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8-10 Oak St, Winchester MA 01890

$1,125,000

Estimated $2,790/month Calculator

Multi Family

Total Units: 2

Price Per Unit: $562,500

Total Rent: 0/year

Estimated CAP Rate:

5 Bedrooms

Baths

2391

Total Parking: 3

4,674 (0.11)

Elegantly updated, two-family home offers flexibility for multi-generational living, rental income, or as a spacious single-family. Thoughtful renovations preserve the home's original character while adding modern comforts. A charming farmer's porch leads to an inviting patio. The larger side, 8 Oak, features 8 rooms, 4 beds, 1.5 baths, a 2024 eat-in kitchen with timeless cabinetry, quartz countertops, butcher block island, blue-and-white tile backsplash, exterior-vented gas range, and direct access to a 2024 TimberTech deck. Highlights include an inviting living room with embossed tin ceiling, a first-floor bedroom or office with floor-to-ceiling windows, wide-plank floors, a lower level family room that has a full walk-out to back yard, and 3 second-floor bedrooms. The full bath was beautifully renovated in 2020 with vintage-inspired washstand sinks. The unfinished basement includes laundry and ample storage. The apartment, 10 Oak, is a bright 3 rooms, 1 bed, 1 bath featuring original pine floors, a living room with access to deck, an eat-in kitchen, and a second-floor bedroom suite. Both sides feature mini-split heat and A/C. 8 Oak also offers gas baseboard and radiator heat and 10 Oak also has radiator heat. Three off-street parking spaces. Enjoy an unbeatable location just a short walk to Winchester Center, two MBTA Commuter Rail stations (only two stops to North Station), restaurants, cafés, and shops. Located in the sought-after Lynch Elementary School district and Winchester's top-rated school system. This special property blends timeless charm, modern updates, and exceptional versatility.

This home has been viewed 6 times

Last Checked: July 27th, 2026 at 7:39pm (Source: MLS PIN #73555245)

Gross Income: $0

Gross Expenses: $11,586

Net Income Calc: $11,586

Annual Expenses for 8-10 Oak St, Winchester MA 01890

Total Gross Expenses (Calculated)$11,586/year

APOD AvailableNo

Heating

Electricity

Water

Gas

Insurance

Sewer

Trash Removal

Repair & Maintenance

Management

Miscellaneous

Real Estate Tax11586

Annual Income & Unit Breakdown for 8-10 Oak St, Winchester MA 01890

Total Gross Income (Calculated)$0

Unit 1

Rental Income$0

LeaseN

Bedrooms4

Bathrooms1 Full, 1 Half

Floor0

Levels in Unit2

Rent IncludesHeat

Unit 2

Rental Income$0

LeaseN

Bedrooms1

Bathrooms1 Full

Floor0

Levels in Unit2

Rent IncludesHeat

General Information for 8-10 Oak St, Winchester MA 01890

Listing ID73555245

Property TypeMulti Family

Price1125000 ($470.51/SqFt)

StyleMulti Family

CityWinchester

CountyMiddlesex

Neighborhood(s)

Approximate Living Area Total2391

Approximate Lot Size (Acres)0.11

Total Parking3

Garage Parking0

Year Built1870

Year Built SourcePublic Records

Year Built DetailsActual

WaterPublic

SewerPublic Sewer

Electric

Hot Water

Roof MaterialAsphalt/fiberglass Shingles

BasementFull

Construction MaterialsFrame

Lot FeaturesGentle Sloping

Foundation Description

Accessible Features

Outdoor SpaceCovered

ZoningRG

Water Views

Water Views Features

Waterfront0

Waterfront Features

Terms

Disclosures for 8-10 Oak St, Winchester MA 01890

Lead PaintNone

UFFI

Living Area Includes BasementYes

Living Area Disclosure

Building Area SourceMeasured

ExclusionsElectric Fireplace

Financial Data Source

Total Gross Expenses By Broker

Total Gross Income By Broker

Total Net Income By Broker

Short Sale / Forclosure (Bank Owned)

Compensation Based On

Financial Information for 8-10 Oak St, Winchester MA 01890

Real Estate Taxes11586

Tax Year2026

Assessed Value$1,045,600

Financial Data Source

Total Gross Expenses By Broker

BostonRealEstate.com Gross Expenses

Total Gross Income By Broker

BostonRealEstate.com Gross Income

Total Net Income By Broker

BostonRealEstate.com Gross NOI

CAP Rate (based on Broker info)

Location Information for 8-10 Oak St, Winchester MA 01890

Elementary SchoolLynch Elementary School

Middle SchoolMccall Middle School

High SchoolWinchester Highschool

Neighborhood(s)

Area AmenitiesWalk/jog Trails

Contact Information for 8-10 Oak St, Winchester MA 01890

Agent

Name: The Synergy Group

Office

Name: The Synergy Group

Phone: 888-410-5454

Team Members

Payment Calculator

, Interest

Property Taxes 965.5

Principal & Interest 6931.89

HOA Dues

Term

Interest

Home Price

Down Payment

Exclusive Listing Agent

The Synergy Group

Agent Phone

Office Phone

(888) 410-5454

Text Agent Call Agent Call Office

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    [unparsed] => 8-10 Oak St, Winchester MA 01890
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EXIT

35 More Photos

Active

8-10 Oak St, Winchester MA 01890

$1,125,000

Annual Expenses for 8-10 Oak St, Winchester MA 01890

Annual Income & Unit Breakdown for 8-10 Oak St, Winchester MA 01890

General Information for 8-10 Oak St, Winchester MA 01890

Disclosures for 8-10 Oak St, Winchester MA 01890

Financial Information for 8-10 Oak St, Winchester MA 01890

Location Information for 8-10 Oak St, Winchester MA 01890

Contact Information for 8-10 Oak St, Winchester MA 01890

Agent

Office

Team Members

Payment Calculator

Exclusive Listing Agent

The Synergy Group

The Synergy Group