20 Winter Street Medfield — Photo 1 of 42
Recent Drop: $51,000
$1,699,000
Investment Analysis — 20 Winter Street
Medfield, MA 02052
Based on HUD Small Area Fair Market Rent for Boston-Cambridge-Quincy, MA-NH HUD Metro FMR Area, a 5-bedroom in 02052 carries an estimated $3,390/mo in gross rent — about a 0.68% cap rate and $11,550/yr in estimated NOI at the $1,699,000 list price. Adjust every assumption in the calculator below.
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.
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.
Estimates — not financial advice
These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.
Open Houses
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
Master 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
$1,699,000
Was $1,750,000
Sep 1, 2026
MLS® 73548388
$1,750,000
Jul 13, 2026
MLS® 73548388
Listing Agent: Gail Lidonni
Listing Office: Legacy Properties
MLS® Number: 73548388
