6 Winthrop Hls · Weston, CT 06883

$2,350,000

5 bd · 5.0 ba · 6,684 sqft · SingleFamily public records · 55 Days on market

Built 1998 2.03 ac lot Est $2132k · 10% over

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Why this score? — see what drove the C- 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 +22.1/30.0
• Schools +7.5/10.0
• DSCR +7.1/10.0
• 1% rule +5.7/10.0
• ARV discount +2.9/15.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks

THANK YOU FOR YOUR INTEREST, SELLER REQUESTS HIGHEST/BEST OFFERS BY 5PM MONDAY 3/30. Welcome to this Modern Colonial, a sanctuary where luxury, comfort & tranquility converge on a premier cul-de-sac, conveniently located to the Merritt Parkway, Weston Center & the campus of award-winning schools and downtown Westport plus beaches. With 5 BRs plus a potential 6th BR/au-pair or in-law suite, this refined retreat offers elegant living & impressive entertaining. The newly reimagined kitchen is a showpiece of style & substance: a spacious island anchors the room, surrounded by premier appliances & abundant storage, all beautifully designed, expertly equipped, and re

Key facts

• 2.03 acre lot
• 4 garage spots
• Pool

Property features AI

Exterior

• Parking: Attached garage with 4 parking spaces
• Utilities: Private well water; Septic system; Oil hot water; Electric power (standard); Thermopane windows for energy efficiency
• Home design: Single-family home; Grey exterior
• Construction: Frame construction; Concrete foundation; Asphalt shingle roof; Wood and shingle siding
• Exterior features: Wrap-around porch including screened porch; Patio; Exterior lighting; Partially fenced, level lot on a cul-de-sac; Cleared and professionally landscaped; Beach rights; In-ground heated swimming pool

Interior

• Kitchen: Gas cooktop; Gas range; Microwave; Range hood; Refrigerator; Dishwasher
• Bedrooms: 5 bedrooms
• Bathrooms: 4 full bathrooms; 2 half bathrooms
• Heating & cooling: Central air with zoned cooling; Hot air heating; Oil-fired hot water; Above-ground fuel tank; Thermopane windows
• Interior features: Audio system; Cable available; Possible in-law apartment over the garage; Two fireplaces; Full, fully finished basement; 11 total rooms; Foyer, mud room, staff quarters
• Laundry & utility: Washer; Dryer; Upper-level laundry room

What this means for you Summary

Snapshot

• This is a 5-bed/5.0-bath single-family listed at $2.35M.

Deal economics

• At list price, monthly cash flow is $4k ($45k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($25k rent vs $2.35M).
• Recommended offer: $2.28M (3.0% below list) — sets the bar for market timing.
• Cap rate 8.2% vs local median 2.9% in Weston — 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: area grade C — affects rentability + tenant quality, not the cash-flow math above.
• Weston School District (suburban): math 68% / reading 77% proficiency, ranked #4 of 153 in CT (top 3%) — strong family-tenant draw, lease renewals of 3-5y typical; only 1% free/reduced lunch — higher-income household profile.
• Zoned schools: Hurlbutt Elementary School (473 students, 1% FRL); Weston Middle School (math 60% / reading 73%, grade A-, #23 of 175 statewide, top 13%, 534 students, 1% FRL); Weston High School (math 82% / reading 87%, grade A, #1 of 194 statewide, top 1%, 722 students, 1% FRL) — zoned schools at 1% FRL track the district average.
• Market conditions: 73 active listings in the ZIP; 2 comparable units currently listed for rent nearby; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $16k of loan paydown is wiped out by about $70k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 55 days — a 3% lower offer ($2.28M) is reasonable based on typical stale-listing flexibility.
• 9 sale attempts since 21y 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.

Recommended offer $2,279,500 (3.0% below list)

Questions for the listing agent

1. It's been on market 55 days. Have you received any prior offers? Is the seller open to a 3% concession, seller financing, or rate buy-down credit?
2. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
3. 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.
4. 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.
5. 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: 1.07% ✓
• Cap rate: 8.22%
• Cash-on-cash: 6.88%
• DSCR: 1.31
• GRM: 7.8

CMA / ARV

• ARV (on-the-fly): $2,132,196
• Comps found: 5

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
6 Winthrop Hls	0.00mi	5/5.0	6,684 (0%)	0mo	$2,400,000	$359	100
10 Winthrop Hls	0.01mi	4/6.0 (-1)	7,069 (+6%)	13mo	$2,255,000	$319	70
11 Winthrop Hls	0.02mi	5/5.0	6,131 (-8%)	23mo	$2,006,000	$327	66
17 Tannery Ln N	0.37mi	5/4.5	5,685 (-15%)	12mo	$1,600,000	$281	46
24 Oakwood Dr	0.59mi	6/7.0 (+1)	6,891 (+3%)	23mo	$1,775,000	$258	35

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

Projected returns pro-forma

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

5-year hold

• IRR: -5.7%
• Equity multiple: 0.79×
• Total profit: $-140,114
• Equity at exit: $350,393

10-year hold

• IRR: 3.9%
• Equity multiple: 1.29×
• Total profit: $188,656
• Equity at exit: $203,185

Cash invested: $658,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 27 Tenant-Leaning
• State Connecticut: 27 Tenant-Leaning · D+7
• County: — inherits STATE
• City: — inherits STATE

Strong tenant statutes; rent commissions in some towns; courts slow especially in cities.

Methodology + full state rankings →

ZIP-level market 06883

• Active inventory: 73
• Price-to-rent: 7.8×

Monthly cashflow live

• Estimated rent: $25,106 medium
• Mortgage (P&I): −$12,324
• Tax from tax record: −$2,756 /mo · $33,071/yr
• Insurance: −$979
• HOA: −$0
• Vacancy / Maint / Mgmt: −$5,272
• Net cashflow: $3,775

Break-even live

Break-even rent $20,328

Max offer price $2,350,000

Occupancy floor 80%

Sensitivity live

Price	-10% $5,105	-5% $4,440	+0% $3,775	+5% $3,110	+10% $2,445
Rent	-10% $1,791	-5% $2,783	+0% $3,775	+5% $4,766	+10% $5,758
Rate	-1.0pp $4,958	-0.5pp $4,373	base $3,775	+0.5pp $3,166	+1.0pp $2,546

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: $587,500
• Closing costs: $70,500
• Reserves months: —
• Total cash needed: —

Rent comps 2 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
29 Rogues Rdg Weston, CT	6.0	6.5	7649	$17,000	$2.22	4d	1	0.57mi
37 Beaverbrook Rd Weston, CT	5.0	4.5	6734	$35,000	$5.20	45d	1	0.79mi

Listing history 24 events

1. 2026-05-21
   status Under Contract
2. 2026-04-09
   historical Under Contract - Continue to Show
3. 2026-03-27
   listed $2,350,000 Active
4. 2026-03-19
   historical $2,350,000
5. 2025-11-21
   historical
6. 2025-10-23
   listed $2,099,000 Active
7. 2025-07-22
   historical
8. 2025-06-05
   price $2,190,000
9. 2025-05-13
   price $2,300,000
10. 2025-04-19
    listed $2,450,000 Active
11. 2025-04-08
    historical
12. 2024-11-02
    historical
13. 2024-09-11
    historical $6,900
14. 2024-07-13
    listed $2,385,000 Active
15. 2024-07-10
    listed $6,900
16. 2024-06-04
    historical $30,000
17. 2024-06-03
    historical
18. 2024-02-26
    listed $2,350,000 Active
19. 2024-01-07
    listed $30,000
20. 2024-01-07
    historical $7,500
21. 2023-12-20
    listed $7,500
22. 2005-09-19
    soldstatus $2,100,000
23. 2005-09-19
    soldstatus $2,100,000
24. 2005-04-21
    listed $2,225,000

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $33,071 · $2,756/mo
• Projected year-2 tax: $41,680 · $3,473/mo
• Expected delta: +$8,610/yr (+$717/mo · 26.0%)

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

Taxation est. · year 1

• Rental income: $301,269
• − Mortgage interest: −$131,637
• − Property taxes: −$33,071
• − Insurance: −$11,750
• − Repairs & maintenance: −$24,102
• − Management: −$24,102
• − Depreciation: −$68,364
• Taxable income: $8,245
• Est. tax owed @ 24.0%: −$1,979
• After-tax cash flow: $43,319/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 School District
• NCES district ID: 0905010
• Math proficiency: 68% ▼ -6.00%
• Reading proficiency: 77% ▼ -1.00%
• Median HH income: $194,414
• Composite: 75.21/100
• National rank: #137
• State rank: #4 of 153 in CT

Livability — Weston

No livability data for this city. (Only ~50 U.S. cities are tracked.)

Census & demographics

• Population (ZIP): 10,335

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (78%)
• Race & ethnicity: White 78% Two or more races 10% Hispanic / Latino 9% Asian 5% Black 3%
• Hispanic origin (detail): Mexican 1% Puerto Rican 2% Dominican 1% Salvadoran 2%
• Common ancestry: Romanian 7% Scotch-Irish 5% Italian 5%
• Foreign-born: 16% · Canada, China, Dominican Republic
• Languages at home: 83% English-only · Spanish 5% Chinese 3% Other Indo-European 3%

Political lean MEDSL · Western Connecticut

• 2024 margin: D (+19.1) · D 58.8% · R 39.7% · Other 1.6%
• All cycles: 2024: D+19.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -316.44%
• Current HPI: 208.835
• Rent YoY: —
• Metro: —
• State GDP YoY: ▲ 1.06%
• F500 in state: 38

Industry mix (Fortune 500 HQ in CT)

Industry	F500 HQs	Revenue
▸Industrial Machinery	4	$38B
▸Insurance	3	$71B
▸Financial Services	2	$25B
▸Transportation / Logistics	2	$18B
▸Healthcare	1	$247B
▸Telecommunications	1	$55B

Price history

+5.6% since first listed

24 events — show timeline

• 2026-05-21 Pending — Smart MLS
• 2026-04-09 Contingent — Smart MLS
• 2026-03-27 Listed $2,350,000 Smart MLS
• 2026-03-19 Coming Soon $2,350,000 Smart MLS
• 2025-11-21 Listing Removed — Smart MLS
• 2025-10-23 Listed $2,099,000 Smart MLS
• 2025-07-22 Listing Removed — Smart MLS
• 2025-06-05 Price Changed $2,190,000 Smart MLS
• 2025-05-13 Price Changed $2,300,000 Smart MLS
• 2025-04-19 Listed $2,450,000 Smart MLS
• 2025-04-08 Coming Soon — Smart MLS
• 2024-11-02 Listing Removed — Smart MLS
• 2024-09-11 Rental Removed $6,900 SMARTMLS
• 2024-07-13 Listed $2,385,000 Smart MLS
• 2024-07-10 Listed for Rent $6,900 SMARTMLS
• 2024-06-04 Rental Removed $30,000 SMARTMLS
• 2024-06-03 Listing Removed — Smart MLS
• 2024-02-26 Listed $2,350,000 Smart MLS
• 2024-01-07 Listed for Rent $30,000 SMARTMLS
• 2024-01-07 Rental Removed $7,500 SMARTMLS
• 2023-12-20 Listed for Rent $7,500 SMARTMLS
• 2005-09-19 Sold (Public Records) $2,100,000 Public Records
• 2005-09-19 Sold (MLS) $2,100,000 Smart MLS
• 2005-04-21 Listed $2,225,000 Smart MLS

Property tax history

+0.6%/yr

Latest (2023): $33,071 · +0.3% YoY. Source: county tax records.