163-165 Main St · Deep River, CT 06417

$825,000

30 bd · 15.0 ba · 4,184 sqft · MultiFamily · 21 Days on market

Built 1850 Good condition 3,049 sqft lot

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Why this score? — see what drove the B 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 +30.0/30.0
• 1% rule +10.0/10.0
• DSCR +10.0/10.0
• ARV discount +7.5/15.0
• Schools +4.5/10.0
• Condition / age +3.8/5.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Appreciation +0.0/10.0

Multi-family units

County records classify this as Multi-Family (5+ Unit). Listing-text estimate: 5 units. confirmed

5+ unit building — per-unit beds/baths from public records are typically unavailable; the breakdown below (if shown) is an estimate from the listing text.

Listing remarks

Rare mixed-use investment opportunity located in the heart of desirable Deep River Village. Positioned directly on Main Street, this 5-unit asset offers a strong blend of residential and commercial income within one of the Connecticut shoreline region's most sought-after rental and retail markets. The property consists of 3 residential apartments and 2 commercial storefronts occupied by long-term local tenants, providing stable in-place cash flow with additional upside through lease-up and rent optimization. Deep River continues to experience strong demand driven by its walkable downtown, restaurant scene, boutique retail presence, and proximity to the Connecticut River and shoreline commun

Key facts

• Walkable downtown
• Restaurant scene
• 3,049 sq ft lot

Tags

• MAIN STREET VISIBILITY
• WALKABLE DOWNTOWN
• RESTAURANT SCENE
• BOUTIQUE RETAIL PRESENCE
• PROXIMITY TO CONNECTICUT RIVER
• STABILIZED MIXED-USE ASSET

Property features AI

Finance

• Financial info: Multi-family for sale (5-family+)

Exterior

• Utilities: Public water connected; Public sewer connected; Fuel tank located in basement
• Home design: Multi-family property (5+ units)
• Construction: Frame construction; Stone foundation
• Exterior features: Corner lot on a level parcel within a historic district; Aluminum siding; Asphalt shingle roof

Interior

• Bedrooms: 6 bedrooms
• Bathrooms: 3 full bathrooms
• Heating & cooling: Hot air heating; Oil and propane fuel options; 50-gallon hot water tank (oil)
• Interior features: 12 total rooms; Full basement with interior access and hatchway; Has attic with walk-up access; partially finished storage space; Window unit cooling

What this means for you Summary

Snapshot

• This is a 5 × 6-bed/3.0-bath units multifamily listed at $825k. Condition is rated good.

Deal economics

• At list price, monthly cash flow is $5k ($62k/yr) — positive. Per door: $1k/mo.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($14k rent vs $825k).
• Recommended offer: $813k (1.5% below list) — sets the bar for market timing.

Location & tenants

• Location reads: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Regional School District 04 (rural): math 37% / reading 63% proficiency, ranked #80 of 153 in CT (top 52%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 8% free/reduced lunch — higher-income household profile.
• Market conditions: 31 active listings in the ZIP; 278 units permitted in Lower Connecticut River Valley Planning Region in 2024 (89 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $6k of loan paydown is wiped out by about $25k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $231k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• It's been on market 21 days — a 2% lower offer ($813k) is reasonable based on typical stale-listing flexibility.
• 2 sale attempts 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.

Risks & watch-outs

• Watch-outs: built in 1850 — expect roof / HVAC / electrical / plumbing capex.

Recommended offer $812,625 (1.5% below list)

Questions for the listing agent

1. Can we see the unit-by-unit rent roll, current vacancy, and any below-market leases? What's the average tenancy length?
2. What capital expenditures (roof, boiler, parking lot, exteriors) have been made in the last 5 years, and what's planned in the next 2?
3. Built in 1850 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
5. 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.
6. 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.
7. 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.

Investment metrics

• 1% rule: 1.67% ✓
• Cap rate: 13.83%
• Cash-on-cash: 26.93%
• DSCR: 2.20
• GRM: 5.0

CMA / ARV

No comps found within radius.

Projected returns pro-forma

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

5-year hold

• IRR: 20.9%
• Equity multiple: 1.85×
• Total profit: $196,645
• Equity at exit: $123,010

10-year hold

• IRR: 29.0%
• Equity multiple: 3.59×
• Total profit: $597,165
• Equity at exit: $71,331

Cash invested: $231,000 (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 06417

• Home prices YoY: -12.3%
• Active inventory: 31
• Price-to-rent: 24.9×

Monthly cashflow live

• Estimated rent: $13,778 medium
• Mortgage (P&I): −$4,326
• Tax est. 1.5%: −$1,031 /mo · $12,375/yr
• Insurance: −$344
• HOA: −$0
• Vacancy / Maint / Mgmt: −$2,893
• Net cashflow: $5,183

Break-even live

Break-even rent $7,217

Max offer price $825,000

Occupancy floor 57%

5-unit breakdown (identical units grouped — click to expand)

Units	Beds	Baths	Est. rent
▸ 5× units	6	3	$13,780
Total (5 units)			$13,778

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: $206,250
• Closing costs: $24,750
• Reserves months: —
• Total cash needed: —

Listing history 18 events

1. 2026-06-18
   days on market $825,000 Active 21 DOM
2. 2026-06-17
   days on market $825,000 Active 20 DOM
3. 2026-06-16
   days on market $825,000 Active 19 DOM
4. 2026-06-15
   days on market $825,000 Active 18 DOM
5. 2026-06-13
   days on market $825,000 Active 16 DOM
6. 2026-06-12
   days on market $825,000 Active 15 DOM
7. 2026-06-10
   days on market $825,000 Active 13 DOM
8. 2026-06-09
   days on market $825,000 Active 12 DOM
9. 2026-06-08
   days on market $825,000 Active 11 DOM
10. 2026-06-07
    days on market $825,000 Active 10 DOM
11. 2026-06-05
    days on market $825,000 Active 7 DOM
12. 2026-06-03
    days on market $825,000 Active 6 DOM
13. 2026-06-02
    days on market $825,000 Active 5 DOM
14. 2026-06-01
    days on market $825,000 Active 4 DOM
15. 2026-05-31
    days on market $825,000 Active 3 DOM
16. 2026-05-27
    listed $825,000 Active
17. 2026-03-23
    historical $1,500
18. 2026-03-12
    listed $1,500

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

Taxation est. · year 1

• Rental income: $165,336
• − Mortgage interest: −$46,213
• − Property taxes: −$12,375
• − Insurance: −$4,125
• − Repairs & maintenance: −$13,227
• − Management: −$13,227
• − Depreciation: −$24,000
• Taxable income: $52,169
• Est. tax owed @ 24.0%: −$12,521
• After-tax cash flow: $49,678/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.

Condition & rehab AI · 13 photos

Good 75/100 Cosmetic rehab

This multi-family property is in good condition with no major repairs needed. It has a good roof, exterior, and interior, and is located in a desirable area with strong demand. Painting the exterior siding and cleaning the windows and HVAC system can further increase its value.

Value-add opportunities

• Both Paint the exterior siding — Painting the exterior siding can improve the curb appeal and increase the property's value.
• Both Clean the windows — Clean windows can improve the property's appearance and increase its value.
• Both Inspect and clean the HVAC system — A clean and functioning HVAC system can improve the property's comfort and energy efficiency, increasing its value.

Renovation cost estimate screening

Value-add ROI direction

• Both Paint the exterior siding — Painting the exterior siding can improve the curb appeal and increase the property's value. ↑
• Both Clean the windows — Clean windows can improve the property's appearance and increase its value. ↑
• Both Inspect and clean the HVAC system — A clean and functioning HVAC system can improve the property's comfort and energy efficiency, increasing its value. ↑

ⓘ Cost ranges are severity-bucket heuristics (US national rule-of-thumb). Get contractor quotes + a written scope before underwriting a rehab budget.

Schools (NCES district)

• District: Regional School District 04
• NCES district ID: 0903630
• Math proficiency: 37% ▼ -18.00%
• Reading proficiency: 63% ▼ -8.00%
• Median HH income: $69,421
• Composite: 44.54/100
• National rank: #2789
• State rank: #80 of 153 in CT

Livability — Deep River

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

Census & demographics

• Census place: Deep River Center, CT
• Population (ZIP): 4,432

Population outlook (Lower Connecticut River Valley County) Hauer SSP2

• By 2040: 188,651

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (87%)
• Race & ethnicity: White 87% Two or more races 5% Hispanic / Latino 4% Black 3%
• Common ancestry: Romanian 7% Slovak 6% Lithuanian 2%
• Foreign-born: 9% · Canada
• Languages at home: 90% English-only · Spanish 4% French/Haitian/Cajun 3% Other Indo-European 2%

Political lean MEDSL · Lower Connecticut River Valley

• 2024 margin: D (+13.4) · D 55.9% · R 42.4% · Other 1.7%
• All cycles: 2024: D+13.4

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -26.17%
• Current HPI: 186.0672
• 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

+54900.0% since first listed

3 events — show timeline

• 2026-05-27 Listed $825,000 Smart MLS
• 2026-03-23 Rental Removed $1,500 RENTEC
• 2026-03-12 Listed for Rent $1,500 RENTEC