29 Shady Side Dr , Longmeadow, MA 01106
$644,900
- 4
- beds
- 2 full · 1 half
- baths
- 2,487
- sqft
- 1961
- year built
$644,900
29 Shady Side Dr , Longmeadow, MA 01106
- 4
- beds
- 2 full · 1 half
- baths
- 2,487
- sqft
- 1961
- year built
- Status:
- Active
- MLS #:
- 73556761
- County:
- Hampden
- Listed By:
- Kelley & Katzer Team - Kelley & Katzer Real Estate, LLC
- Agent Phone:
- (413) 209-9933
Sponsoring Broker: Derek Eisenberg, Continental Real Estate Group, Inc
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!
Highlights
- Residential
- Single Family Residence
- Built in 1961
- 0.53 Acre Lot
- 2 Car Garage
- 103 days on Market
-
- Bedrooms
- 4
-
- Bathrooms
- 2 full · 1 half
-
- Year Built
- 1961
-
- Architectural Style
- Cape
-
- Construction Materials
- Frame
-
- Foundation
- Concrete Perimeter
-
- Garage Spaces
- 2.0
-
- Parking Features
- Driveway, Attached, Paved, Oversized, Garage Door Opener, Garage, Off Street, Garage Faces Side
-
- Living Area
- 2487.0
-
- Interior Features
- Ceiling Fan(s), Vaulted Ceiling(s), Master Downstairs, Central Vacuum, Recessed Lighting, Open Floorplan
-
- Appliances
- Dishwasher, Microwave, Refrigerator, Range, Disposal, Gas Water Heater, Water Heater, Wine Refrigerator
-
- Flooring
- Hardwood, Laminate, Tile, Wood
-
- Exterior Features
- Storage, Rain Gutters
-
- Patio And Porch
- Deck
-
- Pool Features
- Heated, Private, Above Ground
-
- Cooling
- Central Air
-
- Heating
- Forced Air, Natural Gas
-
- Basement
- Crawl Space, Full, Partially Finished, Interior Entry, Concrete
-
- Acres
- 0.53
-
- Lot Features
- Level, Cleared, Landscaped
-
- Water
- Public
-
- County
- Hampden
-
- City
- Longmeadow
-
- Zip Code
- 01106
-
- High School
- Longmeadow High
-
- Middle School
- Glenbrook Middle
-
- Elementary School
- Blueberry Hill
-
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Estimated Value
$677,785
Estimated Sales Price Range:
$589,672 - $765,897
Source: Constellation Data Labs
Price History
| 10/29/2026 | Price Changed | $644,900 |
| Source: MLS Property Information Network (MLS PIN) #73556761 | ||
| 07/29/2026 | Listed | $664,900 |
| Source: MLS Property Information Network (MLS PIN) #73556761 | ||
Source: MLS Data
Deed History
| 08/10/2022 | Quit Claim Deed (arm's length) | $150,000 |
| 08/30/2012 | Quit Claim Deed (arm's length) | $367,500 |
| 09/15/1998 | Deed | $231,500 |
Source: Public records via Constellation Data Labs
Mortgage History
| 08/10/2022 | Purchase Money Mortgage | $366,000 |
| 09/22/2016 | Unknown | $309,000 |
| 08/30/2012 | Unknown | $330,750 |
| 06/29/2009 | $100,000 | |
| 05/13/2003 | $110,500 | |
| 09/15/1998 | $120,000 |
Source: Public records via Constellation Data Labs
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There are currently 67 properties available in Longmeadow, with 0 under contract to close soon. Properties in the city have an average sale price of $0 and typically spend 101 days on the market before being sold.
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Source: ez Home Search, MLS Data
Frequently Asked Questions
How do I schedule a tour of 29 Shady Side 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 29 Shady Side 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 29 Shady Side Dr?
Click Ask a Question to talk with our team. You already know it is a 4 bed, 2 bath, listed for $644,900. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Longmeadow, and can even get you in to see the property quickly.
How much is the monthly mortgage payment for 29 Shady Side 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 29 Shady Side Dr at around $4,683. 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 29 Shady Side Dr?
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Can I negotiate the asking price for 29 Shady Side Dr?
In most cases, yes. Whether 29 Shady Side Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Longmeadow'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 29 Shady Side Dr?
We can handle that for you. Our preferred local agent specializes in residentials in Longmeadow 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 $644,900 with 2,487 sqft of space—that comes out to approximately $259 per square foot.
How long has this property been on the market?
29 Shady Side Dr was listed on July 29, 2026, which means it's been on the market for 103 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 1961, making it approximately 65 years old.
What is the lot size of this property?
29 Shady Side Dr sits on a 0.53-acre lot, which is 23,087 square feet.
What schools are assigned to this property?
Based on MLS info, this home is zoned for:
- Elementary: Blueberry Hill
- Middle: Glenbrook Middle
- High: Longmeadow High
Want to see how these schools compare? Check out our Hampden County School Guide to see ratings, reviews, and more for the schools in the area.
What are the property taxes for 29 Shady Side Dr?
The most recent public record shows annual property taxes for 29 Shady Side Dr were approximately $12,154. 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 29 Shady Side 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 09, 2026 at 11:17PM | Source: MLS Property Information Network (MLS PIN) | MLS#: 73556761
