506 Skyline Trail

2,244 Sq. Ft.
$258 / Sq. Ft.
2,244
Sq. Ft.
$258
per Sq. Ft.

Description

Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and an elegant open layout. A long, estate-style concrete approach creates a grand sense of arrival, leading to a beautifully updated interior with porcelain tile floors, modern updates, and two fireplaces that add warmth and character. The finished bonus space just off the main living area offers valuable flexibility: perfect as a family room, creative retreat, fitness room, or easily converted...Set along the scenic Skyline Trail, this fully renovated home offers refined finishes, abundant natural light, and an elegant open layout. A long, estate-style concrete approach creates a grand sense of arrival, leading to a beautifully updated interior with porcelain tile floors, modern updates, and two fireplaces that add warmth and character. The finished bonus space just off the main living area offers valuable flexibility: perfect as a family room, creative retreat, fitness room, or easily converted back to a two-car garage. A charming barn provides optional space for equestrian interests or upscale hobbies without becoming the focal point of the property. The sale also includes a separate buildable lot, offering outstanding potential for future development, guest house plans, or long-term investment. Surrounded by mature rhododendrons and natural landscape, the home delivers privacy, style, and a peaceful mountain setting just minutes from everyday conveniences.
  1. Listed by Oleg Abramchuk • First NationWide Realty Inc.

Property Details for 506 Skyline Trail

Town
Chester
Area
MA-Chester
Architectural Style
Contemporary
Style
Garden, Contemporary
Garage Spaces
2
Parking Spaces
13.00
Parking Spaces Total
15
LISTING UPDATED: 11/29/2025 03:40 AM

Property Details for 506 Skyline Trail

StatusActive
MLS #73457674
Days on Market92
Taxes$3,216 / year
HOA Fees-
Compass TypeSingle Family
MLS TypeSingle Family / Detached
Year Built1969
CountyHampden County

Location

Listing Courtesy of First NationWide Realty Inc., Oleg Abramchuk
Add your commute

Building Information for 506 Skyline Trail

Stories-Year Built1969Building Size-Lot Size7.63 AC / 332,364 SF

Payment Calculator

$3,089 per month

30 year fixed, 6.15% Interest

Principal and Interest

$2,821

Property Taxes

$268

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 506 Skyline Trail

General Details
Property Details
  • Building Area Units: Square Feet
  • Community Features: Shopping, Stables, Medical Facility, Conservation Area, House of Worship, Public School, Other (See Remarks)
  • Living Area: 2244.0
  • Color: Brown
  • SqFt with Basement: Yes
  • Property Attached: No
  • Single Family Type: Detached
  • Waterfront: No
  • Year Built Details: Actual
  • Year Built Source: Public Records
Features
Interior Features
  • Appliances: Tankless Water Heater, Range, Refrigerator, Range Hood
  • Num of Baths: 2.0
  • Num of Full Baths: 2
  • Num of Half Baths: 0
  • Bathrooms Total Decimal: 2.00
  • Bathrooms Total Integer: 2
  • DoorFeatures: Insulated Doors
  • FireplaceFeatures: Family Room, Living Room
  • FireplaceYN: Yes
  • Fireplaces: 2
  • Flooring: Tile
  • Laundry Features: Remodeled, First Floor, Electric Dryer Hookup, Washer Hookup
  • SpaYN: No
  • Window Features: Insulated Windows
Exterior Features
  • Construction: Frame
  • Exterior Features: Porch, Deck, Patio, Rain Gutters, Storage Shed, Barn/Stable, Fruit Trees, Garden
  • Exterior Features: Barn/Stable, Storage Shed, Fruit Trees, Garden Area, Porch, Deck, Patio
  • Lot Description: Wooded, Cleared, Level
  • Other Structures: Barn/Stable
  • Patio And Porch Features: Porch, Deck, Patio
  • Roof Material: Shingle
  • View: Scenic View(s)
  • View: Yes
Parking Features
  • Attached Garage: Yes
  • Carport: No
  • Covered Spaces: 2.00
  • Garage: Yes
  • Garage Parking: Attached, Storage, Work Area, Paved Drive, Off-Street, Improved Driveway, Paved Driveway
  • Open Parking: Yes
  • Parking Features: Attached, Storage, Work Area, Paved Drive, Off-Street, Improved Driveway, Paved Driveway
  • Parking Features: Work Area, Off-Street, Improved Driveway, Paved Driveway
Utilities
  • Cooling: Ductless Mini-Split System
  • Cooling: Yes
  • Electric: 110 Volts, 220 Volts, Circuit Breakers, 200+ Amp Service
  • Heating: Electric Baseboard, Radiant, Electric, Ductless
  • Heating: Yes
  • Sewer: Private Sewerage
  • Utility Connections: for Gas Range, for Electric Dryer, Washer Hookup
  • Water: Private
Room Information
Primary Bedroom
  • Room Primary Bedroom Features: Slider
  • Primary Bedroom Level: Second Floor
Bedroom 2
  • Bedroom2 Features: Recessed Lighting
  • Bedroom2 Level: First
Bedroom 3
  • Bedroom3 Features: Recessed Lighting
  • Bedroom3 Level: First
Bedroom 4
  • Bedroom4 Features: Recessed Lighting
  • Bedroom4 Level: First
Dining Room
  • Dining Room Features: Cathedral Ceiling(s),Flooring - Stone/Ceramic Tile,Open Floorplan,Recessed Lighting,Remodeled,Slider
  • Dining Room Level: Main,Second
Family Room
  • Family Room Features: Recessed Lighting
  • Family Room Level: First
Kitchen
  • Kitchen Features: Flooring - Stone/Ceramic Tile,Countertops - Stone/Granite/Solid,Open Floorplan,Stainless Steel Appliances
  • Kitchen Level: Second
Living Room
  • Room Living Room Features: Cathedral Ceiling(s),Flooring - Stone/Ceramic Tile,Open Floorplan,Recessed Lighting,Remodeled,Slider
  • Room Living Room Level: Main,Second
Property Information
Property Info
  • Farm Land Area Units: Square Feet
  • WARRANTY: No
  • Lot Size Units: Acres
  • Road Frontage Type: Public
  • Road Responsibility: Public Maintained Road
  • Road Surface Type: Paved
  • Disclosures: Buyer/buyer agent must conduct their own due diligence,verification(s) and research and rely solely on the results thereof. Measurements are approximate and need to be verified by buyer/buyer's agent.
Tax Information
  • Listing Terms: Contract
  • Tax ID: M:405.0 B:0000 P:0108.0,3972170
  • Assessments: $178,100
  • Book: 21968
  • Tax Year: 2025
  • Zoning: AR
Building / Association Information
Living Characteristics
  • Beds Total: 4
Other Building Characteristics
  • Foundation: Concrete Perimeter
  • Foundation Area: 1122.0
  • Cooling Zones: 3
Complex & Association Information
  • Adult Community: No

Property History for 506 Skyline Trail

DateEvent & SourcePriceAppreciation
Nov 25, 2025

Listed (Active)

MLS PIN #73457674

$578,900—
Mar 25, 2025

Expired

MLS PIN #73270244

$600,000—
Jul 25, 2024

Listed (Active)

MLS PIN #73270244

$600,000—
Nov 29, 2017

Sold

MLS PIN #72191526

$101,000—
Sep 28, 2017

Under Agreement

MLS PIN #72191526

—
Sep 28, 2017

Contingent

MLS PIN #72191526

—
Jun 30, 2017

Listed (Active)

MLS PIN #72191526

$129,900—
Jun 28, 2017

Canceled

MLS PIN #72156613

$129,900—
May 2, 2017

Listed (Active)

MLS PIN #72156613

$139,900—
May 1, 2017

Expired

MLS PIN #72113220

$139,900—
Jan 20, 2017

Listed (Active)

MLS PIN #72113220

$149,900—
Jan 13, 2017

Expired

MLS PIN #72067244

$145,000—
Sep 14, 2016

Listed (Active)

MLS PIN #72067244

$154,500—
Apr 29, 1997

Sold (Public Record)

Public Record #89479693

$145,900—
Apr 29, 1997

Sold

MLS PIN #30096297

$145,900—
Dec 11, 1996

Contingent

MLS PIN #30096297

—
Mar 26, 1996

Listed (Active)

MLS PIN #30096297

$159,900—
DateEvent & SourcePrice
11/25/2025

Listed (Active)

MLS PIN #73457674

$578,900
03/25/2025

Expired

MLS PIN #73270244

$600,000
07/25/2024

Listed (Active)

MLS PIN #73270244

$600,000
11/29/2017

Sold

MLS PIN #72191526

$101,000
09/28/2017

Under Agreement

MLS PIN #72191526

—
09/28/2017

Contingent

MLS PIN #72191526

—
06/30/2017

Listed (Active)

MLS PIN #72191526

$129,900
06/28/2017

Canceled

MLS PIN #72156613

$129,900
05/02/2017

Listed (Active)

MLS PIN #72156613

$139,900
05/01/2017

Expired

MLS PIN #72113220

$139,900
01/20/2017

Listed (Active)

MLS PIN #72113220

$149,900
01/13/2017

Expired

MLS PIN #72067244

$145,000
09/14/2016

Listed (Active)

MLS PIN #72067244

$154,500
04/29/1997

Sold (Public Record)

Public Record #89479693

$145,900
04/29/1997

Sold

MLS PIN #30096297

$145,900
12/11/1996

Contingent

MLS PIN #30096297

—
03/26/1996

Listed (Active)

MLS PIN #30096297

$159,900

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 506 Skyline Trail

Taxable ValueLand$42,900Additions$135,200Total$178,100
Tax Record2025$3,216 ($268 / month)
Home Facts
Beds4Baths2Total Finished SqFt1,122 SqFtAbove Grade Finished SqFt1,122 SqFtUnfinished Basement SqFt122 SqFtStories1Lot Size79,715 SqFtStyleSingle Family ResidenceYear Built1969ZoningARCountyHAMPDENAPNCHES M:405.0 B:0000 P:0108.0Fireplace TypeHas Fireplace

Schools near 506 Skyline Trail

This home is within Gateway School District.
Rating
School
Type
Grades
Distance
Public - PK to 5
Public - 6 to 8
Public - 9 to 12
Public - PK to 5
Rating
School
Distance
Chester Elementary School
PublicPK to 5

Gateway Regional Junior High School
Public6 to 8

Gateway Regional High School
Public9 to 12

Littleville Elementary School
PublicPK to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Similar Sold Homes

506 Skyline Trail is a single family home for sale in Chester, MA 01011. This property was listed for sale on November 25, 2025 by First NationWide Realty Inc., it's currently listed at $578,900. It has been on the market for a total of 92 days and was last sold on November 29, 2017. This listing's school district is Gateway School District. Nearby schools include Chester Elementary School, Gateway Regional Junior High School and Gateway Regional High School. 506 Skyline Trail is a 4-bed, 2-bath, 2,244 sqft single family home built in 1969.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity.

Listing Courtesy of First NationWide Realty Inc., Oleg Abramchuk

The property listing data and information, or the images, set forth herein were provided to MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS. The property listing data and information, and the images, are for the personal, non-commercial use of consumers having a good faith interest in purchasing or leasing listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing or leasing. MLS Property Information Network, Inc., Martha's Vineyard MLS, CCIMLS, Link MLS, and Berkshire County Board of REALTORS and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the images, set forth herein.