28 Old Orchard Dr · Weston, CT 06883

$1,779,000

4 bd · 4.5 ba · 4,079 sqft · SingleFamily public records · 421 Days on market

Built 1986 2.00 ac lot $436/sqft · 37% above area Est $2427k · 27% under

---

Why this score? — see what drove the F 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 +7.5/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Cash flow +0.2/30.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.

Key facts

• Cathedral-ceil lr
• Two-story foyer
• Gunite pool

Tags

• GUNITE POOL
• BELGIUM BLOCK-LINED DRIVE
• SPECIMEN LANDSCAPING
• TWO-STORY FOYER
• CATHEDRAL-CEIL LR
• WIDE PLANK FLOORS

What this means for you Summary

Snapshot

• This is a 4-bed/4.5-bath single-family listed at $1.78M.

Deal economics

• At list price, monthly cash flow is $-8k ($-96k/yr) — negative.
• To cash-flow at today's rent, offer at most $427k (76.0% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $488k (72.6% below list).
• Recommended offer: $427k (76.0% below list) — sets the bar for cash-flow.
• Cap rate 0.9% vs local median 3.1% in Weston — below-typical yield; the buyer is paying a premium for something (appreciation thesis, condition, location) that the cap rate doesn't capture.

Location & tenants

• Location reads: area grade F — 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.
• Market conditions: 73 active listings in the ZIP; 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 $12k of loan paydown is wiped out by about $53k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 421 days — a 12% lower offer ($1.57M) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts since 32y 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 $620k; list at $1.78M implies a 187% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 27% 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 $426,720 (76.0% 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 421 days. Have you received any prior offers? Is the seller open to a 76% 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. 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?
6. 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.
7. 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.
8. 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: 0.27% ✗
• Cap rate: 0.90%
• Cash-on-cash: -19.25%
• DSCR: 0.14
• GRM: 30.4

CMA / ARV

• ARV (median comp): $2,427,000
• List price: $1,779,000
• Delta: -26.70%
• Verdict: UNDERPRICED
• Comps: 15 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
7 Hills End Ln	0.05mi	5/5.0 (+1)	4,500 (+10%)	16mo	$2,310,000	$513	60
11 Glory Rd	0.27mi	5/4.0 (+1)	4,370 (+7%)	14mo	$2,200,000	$503	57
4 Trails End Rd	0.73mi	5/3.5 (+1)	3,888 (-5%)	2mo	$1,440,000	$370	48
4 November Trl	0.58mi	4/3.0	4,368 (+7%)	9mo	$1,585,000	$363	48

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: -55.8%
• Equity multiple: -0.60×
• Total profit: $-797,518
• Equity at exit: $265,255

10-year hold

• IRR: —
• Equity multiple: -1.71×
• Total profit: $-1,350,752
• Equity at exit: $153,815

Cash invested: $498,120 (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: 30.4×

Monthly cashflow live

• Estimated rent: $4,881 medium
• Mortgage (P&I): −$9,329
• Tax from tax record: −$1,778 /mo · $21,336/yr
• Insurance: −$741
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,025
• Net cashflow: $-7,992

Break-even live

Break-even rent $14,998

Max offer price $426,720

Occupancy floor —

Sensitivity live

Price	-10% $-6,985	-5% $-7,489	+0% $-7,992	+5% $-8,496	+10% $-8,999
Rent	-10% $-8,378	-5% $-8,185	+0% $-7,992	+5% $-7,800	+10% $-7,607
Rate	-1.0pp $-7,097	-0.5pp $-7,540	base $-7,992	+0.5pp $-8,453	+1.0pp $-8,922

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: $444,750
• Closing costs: $53,370
• Reserves months: —
• Total cash needed: —

Listing history 18 events

1. 2026-06-18
   days on market $1,779,000 Active 421 DOM
2. 2026-06-17
   days on market $1,779,000 Active 420 DOM
3. 2026-06-16
   days on market $1,779,000 Active 419 DOM
4. 2026-06-15
   days on market $1,779,000 Active 418 DOM
5. 2026-06-13
   days on market $1,779,000 Active 416 DOM
6. 2026-06-13
   days on market $1,779,000 Active 415 DOM
7. 2026-06-10
   days on market $1,779,000 Active 413 DOM
8. 2026-06-09
   days on market $1,779,000 Active 412 DOM
9. 2026-06-08
   days on market $1,779,000 Active 411 DOM
10. 2026-06-07
    days on market $1,779,000 Active 410 DOM
11. 2026-06-03
    days on market $1,779,000 Active 406 DOM
12. 2026-06-03
    days on market $1,779,000 Active 405 DOM
13. 2026-06-01
    days on market $1,779,000 Active 404 DOM
14. 2026-05-31
    days on market $1,779,000 Active 403 DOM
15. 2025-04-23
    listed $1,779,000 Active 1535-char remark

    Show marketing remark (1535 chars)

    Experience dramatic, modern living in this grand home with a glorious gunite pool & exceptional architectural appeal. Custom-designed, the quality of this residence is readily apparent as you approach from the centrally-located, multi-million dollar neighborhood of fine homes. The stone front, Belgium block-lined drive and specimen landscaping greet you, leading to the soaring two-story foyer. Large windows that fill the rooms w/sunlight are a defining characteristic of the home, including the cathedral-ceil LR w/stone fpl & wide plank floors, holiday-sized DR w/bay window, fam rm w/wet bar and wall of glass to deck. The dine-in kitchen w/ center island, updated stainless steel appls incl gas cooktop & Sub Zero, also opens out to the large deck. A main flr office & 1.5 bths complete the main lvl. Front & rear staircases lead up to the spacious 2nd level where you will find a grand primary suite w/lrg walk-in clst & en-suite bth plus 3 addl BRs & 2 full baths. The incredible finished, walk-out lower level is a highlight, with sun-drenched spaces that add spacious comfort, flexibility and can meet any need - while still offering great storage. The rec rm w/fpl and a pair of offices or bonus rms each have doors to the rear property. The gym has an adjacent full bth, making it an ideal cabana for swimming guests using the pool when entertaining in these splendid surroundings. Enjoy gorgeous views & tranquil privacy, just minutes to the town Center & school campus plus commuting.

16. 1994-04-12
    historical
17. 1994-02-08
    listed $949,000
18. 1987-02-23
    soldstatus $620,000

ⓘ 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: $21,336 · $1,778/mo
• Projected year-2 tax: $29,703 · $2,475/mo
• Expected delta: +$8,367/yr (+$697/mo · 39.2%)

ⓘ 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 4/10 Moderate
• 🌡 Heat 5/10 Major 7 d/yr ≥99°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 27% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 3 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $58,573
• − Mortgage interest: −$99,652
• − Property taxes: −$21,336
• − Insurance: −$8,895
• − Repairs & maintenance: −$4,686
• − Management: −$4,686
• − Depreciation: −$51,753
• Taxable loss: −$132,434
• Est. tax savings @ 24.0%: +$31,784
• After-tax cash flow: $-64,125/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

+186.9% since first listed

4 events — show timeline

• 2025-04-23 Listed $1,779,000 Smart MLS
• 1994-04-12 Listing Removed — Smart MLS
• 1994-02-08 Listed $949,000 Smart MLS
• 1987-02-23 Sold (Public Records) $620,000 Public Records

Property tax history

+1.0%/yr

Latest (2023): $21,336 · +0.3% YoY. Source: county tax records.