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One of Winchester’s most beloved neighborhoods sets the tone for 30 Prospect Street, a beautifully reimagined home transformed by an extensive remodel less than five years ago. A spectacular, fully renovated Chef’s kitchen anchors the main level with high-end finishes and a seamless flow for living and entertaining. The living room is sunny and inviting, featuring an impressive fireplace, timeless details, and a beautiful view of the gorgeous backyard. The adjoining dining room offers a refined space for gatherings with its classic architectural charm. The new primary suite includes a spa-inspired bath and custom walk-in closet, while additional bathrooms have been fully renewed with elegant finishes. Architectural extensions enhance natural light and expand the home’s functionality. Outside, the refreshed exterior and professionally designed landscaping deliver exceptional curb appeal and serene outdoor living. A rare opportunity for turnkey sophistication in Winchester.
Current real estate data for Single Family in Winchester as of Nov 17, 2025
63
Single Family Listed
69
Avg DOM
554
Avg $ / SqFt
$2,056,473
Avg List Price

Property Details

Price:
$2,099,000
MLS #:
73455307
Status:
Active
Beds:
4
Baths:
3
Type:
Single Family
Subtype:
Single Family Residence
Listed Date:
Nov 15, 2025
Finished Sq Ft:
2,519
Total Sq Ft:
2,519
Lot Size:
21,589 sqft / 0.50 acres (approx)
Year Built:
1934
WoodedPoolTennisLincolnMccall MiddleWinchester High

Schools

Elementary School:
Lincoln
Middle School:
Mccall Middle
High School:
Winchester High

Interior

Appliances
Gas Water Heater, Water Heater, Range, Dishwasher, Microwave, Refrigerator
Bathrooms
3 Full Bathrooms
Cooling
Central Air
Fireplaces Total
1
Flooring
Tile, Hardwood
Heating
Forced Air, Natural Gas
Laundry Features
Electric Dryer Hookup, Washer Hookup

Exterior

Architectural Style
Tudor
Community Features
Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Bike Path, Conservation Area, Highway Access, House of Worship, Public School, T-Station
Construction Materials
Frame, Brick
Exterior Features
Deck
Parking Features
Attached, Paved Drive, Paved
Parking Spots
3

Financial

Tax Year
2019
Taxes
$18,198

Map

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Community

Property Summary

    30 Prospect St Winchester MA is a Single Family for sale in Winchester, MA, 01890. It is listed for $2,099,000 and features 4 beds, 3 baths, and has approximately 2,519 square feet of living space, and was originally constructed in 1934. The current price per square foot is $833. The average price per square foot for Single Family listings in Winchester is $554. The average listing price for Single Family in Winchester is $2,056,473. To schedule a showing of MLS#73455307 at 30 Prospect St in Winchester, MA, contact your Boardwalk Real Estate Corp. agent at 781-944-7820.

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CRP: Certified Relocation Professional
CRS: Certified Residential Specialist
GRI: Graduate of Realtors Institute
CBR: Certified Buyers Representative
BSBA: Bachelor of Science in Business Administration. Babson College 1979
MBA: Master of Business Administration. Babson College 2002

James M. Joly is President and Principal-Owner of Boardwalk Real Estate Corp.,…

More About James
30 Prospect St
Winchester, MA