2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 2 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 3 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 4 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 5 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 6 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 7 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 8 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 9 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 10 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 11 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 12 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 13 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 14 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 15 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 16 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 17 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 18 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 19 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 20 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 21 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 22 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 23 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 24 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 25 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 26 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 27 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 28 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 29 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 30 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 31 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 32 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 33 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 34 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 35 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 36 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 37 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 38 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 39 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 40 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 41 of 42
2 Family - 2 Units Up/Down at 37-39 Upland St, Springfield MA 01104, Springfield, photo 42 of 42
42 photos

$399,900

37-39 Upland St, Springfield MA 01104
Springfield, MA 01104
Listed by Taylor Hildack
Bedrooms
6
Bathrooms
2
Living area
2,174 sqft
Year built
1920

About this home

BACK ON MARKET — NO FAULT OF THE PROPERTY! Previous transactions did not fall through due to property-related issues. First buyer was unable to obtain financing. Second buyer got cold feet. Their loss is your opportunity! This rare, beautifully updated 2-Family is tucked into an established residential neighborhood in East Springfield and ready for its new owner! Perfect for owner-occupants looking to offset their mortgage or investors looking to expand their portfolio. The first unit features a spacious living room and 3 bedrooms, all with hardwood floors, a kitchen with stainless steel appliances, and a full bath with a new vanity & updated plumbing. The updated second unit is vacant and move-in ready, featuring a spacious living room with hardwood floors & charming barn door, 3 bedrooms, plus a finished walk-up attic offering fantastic bonus space for an extra bedroom, office, playroom & more! The updated kitchen features granite countertops, vinyl flooring & stainless steel appliances, while the fully renovated bath offers ceramic tile, a new tub & vanity. This unit also features an enclosed porch & balcony. (Previous 2nd unit tenants were paying $2,200/mo.) Outside, enjoy a freshly painted front porch, newly seal-coated driveway, 2-car garage with storage space, fenced yard, patio & storage shed. All appliances to remain.Recent improvements by licensed professionals! Seller has completed numerous updates, including servicing of both steam boilers, a new oil supply line, updated boiler and water-heater flue piping, chimney cleaning and repairs, code-compliant smoke/CO detectors, stove repairs, and correction of third-floor power ventilation. Documentation available upon request. Don't wait, schedule your showing today!

Property details

MLS #
73564327
Property type
2 Family - 2 Units Up/Down
Subdivision
N/A
Status
Active
Days on market
53
On market date
August 16, 2026
Stories
3
Total bathrooms
2
Garage spaces
2
Parking spaces
6
Lot size
0.12 acres
Loading map…

Nearby schools

Within 10 miles. School directory data from the National Center for Education Statistics (NCES), accessed via the Urban Institute Education Data API. Local Score is calculated by INNOVATE Real Estate; where a state rating is shown, it comes from that state's own official school report card (e.g. NC Dept. of Public Instruction, SC Report Card).

Elementary
Liberty
0.41 mi away · Grades 0-5
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
264
Student:teacher ratio
10.2:1
District
Springfield
Middle
Emergence Academy
0.12 mi away · Grades 6-8
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
45
Student:teacher ratio
9.0:1
District
Springfield
High
The Springfield Renaissance School an Expeditionary Learning
0.12 mi away · Grades 6-12
Nearest school -- attendance-zone data not available here
5.0
Local Score (student-teacher ratio only (preliminary -- will incorporate state test-score data once available)) -- not an official state rating
Enrollment
608
Student:teacher ratio
11.9:1
District
Springfield

Walkability

Blended score for Springfield's center, calculated by INNOVATE Real Estate from two sources: the EPA's National Walkability Index (street network, transit, land-use mix) and Google Places amenity data (what's actually reachable on foot from this point). 60% EPA National Walkability Index + 40% nearby-amenity density (Google Places).

91
Highly walkable
out of 100
EPA National Walkability Index
16.8 / 20 -- Most walkable
Google Places amenity density
100 / 100
Restaurants & cafes20
Grocery stores8
Parks5
Schools16
Transit stops20
Pharmacies4

Market position

How this listing compares to current activity in Springfield, from live MLS data.

On the market 53 days -- 57 fewer days than Springfield's current average of 110 days.
For reference, the median list price across 723 active listings in Springfield right now is $305,000.

Mortgage calculator

Estimate only - actual rate and payment depend on your lender, credit, and loan program.

$
%
%
Adjust tax / insurance estimates
% / yr
$
/mo
Est. monthly payment
$2,558/mo
$79,980 down
$319,920 loan
Principal & interest$2,075
Property tax (est.)$333
Home insurance (est.)$150

Similar homes you might like

Data source: Listing information provided by MLS Property Information Network via Trestle/CoreLogic. Last updated 1 days ago.

Information herein deemed reliable but not guaranteed; all measurements, school assignments, HOA fees, taxes, and feature lists are approximate and should be independently verified. Equal Housing Opportunity.