Active
58 Days on market
20 Winter Street Medfield — Photo 1 of 42

20 Winter Street Medfield — Photo 1 of 42

Recent Drop: $51,000

$1,750,000
$1,699,000

$1,699,000

20 Winter Street, Medfield, MA 02052

Medfield, MA 02052

Beds

5

Baths

2.5

SqFt

4,208

Style

Single Family

Built

2001

Exquisite home located on a beautifully landscaped one-acre lot just minutes from Medfield's vibrant town center, and top-rated schools. Quality craftsmanship shines throughout with hardwood floors, custom millwork and elegant finishes. A welcoming mahogany farmer's porch leads to a dramatic two-story foyer. The granite kitchen with stainless steel appliances, wall oven, electric cooktop and dining area opens to a vaulted fireplaced family room with a wall of windows and French doors to a bluestone patio with retractable awning and hot tub overlooking the private backyard. The main level also features a formal dining room, fireplaced living room, half bath, mudroom and a versatile first-floor bedroom or home office. Upstairs offers a spacious primary suite with walk-in closet and spa-like bath, plus three additional bedrooms, full bath and laundry. Walkout lower level with recreation space, workshop and ample storage. A wonderful combination of quality, comfort and outdoor living.

Market Value Analysis

This Property
Size (SqFt) →Price →
This Property$404/sqft
Local Avg (Medfield)$415/sqft
3% BelowMarket Average

* Analysis is based on 8 actively listed and recently sold comparable properties strictly within Medfield, MA.

Property Details

Financials

Original Price$1,750,000
Annual Taxes$19,367

Parking

Garage2
Off-Street12

Interior Specifications

Total Rooms12
Fireplaces3
FlooringTile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
BasementFull, Finished, Interior Entry, Sump Pump

Climate & Utilities

HeatingBaseboard, Oil
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRES

Property & Lot

Acres1
SqFt Lot43,503
Lot FeaturesLevel

Amenities & Appliances

Oven • Dishwasher • Disposal • Microwave • Range • Refrigerator • Washer • Dryer • Plumbed For Ice Maker

Neighborhood

Shopping • Tennis Court(s) • Park • Walk/Jog Trails • Conservation Area • House of Worship

Geography

Floorplan Breakdown

Structural Layout

Second
Master BedroomBedroom 2Bedroom 3Bedroom 4Bathroom 2Bathroom 3
First
KitchenBedroom 5Bathroom 1
Main,First
Living RoomDining RoomFamily Room
Living Room
Lvl Main,First

Flooring - Hardwood, Recessed Lighting, Crown Molding

Dining Room
Lvl Main,First

Flooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Decorative Molding

Kitchen
Lvl First

Flooring - Stone/Ceramic Tile, Dining Area, Countertops - Stone/Granite/Solid, French Doors, Cabinets - Upgraded, Exterior Access, Recessed Lighting, Stainless Steel Appliances, Crown Molding

Family Room
Lvl Main,First

Cathedral Ceiling(s), Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting

Master Bedroom
Lvl Second

Bathroom - Full, Bathroom - Double Vanity/Sink, Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Recessed Lighting, Lighting - Pendant, Half Vaulted Ceiling(s), Decorative Molding

Bedroom 2
Lvl Second
Bedroom 3
Lvl Second

Walk-In Closet(s), Flooring - Hardwood, Crown Molding

Bedroom 4
Lvl Second

Closet, Crown Molding

Bedroom 5
Lvl First

Walk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Crown Molding

Bathroom 1
Lvl First

Bathroom - Half, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Recessed Lighting

Bathroom 2
Lvl Second

Bathroom - Full, Bathroom - Tiled With Tub & Shower, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Crown Molding

Bathroom 3
Lvl Second

Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub

Property History

Price Drop
$1,699,000

Was $1,750,000

Sep 1, 2026

MLS® 73548388

Listed
$1,750,000

Jul 13, 2026

MLS® 73548388

Population

13,068

U.S. Census Bureau, ACS 2024 5-Year Estimates (B01003)

Median Household Income

$236K

U.S. Census Bureau, ACS 2024 5-Year Estimates (B19013)

Renter-Occupied Homes

13.9%

U.S. Census Bureau, ACS 2024 5-Year Estimates (B25003)

New Construction Permits — Norfolk County

1,189 housing units permitted in the last 12 months (+21% vs the prior 12 months) — 706 in 5+ unit buildings

U.S. Census Bureau, Building Permits Survey (through Jun '26)

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 4,208 sq ft principal dwelling). Lot size: 43,503 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Full Medfield, MA market report ZIP 02052 market data
Listing Provided By

Listing Agent: Gail Lidonni

Listing Office: Legacy Properties

MLS® Number: 73548388

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