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112 Oakwood Trail #112

Chester, Connecticut 06412

ACTIVE - NEW$599,900
Beds
2
Baths
2 | 1
SqFt
2,521
Year Built
2006
Matt Caiola

Matt Caiola

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2-Car Garage1 Fireplace

About This Home

A distinctive offering in Chester's only 55+ condominium community, privately set along a quiet cul-de-sac. This beautifully appointed two-bedroom, two-and-a-half-bath residence pairs custom details with an open, light-filled design and a well-planned first-floor layout. The main living space features hardwood floors, abundant windows, and a gas fireplace creating a warm architectural focal point. The chef's kitchen is finished with rich cherry cabinetry, corian countertops, a generous island, and custom details throughout. The first-floor primary suite features a private full bath and two ample closets. Upstairs, a spacious open family room/loft with custom built-ins creates an inviting library, reading area, or study, accompanied by a private bedroom, full bath, and separate office/flex room. Just off the kitchen, a three-season sunroom overlooks the private backyard and lightly wooded surroundings, while a bluestone patio offers additional outdoor living space. An attached two-car garage and full basement provide additional storage. Set in the quintessential town of Chester, known for acclaimed restaurants, independent shops, galleries, and its celebrated village atmosphere. A rare opportunity for refined, low-maintenance living with exceptional space and craftsmanship.

Key Facts

City/Town
Chester
Neighborhood
N/A
Property / Style
Condo · Townhouse
Year Built
2006
Days on Market
0 days
Beds
2
Baths
2 full · 1 half
Living Area
2,521 sq ft
Garage / Parking
2 garage
Property Taxes
$6,980 / Annually
HOA Fee
$600 / Monthly

Market Snapshot

The Chester Market

Condo · trailing 12 months

Median Days on Market

0

1 active listing

Median $ / Sq Ft

$238

1 active listing

Sale-to-List Ratio

--

0 sales

How this home compares

List Price

$599,900

vs $599,900 median

In line with median

Price / Sq Ft

$238

vs $238 median

In line with median

Days on Market

--

vs 0 days median

Limited comparable data

Based on 1 active and 0 closed sales (trailing 12 mo) of condo in Chester. Source: SmartMLS · As of September 2, 2026.

Location

112 Oakwood Trail #112, Chester, Connecticut

Property

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,466

per month

  • Principal & Interest$3,084
  • Property Taxes$582
  • Insurance$200
  • HOA$600

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Chester
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Condo
Subtype
Condominium
Style
Townhouse
Year Built
2006
New Construction
No/Resale
Living Area
2,521 sq ft

Schools

Elementary
Chester
High
Valley

Interior

Heating
Hot Air
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
1
Laundry
Main Level
Appliances
Oven/RangeMicrowaveRefrigeratorDishwasherWasherDryer
Basement
FullUnfinished
In-Law Apartment
No
Interior Features
Cable - AvailableCentral VacuumOpen Floor Plan
Additional Rooms
Bonus RoomFoyer

Exterior & Lot

Zoning
R-2
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Shared Well
Sewer
Shared Septic
Construction
Vinyl Siding
Exterior Features
Covered DeckPatio
Lot Description
Corner LotLightly WoodedLevel LotOn Cul-De-Sac

HOA / Association

Fee
$600 / Monthly

Listing & Financials

Property Taxes
$6,980 / Annually
Days on Market
0
MLS #
24202649
MLS Status
Active

Similar Properties

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Listed By

Kelly Puorro

(860) 575-8666

Puorro Realty Group

(860) 558-9740

Co-Listed By

Brandon Puorro

Puorro Realty Group

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/2/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 9/2/2026 at 4:10 PM UTC.