20 Winter Street Medfield — Photo 1 of 41
Recent Drop: $30,000
$1,649,000
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.
Key facts
It was listed on September 15, 2026. The price has come down from an original $1,679,000 to $1,649,000, most recently on September 27, 2026. The annual property taxes are $19,367 (2026 tax year). It sits on a 1-acre (43,503 sq ft) lot.
Open Houses
Market Value Analysis
* Analysis is based on 12 actively listed and recently sold comparable properties strictly within Medfield, MA.
Property Details
Financials
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl Main,FirstFlooring - Hardwood, Recessed Lighting, Crown Molding
Dining Room
Lvl Main,FirstFlooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Decorative Molding
Kitchen
Lvl FirstFlooring - 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,FirstCathedral Ceiling(s), Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting
Primary Bedroom
Lvl SecondBathroom - 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 SecondBedroom 3
Lvl SecondWalk-In Closet(s), Flooring - Hardwood, Crown Molding
Bedroom 4
Lvl SecondCloset, Crown Molding
Bedroom 5
Lvl FirstWalk-In Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Crown Molding
Bathroom 1
Lvl FirstBathroom - Half, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Recessed Lighting
Bathroom 2
Lvl SecondBathroom - Full, Bathroom - Tiled With Tub & Shower, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Crown Molding
Bathroom 3
Lvl SecondBathroom - 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
$1,649,000
Was $1,679,000
Sep 27, 2026
MLS® 73577110
$1,679,000
Sep 15, 2026
MLS® 73577110
$1,699,000
Sep 13, 2026
MLS® 73548388
$1,699,000
Jul 13, 2026
MLS® 73548388
Questions about this home
When was 20 Winter Street, Medfield listed?
20 Winter Street, Medfield was listed on September 15, 2026.
Has the price of 20 Winter Street, Medfield changed?
The price has come down from an original $1,679,000 to $1,649,000, most recently on September 27, 2026.
What are the property taxes for 20 Winter Street, Medfield?
The annual property taxes for 20 Winter Street, Medfield are $19,367 (2026 tax year).
How big is the lot at 20 Winter Street, Medfield?
20 Winter Street, Medfield sits on a 1-acre (43,503 sq ft) lot.
What is the status of 20 Winter Street, Medfield?
20 Winter Street, Medfield is actively listed for sale.
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
1,524 housing units permitted in the last 12 months (+52% vs the prior 12 months) — 1,030 in 5+ unit buildings
U.S. Census Bureau, Building Permits Survey (through Jul '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.
Listing Agent: Gail Lidonni
Listing Office: Legacy Properties
MLS® Number: 73577110
