104 Woodland Dr #104

Middletown, CT 06416

$165,000C-

1 bd · 1.0 ba · 720 sqft · Built 1974 · Condo · Under Contract · 5 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $1,989/mo
• Mortgage (P&I): −$865
• Tax + insurance: −$275
• HOA: −$297
• Vac / Maint / Mgmt: −$418
• Net cashflow: $134/mo
• Annual: $1,611/yr
• Cap rate: 7.27%
• Cash-on-cash: 3.49%
• DSCR: 1.16
• 1% rule: 1.21%
• Cash to close: $46,200

Investor read

• This is a 1-bed/1.0-bath condo listed at $165k. Condition is rated fair.
• At list price, monthly cash flow is $134 ($2k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($2k rent vs $165k).
• Only 5 days on market — expect competitive offers; lowballing is unlikely to land.
• Local home prices are declining (-3.0%/yr); year-one equity from $1k of loan paydown is wiped out by about $5k of value loss. Plan a longer hold.
• Location reads 81/100 on livability (#17 in CT, #1,390 nationally) — a professional / high-income tenant draw. Strengths: crime A+, amenities A+, health & safety A+; Watch: commute F.
• Cromwell School District (suburban): math 51% / reading 58% proficiency, ranked #63 of 153 in CT (top 41%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 14% free/reduced lunch — higher-income household profile.
• Zoned schools: Edna C. Stevens School (473 students, 27% FRL); Cromwell High School (math 52% / reading 67%, grade C+, #45 of 194 statewide, top 25%, 536 students, 25% FRL).
• Market conditions: 58 active listings in the ZIP; high-income renter base; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 in 5+ unit buildings).
• 2 sale attempts since 19y 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 $86k; list at $165k implies a 92% gain — meaningful room to come down on a strong offer.
• Cap rate 7.3% vs local median 3.7% in Middletown — 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.

Questions for listing agent

• Have any recent inspections been done? Can we get a copy of the seller's disclosures and any deferred-maintenance estimates?
• Built in 1974 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
• What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
• Any open or pending special assessments — roof, HVAC, plumbing, elevator, façade? What's the per-unit balance and payoff schedule, and is the seller paying it off at close or rolling it to the buyer?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• 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.
• 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.
• How much new apartment / multifamily construction is in the pipeline within 1–3 miles? Heavy new supply (>2% of stock underway) typically softens rents 12–24 months out; light construction supports rent growth.

Repairs flagged (vision-AI assessment)

• Minor: Paint touch-ups — There is some minor discoloration and wear visible on the siding and interior walls.
• Minor: Carpet cleaning — The carpet in the living room and kitchen appears to be in fair condition, with some wear visible.