568 Wellesley St · Wellesley, MA 02493

$4,388,000

5 bd · 6.0 ba · 8,152 sqft · SingleFamily public records · 131 Days on market

Built 1988 1.79 ac lot $538/sqft · 10% below area Est $5275k · 17% under

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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).

• ARV discount +15.0/15.0
• Schools +7.4/10.0
• Cash flow +6.2/30.0
• Appreciation +5.8/10.0
• Livability +4.2/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.7/10.0
• DSCR +0.5/10.0

Listing remarks MLS

Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded appliances flows into a spacious family room and sunroom, both with fireplaces. A luxurious first-floor primary suite offers a spa-like bath, dual walk-in closets, private office, and gym. Residents and guests can unwind in the spacious private theater, perfect for an immersive entertainment experience. The expansive finished basement offers an additional comfortable living area, ideal for recreation, relaxation, or extended guest stays.Outdoors, enjoy a bluestone patio with built-in grill and fire pit, plus a resort-style pool with waterfall spa, surrounded by elegant stonework. Very near to schools.

Key facts

• 1.79 acre lot
• 3 garage spots
• Pool

What this means for you Summary

Snapshot

• This is a 5-bed/6.0-bath single-family listed at $4.39M.

Deal economics

• At list price, monthly cash flow is $-8k ($-96k/yr) — negative.
• To cash-flow at today's rent, offer at most $2.98M (32.1% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $2.50M (43.0% below list).
• Recommended offer: $2.50M (43.0% below list) — sets the bar for 1% rule.
• Cap rate 4.1% vs local median 1.6% in Wellesley — 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 85/100 on livability (#13 in MA, #568 nationally) — a professional / high-income tenant draw. Strengths: crime A+, commute A+, employment A+; Watch: amenities C-, cost of living F.
• Weston (suburban): math 71% / reading 77% proficiency, ranked #7 of 302 in MA (top 2%) — strong family-tenant draw, lease renewals of 3-5y typical; only 4% free/reduced lunch — higher-income household profile.
• Zoned schools: Country (math 44% / reading 74%, grade B-, #167 of 938 statewide, top 21%, 331 students, 0% FRL); Weston Middle (math 72% / reading 76%, grade A, #5 of 305 statewide, top 2%, 444 students, 0% FRL); Weston High (math 87% / reading 82%, grade A, #22 of 343 statewide, top 8%, 639 students, 0% FRL) — zoned schools at 0% FRL track the district average.
• Market conditions: 53 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 3,670 units permitted in Middlesex County in 2024 (2,611 in 5+ unit buildings).

Forward outlook

• In year one you build about $97k of equity ($30k loan paydown + $66k appreciation (1.5% local appreciation)).
• Middlesex County population projected at +20% by 2050 — long-run rental-demand tailwind backs the buy-and-hold thesis.
• By year 3, paydown + projected appreciation supports a ~$249k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 131 days — a 12% lower offer ($3.86M) is reasonable based on typical stale-listing flexibility.
• 7 sale attempts since 19y ago; this cycle's ask has dropped $300k (6%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $635k; list at $4.39M implies a 591% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 50% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $2,500,000 (43.0% 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. It's been on market 131 days. Have you received any prior offers? Is the seller open to a 43% concession, seller financing, or rate buy-down credit?
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 A-rated — typically a magnet for longer-tenancy family renters. What's the average tenant stay here, and is there a school-zone premium baked into asking?
6. 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?
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: 0.57% ✗
• Cap rate: 4.11%
• Cash-on-cash: -7.79%
• DSCR: 0.65
• GRM: 14.6

CMA / ARV

• ARV (median comp): $5,274,872
• List price: $4,388,000
• Delta: -16.81%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
57 Westcliff Rd	0.55mi	6/7.0 (+1)	8,005 (-2%)	12mo	$5,420,000	$677	53
55 Radcliffe Rd	0.42mi	6/7.5 (+1)	8,000 (-2%)	23mo	$4,520,000	$565	47
168 Beaver Rd	0.67mi	5/7.0	7,369 (-10%)	7mo	$4,075,000	$553	43

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

Projected returns pro-forma

1.51% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -4.9%
• Equity multiple: 0.74×
• Total profit: $-316,968
• Equity at exit: $1,615,335

10-year hold

• IRR: 0.2%
• Equity multiple: 1.02×
• Total profit: $27,532
• Equity at exit: $2,240,497

Cash invested: $1,228,640 (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 02493

• Home prices YoY: 0.6%
• Active inventory: 53
• Price-to-rent: 14.6×

Monthly cashflow live

• Estimated rent: $25,000 medium
• Mortgage (P&I): −$23,011
• Tax from tax record: −$2,888 /mo · $34,660/yr
• Insurance: −$1,828
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,250
• Net cashflow: $-7,978

Break-even live

Break-even rent $35,099

Max offer price $2,978,685

Occupancy floor —

Sensitivity live

Price	-10% $-5,494	-5% $-6,736	+0% $-7,978	+5% $-9,220	+10% $-10,462
Rent	-10% $-9,953	-5% $-8,965	+0% $-7,978	+5% $-6,990	+10% $-6,003
Rate	-1.0pp $-5,768	-0.5pp $-6,862	base $-7,978	+0.5pp $-9,115	+1.0pp $-10,272

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: $1,097,000
• Closing costs: $131,640
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
63 Sylvan Ln Weston, MA	5.0	5.5	11990	$25,000	$2.09	0d	1	0.25mi

Listing history 38 events

1. 2026-06-21
   days on market $4,388,000 Active 131 DOM
2. 2026-06-18
   days on market $4,388,000 Active 128 DOM
3. 2026-06-17
   days on market $4,388,000 Active 127 DOM
4. 2026-06-16
   days on market $4,388,000 Active 126 DOM
5. 2026-06-15
   days on market $4,388,000 Active 125 DOM
6. 2026-06-13
   days on market $4,388,000 Active 123 DOM
7. 2026-06-09
   days on market $4,388,000 Active 119 DOM
8. 2026-06-08
   days on market $4,388,000 Active 118 DOM
9. 2026-06-07
   days on market $4,388,000 Active 117 DOM
10. 2026-06-04
    days on market $4,388,000 Active 114 DOM
11. 2026-06-03
    days on market $4,388,000 Active 113 DOM
12. 2026-06-02
    days on market $4,388,000 Active 112 DOM
13. 2026-06-01
    days on market $4,388,000 Active 111 DOM
14. 2026-05-31
    days on market $4,388,000 Active 110 DOM
15. 2026-03-25
    price $4,388,000 1003-char remark

    Show marketing remark (1003 chars)

    Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded appliances flows into a spacious family room and sunroom, both with fireplaces. A luxurious first-floor primary suite offers a spa-like bath, dual walk-in closets, private office, and gym. Residents and guests can unwind in the spacious private theater, perfect for an immersive entertainment experience. The expansive finished basement offers an additional comfortable living area, ideal for recreation, relaxation, or extended guest stays.Outdoors, enjoy a bluestone patio with built-in grill and fire pit, plus a resort-style pool with waterfall spa, surrounded by elegant stonework. Very near to schools.

16. 2026-02-10
    listed $4,688,000 New 1003-char remark

    Show marketing remark (1003 chars)

    Elegant Custom Estate on 1.8 Acres in Weston! This stunning 8,000+ sq ft Colonial sits on a beautifully landscaped, level 1.8-acre lot with a private drive and circular entry. Inside, a grand foyer with a sweeping staircase opens to formal living and dining rooms with soaring ceilings, crown moldings, and French doors. The gourmet kitchen with marble countertops, super high-end & branded appliances flows into a spacious family room and sunroom, both with fireplaces. A luxurious first-floor primary suite offers a spa-like bath, dual walk-in closets, private office, and gym. Residents and guests can unwind in the spacious private theater, perfect for an immersive entertainment experience. The expansive finished basement offers an additional comfortable living area, ideal for recreation, relaxation, or extended guest stays.Outdoors, enjoy a bluestone patio with built-in grill and fire pit, plus a resort-style pool with waterfall spa, surrounded by elegant stonework. Very near to schools.

17. 2023-04-21
    soldstatus $635,000 Sold 1002-char remark

    Show marketing remark (1002 chars)

    Finally, a home that presents every bit as well in person as it does in its professional photos... In fact, 33 Pupkis Road will likely exceed your expectations. Charm and care are evident throughout this 3 bed, 2 full bath home in Tewksbury. Learn to love cooking again in your custom kitchen featuring granite counters, stainless appliances and thoughtfully designed with a perfect and practical work triangle. Bright and spacious, the large living room and dining room area feels open and inviting. 3 generous bedrooms, full hallway bath and laundry offer comfort and refuge after a long day...but only after a dip in the above ground pool or catching some rays on the patio deck or perhaps unwind with a cocktail under the gazebo. As you tour this lovely home it will become more apparent that 33 Pupkis Road feels more like an oasis than just a home both inside and out. Sellers hoping for flexibility with respect to closing and requesting a Use & Occupancy Agreement. Book your showing today!

18. 2023-03-16
    status Under Agreement 1002-char remark

    Show marketing remark (1002 chars)

    Finally, a home that presents every bit as well in person as it does in its professional photos... In fact, 33 Pupkis Road will likely exceed your expectations. Charm and care are evident throughout this 3 bed, 2 full bath home in Tewksbury. Learn to love cooking again in your custom kitchen featuring granite counters, stainless appliances and thoughtfully designed with a perfect and practical work triangle. Bright and spacious, the large living room and dining room area feels open and inviting. 3 generous bedrooms, full hallway bath and laundry offer comfort and refuge after a long day...but only after a dip in the above ground pool or catching some rays on the patio deck or perhaps unwind with a cocktail under the gazebo. As you tour this lovely home it will become more apparent that 33 Pupkis Road feels more like an oasis than just a home both inside and out. Sellers hoping for flexibility with respect to closing and requesting a Use & Occupancy Agreement. Book your showing today!

19. 2023-03-08
    historical Contingent 1002-char remark

    Show marketing remark (1002 chars)

    Finally, a home that presents every bit as well in person as it does in its professional photos... In fact, 33 Pupkis Road will likely exceed your expectations. Charm and care are evident throughout this 3 bed, 2 full bath home in Tewksbury. Learn to love cooking again in your custom kitchen featuring granite counters, stainless appliances and thoughtfully designed with a perfect and practical work triangle. Bright and spacious, the large living room and dining room area feels open and inviting. 3 generous bedrooms, full hallway bath and laundry offer comfort and refuge after a long day...but only after a dip in the above ground pool or catching some rays on the patio deck or perhaps unwind with a cocktail under the gazebo. As you tour this lovely home it will become more apparent that 33 Pupkis Road feels more like an oasis than just a home both inside and out. Sellers hoping for flexibility with respect to closing and requesting a Use & Occupancy Agreement. Book your showing today!

20. 2023-02-27
    listed $619,900 New 1002-char remark

    Show marketing remark (1002 chars)

    Finally, a home that presents every bit as well in person as it does in its professional photos... In fact, 33 Pupkis Road will likely exceed your expectations. Charm and care are evident throughout this 3 bed, 2 full bath home in Tewksbury. Learn to love cooking again in your custom kitchen featuring granite counters, stainless appliances and thoughtfully designed with a perfect and practical work triangle. Bright and spacious, the large living room and dining room area feels open and inviting. 3 generous bedrooms, full hallway bath and laundry offer comfort and refuge after a long day...but only after a dip in the above ground pool or catching some rays on the patio deck or perhaps unwind with a cocktail under the gazebo. As you tour this lovely home it will become more apparent that 33 Pupkis Road feels more like an oasis than just a home both inside and out. Sellers hoping for flexibility with respect to closing and requesting a Use & Occupancy Agreement. Book your showing today!

21. 2020-04-30
    soldstatus $499,900 Sold
22. 2020-03-27
    status Under Agreement
23. 2020-03-18
    listed $499,900 New
24. 2015-02-25
    soldstatus $285,000 Sold
25. 2014-12-15
    historical Contingent
26. 2014-12-07
    status Back On Market
27. 2014-11-28
    historical Contingent
28. 2014-11-05
    price $295,000
29. 2014-10-30
    status Back On Market
30. 2014-10-16
    historical Contingent
31. 2014-09-23
    price $299,900
32. 2014-08-20
    listed $329,900 New
33. 2007-11-14
    historical
34. 2007-11-13
    soldstatus $318,000 Sold
35. 2007-11-13
    soldstatus $318,000
36. 2007-09-19
    price $324,900
37. 2007-09-12
    price $328,000
38. 2007-08-25
    listed $334,900

ⓘ 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: $34,660 · $2,888/mo
• Projected year-2 tax: $44,316 · $3,693/mo
• Expected delta: +$9,656/yr (+$805/mo · 27.9%)

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥97°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 50% chance of damaging wind over 30 yrs
• 🫁 Air quality 2/10 Low 1 unhealthy d/yr today · 2 by 30 yrs out

Taxation est. · year 1

• Rental income: $300,000
• − Mortgage interest: −$245,796
• − Property taxes: −$34,660
• − Insurance: −$21,940
• − Repairs & maintenance: −$24,000
• − Management: −$24,000
• − Depreciation: −$127,651
• Taxable loss: −$178,047
• Est. tax savings @ 24.0%: +$42,731
• After-tax cash flow: $-53,002/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: Weston
• NCES district ID: 2512750
• Math proficiency: 71% ▼ -11.00%
• Reading proficiency: 77% ▼ -6.00%
• Median HH income: $164,610
• Composite: 73.62/100
• National rank: #175
• State rank: #7 of 302 in MA

Livability — Wellesley

• Score: 85/100
• State rank: #13
• US rank: #568

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 17,415
• Population (ZIP): 11,443

Population outlook (Middlesex County) Hauer SSP2

• Today (2025): 1,740,269 people
• By 2030: 1,817,187 · +4.4%
• By 2040: 1,963,195 · +12.8%
• By 2050: 2,087,461 · +20.0%
• By 2075: 2,344,036 · +34.7%
• By 2100: 2,383,776 · +37.0%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (74%)
• Race & ethnicity: White 74% Asian 13% Two or more races 6% Hispanic / Latino 4% Black 3%
• Common ancestry: Romanian 6% Iranian 5% Scotch-Irish 4%
• Foreign-born: 21% · Canada, China, South Korea
• Languages at home: 73% English-only · Other Indo-European 9% Chinese 5% Russian/Polish/Slavic 2%

Political lean MEDSL · Middlesex

• 2024 margin: Solid D (+39.5) · D 68.5% · R 29.0% · Other 2.5%
• 2008→2024 swing: +9.3pp toward D · 2008: 30.1pp · 2024: 39.5pp
• All cycles: 2024: D+39.5 2020: D+45.2 2016: D+38.1 2012: D+26.9 2008: D+30.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 1.51%
• Current HPI: 272.692
• 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

+1210.2% since first listed

24 events — show timeline

• 2026-03-25 Price Changed $4,388,000 MLS PIN
• 2026-02-10 Listed $4,688,000 MLS PIN
• 2023-04-21 Sold (MLS) $635,000 MLS PIN
• 2023-03-16 Pending — MLS PIN
• 2023-03-08 Contingent — MLS PIN
• 2023-02-27 Listed $619,900 MLS PIN
• 2020-04-30 Sold (MLS) $499,900 MLS PIN
• 2020-03-27 Pending — MLS PIN
• 2020-03-18 Listed $499,900 MLS PIN
• 2015-02-25 Sold (MLS) $285,000 MLS PIN
• 2014-12-15 Contingent — MLS PIN
• 2014-12-07 Relisted — MLS PIN
• 2014-11-28 Contingent — MLS PIN
• 2014-11-05 Price Changed $295,000 MLS PIN
• 2014-10-30 Relisted — MLS PIN
• 2014-10-16 Contingent — MLS PIN
• 2014-09-23 Price Changed $299,900 MLS PIN
• 2014-08-20 Listed $329,900 MLS PIN
• 2007-11-14 Listing Removed — MLS PIN
• 2007-11-13 Sold (Public Records) $318,000 Public Records
• 2007-11-13 Sold (MLS) $318,000 MLS PIN
• 2007-09-19 Price Changed $324,900 MLS PIN
• 2007-09-12 Price Changed $328,000 MLS PIN
• 2007-08-25 Listed $334,900 MLS PIN

Property tax history

+14.6%/yr

Latest (2026): $34,660 · +387.1% YoY. Source: county tax records.