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Bean Group
Offered at $644,900Active
beds
4
baths
3
sq ft
2,487
Built
1961

29 Shady Side Dr

Longmeadow, MA 01106

About this home

Second Chance at this gorgeous home with an NEW attractive price! Back On Market Due to Buyer Financing. Found In the heart of one of Longmeadow's most coveted neighborhoods is this Exceptionally Maintained Cape that's situated on a beautifully landscaped with a private setting offering sophisticated living designed for today's lifestyle. Blended with warmth and charm with over 2,400 square feet of comfortable living ideal for family and friends to gather. Once inside you are welcomed into a stunning family room with soaring vaulted ceilings with views of the private backyard oasis complete with an oversized composite deck, cabanas, and a heated above ground salt water pool that makes entertaining a dream. The open kitchen features many traditional cabinets, lots of counterspace with stainless appliances and tile floor. The kitchen flows effortlessly into the formal dining room accented with a chair rail and hardwood floors will make every day dining feel like a special occasion. The inviting living room is perfect for relaxing by the cozy wood burning fireplace, gleaming hardwood floors and picture window fills the room with sunlight. A highly desirable first floor primary bedroom has abundant closets and rich hardwood floors. Also on the first floor a second bedroom provides ease for guests, family or as a home office. The main first floor bathroom is where you can unwind in the spa inspired bath featuring a luxurious soaking tub and shower. Also for an added convenience on the first floor is the sparkling half bathrm. Upstairs on the 2nd floor you'll find two exceptionally spacious bedrooms with roomy closets. One of the bedrooms features a tandem bonus room which is ideal for a dressing room, playroom, office or private guest room. If you need more room the partially finished basement offers additional living area for recreational room or a home gym. Additional highlights include mostly Anderson replacement windows, freshly painted exterior, newer gutters, upgraded concrete driveway and energy saving solar panels for added efficiency. This captivating home is all about comfort, style, indoor and outdoor living at its finest in one of Longmeadow's premier locations. It's a Dream Come True!

Listing last checked: Listing updated:

Listed by Kelley & Katzer Team · Kelley & Katzer Real Estate, LLC · MLS #73556761

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Details at a glance

Interior6 property facts
Rooms
9
Heating
Forced Air, Natural Gas
Cooling
Central Air
Flooring
Wood, Tile, Hardwood, Flooring - Hardwood, Laminate
Basement
Yes · Full, Crawl Space, Partially Finished, Interior Entry, Bulkhead, Concrete
Fireplaces
1
Building6 property facts
Style
Single Family Residence
Year built
1961
Garage
2
Parking
8
Foundation
Concrete Perimeter
Roof
Shingle
Land & utilities5 property facts
Lot size
0.53 acres
Water
Public
Sewer
Public Sewer
Pool
Yes · Heated, Private
Zoning
RA2
Financial2 property facts
Annual taxes
$12,154
Assessment year
2026

Location

Estimated monthly cost

Explore costs at the $644,900 asking price. Adjust the assumptions to your situation.

Known monthly costs$4,274 / monthAdjust
Principal & interest
$3,261
Property tax
$1,013
Insurance
Not entered
HOA
Not entered

Listing annual taxes: $12,154. Initial monthly tax is one twelfth of that amount. HOA amount was not supplied.

Partial estimate: add insurance, monthly HOA to include those costs. Blank amounts are unknown.

The initial 6.5% rate is illustrative, not a current rate or lender quote. Excludes utilities, maintenance, closing costs and mortgage insurance, which may apply with a down payment below 20%. Taxes and insurance can change.

More property insights

Automated value estimate $670,000

Estimated range $620,000–$725,000.

Automated estimates are not appraisals or guarantees of market value.

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Comparable properties 3 supplied

Sold Aug 7, 2026

$693,000

65 Blackberry Lane

Sold Sep 18, 2026

$680,000

20 Wachusett Street

Sold Sep 14, 2026

$640,000

164 Ridge Street

Photo-based condition insights

Overall presentation: above average

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About 29 Shady Side Dr

Can I request a private showing?

Request a tour of 29 Shady Side Dr and a Bean Group agent will help coordinate an available time with the listing side.

Can you help me evaluate this property?

Yes. We can discuss condition, comparable sales, offer strategy and the questions worth asking before you decide whether to proceed.

Are property documents available?

Availability varies by property and source. Request the documents you need and we will help obtain what is available.