27 Chester St · Springfield, MA 01105

$199,000

5 bd · 1.5 ba · 1,378 sqft · SingleFamily public records · 70 Days on market

Built 1913 4,378 sqft lot $144/sqft · 12% below area Est $246k · 19% under

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Why this score? — see what drove the B grade

The composite is a weighted blend of 9 inputs, each scored 0–100. Each bar is that input's sub-score; the figure is the points it added to the 100-point composite (weight × sub-score).

• Cash flow +26.9/30.0
• ARV discount +15.0/15.0
• DSCR +9.3/10.0
• 1% rule +7.0/10.0
• Appreciation +5.5/10.0
• Livability +3.7/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• Schools +1.6/10.0

Listing remarks MLS

Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

Key facts

• Vinyl sided home
• Hot water tank
• Lead compliant

Tags

• VINYL SIDED HOME
• HOT WATER TANK
• UPDATED KITCHEN
• REPLACEMENT WINDOWS
• LEAD COMPLIANT

What this means for you Summary

Snapshot

• This is a 5-bed/1.5-bath single-family listed at $199k.

Deal economics

• At list price, monthly cash flow is $552 ($7k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $199k).
• Recommended offer: $187k (6.0% below list) — sets the bar for market timing.
• Cap rate 9.6% vs local median 5.1% in Springfield — top-decile yield for the area; either an underpriced asset or a hidden risk that comps aren't pricing in. Stress-test before assuming the spread holds.

Location & tenants

• Location reads 73/100 on livability (#97 in MA) — a middle-class / working-renter tenant base. Strengths: commute A+, health & safety A+, amenities A; Watch: schools D, crime F, employment D-.
• Springfield (urban): math 13% / reading 25% proficiency, ranked #296 of 302 in MA (top 98%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover; 81% free/reduced lunch — lower-income household profile, screen leases tightly.
• Market conditions: 18 active listings in the ZIP; 4 comparable units currently listed for rent nearby; rentals lingering (median 45d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% of comp listings sitting > 30 days — soft ceiling on asking rent; 453 units permitted in Hampden County in 2024 (116 in 5+ unit buildings).

Forward outlook

• In year one you build about $4k of equity ($1k loan paydown + $2k appreciation (1.1% local appreciation)).
• Hampden County population projected at +5% by 2050 — modest demand growth; plan on rents tracking national, not racing it.
• At projected returns (1.1% appreciation + 3.0% rent growth), your $56k cash investment doubles in ~5 years — after that, you're playing with house money.
• By year 9, paydown + projected appreciation supports a ~$32k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 70 days — a 6% lower offer ($187k) is reasonable based on typical stale-listing flexibility.
• 9 sale attempts since 24y ago; this cycle's ask has dropped $16k (7%) from the opening price — seller is motivated, your offer sets the floor, not the list.

Risks & watch-outs

• Watch-outs: built in 1913 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $187,060 (6.0% below list)

Questions for the listing agent

1. It's been on market 70 days. Have you received any prior offers? Is the seller open to a 6% concession, seller financing, or rate buy-down credit?
2. Built in 1913 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
6. Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
7. What's the average days-on-market for RENTAL listings here right now (not sales)? A rising rental-DOM trend means longer vacancies and softer asking-rent achievability than the comps imply.
8. What's the recent tenant-quality profile in this submarket — average credit score on applications, eviction rate, late-payment / NSF rate, and stable-employment percentage? A property-management company in the area should have these aggregated.
9. How much new for-sale + rental construction is in the pipeline within 1–3 miles? Heavy new supply typically softens prices + rents 12–24 months out; constrained supply supports both.

Investment metrics

• 1% rule: 1.20% ✓
• Cap rate: 9.62%
• Cash-on-cash: 11.88%
• DSCR: 1.53
• GRM: 7.0

CMA / ARV

• ARV (median comp): $245,899
• List price: $199,000
• Delta: -19.07%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 6 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
307 Oakland St	0.24mi	4/2.5 (-1)	1,366 (-1%)	7mo	$295,000	$216	72
127 Orange St	0.29mi	4/1.5 (-1)	1,583 (+15%)	1mo	$223,000	$141	56
17 Ashley St	0.43mi	4/1.0 (-1)	1,306 (-5%)	14mo	$285,000	$218	53
34 Collins St	0.53mi	4/1.5 (-1)	1,356 (-2%)	18mo	$299,900	$221	52
207 Euclid Ave	0.24mi	4/2.0 (-1)	1,560 (+13%)	13mo	$265,000	$170	49
23 Mary St	0.75mi	4/2.0 (-1)	1,308 (-5%)	5mo	$295,000	$226	46

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

1.08% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 13.9%
• Equity multiple: 1.71×
• Total profit: $39,649
• Equity at exit: $68,762

10-year hold

• IRR: 17.4%
• Equity multiple: 3.12×
• Total profit: $118,142
• Equity at exit: $92,021

Cash invested: $55,720 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 20 Strongly Tenant-Friendly
• State Massachusetts: 20 Strongly Tenant-Friendly · D+15
• County: — inherits STATE
• City: — inherits STATE

Cambridge / Boston historically rent-controlled (preempted 1994 but consideration ongoing); strong tenant protections; court backlogs.

Methodology + full state rankings →

ZIP-level market 01105

• Home prices YoY: 0.3%
• Active inventory: 18
• Price-to-rent: 7.0×

Monthly cashflow live

• Estimated rent: $2,383 medium
• Mortgage (P&I): −$1,044
• Tax from tax record: −$204 /mo · $2,453/yr
• Insurance: −$83
• HOA: −$0
• Vacancy / Maint / Mgmt: −$500
• Net cashflow: $552

Break-even live

Break-even rent $1,685

Max offer price $199,000

Occupancy floor 72%

Sensitivity live

Price	-10% $664	-5% $608	+0% $552	+5% $495	+10% $439
Rent	-10% $363	-5% $458	+0% $552	+5% $646	+10% $740
Rate	-1.0pp $652	-0.5pp $602	base $552	+0.5pp $500	+1.0pp $448

UW: 25.0% down · 7.5% · 30yr · 1.5% tax · 5.0% vac · 8.0% maint · 8.0% mgmt

Financing live

Cash to close

• Down payment: $49,750
• Closing costs: $5,970
• Reserves months: —
• Total cash needed: —

Rent comps 4 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
94 Hancock St Unit 2 Springfield, MA	5.0	2.0	1200	$2,400	$2.00	44d	1	0.81mi
210 Fort Pleasant Ave Springfield, MA	4.0	1.5	1600	$2,350	$1.47	21d	1	0.87mi
41 Clarendon St Unit 2 Springfield, MA	5.0	1.5	1600	$2,350	$1.47	44d	1	1.37mi
834 Worthington St Unit 2nd Fl Springfield, MA	5.0	1.0	1841	$2,450	$1.33	21d	1	1.42mi

Listing history 50 events

1. 2026-06-18
   days on market $199,000 Active 70 DOM
2. 2026-06-17
   days on market $199,000 Active 69 DOM
3. 2026-06-16
   days on market $199,000 Active 68 DOM
4. 2026-06-15
   days on market $199,000 Active 67 DOM
5. 2026-06-14
   days on market $199,000 Active 65 DOM
6. 2026-06-13
   statusdays on market $199,000 Active 64 DOM
7. 2026-06-10
   days on market $199,000 Price Changed 62 DOM
8. 2026-06-09
   days on market $199,000 Price Changed 61 DOM
9. 2026-06-09
   pricestatus $199,000 Price Changed 60 DOM
10. 2026-06-08
    days on market $205,000 Active 60 DOM
11. 2026-06-07
    days on market $205,000 Active 59 DOM
12. 2026-06-05
    days on market $205,000 Active 56 DOM
13. 2026-06-03
    days on market $205,000 Active 55 DOM
14. 2026-06-02
    days on market $205,000 Active 54 DOM
15. 2026-06-01
    days on market $205,000 Active 53 DOM
16. 2026-05-31
    days on market $205,000 Active 52 DOM
17. 2026-05-30
    days on market $205,000 Active 51 DOM
18. 2026-05-15
    status Back On Market 160-char remark

    Show marketing remark (160 chars)

    Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

19. 2026-05-13
    status Under Agreement 160-char remark

    Show marketing remark (160 chars)

    Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

20. 2026-05-06
    price $210,000 160-char remark

    Show marketing remark (160 chars)

    Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

21. 2026-05-02
    status Back On Market 160-char remark

    Show marketing remark (160 chars)

    Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

22. 2026-04-23
    historical Contingent 160-char remark

    Show marketing remark (160 chars)

    Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

23. 2026-04-07
    listed $215,000 New 160-char remark

    Show marketing remark (160 chars)

    Large vinyl sided home features newer gas forced air heating system, hot water tank, updated kitchen and replacement windows and property is also lead compliant

24. 2023-11-12
    historical $2,250
25. 2023-11-04
    listed $2,250
26. 2023-11-03
    soldstatus $207,000 Sold 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

27. 2023-10-06
    status Under Agreement 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

28. 2023-09-26
    historical Contingent 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

29. 2023-09-22
    price $209,000 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

30. 2023-09-11
    price $214,900 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

31. 2023-08-23
    price $215,000 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

32. 2023-08-11
    price $219,900 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

33. 2023-08-09
    price $224,000 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

34. 2023-08-01
    price $225,000 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

35. 2023-07-19
    status Back On Market 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

36. 2023-07-18
    historical Contingent 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

37. 2023-07-10
    status Back On Market 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

38. 2023-07-06
    status Under Agreement 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

39. 2023-06-22
    historical Contingent 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

40. 2023-06-21
    price $229,900 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

41. 2023-06-15
    listed $235,000 New 353-char remark

    Show marketing remark (353 chars)

    Looking for a great investment property? Tired of paying rent? Check out this recently remodeled 5 bedroom and 1.5 bath home. Many upgrades have been done to this house in the past few years including heating system, hot water heater, new water meter from the city, new flooring throughout the home and new appliances. Schedule an appointment today.

42. 2023-03-28
    soldstatus $104,000 Sold
43. 2023-02-20
    status Under Agreement
44. 2023-02-15
    historical Contingent
45. 2023-01-21
    price $124,900
46. 2022-12-22
    price $134,900
47. 2022-11-16
    listed $144,900 New
48. 2002-11-12
    soldstatus $70,000
49. 2002-11-12
    soldstatus $70,500
50. 2002-10-01
    listed $70,000

ⓘ Source: listings_history table (triggers on properties + properties_extension) + one-shot backfill from property_details.listing_events for pre-trigger history.

Tax reassessment forecast MA · Partial reset (capped growth)

• Current annual tax: $2,453 · $204/mo
• Projected year-2 tax: $2,453 · $204/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Taxation est. · year 1

• Rental income: $28,598
• − Mortgage interest: −$11,147
• − Property taxes: −$2,453
• − Insurance: −$995
• − Repairs & maintenance: −$2,288
• − Management: −$2,288
• − Depreciation: −$5,789
• Taxable income: $3,638
• Est. tax owed @ 24.0%: −$873
• After-tax cash flow: $5,748/yr

For passive investors: Depreciation is non-cash, so a rental often shows a tax loss while cash-flowing — sheltering income. Rental losses are passive: they offset passive income freely, and up to $25,000/yr can offset ordinary (W-2) income if you actively participate and your MAGI is under $100k (phasing out to $0 by $150k); unused losses carry forward. On sale, claimed depreciation is recaptured at up to 25%, and gains may owe capital-gains tax (a 1031 exchange can defer both). Figures are a year-1 estimate at your 24.0% rate — not tax advice; consult a CPA.

Schools (NCES district)

• District: Springfield
• NCES district ID: 2511130
• Math proficiency: 13% ▼ -12.00%
• Reading proficiency: 25% ▼ -5.00%
• Median HH income: $34,938
• Composite: 15.6/100
• National rank: #9293
• State rank: #296 of 302 in MA

Livability — Springfield

• Score: 73/100
• State rank: #97
• US rank: #5195

Category grades

Amenities A Commute A+ Cost of living B- Crime F Employment D- Housing A Health & safety A+ User ratings F

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Springfield, MA
• City population: 61,006
• Population (ZIP): 11,469

Population outlook (Hampden County) Hauer SSP2

• Today (2025): 485,646 people
• By 2030: 491,517 · +1.2%
• By 2040: 500,539 · +3.1%
• By 2050: 508,827 · +4.8%
• By 2075: 539,167 · +11.0%
• By 2100: 545,698 · +12.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly Hispanic (74%)
• Race & ethnicity: Hispanic / Latino 74% Two or more races 37% Black 14% White 10%
• Hispanic origin (detail): Puerto Rican 63% Dominican 5%
• Common ancestry: Lithuanian 1% Romanian 1%
• Foreign-born: 8% · Canada
• Languages at home: 44% English-only · Spanish 53% Other Indo-European 2% French/Haitian/Cajun 1%

Political lean MEDSL · Hampden

• 2024 margin: Lean D (+8.9) · D 53.4% · R 44.5% · Other 2.1%
• 2008→2024 swing: -16.4pp toward R · 2008: 25.3pp · 2024: 8.9pp
• All cycles: 2024: D+8.9 2020: D+17.7 2016: D+16.0 2012: D+25.4 2008: D+25.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 1.08%
• Current HPI: 322.6127
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 2.28%
• F500 in state: 38

Industry mix (Fortune 500 HQ in MA)

Industry	F500 HQs	Revenue
▸Technology	3	$17B
▸Insurance	2	$84B
▸Retail	2	$76B
▸Life Sciences	1	$43B
▸Energy Technology	1	$31B
▸Aerospace / Defense	1	$18B

Price history

+200.0% since first listed

33 events — show timeline

• 2026-05-15 Relisted — MLS PIN
• 2026-05-13 Pending — MLS PIN
• 2026-05-06 Price Changed $210,000 MLS PIN
• 2026-05-02 Relisted — MLS PIN
• 2026-04-23 Contingent — MLS PIN
• 2026-04-07 Listed $215,000 MLS PIN
• 2023-11-12 Rental Removed $2,250 BUILDIUM
• 2023-11-04 Listed for Rent $2,250 BUILDIUM
• 2023-11-03 Sold (MLS) $207,000 MLS PIN
• 2023-10-06 Pending — MLS PIN
• 2023-09-26 Contingent — MLS PIN
• 2023-09-22 Price Changed $209,000 MLS PIN
• 2023-09-11 Price Changed $214,900 MLS PIN
• 2023-08-23 Price Changed $215,000 MLS PIN
• 2023-08-11 Price Changed $219,900 MLS PIN
• 2023-08-09 Price Changed $224,000 MLS PIN
• 2023-08-01 Price Changed $225,000 MLS PIN
• 2023-07-19 Relisted — MLS PIN
• 2023-07-18 Contingent — MLS PIN
• 2023-07-10 Relisted — MLS PIN
• 2023-07-06 Pending — MLS PIN
• 2023-06-22 Contingent — MLS PIN
• 2023-06-21 Price Changed $229,900 MLS PIN
• 2023-06-15 Listed $235,000 MLS PIN
• 2023-03-28 Sold (MLS) $104,000 MLS PIN
• 2023-02-20 Pending — MLS PIN
• 2023-02-15 Contingent — MLS PIN
• 2023-01-21 Price Changed $124,900 MLS PIN
• 2022-12-22 Price Changed $134,900 MLS PIN
• 2022-11-16 Listed $144,900 MLS PIN
• 2002-11-12 Sold (Public Records) $70,500 Public Records
• 2002-11-12 Sold (MLS) $70,000 MLS PIN
• 2002-10-01 Listed $70,000 MLS PIN

Property tax history

+3.6%/yr

Latest (2023): $2,453 · +13.4% YoY. Source: county tax records.