen, where warm cabinetry and granite countertops invite culinary exploration made easy with a pot filler, warming drawer and 7 foot island with sink. Alfresco dining is steps away through the sliders to the trex deck. Upstairs, three additional generously sized bedrooms , including one with a private bath. The home's versatility shines with a bonus room accessed by a separate staircase- perfect for a home office, media room or family room. Additional living space awaits your finishing touches in the basement, complete with sliders that open to the backyard oasis with a Koi pond and rolling lush lawns. This Chester gem combines the warmth of a family home with the sophistication of upscale living. Don't miss the opportunity to make this house your forever home
Listing Agent
William Pitt Sotheby's Int'l License #RES.0814595 Listed on: 07/10/2025

Home Details
Home Type
- Single Family
Est. Annual Taxes
- $11,402
Year Built
- Built in 2008
Lot Details
- 2.01 Acre Lot
- Property is zoned R-2
Home Design
- Cape Cod Architecture
- Concrete Foundation
- Frame Construction
- Asphalt Shingled Roof
- Vinyl Siding
Interior Spaces
- Central Vacuum
- 1 Fireplace
- Thermal Windows
- Entrance Foyer
- Bonus Room
- Smart Thermostat
Kitchen
- Oven or Range
- Range Hood
- Dishwasher
- Disposal
Bedrooms and Bathrooms
- 4 Bedrooms
Laundry
- Laundry in Mud Room
- Laundry Room
- Laundry on main level
- Washer
Attic
- Storage In Attic
- Attic or Crawl Hatchway Insulated
Unfinished Basement
- Walk-Out Basement
- Basement Fills Entire Space Under The House
Parking
- 2 Car Garage
- Parking Deck
- Automatic Garage Door Opener
Outdoor Features
- Deck
- Exterior Lighting
- Rain Gutters
Location
- Property is near shops
Schools
- Chester Elementary School
- Winthrop Middle School
- Valley High School
Utilities
- Zoned Heating and Cooling System
- Hydro-Air Heating System
- Heating System Uses Propane
- Programmable Thermostat
- Underground Utilities
- Private Company Owned Well
- Tankless Water Heater
- Propane Water Heater
- Fuel Tank Located in Ground
- Cable TV Available
Listing and Financial Details
- Assessor Parcel Number 2465596
Map
Home Values in the Area
Average Home Value in this Area
Tax History
Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
---|---|---|---|---|
2025 | $11,402 | $421,050 | $66,570 | $354,480 |
2024 | $10,295 | $421,050 | $66,570 | $354,480 |
2023 | $9,547 | $321,450 | $66,560 | $254,890 |
2022 | $9,483 | $321,450 | $66,560 | $254,890 |
2021 | $9,483 | $321,450 | $66,560 | $254,890 |
2020 | $9,200 | $321,450 | $66,560 | $254,890 |
2019 | $9,255 | $321,450 | $66,560 | $254,890 |
2018 | $9,018 | $332,650 | $70,070 | $262,580 |
2017 | $8,769 | $332,650 | $70,070 | $262,580 |
2016 | $6,706 | $332,650 | $70,070 | $262,580 |
2015 | $8,423 | $332,650 | $70,070 | $262,580 |
2014 | $8,256 | $332,650 | $70,070 | $262,580 |
Property History
Date | Event | Price | Change | Sq Ft Price |
---|---|---|---|---|
07/10/2025 07/10/25 | For Sale | $799,000 | +66.5% | $235 / Sq Ft |
04/03/2020 04/03/20 | Sold | $480,000 | -2.0% | $141 / Sq Ft |
02/04/2020 02/04/20 | Pending | -- | -- | -- |
12/14/2019 12/14/19 | Price Changed | $489,999 | -2.0% | $144 / Sq Ft |
10/08/2019 10/08/19 | Price Changed | $499,999 | -3.7% | $147 / Sq Ft |
09/26/2019 09/26/19 | Price Changed | $519,000 | -3.0% | $153 / Sq Ft |
09/23/2019 09/23/19 | For Sale | $535,000 | +9.2% | $158 / Sq Ft |
06/14/2016 06/14/16 | Sold | $489,900 | 0.0% | $192 / Sq Ft |
04/06/2016 04/06/16 | Pending | -- | -- | -- |
02/29/2016 02/29/16 | For Sale | $489,900 | -- | $192 / Sq Ft |
Purchase History
Date | Type | Sale Price | Title Company |
---|---|---|---|
Warranty Deed | $480,000 | None Available | |
Warranty Deed | $480,000 | None Available | |
Warranty Deed | $489,000 | -- | |
Warranty Deed | $489,000 | -- | |
Warranty Deed | $599,000 | -- | |
Warranty Deed | $599,000 | -- |
Mortgage History
Date | Status | Loan Amount | Loan Type |
---|---|---|---|
Open | $100,000 | Stand Alone Refi Refinance Of Original Loan | |
Open | $456,000 | Purchase Money Mortgage | |
Closed | $456,000 | New Conventional | |
Previous Owner | $239,900 | Purchase Money Mortgage | |
Previous Owner | $360,000 | Credit Line Revolving |
Similar Homes in Chester, CT
Source: SmartMLS
MLS Number: 24104682

APN: CHES-000013-000000-000108
- 86 Spring St
- 171 Main St
- 10 Phelps Ln
- 52 Essex St
- 105 Bridge Rd
- 3 Brookes Ct
- 489 N Roast Meat Hill Rd
- 23 Main St Unit 5 The Chace Suite
- 23 Main St Unit 2 - The Burton Suite
- 41 Melody Ln
- 82 River Rd
- 26 Sunset Terrace Unit B3
- 26 Sunset Terrace Unit 26C
- 62 N Main St
- 1 Foxboro Rd
- 2 Porges Rd
- 15 Prospect St
- 11 N Main St Unit A
- 14 Pratt St
- 15 Main St Unit 1