Keith Wade
eXp Realty
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For Sale · 32 days↗ Share♡ Favorite
$1,549,000↓ $100K price cut 10-13-2026

20 Winter St, Medfield, MA 02052  Medfield

SFR
5Beds
2.5Baths
4,208Sq Ft
1.00Acres
2001Year Built
32DOMi

Home Highlights

Private Spa
2‑Car Garage
Finished Basement1,925 finished sq ft
Fireplace3 fireplaces
6% Under Estimated ValueCotality estimate: $1,653,100
10% Below Area $/Sq Ft$368 vs $411, the Medfield median
Minimal Flood RiskFEMA Zone X (unshaded)
3 Zoned SchoolsRated up to 9/10

About This Home

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.
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Key Details

MLS #73577110
Monthly HOA$0
Price / Sq Ft$368
Property TypeSingle Family
Subdivision
Tax (2026)$19,367
Assessed Value$1,432,500

How This Home Compares

vs. the 27 homes for sale in Medfield
Price$1,549,000
48% above the median Medfield home ($1,049,000).
Price per Sq Ft$368
10% below the median Medfield home ($411).
Home Size4,208 sq ft
91% larger than the median Medfield home (2,204 sq ft).
Lot Size1.00 acres
64% larger than the median Medfield home (0.61 acres).
Days on Market32 days
About the same as the median Medfield home.

20 Winter St at a Glance

MLS# 73577110

Offered at $1,549,000, this 5 bed, 2.5 bath home has 4,208 square feet of living space and was built in 2001. It sits in Medfield, zoned for Dale Street School, Thomas Blake Middle School and Medfield Senior High School.

Want to see it in person? Schedule a showing or call Keith Wade at 603-818-7976.

Property Details

Interior Features

  • Closet
  • Lighting - Pendant
  • Decorative Molding
  • Closet/Cabinets - Custom Built
  • Beadboard
  • Crown Molding
  • Walk-in Closet(s)
  • Recessed Lighting
  • Lighting - Overhead
  • Entrance Foyer
  • Mud Room
  • Play Room
  • Central Vacuum
  • Door FeaturesFrench Doors
  • FlooringTile, Carpet, Hardwood, Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Flooring - Wall to Wall Carpet
  • Window FeaturesInsulated Windows

Kitchen and Appliances

  • Oven
  • Dishwasher
  • Disposal
  • Microwave
  • Range
  • Refrigerator
  • Washer
  • Dryer
  • Plumbed for Ice Maker
  • Laundry FeaturesDryer Hookup - Electric, Washer Hookup, Countertops - Stone/Granite/Solid, Electric Dryer Hookup, Crown Molding, Second Floor
  • Dining Room FeaturesFlooring - Hardwood, Window(s) - Picture, Lighting - Pendant, Decorative Molding
  • Dining Room LevelMain,First
  • Kitchen FeaturesFlooring - Stone/Ceramic Tile,Dining Area,Countertops - Stone/Granite/Solid,French Doors,Cabinets - Upgraded,Exterior Access,Recessed Lighting,Stainless Steel Appliances,Crown Molding
  • Kitchen LevelFirst

Pool and Spa

  • Spa FeaturesPrivate
  • Spa

Exterior and Lot

  • Porch
  • Patio
  • Rain Gutters
  • Hot Tub/Spa
  • Professional Landscaping
  • Sprinkler System
  • Decorative Lighting
  • Garden
  • Stone Wall
  • Other StructuresWorkshop
  • Patio and Porch FeaturesPorch, Patio
  • Road Frontage TypePublic
  • Road ResponsibilityPublic Maintained Road
  • Road Surface TypePaved
  • Patio
  • Porch

Garage and Parking

  • Attached Garage
  • Covered Spaces2
  • Garage Spaces2
  • Open Parking
  • Parking FeaturesAttached, Garage Door Opener, Paved Drive, Off Street
  • Parking Total12

Building and Construction

  • Total Square Feet Living4,208
  • Year Built2001
  • Above Grade Finished Area4,208
  • BelowGradeFinishedArea1,925
  • Building Area Total4,208
  • Building Area UnitsSquare Feet
  • Construction MaterialsFrame
  • Foundation DetailsConcrete Perimeter
  • Property Age25
  • RoofShingle
  • Year Built DetailsActual
  • Year Built SourcePublic Records
  • Architectural StyleCape

Bedrooms and Bathrooms

  • Bedrooms5
  • Primary Bedroom LevelSecond
  • Bedroom 2 LevelSecond
  • Bedroom 3 LevelSecond
  • Bedroom 4 LevelSecond
  • Bedroom 5 LevelFirst
  • Primary Bedroom FeaturesBathroom - 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 FeaturesWalk-in Closet(s), Flooring - Hardwood, Window(s) - Bay/Bow/Box, Crown Molding
  • Bedroom 3 FeaturesWalk-in Closet(s), Flooring - Hardwood, Crown Molding
  • Bedroom 4 FeaturesCloset, Crown Molding
  • Bedroom 5 FeaturesWalk-in Closet(s), Closet/Cabinets - Custom Built, Flooring - Hardwood, Window(s) - Picture, Crown Molding
  • Total Bathrooms2.5
  • Full Bathrooms2
  • 1/2 Bathrooms1
  • Bathroom 1 LevelFirst
  • Bathroom 2 LevelSecond
  • Bathroom 3 LevelSecond
  • Primary Bathroom Features
  • Bathroom 1 FeaturesBathroom - Half, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Recessed Lighting
  • Bathroom 2 FeaturesBathroom - Full, Bathroom - Tiled with Tub & Shower, Closet - Linen, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Crown Molding
  • Bathroom 3 FeaturesBathroom - 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

Other Rooms

  • Total Rooms12
  • Basement FeaturesFull, Finished, Interior Entry, Sump Pump
  • Family Room LevelMain,First
  • Living Room LevelMain,First
  • Family Room FeaturesCathedral Ceiling(s), Flooring - Hardwood, French Doors, Exterior Access, Recessed Lighting
  • Living Room FeaturesFlooring - Hardwood, Recessed Lighting, Crown Molding

Heating and Cooling

  • Cooling FeaturesCentral Air
  • Fireplace FeaturesFamily Room, Living Room
  • Heating FeaturesBaseboard, Oil
  • Heating
  • Number of Fireplaces3

Land Info

  • Lot DescriptionLevel
  • Lot Size Acres1
  • Lot Size Square Feet43,503

Homeowners Association

  • AssociationNo
  • Calculated Total Monthly Association Fees0

School Information

  • Elementary SchoolMem, Whee, Dale
  • High SchoolMedfield High
  • Middle SchoolBlake Middle

Amenities and Community Features

  • Community FeaturesShopping, Tennis Court(s), Park, Walk/Jog Trails, Conservation Area, House of Worship, Private School, Public School

Other Property Info

  • Annual Tax Amount19,367
  • Source Listing StatusPrice Changed
  • CountyNorfolk County
  • DirectionsFrom Center of Medfield Take North Street. Right Onto Winter. Home Is #20 on the Left.
  • Tax Year2026
  • Source Property TypeResidential
  • ExclusionsAll Personal Property.
  • Home WarrantyNo
  • Parcel Number114840
  • Postal Code Plus 41311
  • ZoningRES
  • Property SubtypeSingle Family Residence

Utilities

  • ElectricCircuit Breakers, 200+ Amp Service
  • SewerPublic Sewer
  • For Electric Range
  • For Electric Oven
  • For Electric Dryer
  • Washer Hookup
  • Icemaker Connection
  • Water SourcePublic

Home Features

  • Green Energy EfficientThermostat
  • Security FeaturesSecurity System

Schools Zoned for This Home

Medfield School District
Dale Street Schoolelementary · 4-5Photo: web
Dale Street School
0.5 mi away383 studentsPublic
Thomas Blake Middle Schoolmiddle · 6-8Photo: web
Thomas Blake Middle School
1.1 mi away567 studentsPublic
Medfield Senior High Schoolhigh · 9-12Photo: web
Medfield Senior High School
1.1 mi away713 studentsPublic

Mortgage Calculator

For 20 Winter St, Medfield, MA 02052
Estimated Monthly Payment
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Rate from today's national average (7.28%). Includes estimated property taxes and HOA; homeowners insurance not included. An estimate, not a loan offer.

Price History

Listed For
$1,549,000on 10-13-2026
Last Sold $1,330,000 on 06-24-2021
First Recorded Sale $263,000 in 1994
SoldListed
DateEventPriceChange
10-13-2026MLSPrice ChangedPrice Changed$1,549,000−$100,000−6.1%
09-27-2026MLSPrice ChangedPrice Changed$1,649,000−$30,000−1.8%
MLSListedListed$1,679,000−$20,000−1.2%
09-13-2026MLSListing RemovedListing Removed——
09-01-2026MLSPrice ChangedPrice Changed$1,699,000−$51,000−2.9%
MLSListedListed$1,750,000+$420,000+31.6%
06-24-2021MLSSoldSold$1,330,000+$1,067,000+405.7%
10-27-1994Public RecordSoldSold$263,000—

Sale prices from public records; list prices from the MLS. Taxes shown are for the prior owner and can change after a sale.

20 Winter St FAQ

At $1,549,000, the asking price of 20 Winter St is 47.7% above the median asking price of $1,049,000 for homes for sale in Medfield.

  • Its price per square foot is $368, 10.4% below the median of $411 for homes for sale in Medfield.
  • That is the 9th lowest price per square foot of the 26 homes for sale in Medfield that list their size.

More Homes in Medfield

Listed by Gail LiDonni of Legacy Properties

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting 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, leasing or renting. 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, or as to the accuracy of any of the Images, set forth herein.

©2026 MLS Property Information Network (MLS PIN). All rights reserved.

Listing Information Last Updated 10-17-2026

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