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2 Chestnut St, Winchester MA 01890

$3,599,000

Estimated $37,816.89/month Calculator

Single Family

6 Bedrooms

5 Full Baths

5,500 SqFt

4 Parking Spots

0.25 acres

Built in 2025

Welcome to 2 Chestnut Street, an exquisite new construction home in progress by Mark Stephen Development. Situated off coveted Main Street in one of Winchester’s most sought-after neighborhoods, this residence is thoughtfully designed to blend timeless charm with modern conveniences. The home will feature five spacious bedrooms, five full bathrooms, a first-floor office, and a basement offering flexible space for an additional office, playroom, exercise room, or living area. The open-concept kitchen will include premium appliances, a grand nine-foot island, and custom cabinetry, while the primary suite will boast luxurious his-and-her closets and a spa-like bathroom with a soaking tub and marble-tiled shower. A third-floor bonus space adds versatility. With mature landscaping providing privacy and a spacious patio for outdoor living, this property is conveniently located near Winchester town center, top-rated schools, offers easy access to Boston, and promises an unparalleled lifestyle

This home has been viewed 24 times

Last Updated: March 11th, 2025 at 6:48am

Garage Parking

Air Conditioning

General Information for 2 Chestnut St, Winchester MA 01890

Listing ID73333668

Property TypeSingle Family / Detached

Price$3,599,000 ($654.36/SqFt)

StyleColonial

CityWinchester

CountyMiddlesex

MLS Area

Neighborhood(s)

Total Parking4 (2 Garage)

Garage Parking2

ZoningRDB

AssociationNo

Year Built2025

Year Built SourceOwner

Year RenovatedN/A

Year Built DetailsActual

Handicap Access / FeaturesNo

Energy Features

Interior Features for 2 Chestnut St, Winchester MA 01890

Approximate Living Area Total5,500 SqFt

Living Area Includes BasementYes

Rooms15

Bedrooms6

Full Baths5

Half Baths0

Primary En Suite BathroomYes

BasementFull, Partially Finished, Walk-out Access

HeatingYes / Central, Electric

CoolingYes / Central Air, Heat Pump

Fireplaces1

AppliancesElectric Water Heater

FlooringWood, Flooring - Wall To Wall Carpet, Flooring - Stone/ceramic Tile, Flooring - Hardwood, Flooring - Wood

Electric

Exterior Features for 2 Chestnut St, Winchester MA 01890

Approximate Lot Size (Acres)0.25 acres

Approximate Lot Size (Square Feet)11,090

Total Parking4

Garage Parking2 / Detached

WaterPublic

SewerPublic Sewer

Lot FeaturesCorner Lot, Off Street, Attached

Exterior FeaturesSprinkler System, Professional Landscaping, Stone Wall, Patio, Decorative Lighting

Foundation Area

Foundation MaterialsConcrete Perimeter

Construction MaterialsFrame

Approximate Street Frontage

Road Frontage Type

Patio & PorchPatio

Roof MaterialShingle

Utility Connections

Water Views

Water Views Features

WaterfrontNo

Waterfront Features

Private PoolNo

Pool Features

Horse PermittedNo

Horse Amenities

Disclosures for 2 Chestnut St, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourceOwner

Senior CommunityNo

Special Listing Conditions

For Sale By OwnerNo

Exclusions

Disclosures

Title 5

Buyer Agent Compensation

Facilitator Compensation

Sub-Agent Compensation

Compensation Based OnNet Sale Price

Financial Information for 2 Chestnut St, Winchester MA 01890

AssociationNo

Association Fee$0

Association Fee Frequency

Association Fee Includes

Real Estate Tax$15,641

Tax Year2025

Assessed Value$1,410,400

Location information for 2 Chestnut St, Winchester MA 01890

Elementary School

Middle School

High School

Neighborhood(s)

MLS Area

Area Amenities

Contact Information for 2 Chestnut St, Winchester MA 01890

Agent

Name: Mark Donnellan

MLS ID: NB112231

Office ID: AN8756

National Association ID: 449537583

Phone: 781-608-9970

Address: 22 Grove Place Unit 25

City: Winchester

State: MA

Zip: 01890

Office

Name: Advisors Living - Winchester

MLS Office ID: AN8756

Phone: 978-423-5235

Payment Calculator

, Interest

Property Taxes $15,641

Principal & Interest 22175.89

HOA Dues $0

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

Advisors Living - Winchester

Mark Donnellan

Agent Phone

(781) 608-9970

Office Phone

(978) 423-5235

Text Agent Call Agent Call Office

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[field_3189] => Array
                (
                    [field_id] => 3189
                    [type] => price
                    [name] => ConcessionsAmount
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[f_3190] => Array
                (
                    [field_id] => 3190
                    [type] => feature
                    [name] => ConstructionMaterials
                    [values] => Array
                        (
                            [0] => Frame
                        )

)

[field_3191] => Array
                (
                    [field_id] => 3191
                    [type] => select
                    [name] => CoolingYN
                    [value] => 1
                )

[field_3192] => Array
                (
                    [field_id] => 3192
                    [type] => number
                    [name] => ParkingTotal
                    [value] => 2
                )

[field_3193] => Array
                (
                    [field_id] => 3193
                    [type] => number
                    [name] => CoveredSpaces
                    [value] => 2
                )

[field_3200] => Array
                (
                    [field_id] => 3200
                    [type] => price
                    [name] => ElectricExpense
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3205] => Array
                (
                    [field_id] => 3205
                    [type] => date
                    [name] => ExpirationDate
                    [value] => 01/01/1900
                )

[field_3206] => Array
                (
                    [field_id] => 3206
                    [type] => select
                    [name] => FarmLandAreaUnits
                    [value] => Square Feet
                )

[field_3208] => Array
                (
                    [field_id] => 3208
                    [type] => select
                    [name] => FireplaceYN
                    [value] => 1
                )

[field_3209] => Array
                (
                    [field_id] => 3209
                    [type] => text
                    [name] => FoundationDetails
                    [value] => Concrete Perimeter
                )

[field_3211] => Array
                (
                    [field_id] => 3211
                    [type] => number
                    [name] => GarageSpaces
                    [value] => 2
                )

[field_3212] => Array
                (
                    [field_id] => 3212
                    [type] => select
                    [name] => GarageYN
                    [value] => 1
                )

[field_3216] => Array
                (
                    [field_id] => 3216
                    [type] => price
                    [name] => GrossIncome
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3217] => Array
                (
                    [field_id] => 3217
                    [type] => select
                    [name] => HeatingYN
                    [value] => 1
                )

[field_3220] => Array
                (
                    [field_id] => 3220
                    [type] => price
                    [name] => InsuranceExpense
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3222] => Array
                (
                    [field_id] => 3222
                    [type] => text
                    [name] => ListingAgreement
                    [value] => Exclusive Right To Sell
                )

[field_3223] => Array
                (
                    [field_id] => 3223
                    [type] => date
                    [name] => ListingContractDate
                    [value] => 09/02/2025
                )

[f_3225] => Array
                (
                    [field_id] => 3225
                    [type] => feature
                    [name] => LotFeatures
                    [values] => Array
                        (
                            [0] => Corner Lot
                        )

)

[field_3226] => Array
                (
                    [field_id] => 3226
                    [type] => area
                    [name] => LotSizeSquareFeet
                    [value] => 11,090 Sqft
                    [raw] => 11090
                    [unit_id] => 1
                )

[field_3230] => Array
                (
                    [field_id] => 3230
                    [type] => price
                    [name] => OperatingExpense
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3231] => Array
                (
                    [field_id] => 3231
                    [type] => price
                    [name] => OriginalListPrice
                    [raw] => 3599000
                    [unit_id] => 260
                    [value] => $3,599,000
                    [price_only] => $3,599,000
                )

[field_3240] => Array
                (
                    [field_id] => 3240
                    [type] => text
                    [name] => UnparsedAddress
                    [value] => 2 Chestnut St, Winchester MA 01890
                )

[field_3241] => Array
                (
                    [field_id] => 3241
                    [type] => price
                    [name] => WaterSewerExpense
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3243] => Array
                (
                    [field_id] => 3243
                    [type] => text
                    [name] => YearBuiltDetails
                    [value] => Actual
                )

[field_3245] => Array
                (
                    [field_id] => 3245
                    [type] => text
                    [name] => YearBuiltSource
                    [value] => Owner
                )

[field_3248] => Array
                (
                    [field_id] => 3248
                    [type] => datetime
                    [name] => OriginalEntryTimestamp
                    [value] => 09/02/2025 13:02:00
                )

[field_3260] => Array
                (
                    [field_id] => 3260
                    [type] => text
                    [name] => MLSPIN_DISCLOSURE
                    [value] => Y
                )

[field_3265] => Array
                (
                    [field_id] => 3265
                    [type] => price
                    [name] => MLSPIN_GRE
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3266] => Array
                (
                    [field_id] => 3266
                    [type] => price
                    [name] => MLSPIN_HTE
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3272] => Array
                (
                    [field_id] => 3272
                    [type] => text
                    [name] => MLSPIN_LEAD_PAINT
                    [value] => None
                )

[field_3277] => Array
                (
                    [field_id] => 3277
                    [type] => text
                    [name] => MLSPIN_MAIN_LO
                    [value] => AN1921
                )

[field_3280] => Array
                (
                    [field_id] => 3280
                    [type] => number
                    [name] => MLSPIN_MARKET_TIME_PROPERTY
                    [value] => 29
                )

[field_3281] => Array
                (
                    [field_id] => 3281
                    [type] => price
                    [name] => MLSPIN_MGF
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3282] => Array
                (
                    [field_id] => 3282
                    [type] => price
                    [name] => MLSPIN_MSE
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3285] => Array
                (
                    [field_id] => 3285
                    [type] => price
                    [name] => MLSPIN_OPTIONAL_FEE
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3290] => Array
                (
                    [field_id] => 3290
                    [type] => price
                    [name] => MLSPIN_PRICE_PER_SQFT
                    [raw] => 654.36
                    [unit_id] => 260
                    [value] => $654
                    [price_only] => $654
                )

[field_3292] => Array
                (
                    [field_id] => 3292
                    [type] => price
                    [name] => MLSPIN_RFS
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3293] => Array
                (
                    [field_id] => 3293
                    [type] => price
                    [name] => MLSPIN_RME
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3301] => Array
                (
                    [field_id] => 3301
                    [type] => select
                    [name] => RoomMasterBathroomFeatures
                    [value] => Yes
                )

[field_3306] => Array
                (
                    [field_id] => 3306
                    [type] => price
                    [name] => GrossScheduledIncome
                    [raw] => 0
                    [unit_id] => 260
                    [value] => $0
                    [price_only] => $0
                )

[field_3311] => Array
                (
                    [field_id] => 3311
                    [type] => number
                    [name] => BRE_Total_Parking
                    [value] => 4
                )

[f_3319] => Array
                (
                    [field_id] => 3319
                    [type] => feature
                    [name] => PatioAndPorchFeatures
                    [values] => Array
                        (
                            [0] => Patio
                        )

)

[field_3320] => Array
                (
                    [field_id] => 3320
                    [type] => boolean
                    [name] => Waterfront
                    [value] => No
                )

)

EXIT

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