102 Wykeham Rd · New Preston, CT 06793

$1,195,000

4 bd · 2.5 ba · 2,113 sqft · SingleFamily public records · 94 Days on market

Built 1964 1.80 ac lot

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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 +7.5/15.0
• Schools +6.3/10.0
• Appreciation +5.4/10.0
• Cash flow +4.6/30.0
• Livability +3.5/5.0
• Rent growth +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +0.0/10.0
• DSCR +0.0/10.0

Listing remarks MLS

Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

Key facts

• 1.8 acre lot
• 2 garage spots
• Built 1964

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $1.20M.

Deal economics

• At list price, monthly cash flow is $-3k ($-36k/yr) — negative.
• To cash-flow at today's rent, offer at most $662k (44.6% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $514k (57.0% below list).
• Recommended offer: $514k (57.0% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads 69/100 on livability (#105 in CT) — a middle-class / working-renter tenant base. Strengths: crime A+, employment A+, housing A+; Watch: amenities F, commute F, cost of living F.
• Regional School District 12 (rural): math 64% / reading 77% proficiency, ranked #20 of 153 in CT (top 13%) — strong family-tenant draw, lease renewals of 3-5y typical; only 8% free/reduced lunch — higher-income household profile.
• Zoned schools: Washington Primary School (math 64% / reading 84%, grade A, #44 of 553 statewide, top 10%, 162 students, 25% FRL); Shepaug Valley School (math 61% / reading 76%, grade B, #23 of 194 statewide, top 12%, 494 students, 21% FRL) — zoned schools average 23% FRL vs 8% district-wide (15 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 10 active listings in the ZIP; 154 units permitted in Northwest Hills Planning Region in 2024 (6 in 5+ unit buildings).

Forward outlook

• In year one you build about $19k of equity ($8k loan paydown + $10k appreciation (0.9% local appreciation)).
• By year 4, paydown + projected appreciation supports a ~$68k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.

Negotiation context

• It's been on market 94 days — a 9% lower offer ($1.09M) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 2y ago; this cycle's ask has dropped $80k (6%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $582k; list at $1.20M implies a 105% gain — meaningful room to come down on a strong offer.

Recommended offer $514,150 (57.0% 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 94 days. Have you received any prior offers? Is the seller open to a 57% concession, seller financing, or rate buy-down credit?
3. Built in 1964 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
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: 0.43% ✗
• Cap rate: 3.26%
• Cash-on-cash: -10.83%
• DSCR: 0.52
• GRM: 19.4

CMA / ARV

• ARV (on-the-fly): $528,250
• Comps found: 1

Show comp detail 1 sale within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
27 Old Litchfield Rd	0.41mi	3/1.0 (-1)	1,900 (-10%)	13mo	$475,000	$250	42

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

Projected returns pro-forma

0.86% appreciation · 3.0% rent growth · sell at horizon

5-year hold

• IRR: -10.7%
• Equity multiple: 0.47×
• Total profit: $-178,705
• Equity at exit: $399,373

10-year hold

• IRR: -4.8%
• Equity multiple: 0.43×
• Total profit: $-191,373
• Equity at exit: $524,159

Cash invested: $334,600 (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 06793

• Home prices YoY: 0.3%
• Active inventory: 10
• Price-to-rent: 19.4×

Monthly cashflow live

• Estimated rent: $5,142 medium
• Mortgage (P&I): −$6,267
• Tax from tax record: −$317 /mo · $3,805/yr
• Insurance: −$498
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,080
• Net cashflow: $-3,020

Break-even live

Break-even rent $8,964

Max offer price $661,517

Occupancy floor —

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: $298,750
• Closing costs: $35,850
• Reserves months: —
• Total cash needed: —

Listing history 11 events

1. 2026-04-08
   status Under Contract
2. 2026-03-13
   historical Under Contract - Continue to Show
3. 2026-03-09
   price $1,195,000
4. 2026-01-05
   listed $1,275,000 Active
5. 2025-12-30
   historical $1,275,000
6. 2025-05-23
   soldstatus $582,500 Closed 684-char remark

   Show marketing remark (684 chars)

   Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

7. 2025-05-19
   status Under Contract 684-char remark

   Show marketing remark (684 chars)

   Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

8. 2025-03-14
   historical Under Contract - Continue to Show 684-char remark

   Show marketing remark (684 chars)

   Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

9. 2025-03-08
   status Active 684-char remark

   Show marketing remark (684 chars)

   Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

10. 2024-12-21
    historical 684-char remark

    Show marketing remark (684 chars)

    Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

11. 2024-11-20
    listed $695,000 Active 684-char remark

    Show marketing remark (684 chars)

    Private 4 bedroom/2.5 bath home on 1.8 +/- tranquil, lightly wooded acres featuring many old growth trees, mature vegetation and gorgeous rock outcroppings. Super location near Washington Green and minutes to Washington Depot. One-floor living with hardwood floors throughout. A large eat-in country kitchen/family room with a fireplace/woodburning stove leads out to a lovely stone patio and open surrounding lawn. A cozy dining room adjoins a large living room with a handsome stone fireplace. A separate bedroom wing includes a primary ensuite and three other well-proportioned bedrooms that share a hall bath. Amazing seasonal sunset views. Room for a pool. Wonderful opportunity.

ⓘ 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: $3,805 · $317/mo
• Projected year-2 tax: $14,689 · $1,224/mo
• Expected delta: +$10,884/yr (+$907/mo · 286.0%)

ⓘ 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 · 0% chance over 30 yrs
• 🔥 Wildfire 4/10 Moderate
• 🌡 Heat 3/10 Moderate 7 d/yr ≥94°F today · 14 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 22% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $61,698
• − Mortgage interest: −$66,939
• − Property taxes: −$3,805
• − Insurance: −$5,975
• − Repairs & maintenance: −$4,936
• − Management: −$4,936
• − Depreciation: −$34,764
• Taxable loss: −$59,656
• Est. tax savings @ 24.0%: +$14,317
• After-tax cash flow: $-21,922/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: Regional School District 12
• NCES district ID: 0903530
• Math proficiency: 64% ▼ -9.00%
• Reading proficiency: 77% ▬ 0.00%
• Median HH income: $86,065
• Composite: 63.18/100
• National rank: #638
• State rank: #20 of 153 in CT

Livability — New Preston

• Score: 69/100
• State rank: #105
• US rank: #9031

Category grades

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

Schools grade is shown separately in the Schools card above.

Census & demographics

• City population: 1,802
• Population (ZIP): 1,270

Population outlook (Northwest Hills County) Hauer SSP2

• By 2040: 118,998

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (81%)
• Race & ethnicity: White 81% Hispanic / Latino 17% Two or more races 3% Asian 2%
• Hispanic origin (detail): Cuban 3%
• Common ancestry: Romanian 5% Slovak 4% Lithuanian 4%
• Foreign-born: 22% · Canada, Jamaica
• Languages at home: 81% English-only · Spanish 15% French/Haitian/Cajun 2% German/W. Germanic 1%

Political lean MEDSL · Northwest Hills

• 2024 margin: Toss-up / Even · D 48.6% · R 49.9% · Other 1.6%
• All cycles: 2024: R+1.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▲ 0.86%
• Current HPI: 260.8543
• 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

+71.9% since first listed

11 events — show timeline

• 2026-04-08 Pending — Smart MLS
• 2026-03-13 Contingent — Smart MLS
• 2026-03-09 Price Changed $1,195,000 Smart MLS
• 2026-01-05 Listed $1,275,000 Smart MLS
• 2025-12-30 Coming Soon $1,275,000 Smart MLS
• 2025-05-23 Sold (MLS) $582,500 Smart MLS
• 2025-05-19 Pending — Smart MLS
• 2025-03-14 Contingent — Smart MLS
• 2025-03-08 Relisted — Smart MLS
• 2024-12-21 Listing Removed — Smart MLS
• 2024-11-20 Listed $695,000 Smart MLS

Property tax history

-0.8%/yr

Latest (2023): $3,805 · +0.0% YoY. Source: county tax records.