Active
45 Days on market
29 Shady Side Dr Longmeadow — Photo 1 of 42

29 Shady Side Dr Longmeadow — Photo 1 of 42

Recent Drop: $15,000

$664,900
$649,900

$649,900

Investment Analysis — 29 Shady Side Dr

Longmeadow, MA 01106

Based on HUD Small Area Fair Market Rent for Springfield, MA MSA, a 4-bedroom in 01106 carries an estimated $3,440/mo in gross rent — about a 2.96% cap rate and $19,219/yr in estimated NOI at the $649,900 list price. Adjust every assumption in the calculator below.

View Standard Listing

Beds

4

Baths

2.5

SqFt

2,487

Style

Single Family

Built

1961

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!

ADU Potential

Massachusetts allows one accessory dwelling unit by right in single-family zoning districts statewide (M.G.L. c. 40A §3; 760 CMR 71.00, effective Feb 2025). Estimated maximum ADU size for this property: 900 sq ft (the lesser of 900 sq ft or half the 2,487 sq ft principal dwelling). Lot size: 23,210 sq ft.

Based on listing data, which indicates the property type — not the zoning district. Local dimensional, septic (Title 5), and historic-district requirements still apply. Not legal advice — verify with the municipality.

Estimates — not financial advice

These figures are illustrative estimates for informational purposes only — not an appraisal, valuation, or guarantee of rent, income, or returns, and not financial, tax, or investment advice. Rent is either the figure reported on the MLS listing — in-place rent that may differ from market and is not verified against the actual leases — or, where the listing reports none, an estimate from HUD Small Area Fair Market Rents, a government benchmark that may differ from actual market rent. Each figure is labelled with its source. Cap rate, NOI, and returns depend on the assumptions shown, which you can change. MLS and other third-party data may be inaccurate or out of date. Verify all figures independently and consult your own financial, tax, and legal advisors before making any investment decision.

Immersive Experience

Property Details

Financials

Original Price$664,900
Annual Taxes$12,154

Parking

Garage2
Off-Street8

Interior Specifications

Total Rooms9
Fireplaces1
FlooringWood, Tile, Hardwood, Flooring - Hardwood, Laminate
BasementFull, Crawl Space, Partially Finished, Interior Entry, Bulkhead, Concrete

Climate & Utilities

HeatingForced Air, Natural Gas
CoolingCentral Air
WaterPublic
SewerPublic Sewer

Building & Exterior

ConstructionFrame
RoofShingle
FoundationConcrete Perimeter
ZoningRA2

Property & Lot

Acres0.53
SqFt Lot23,210
Lot FeaturesCleared, Level

Amenities & Appliances

Gas Water Heater • Water Heater • Range • Dishwasher • Disposal • Microwave • Refrigerator • Wine Refrigerator • Vacuum System

Neighborhood

Public Transportation • Shopping • Pool • Tennis Court(s) • Park • Walk/Jog Trails

Geography

Floorplan Breakdown

Structural Layout

Second
Bedroom 3Bedroom 4Bathroom 3
Main,First
Living RoomDining RoomKitchenFamily RoomMaster BedroomBedroom 2Bathroom 1Bathroom 2
Living Room
Lvl Main,First

21 x 12

Flooring - Hardwood, Window(s) - Picture, Exterior Access, Pocket Door

Dining Room
Lvl Main,First

11 x 13

Flooring - Hardwood, Chair Rail, Lighting - Pendant, Pocket Door

Kitchen
Lvl Main,First

10 x 12

Flooring - Stone/Ceramic Tile, Breakfast Bar / Nook, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Lighting - Overhead

Family Room
Lvl Main,First

14 x 18

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

Master Bedroom
Lvl Main,First

14 x 15

Ceiling Fan(s), Cedar Closet(s), Closet, Flooring - Hardwood, Lighting - Overhead, Closet - Double

Bedroom 2
Lvl Main,First

10 x 13

Bedroom 3
Lvl Second

15 x 22

Flooring - Hardwood, Recessed Lighting, Remodeled, Closet - Double

Bedroom 4
Lvl Second

16 x 14

Closet, Flooring - Hardwood

Bathroom 1
Lvl Main,First

9 x 10

Bathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Pedestal Sink

Bathroom 2
Lvl Main,First

5 x 4

Bathroom - Full, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Jacuzzi / Whirlpool Soaking Tub, Enclosed Shower - Fiberglass, Remodeled, Steam / Sauna, Lighting - Sconce, Lighting - Overhead

Bathroom 3
Lvl Second

7 x 7

Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead

Property History

Price Drop
$649,900

Was $664,900

Aug 21, 2026

MLS® 73556761

Listed
$664,900

Jul 29, 2026

MLS® 73556761

Listing Provided By

Listing Agent: Kelley & Katzer Team

Listing Office: Kelley & Katzer Real Estate, LLC

MLS® Number: 73556761