
29 Shady Side Dr Longmeadow — Photo 1 of 42
Recent Drop: $15,000
$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.
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
Parking
Interior Specifications
Climate & Utilities
Building & Exterior
Property & Lot
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
Living Room
Lvl Main,First21 x 12
Flooring - Hardwood, Window(s) - Picture, Exterior Access, Pocket Door
Dining Room
Lvl Main,First11 x 13
Flooring - Hardwood, Chair Rail, Lighting - Pendant, Pocket Door
Kitchen
Lvl Main,First10 x 12
Flooring - Stone/Ceramic Tile, Breakfast Bar / Nook, Recessed Lighting, Stainless Steel Appliances, Wine Chiller, Lighting - Overhead
Family Room
Lvl Main,First14 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,First14 x 15
Ceiling Fan(s), Cedar Closet(s), Closet, Flooring - Hardwood, Lighting - Overhead, Closet - Double
Bedroom 2
Lvl Main,First10 x 13
Bedroom 3
Lvl Second15 x 22
Flooring - Hardwood, Recessed Lighting, Remodeled, Closet - Double
Bedroom 4
Lvl Second16 x 14
Closet, Flooring - Hardwood
Bathroom 1
Lvl Main,First9 x 10
Bathroom - Half, Flooring - Stone/Ceramic Tile, Lighting - Sconce, Pedestal Sink
Bathroom 2
Lvl Main,First5 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 Second7 x 7
Bathroom - Full, Bathroom - With Tub & Shower, Flooring - Stone/Ceramic Tile, Countertops - Stone/Granite/Solid, Lighting - Overhead
Property History
$649,900
Was $664,900
Aug 21, 2026
MLS® 73556761
$664,900
Jul 29, 2026
MLS® 73556761
Listing Agent: Kelley & Katzer Team
Listing Office: Kelley & Katzer Real Estate, LLC
MLS® Number: 73556761
