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Offering nearly 2,600 sq. ft. of living space, this impressive Cape combines timeless charm, generous room sizes & an incredible layout designed for both everyday living & entertaining! Beautiful hardwood flooring flows throughout the main living areas, beginning with an oversized formal living room filled with natural light. The massive family room is sure to impress with a wood-burning fireplace framed by beautiful custom built-in cabinetry, creating a warm & inviting space to gather. The updated, fully applianced kitchen features granite countertops, gas range, ample cabinetry & a comfortable eat-in area for casual dining. Hosting holidays & special occasions will be a joy in the traditional dining room, complete with a charming built-in corner hutch & double Andersen window overlooking the backyard. Desirable first-floor primary suite offers generous closet space & private en-suite bath, while an additional spacious bedroom with double closet & full bath provides flexibility for a variety of living arrangements. Upstairs, you'll find TWO oversized bedrooms, one featuring a custom built-in armoire, along with a beautifully renovated full bath boasting a Jacuzzi tub. Need MORE space? The expansive lower level delivers! A massive recreation room with sliders to the exterior & garage offers endless possibilities for entertaining, game nights or additional living space. A separate flex area is ideal for a home office, fitness space or hobby room, while dedicated laundry hookups, abundant built-in shelving & an additional workshop or storage area with utility sink provide exceptional functionality. And the outdoor space is equally impressive! Enjoy summer days poolside in your very own inground pool, surrounded by a fully fenced yard with plenty of room for outdoor entertaining, recreation & relaxation. A storage shed adds even more convenience. With nearly 2,600 sq. ft., four generously sized bedrooms, three full baths, versatile lower-level space & a backyard designed for making memories, this home truly offers something for everyone! Just minutes to Interstate 91 & the Mass Pike, with convenient access to area amenities, this commuter's DREAM delivers the space, comfort & location you've been waiting for!

Highlights

  • Residential
  • Single Family Residence
  • Built in 1965
  • 0.34 Acre Lot
  • 2 Car Garage
  • 7 days on Market

Open House

  • November 14, 2026
    12:00pm - 1:30pm
  • November 15, 2026
    12:00pm - 1:30pm

This open house information was last updated on 11/12/2026 03:34AM

  • Bedrooms
    4
  • Bathrooms
    3
  • Year Built
    1965
  • Architectural Style
    Cape
  • Construction Materials
    Frame
  • Foundation
    Concrete Perimeter
  • Garage Spaces
    2.0
  • Parking Features
    Attached, Paved, Garage Door Opener, Garage, Off Street, Garage Faces Side
  • Living Area
    2596.0
  • Interior Features
    Master Downstairs
  • Appliances
    Dishwasher, Microwave, Refrigerator, Range, Disposal, Gas Water Heater, Water Heater
  • Flooring
    Hardwood, Tile, Vinyl, Carpet, Concrete
  • Exterior Features
    Storage
  • Patio And Porch
    Patio, Porch
  • Pool Features
    In Ground, Private
  • Cooling
    Ductless, Zoned, Wall Unit(s)
  • Heating
    Natural Gas, Baseboard, Zoned
  • Basement
    Full, Walk-Out Access, Partially Finished, Interior Entry, Concrete

  • Acres
    0.34
  • Lot Features
    Cul-De-Sac, Gentle Sloping
  • Water
    Public

  • Area
    Tatham
  • County
    Hampden
  • City
    West Springfield
  • Zip Code
    01089

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Frequently Asked Questions

How do I schedule a tour of 104 Winona Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 104 Winona Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 104 Winona Dr?

Click Ask a Question to talk with our team. You already know it is a 4 bed, 3 bath, listed for $499,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in West Springfield, and can even get you in to see the property quickly.

Are there any upcoming open houses for this property?

Yes—an open house is scheduled for . Let us connect you with our local expert before you go so they can help you prepare questions, highlight key features, and arrange a private tour if that time doesn't work.

How much is the monthly mortgage payment for 104 Winona Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 104 Winona Dr at around $3,378. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 104 Winona Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Hampden County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 104 Winona Dr?

In most cases, yes. Whether 104 Winona Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in West Springfield's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 104 Winona Dr?

We can handle that for you. Our preferred local agent specializes in residentials in West Springfield and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $499,000 with 2,596 sqft of space—that comes out to approximately $192 per square foot.

How long has this property been on the market?

104 Winona Dr was listed on November 06, 2026, which means it's been on the market for 7 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1965, making it approximately 61 years old.

What is the lot size of this property?

104 Winona Dr sits on a 0.34-acre lot, which is 14,810 square feet.

What are the property taxes for 104 Winona Dr?

The most recent public record shows annual property taxes for 104 Winona Dr were approximately $6,459. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 104 Winona Dr still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, MLS Property Information Network (MLS PIN). All rights reserved.

Last Updated: November 13, 2026 at 06:52AM | Source: MLS Property Information Network (MLS PIN) | MLS#: 73599732