101 Friar Tuck Dr · Chester, MA 01223

$199,900

2 bd · 1.0 ba · 760 sqft · SingleFamily public records · 23 Days on market

Built 1974 0.53 ac lot Est $187k · 7% over

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Why this score? — see what drove the D- 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).

• Appreciation +10.0/10.0
• Cash flow +8.1/30.0
• ARV discount +4.4/15.0
• Livability +3.7/5.0
• Schools +3.5/10.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• DSCR +2.2/10.0
• 1% rule +1.6/10.0

Listing remarks MLS

Affordable 2 bedroom 1 bath home located in Sherwood Forest. Enjoy deeded lake access and a nice fenced in back yard with large fire pit. Updates include - new roof and shed roof in 2020 and new flooring.

Key facts

• Open concept ranch
• Half acre
• 0.53 acre lot

Tags

• OPEN CONCEPT RANCH
• RECENTLY TILED SHOWER
• SOUTH FACING DINING ROOM
• HALF ACRE
• ACCESSORY DWELLING UNITS

Property features AI

Finance

• HOA & community: Not a senior community

Exterior

• Parking: 4 off-street parking spaces
• Utilities: Private water; Private sewer; 110-volt electric; Gas connections available for range and oven
• Home design: Single family residence; Single-story (entry level and exact stories not specified)
• Construction: Shingle roof; Irregular foundation; Built year per public records
• Exterior features: Porch; Fenced yard; Fenced/enclosed; Cleared lot; Private road frontage; Private maintained road; Unimproved road surface; Lake/pond access; Nearby beach with deeded beach rights (1/10 to 3/10 mile)

Interior

• Kitchen: Range; Microwave; Refrigerator; Water heater
• Flooring: Wood flooring; Carpet
• Bathrooms: 1 full bathroom
• Heating & cooling: Window air conditioning units
• Interior features: Insulated doors; Insulated windows; Total of 4 rooms
• Laundry & utility: Washer and dryer included; Washer hookup; Electric dryer hookup

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $200k.

Deal economics

• At list price, monthly cash flow is $-192 ($-2k/yr) — negative.
• To cash-flow at today's rent, offer at most $166k (17.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $133k (33.7% below list).
• Recommended offer: $133k (33.7% below list) — sets the bar for 1% rule.
• Cap rate 5.1% vs local median 1.8% in Chester — 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 74/100 on livability (#91 in MA, #4,646 nationally) — a middle-class / working-renter tenant base. Strengths: crime A+, housing A+, employment A; Watch: schools C-, amenities F, commute F.
• Central Berkshire (rural): math 32% / reading 47% proficiency, ranked #206 of 302 in MA (top 68%) — families likely to look elsewhere, expect single-tenant / working-renter base with shorter leases.
• Market conditions: 73 active listings in the ZIP; 130 units permitted in Berkshire County in 2024 (10 in 5+ unit buildings).

Forward outlook

• In year one you build about $21k of equity ($1k loan paydown + $20k appreciation (10.0% local appreciation)).
• Berkshire County population projected at -24% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• By year 2, paydown + projected appreciation supports a ~$34k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 23 days — a 2% lower offer ($197k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 10y ago with the ask held roughly flat each time — persistent listings suggest the price (not the market) is what's stuck; bring a comps-based counter.
• Current owner paid $150k; 33% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Recommended offer $132,527 (33.7% below list)

Questions for the listing agent

1. What do current leases actually rent for vs. the listed asking? Can we see a recent rent roll and the last 12 months of T-12 income?
2. Built in 1974 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. The area grade is low — what's the realistic commute time and amenity access for the typical tenant pool here? Any planned neighborhood developments (good or bad) we should know about?
5. 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.
6. 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.
7. 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: 0.66% ✗
• Cap rate: 5.14%
• Cash-on-cash: -4.12%
• DSCR: 0.82
• GRM: 12.6

CMA / ARV

• ARV (on-the-fly): $186,960
• Comps found: 3

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
48 King Arthur Dr	0.28mi	1/1.0 (-1)	765 (+1%)	17mo	$180,000	$235	67
40 Dragon Way	0.68mi	2/1.0	651 (-14%)	9mo	$198,000	$304	37
73 Porcupine Ct	0.68mi	2/1.0	852 (+12%)	20mo	$210,000	$246	31

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

Projected returns pro-forma

10.0% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 21.3%
• Equity multiple: 2.73×
• Total profit: $96,577
• Equity at exit: $180,086

10-year hold

• IRR: 19.3%
• Equity multiple: 6.25×
• Total profit: $293,884
• Equity at exit: $388,362

Cash invested: $55,972 (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 01223

• Home prices YoY: 6.8%
• Active inventory: 73
• Price-to-rent: 12.6×

Monthly cashflow live

• Estimated rent: $1,325 medium
• Mortgage (P&I): −$1,048
• Tax from tax record: −$107 /mo · $1,288/yr
• Insurance: −$83
• HOA: −$0
• Vacancy / Maint / Mgmt: −$278
• Net cashflow: $-192

Break-even live

Break-even rent $1,568

Max offer price $165,990

Occupancy floor —

Sensitivity live

Price	-10% $-79	-5% $-135	+0% $-192	+5% $-249	+10% $-305
Rent	-10% $-297	-5% $-244	+0% $-192	+5% $-140	+10% $-87
Rate	-1.0pp $-91	-0.5pp $-141	base $-192	+0.5pp $-244	+1.0pp $-296

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: $49,975
• Closing costs: $5,997
• Reserves months: —
• Total cash needed: —

Listing history 26 events

1. 2026-06-19
   days on market $199,900 Active 23 DOM
2. 2026-06-18
   days on market $199,900 Active 22 DOM
3. 2026-06-17
   days on market $199,900 Active 21 DOM
4. 2026-06-16
   days on market $199,900 Active 20 DOM
5. 2026-06-15
   days on market $199,900 Active 19 DOM
6. 2026-06-14
   days on market $199,900 Active 17 DOM
7. 2026-06-12
   days on market $199,900 Active 16 DOM
8. 2026-06-09
   days on market $199,900 Active 13 DOM
9. 2026-06-08
   days on market $199,900 Active 12 DOM
10. 2026-06-07
    days on market $199,900 Active 11 DOM
11. 2026-06-05
    days on market $199,900 Active 8 DOM
12. 2026-06-03
    days on market $199,900 Active 7 DOM
13. 2026-06-02
    days on market $199,900 Active 6 DOM
14. 2026-06-01
    statusdays on market $199,900 Active 5 DOM
15. 2026-05-31
    days on market $199,900 New 4 DOM
16. 2026-05-30
    days on market $199,900 New 3 DOM
17. 2026-05-28
    listed $199,900 New
18. 2022-09-30
    soldstatus $150,000 Closed 204-char remark

    Show marketing remark (204 chars)

    Affordable 2 bedroom 1 bath home located in Sherwood Forest. Enjoy deeded lake access and a nice fenced in back yard with large fire pit. Updates include - new roof and shed roof in 2020 and new flooring.

19. 2022-09-13
    status Pending 204-char remark

    Show marketing remark (204 chars)

    Affordable 2 bedroom 1 bath home located in Sherwood Forest. Enjoy deeded lake access and a nice fenced in back yard with large fire pit. Updates include - new roof and shed roof in 2020 and new flooring.

20. 2022-09-06
    listed $150,000 Active 204-char remark

    Show marketing remark (204 chars)

    Affordable 2 bedroom 1 bath home located in Sherwood Forest. Enjoy deeded lake access and a nice fenced in back yard with large fire pit. Updates include - new roof and shed roof in 2020 and new flooring.

21. 2017-01-31
    soldstatus $73,400 216-char remark

    Show marketing remark (216 chars)

    Close to southern Berkshire cultural attractions. Bring your own personal touches. Open concept, single level living. Comes with extra lot across the street. Title V to be determined. Agent is related to seller.

22. 2017-01-31
    soldstatus $73,400

    Show marketing remark (216 chars)

    Close to southern Berkshire cultural attractions. Bring your own personal touches. Open concept, single level living. Comes with extra lot across the street. Title V to be determined. Agent is related to seller.

23. 2016-11-07
    listed $69,900 216-char remark

    Show marketing remark (216 chars)

    Close to southern Berkshire cultural attractions. Bring your own personal touches. Open concept, single level living. Comes with extra lot across the street. Title V to be determined. Agent is related to seller.

24. 2016-11-07
    listed $69,900

    Show marketing remark (216 chars)

    Close to southern Berkshire cultural attractions. Bring your own personal touches. Open concept, single level living. Comes with extra lot across the street. Title V to be determined. Agent is related to seller.

25. 2016-06-13
    historical
26. 2016-05-01
    listed $55,500

ⓘ 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: $1,288 · $107/mo
• Projected year-2 tax: $1,873 · $156/mo
• Expected delta: +$585/yr (+$49/mo · 45.4%)

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

Taxation est. · year 1

• Rental income: $15,903
• − Mortgage interest: −$11,198
• − Property taxes: −$1,288
• − Insurance: −$1,000
• − Repairs & maintenance: −$1,272
• − Management: −$1,272
• − Depreciation: −$5,815
• Taxable loss: −$5,942
• Est. tax savings @ 24.0%: +$1,426
• After-tax cash flow: $-878/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: Central Berkshire
• NCES district ID: 2503390
• Math proficiency: 32% ▼ -13.00%
• Reading proficiency: 47% ▲ 1.00%
• Median HH income: $58,145
• Composite: 34.8/100
• National rank: #5108
• State rank: #206 of 302 in MA

Livability — Chester

• Score: 74/100
• State rank: #91
• US rank: #4646

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• Population (ZIP): 2,588

Population outlook (Berkshire County) Hauer SSP2

• Today (2025): 119,723 people
• By 2030: 114,608 · -4.3%
• By 2040: 102,806 · -14.1%
• By 2050: 91,305 · -23.7%
• By 2075: 71,517 · -40.3%
• By 2100: 57,988 · -51.6%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (91%)
• Race & ethnicity: White 91% Two or more races 6% Hispanic / Latino 3% Asian 1%
• Common ancestry: Lithuanian 10% Romanian 6% Slovak 2%
• Foreign-born: 5%
• Languages at home: 93% English-only · Russian/Polish/Slavic 2% Other Indo-European 1% Spanish 1%

Political lean MEDSL · Berkshire

• 2024 margin: Solid D (+39.9) · D 68.9% · R 29.0% · Other 2.1%
• 2008→2024 swing: -12.5pp toward R · 2008: 52.4pp · 2024: 39.9pp
• All cycles: 2024: D+39.9 2020: D+47.1 2016: D+41.5 2012: D+53.7 2008: D+52.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 19.33%
• Current HPI: 305.8977
• 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

+260.2% since first listed

10 events — show timeline

• 2026-05-28 Listed $199,900 MLS PIN
• 2022-09-30 Sold (MLS) $150,000 BCMLS
• 2022-09-13 Pending — BCMLS
• 2022-09-06 Listed $150,000 BCMLS
• 2017-01-31 Sold (MLS) $73,400 BCMLS
• 2017-01-31 Sold (MLS) $73,400 MLS PIN
• 2016-11-07 Listed $69,900 BCMLS
• 2016-11-07 Listed $69,900 MLS PIN
• 2016-06-13 Listing Removed — BCMLS
• 2016-05-01 Listed $55,500 BCMLS

Property tax history

+3.2%/yr

Latest (2023): $1,288 · +37.2% YoY. Source: county tax records.