$2,380,000
14 Hillside Ave
Winchester, MA, 01890
Fully gutted in 2026, this exceptional Winchester home offers the perfect blend of luxury, craftsmanship, and location. Featuring a brand-new roof, upgraded 400-amp electrical service, designer kitchen, beautifully renovated baths, and HVAC systems and all-new finishes throughout. First floor featuring wide open large living & dinning area with a family room. 2nd floor featuring (3) main bedroom with full baths suites. The stunning finished lower level includes a custom wine cellar and recreation area, and flexible rooms perfect for a home office, gym, media room, or guest accommodations.. Ideally located just minutes from Winchester’s highly rated schools, town center, parks, dining, and commuter routes. Move-in ready and thoughtfully redesigned for modern living—this is a rare opportunity in one of Winchester’s most sought-after neighborhoods.
Property Details
Price:
$2,380,000
MLS #:
73541163
Status:
Active
Beds:
4
Baths:
4.5
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Jun 24, 2026
Finished Sq Ft:
3,881
Total Sq Ft:
3,881
Lot Size:
12,057 sqft / 0.28 acres (approx)
Year Built:
1870
Schools
Elementary School:
Lincoln
Middle School:
Mccall Middle
High School:
Winchester Hs
Interior
Above Grade Finished Area
2615
Appliances
Electric Water Heater, Range, Oven, Dishwasher, Disposal, Refrigerator
Bathrooms
4 Full Bathrooms, 1 Half Bathroom
Below Grade Finished Area
1266
Cooling
Central Air, Heat Pump
Fireplaces Total
2
Flooring
Vinyl, Hardwood
Heating
Central, Electric
Interior Features
Bonus Room, Wine Cellar
Laundry Features
First Floor, Electric Dryer Hookup, Washer Hookup
Exterior
Architectural Style
Colonial, Victorian, Italianate
Community Features
Park, Public School
Covered Spaces
1
Exterior Features
Deck
Garage Spaces
1
Open Parking Spaces
9
Open Parking YN
1
Parking Features
Detached, Paved Drive, Off Street
Parking Spots
10
Parking Total
10
Patio And Porch Features
Deck
Financial
Tax Year
2025
Taxes
$16,639
Marie Andrews is an award-winning, licensed real estate broker with licenses in Massachusetts and Florida. She has been selling real estate in the greater Boston area for over 20 years. Over the past two decades, Marie has worked for Century 21 Advanced Realty, building a reputation as a multi-million dollar producer. She has developed an extensive network of investors, lenders, and attorneys. Marie has a wide knowledge base on property management, Massachusetts real estate law, and building…
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Map
Current real estate data for Single Family in Winchester as of Jul 12, 2026
70
Single Family Listed
67
Avg DOM
542
Avg $ / SqFt
$2,029,207
Avg List Price
Community
- Address14 Hillside Ave Winchester MA
- CityWinchester
- CountyMiddlesex
- Zip Code01890
Subdivisions in Winchester
- Brooks / Parkhurst / Town Forest
- Cox Road / High St Extension neighborhood
- Flats
- Flats neighborhood
- Lakeview/Wedgemere~ Near downtown & Wedgemere train station
- Macdonald field neighborhood
- Middlesex / downtown
- Near town/ Pine St neighborhood
- Old Village/ West Side
- Rangeley Historical Estate
- The Flats
- Vinson-Owen School District.
- West Side
- Winning Farm
Similar Listings Nearby
Property Summary
- 14 Hillside Ave Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,380,000 and features 4 beds, 5 baths, and has approximately 3,881 square feet of living space, and was originally constructed in 1870. The current price per square foot is $613. The average price per square foot for Single Family listings in Winchester is $542. The average listing price for Single Family in Winchester is $2,029,207. To schedule a showing of MLS#73541163 at 14 Hillside Ave in Winchester, MA, contact your Pegasus Realty LLC agent at 781-858-3505.
Courtesy of East West Real Estate, LLC. The property listing data and information set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information 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. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information set forth herein.
14 Hillside Ave
Winchester, MA