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Open: Sun 1pm-2:30pm
For salePrice cut: $15K (8/21)
$649,900
4beds
2,487sqft

29 Shady Side Dr, Longmeadow, MA 01106

4beds
2,487sqft
Single family residence
Built in 1961
0.53 Acres
2 Attached garage spaces
$261 price/sqft

What's special

Cozy wood burning fireplaceMostly anderson replacement windowsOversized composite deckGleaming hardwood floorsLots of counterspaceNewer guttersStainless appliances

Second Chance at this gorgeous home! BOM 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!

28 days
|
4,625
|
115
|
Source: MLS PIN,MLS#: 73556761
Travel times

Living Room

Kitchen

Primary Bedroom

Zillow last checked:

Listing updated:

Listed by:

Kelley & Katzer Team 413-209-9933,

Kelley & Katzer Real Estate, LLC 413-209-9933,

Natalie Murphy 413-875-5453

Source: MLS PIN,MLS#: 73556761

Facts & features

Interior

Bedrooms & bathrooms
  • Bedrooms: 4
  • Bathrooms: 3
  • Full bathrooms: 2
  • 1/2 bathrooms: 1
  • Main level bathrooms: 2
  • Main level bedrooms: 2
Primary bedroom
  • Features: Ceiling Fan(s), Cedar Closet(s), Closet, Flooring - Hardwood, Lighting - Overhead, Closet - Double
  • Level: Main,First
  • Area: 210
  • Dimensions: 14 x 15
Bedroom 2
  • Features: Closet, Flooring - Wood, Lighting - Overhead
  • Level: Main,First
  • Area: 130
  • Dimensions: 10 x 13
Bedroom 3
  • Features: Flooring - Hardwood, Recessed Lighting, Remodeled, Closet - Double
  • Level: Second
  • Area: 330
  • Dimensions: 15 x 22
Bedroom 4
  • Features: Closet, Flooring - Hardwood
  • Level: Second
  • Area: 224
  • Dimensions: 16 x 14
Primary bathroom
  • Features: No
Bathroom 1
  • Features: Bathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Pedestal Sink
  • Level: Main,First
  • Area: 90
  • Dimensions: 9 x 10
Bathroom 2
  • Features: Bathroom - Full, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub, Enclosed Shower - Fiberglass, Remodeled, Steam / Sauna, Lighting - Sconce, Lighting - Overhead
  • Level: Main,First
  • Area: 20
  • Dimensions: 5 x 4
Bathroom 3
  • Features: Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead
  • Level: Second
  • Area: 49
  • Dimensions: 7 x 7
Dining room
  • Features: Flooring - Hardwood, Chair Rail, Lighting - Pendant, Pocket Door
  • Level: Main,First
  • Area: 143
  • Dimensions: 11 x 13
Family room
  • Features: Bathroom - Half, Skylight, Ceiling Fan(s), Vaulted Ceiling(s), Flooring - Hardwood, Flooring - Stone/Ceramic Tile, Deck - Exterior, Exterior Access, Open Floorplan, Recessed Lighting, Slider, Lighting - Overhead
  • Level: Main,First
  • Area: 252
  • Dimensions: 14 x 18
Kitchen
  • Features: Flooring - Stone/Ceramic Tile, Breakfast Bar / Nook, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Lighting - Overhead
  • Level: Main,First
  • Area: 120
  • Dimensions: 10 x 12
Living room
  • Features: Flooring - Hardwood, Window(s) - Picture, Exterior Access, Pocket Door
  • Level: Main,First
  • Area: 252
  • Dimensions: 21 x 12
Heating
  • Forced Air, Natural Gas
Cooling
  • Central Air
Appliances
  • Included: Gas Water Heater, Water Heater, Range, Dishwasher, Disposal, Microwave, Refrigerator, Wine Refrigerator, Vacuum System
  • Laundry: Flooring - Laminate, Gas Dryer Hookup, Washer Hookup, Lighting - Overhead, In Basement
Features
  • Recessed Lighting, Open Floorplan, Bonus Room, Central Vacuum, Internet Available - Unknown
  • Flooring: Wood, Tile, Hardwood, Flooring - Hardwood, Laminate
  • Doors: Insulated Doors, Storm Door(s)
  • Windows: Insulated Windows
  • Basement: Full,Crawl Space,Partially Finished,Interior Entry,Bulkhead,Concrete
  • Number of fireplaces: 1
  • Fireplace features: Living Room
Interior area
  • Total structure area: 2,487
  • Total interior livable area: 2,487 sqft
  • Finished area above ground: 2,487
  • Finished area below ground: 561
Video & virtual tour

Property

Parking
  • Total spaces: 8
  • Parking features: Attached, Garage Door Opener, Garage Faces Side, Oversized, Paved Drive, Off Street, Driveway
  • Attached garage spaces: 2
  • Uncovered spaces: 6
Features
  • Patio & porch: Deck - Wood, Deck - Composite
  • Exterior features: Deck - Wood, Deck - Composite, Pool - Above Ground Heated, Rain Gutters, Storage, Professional Landscaping, Sprinkler System
  • Has private pool: Yes
  • Pool features: Heated
Lot
  • Size: 0.53 Acres
  • Features: Cleared, Level
Details
  • Parcel number: M:0642 B:0027 L:0053,2546844
  • Zoning: RA2

Construction

Type & style
  • Home type: SingleFamily
  • Architectural style: Cape
  • Property subtype: Single Family Residence
Materials
  • Frame
  • Foundation: Concrete Perimeter
  • Roof: Shingle
Condition
  • Updated/Remodeled,Remodeled
  • Year built: 1961

Utilities & green energy

  • Electric: Circuit Breakers, 200+ Amp Service
  • Sewer: Public Sewer
  • Water: Public
  • Utilities for property: for Electric Range, for Gas Dryer, Washer Hookup
Green energy
  • Energy efficient items: Partial, Thermostat
  • Energy generation: Solar

Community & HOA

Community
  • Features: Public Transportation, Shopping, Pool, Tennis Court(s), Park, Walk/Jog Trails, Golf, Medical Facility, Laundromat, Highway Access, House of Worship, Private School, Public School, University
HOA
  • Has HOA: No
Location
  • Region: Longmeadow

Financial & listing details

  • Price per square foot: $261/sqft
  • Tax assessed value: $629,100
  • Annual tax amount: $12,154
  • Date on market: 7/30/2026
  • Exclusions: Security System, Washer, Dryer, Basketball Hoop, All Televisions & Mounts. Pool Table Is Negotiable.
  • Road surface type: Paved

Price history

DateEventPrice
8/25/2026Listed for sale$649,900$261/sqft
Source: MLS PIN #73556761 Report a problem
8/21/2026Contingent$649,900$261/sqft
Source: MLS PIN #73556761 Report a problem
8/21/2026Price change$649,900-2.3%$261/sqft
Source: MLS PIN #73556761 Report a problem
7/29/2026Listed for sale$664,900+80.9%$267/sqft
Source: MLS PIN #73556761 Report a problem
8/30/2012Sold$367,500-2%$148/sqft
Source: Public Record Report a problem
7/13/2012Price change$374,900-1.3%$151/sqft
Source: Coldwell Banker Residential Brokerage - Longmeadow #71349909 Report a problem
3/14/2012Listed for sale$379,900+64.1%$153/sqft
Source: Coldwell Banker Residential Brokerage - #71349909 Report a problem
9/15/1998Sold$231,500$93/sqft
Source: Public Record Report a problem

Public tax history

YearProperty taxesTax assessment
2025$11,831 +2.1%$560,200
2024$11,585 +3.5%$560,200 +14.7%
2023$11,190 +5.1%$488,200 +12.9%
2022$10,652 +4.8%$432,300 +5.3%
2021$10,161 -0.7%$410,700 +2%
2020$10,238 +11.9%$402,800 +6.1%
2019$9,149 +3.6%$379,800 +4.7%
2018$8,828 +2.5%$362,700 -0.7%
2017$8,616 +2.6%$365,400 +5.8%
2016$8,401 +3.5%$345,300 +0.5%
2015$8,116 +33%$343,600 +1.9%
2014$6,101 -16.5%$337,200 -0.6%
2013$7,309 +5.9%$339,300 -3.3%
2012$6,904 +2.8%$350,800 -2.1%
2011$6,716 +2.6%$358,200
2010$6,548 +1.7%$358,200 -4.8%
2009$6,438 $376,300 -0.9%
2008$6,438 +9.2%$379,600
2007$5,895 +1.8%$379,600
2006$5,793 +7%$379,600 +20.1%
2005$5,413 +2.9%$316,200 +13.6%
2004$5,259 +4.8%$278,400
2003$5,020 +7.5%$278,400 +20.1%
2002$4,671 $231,800

Find assessor info on the county website

Monthly payment

Est. payment
$4,049/mo
Principal & interest
$3302
Property taxes
$747
More affordability toolsChevron Right

Estimated market value

$641,600

$610,000 - $674,000

$4,212/mo

Climate risks

Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.

Neighborhood: 01106

Nearby schools

Blueberry Hill Elementary School
Grades K-5 • 1.2 miles
7/10
GreatSchools® Rating
Test Score Rating
9/10
Student Progress Rating
5/10
Glenbrook Middle School
Grades 6-8 • 1.1 miles
8/10
GreatSchools® Rating
Test Score Rating
9/10
Student Progress Rating
6/10
Longmeadow High School
Grades 9-12 • 1.2 miles
8/10
GreatSchools® Rating
Test Score Rating
9/10
College Readiness Rating
8/10

Open house

  • Sun, Aug 30

    1:00 PM - 2:30 PM

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