23116 Gilpin Point Rd

Preston, MD 21655

$374,990D

4 bd · 2.0 ba · 1,880 sqft · Built 1989 · SingleFamily · Active · 19 DOM

Cashflow @ list (25.0% down · 7.5%)

• Estimated rent: $2,156/mo
• Mortgage (P&I): −$1,966
• Tax + insurance: −$410
• HOA: −$0
• Vac / Maint / Mgmt: −$453
• Net cashflow: $-673/mo
• Annual: $-8,077/yr
• Cap rate: 4.14%
• Cash-on-cash: -7.69%
• DSCR: 0.66
• 1% rule: 0.58%
• Cash to close: $104,997

Investor read

• This is a 4-bed/2.0-bath single-family listed at $375k.
• At list price, monthly cash flow is $-673 ($-8k/yr) — negative.
• To cash-flow at today's rent, offer at most $256k (31.7% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $216k (42.5% below list).
• It's been on market 19 days — a 2% lower offer ($369k) is reasonable based on typical stale-listing flexibility.
• Recommended offer: $216k (42.5% below list) — sets the bar for 1% rule.
• In year one you build about $39k of equity ($3k loan paydown + $36k appreciation (9.6% local appreciation)).
• Location reads 66/100 on livability (#245 in MD) — a middle-class / working-renter tenant base. Strengths: housing A+, health & safety A+, cost of living B+; Watch: crime F, amenities F, commute F.
• Caroline County Public Schools (rural): math 13% / reading 29% proficiency, ranked #17 of 24 in MD (top 71%) — low school quality limits family demand, transient renter base, plan for 1-2y turnover.
• Zoned schools: Preston Elementary School (math 12% / reading 22%, grade F, #408 of 860 statewide, top 50%, 406 students, 60% FRL); Colonel Richardson Middle School (math 3% / reading 28%, grade F, #190 of 225 statewide, top 85%, 374 students, 72% FRL); Colonel Richardson High School (math 52% / reading 77%, grade B-, #55 of 222 statewide, top 26%, 549 students, 66% FRL) — zoned schools average 66% FRL vs 48% district-wide (18 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: 35 active listings in the ZIP; 59 units permitted in Caroline County in 2024 (0 in 5+ unit buildings).
• Caroline County population projected at -19% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.
• 11 sale attempts since 31y 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.
• By year 2, paydown + projected appreciation supports a ~$62k cash-out refi (75% LTV) — recoverable capital for the next deal without selling this one.
• Climate carrying-cost: major wind risk, 55% chance of damaging wind over 30y; extreme-heat days projected 7→16/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Questions for listing agent

• 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?
• Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
• Crime grade is F in this area — have there been break-ins, vandalism, or insurance claims at this property in the last 3 years? What carrier currently insures it and at what premium?
• 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?
• 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 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.