37-39 Upland St, Springfield MA 01104
Springfield, MA 01104
$399,900
Est. $2,566/month
Estimate assumptions
20% down, a 30-year loan at 6.5%, and $200/month estimated insurance.
Includes the supplied property-tax and HOA inputs; missing inputs contribute $0. HOA fees with an unspecified frequency are treated as monthly. PMI and closing costs are excluded.
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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!
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Recently Sold Nearby
Property History
Market Insights
Property Timeline
Back On Market
Oct 4, 2026
Active
Status: Active under contract
Sep 28, 2026
Active → Active Under Contract
Back On Market
Sep 21, 2026
Active
Status: Active under contract
Aug 23, 2026
Active → Active Under Contract
Pending Sale
Aug 23, 2026
Offer accepted, sale pending
Showing Instructions Updated
Aug 20, 2026
New showing requirements
Listed for Sale
Aug 17, 2026
$399,900
Original listing
Agent: Taylor Hildack
Office: Keller Williams Realty
| Date | Event | Price | Change | $/sqft | Details |
|---|---|---|---|---|---|
| 10/04/2026 | • Back On Market | - | - | - | Active |
| 09/28/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 09/21/2026 | • Back On Market | - | - | - | Active |
| 08/23/2026 | 📋 Status: Active under contract | - | - | - | Active → Active Under Contract |
| 08/23/2026 | ⏳ Pending Sale | - | - | - | Offer accepted, sale pending |
| 08/20/2026 | 👁️ Showing Instructions Updated | - | - | - | New showing requirements |
| 08/17/2026 | 🏠 Listed for Sale | $399,900 | - | - | Original listing |
Tax History
| Year | Taxes | Assessment |
|---|---|---|
| 2025 | $4,130 | $263,400 |
Financial Details
Annual Property Tax
$4,130
Tax Year 2025
Assessed Value
$263,400
Facts & Features
2 Car Garage
Home Facts
Type
Residential Income
Style
2 Family - 2 Units Up/Down
Year Built
1920
Living Area
2,174 sq ft
Lot Size
0.12 acres
Stories
3
Bedrooms
6
Full Baths
2
Total Rooms
11
Investment Metrics
Units
2
Unit 1 Rent
$1,800/mo · Y
Unit 2 Rent
— · N
Total Monthly Rent
$1,800/mo
Gross Income
$21,600
Net Operating Income
$21,600
Cap Rate
5.40%
Interior
Heating
Natural Gas, Oil
Cooling
None
Flooring
Tile, Vinyl, Hardwood
Appliances
Range, Microwave, Refrigerator, Washer, Dryer
Fireplace
None
Basement
Full, Unfinished
Laundry
Washer & Dryer Hookup
Features
Ceiling Fan(s), Pantry, Storage, Bathroom With Tub & Shower, Other, Walk-up Attic, Stone/granite/solid Counters, Remodeled, Living Room, Kitchen, Family Room
Exterior
Construction
Frame
Architecture
None
Roof
Shingle
Features
Balcony/deck, Rain Gutters
Pool
None
Spa
None
Fencing
Fenced
Patio/Porch
Porch, Patio
Parking
Garage Spaces
2
Has Garage
Yes
Features
Paved Drive, Off Street, Paved
Total Spaces
6
Utilities
Electric
Circuit Breakers, 100 Amp Service
Water
Public
Sewer
Public Sewer
Gas
None
Other
For Gas Range
Financial
Annual Tax
$4,130
Assessed Value
$263,400
HOA & Community
Fee Includes
None
Amenities
None
Optional Fee Includes
None
Down Payment Resource
Eligible
MA Disclosures
Lead Paint
Yes, Certified Treated
Seller Disclosures
Deleading Compliance Attached. First Floor Tenant To Remain- Year Lease Expires June 2027. Solar Panels Are Leased. Window Ac Units Remain. Cameras On The Premises.
Additional Details
Possession
None
Accepted Financing
None
Structure Type
[]
House Color
White
Sq Ft Source
Public Record
Documents
None
County
Hampden
Total market time (incl. prior listings)
34 days
Property Overview
Property Type
2 Family - 2 Units Up/Down
Listing Type
For Sale
Year Built
1920
Bedrooms
6
Full Bathrooms
2
Living Area
2,174 sq ft
Total Rooms
11
Stories
3
Levels
3
Floor Layout
Interior Features
Flooring:
Tile, Vinyl, Hardwood
Appliances:
Range, Microwave, Refrigerator, Washer, Dryer
Interior Features:
Ceiling Fan(s), Pantry, Storage, Bathroom With Tub & Shower, Other, Walk-Up Attic, Stone/Granite/Solid Counters, Remodeled, Living Room, Kitchen, Family Room
Windows:
Basement:
Full, Unfinished
Laundry:
Washer & Dryer Hookup
Security:
Security System
Construction & Materials
Year Built:
1920
Structure Type:
Exterior Materials:
Frame
Roof:
Shingle
Foundation:
Block
Stories:
3
Heating, Cooling & Utilities
Heating:
Natural Gas, Oil
Cooling:
Hot Water:
Water Source:
Public
Sewer:
Public Sewer
Energy Features:
Exterior & Lot
Exterior Features:
Balcony/Deck, Rain Gutters
Patio & Porch:
Porch, Patio
Fencing:
Fenced
Other Structures:
Shed(s)
Lot Features:
Level
Road Surface:
Parking & Garage
Garage Spaces:
2
Total Parking Spaces:
6
Parking Features:
Paved Drive, Off Street, Paved
Nearby Schools
School District
Springfield School District local
D
Where Graduates Go
Class of 2021
36%
attend college
20%
4-Year
16%
2-Year
3%
Out of State
3%
Working
School Safety
2024-25
5.9%
Above Average
5.1%
Suspensions
1.4%
In-School
0.8%
Emergency
0.4% above state avg
Elementary Schools
10 schools
Academy Hill School
0.8 mi
Grades PK-08
Grace Academy
1.1 mi
Grades K-12
A
Alfred G. Zanetti Montessori Magnet School
1.1 mi
|
#3 of 16
|
Score: 47.5
Improved 137 spots from last year
-10.7 below state avg
436 students
Diverse
Rising School
Grades PK-08
A+
Springfield Preparatory Charter School
1.4 mi
|
#2 of 16
|
Score: 48.5
Improved 94 spots from last year
-9.8 below state avg
485 students
Moderate
Rising School
Strong Attendance
Grades K-08
D
The Springfield Virtual School
1.6 mi
|
#326 of 346
|
Score: 30.7
Improved 11 spots from last year
-27.5 below state avg
201 students
Moderate
College Ready Curriculum
Grades PK-12
Your Educational Success Academy
2.0 mi
Grades K-12
B
Veritas Preparatory Charter School
2.6 mi
|
#12 of 25
|
Score: 34.5
Improved 339 spots from last year
-23.8 below state avg
769 students
Moderate
Early College Program
Rising School
Grades 05-12
St. Michael's Academy
3.1 mi
Grades PK-08
Pioneer Valley Christian Academy
3.5 mi
Grades PK-12
Mill Pond School
4.2 mi
Grades PK-12
Middle Schools
10 schools
C
John J. Duggan Middle School
2.6 mi
|
#251 of 346
|
Score: 47.1
Improved 35 spots from last year
-11.1 below state avg
843 students
Diverse
High Graduation Rate
Rising School
College Ready Curriculum
Grades 06-12
C-
Van Sickle Prep School
0.1 mi
|
#15 of 16
|
Score: 21.0
Improved 330 spots from last year
-37.2 below state avg
207 students
Moderate
Rising School
Grades 06-08
B-
Van Sickle Academy
0.1 mi
|
#10 of 16
|
Score: 28.1
Improved 340 spots from last year
-30.1 below state avg
256 students
Moderate
Rising School
Grades 06-08
C+
STEM Middle Academy
1.4 mi
|
#12 of 16
|
Score: 24.5
Improved 298 spots from last year
-33.7 below state avg
241 students
Diverse
Rising School
Grades 06-08
Springfield Middle School
1.9 mi
15 students
Moderate
Grades 06-08
F
Springfield Public Day Middle School
1.9 mi
|
#352 of 352
|
Score: 19.5
Improved 14 spots from last year
-38.7 below state avg
45 students
Diverse
Grades 06-08
Springfield Commonwealth Academy
2.3 mi
Grades 06-08
D
Springfield Legacy Academy
2.4 mi
|
#16 of 16
|
Score: 18.8
Improved 340 spots from last year
-39.4 below state avg
243 students
Less Diverse
Rising School
Grades 06-08
C
Impact Prep at Chestnut
2.4 mi
|
#13 of 16
|
Score: 23.7
Improved 350 spots from last year
-34.5 below state avg
314 students
Moderate
Rising School
Grades 06-08
B
Chestnut Accelerated Middle School (Talented and Gifted)
2.4 mi
|
#162 of 352
|
Score: 43.2
Dropped 9 spots from last year
-15 below state avg
291 students
Diverse
Strong Attendance
Grades 06-08
High Schools
10 schools
C
The Springfield Renaissance School an Expeditionary Learning School
0.1 mi
|
#275 of 346
|
Score: 45.0
Improved 6 spots from last year
-13.2 below state avg
596 students
Diverse
High Graduation Rate
College Ready Curriculum
Grades 06-12
C-
Baystate Academy Charter Public School
1.4 mi
|
#306 of 346
|
Score: 37.1
Improved 37 spots from last year
-21.1 below state avg
344 students
Diverse
Rising School
College Ready Curriculum
Grades 06-12
C
Emergence Academy
1.7 mi
|
#21 of 25
|
Score: 26.2
Improved 356 spots from last year
-32 below state avg
376 students
Diverse
Rising School
Diverse Student Body
Grades 06-12
C-
Conservatory of the Arts
1.9 mi
|
#303 of 346
|
Score: 37.6
Improved 2 spots from last year
-20.6 below state avg
292 students
Moderate
High Graduation Rate
College Ready Curriculum
Grades 06-12
C+
Libertas Academy Charter School
2.0 mi
|
#238 of 346
|
Score: 48.5
Improved 106 spots from last year
-9.8 below state avg
592 students
Moderate
7 sports
• 134 athletes
Rising School
Grades 06-12
C
Springfield Central High School
1.2 mi
|
#261 of 346
|
Score: 46.4
Improved 38 spots from last year
-11.8 below state avg
2,015 students
Diverse
17 sports
• 1,176 athletes
Rising School
College Ready Curriculum
Strong Athletics
Grades 09-12
A
Roger L. Putnam Vocational Technical Academy
1.4 mi
|
#6 of 25
|
Score: 50.3
Improved 257 spots from last year
-7.9 below state avg
1,377 students
Moderate
High Graduation Rate
Rising School
Career Tech Programs
College Ready Curriculum
Grades 09-12
F
Phoenix Academy Public Charter High School, Springfield
1.5 mi
|
#343 of 346
|
Score: 20.1
Improved 5 spots from last year
-38.1 below state avg
175 students
Moderate
College Ready Curriculum
Grades 09-12
B+
Gateway to College at Springfield Technical Community College
1.5 mi
|
#123 of 346
|
Score: 74.4
Same rank as last year
30 students
Diverse
College Ready Curriculum
Grades 09-12
F
Springfield International Academy at Sci-Tech
1.5 mi
|
#340 of 346
|
Score: 20.7
Dropped 40 spots from last year
-37.5 below state avg
52 students
Diverse
Career Tech Programs
College Ready Curriculum
Diverse Student Body
Grades 09-12
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Property Tax
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Homeowners Insurance
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95% Interest
Year 15
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Location
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Neighborhood
37-39 Upland St, Springfield MA 01104
Springfield, MA 01104
Listing Information
Listing Agent
Taylor Hildack
Listing Office
Keller Williams Realty
Office Phone
413-642-8650
Agent MLS ID
CN240626
Office MLS ID
M95310
Listing Data Updated
Oct 4, 2026 2:20 PM EDT
Listing information is deemed reliable but not guaranteed. Data provided by MLS Property Information Network, Inc. All information should be independently verified.
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