276 High St, Winchester, MA, 01890
About This Home
Discover this beautiful home with all the space you've been looking for! Set on a private half-acre lot in a serene cul-de-sac near the Winchester/Lexington border. This residence offers unparalleled privacy & is surrounded by nature. This home includes 5 bedrooms, 3.5 bathrooms & an oversized 3 car garage! The spacious grounds feature delightful front & back yards, a generous deck, & a charming gazebo, all beside Whipple Hill & Smith Pond w/ miles of walking trails nearby! Inside you will find a thoughtfully designed floor plan for every day living & entertaining featuring a sunken living room, sunny home office, lovely formal dining room & oversized family kitchen w dining area showcasing walls of windows overlooking the stunning rear yard & an adjacent family room w/ wood burning fireplace. The oversized primary suite incudes a walk in closet & spacious bath. Just 7 miles from Boston, Winchester is known for top-rated schools & great quality of life. Don't miss this fabulous home!
Getting Around
Car-Dependent
Very Limited Transit
Somewhat BikeableSchools
Construction
Condition
- Year built: 1992
Materials
- Foundation: Concrete Perimeter
- Roof: Shingle
- Construction materials: Frame
Type & Style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subType: Single Family Residence
Interior
Appliances
- Appliances included: Water Heater,Range,Oven,Dishwasher,Disposal,Trash Compactor,Microwave,Refrigerator,Freezer,Washer,Dryer,Plumbed For Ice Maker
- Laundry features: Second Floor,Electric Dryer Hookup,Washer Hookup
Basement
- Has basement: Yes
- Basement: Full,Finished,Interior Entry
Bathroom1
- Features: Bathroom - Half
- Level: First
- Area: 40
Bathroom2
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Shower Stall, Bathroom - Tiled With Tub, Closet, Flooring - Stone/Ceramic Tile, Jacuzzi / Whirlpool Soaking Tub
- Level: Second
- Area: 156
Bathroom3
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Bathroom - Tiled With Tub & Shower
- Level: Second
- Area: 81
Bedroom2
- Features: Ceiling Fan(s), Closet, Lighting - Overhead
- Level: Second
- Area: 238
Bedroom3
- Features: Ceiling Fan(s), Closet, Lighting - Overhead
- Level: Second
- Area: 195
Bedroom4
- Features: Ceiling Fan(s), Closet, Lighting - Overhead
- Level: Second
- Area: 168
Bedroom5
- Features: Ceiling Fan(s), Closet, Lighting - Overhead
- Level: Third
- Area: 528
Bedrooms & Bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Dining Room
- Features: Flooring - Hardwood, Window(s) - Picture, French Doors, Lighting - Pendant, Lighting - Overhead
- Level: First
- Area: 225
Family Room
- Features: Ceiling Fan(s), Flooring - Hardwood, Balcony / Deck, Deck - Exterior, Exterior Access, Lighting - Overhead
- Level: First
- Area: 660
Features
- Bathroom - Tiled With Shower Stall,Bathroom - Full,Bathroom - With Shower Stall,Recessed Lighting,Closet,Lighting - Overhead,Bathroom,Game Room,Office,Central Vacuum,Walk-up Attic
- Door features: Insulated Doors
- Window features: Insulated Windows
- Flooring: Tile,Carpet,Hardwood,Flooring - Wall to Wall Carpet,Flooring - Hardwood
- Number of fireplaces: 1
- Fireplace features: Family Room
- Fireplace: Yes
- Finished area below ground: 739
- Finished area above ground: 4,267
Heating & Cooling
- Heating features: Forced Air,Oil
- Cooling features: Central Air,Dual
Interior Area
- Total structure area: 5,006
- Total interior livable area: 5,006 sqft
Kitchen
- Features: Closet/Cabinets - Custom Built, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, French Doors, Kitchen Island, Breakfast Bar / Nook, Exterior Access, Open Floorplan, Recessed Lighting, Stainless Steel Appliances, Lighting - Pendant
- Level: Main,First
- Area: 240
Living Room
- Features: Flooring - Hardwood, Open Floorplan, Sunken, Lighting - Overhead
- Level: First
- Area: 210
Master Bathroom
- Features: Yes
Master Bedroom
- Features: Bathroom - Full, Bathroom - Double Vanity/Sink, Closet - Linen, Flooring - Stone/Ceramic Tile, French Doors, Lighting - Sconce, Lighting - Overhead
- Level: Second
- Area: 598
Office
- Features: Closet, Flooring - Hardwood, Lighting - Overhead
- Level: First
- Area: 154
Property
Details
- Parcel number: M:025 B:0146 L:0,900972
- Zoning: RDA
Features
- Patio & porch: Deck
- Exterior features: Deck,Rain Gutters,Sprinkler System,Gazebo
Lot
- Lot size: 0.46 Acres
Parking
- Total spaces: 9
- Parking features: Attached,Paved Drive,Off Street
- Has garage: Yes
- Attached garage spaces: 3
- Covered spaces: 3
- Has uncovered spaces: Yes
- Uncovered spaces: 6
Climate Risk is Financial Risk
Every home has a financial story beyond the listing price. Below, you’ll see the climate risks that could affect this property — and in Bills & Affordability, how those risks may influence repairs, insurance, utilities, and long-term value.
Biggest Threats for This Home
- Inland Flooding
- Ice Storm
- Tsunami
How This Home’s Risks Compare
FEMA Declared Disasters Across Massachusetts Counties
Understanding the Costs
Financial advisors generally recommend spending no more than 30% of your gross household income on housing costs. In practice, many households stretch to 35% or beyond — especially in high-cost markets.
Estimated Costs Today
| Monthly | Annual | |
|---|---|---|
| Mortgage | $11,099 | $133,188 |
| Home Insurance * | $397 | $4,764 |
| Property Taxes | $2,007 | $24,084 |
| Electricity | $987 | $11,845 |
| Total | $14,490 | $173,880 |
Income You'd Need if You Spent...
Massachusetts FAIR Plan Programs
How Costs Could Change Over Time
Climate risk is quickly impacting all of the major home ownership costs. Adjust the growth rates and percentage of income spent on housing below to see how your housing costs could change over the next 10 years — and what income you'd need to keep up.
Comparing Against the Market
Price Per Sq Ft
vs Other Active Listings
Avg $/sqft
vs Homes Sold Last Month
Median $/sqft
Current Market Trends
Median Price Per Square Foot
The median price per square foot of homes sold in this area each month. Compare this to this listing's price per square foot to gauge whether the home is priced in line with recent sales.
Historicals for This Listing
Zestimate History ($/sqft)
Price History
| Date | Event | Price |
|---|---|---|
| 2026-05-13 | Price change | $2,195,000 |
| 2026-04-06 | Listed for sale | $2,299,000 |
| 2025-12-16 | Listing removed | $2,299,000 |
| 2025-09-25 | Price change | $2,299,000 |
| 2025-07-15 | Listed for sale | $2,350,000 |
| 2025-06-16 | Listing removed | $2,399,000 |
| 2025-04-04 | Price change | $2,399,000 |
| 2025-03-24 | Listed for sale | $2,599,000 |
| 2024-09-15 | Listing removed | $2,750,000 |
| 2024-07-05 | Price change | $2,750,000 |
| 2024-04-25 | Price change | $2,870,000 |
| 2024-04-13 | Price change | $2,830,000 |
| 2024-01-28 | Listed for sale | $2,930,000 |
| 2023-11-29 | Listing removed | $2,590,000 |
| 2023-10-14 | Listed for sale | $2,590,000 |
| 2018-08-27 | Listing removed | $6,800 |
| 2018-08-08 | Price change | $6,800 |
| 2018-07-22 | Listed for rent | $7,500 |
| 2017-07-28 | Listing removed | $5,600 |
| 2017-07-12 | Price change | $5,600 |
| 2017-04-03 | Price change | $6,000 |
| 2017-02-22 | Price change | $5,000 |
| 2017-02-03 | Listed for rent | $5,500 |
| 1999-06-14 | Sold | $772,500 |
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