House Hack Deal Analysis – Two Houses on One Lot in Waterford, CT (Need Feedback)

[Gregory Kohler]

Hey everyone,

I’m analyzing a potential house hack in Waterford, CT and would love some feedback from the community.

This is a unique property because it has two separate single-family homes on one lot. Both will be delivered vacant at closing. Here’s the listing:

--> https://www.zillow.com/homedetails/398-402-Boston-Post-Rd-Wa... price: $350,000

My plan:

Live in the smaller home

Rent the larger home immediately (after light cosmetic work)

Use FHA (3.5% down) + CHFA (down payment assistance)

Reduce my personal housing cost as much as possible

Slowly fix my unit over time

Build equity and eventually refinance to help fund a future business

NUMBERS

Purchase Price Target:

Offer target: $260,000

Expected seller counter: $275,000–$300,000

Currently listed at: $350,000

FINANCING (FHA + CHFA)

FHA 3.5% down

Down payment covered by CHFA assistance program

Estimated interest rate: ~6.5–7%

MONTHLY PAYMENT ESTIMATES (P&I + Taxes + Insurance)

At $275,000 purchase:

Mortgage (P&I): ~$1,775

Taxes: ~$420

Insurance: ~$150

--> Estimated Total: ~$2,350/month

At $300,000 purchase:

Mortgage (P&I): ~$1,940

Taxes: ~$420

Insurance: ~$150

--> Estimated Total: ~$2,510/month

RENTAL INCOME ESTIMATE (Big House)

Based on local comps:

Low: $1,700/month

Typical: $1,800–$1,950/month

Strong (clean/paint/update): $2,000–$2,100/month

MY OUT-OF-POCKET HOUSING COST AFTER RENT

If I rent the big house at $1,900/month:

At $275k: ~$450/month

At $300k: ~$610/month

If I rent at $2,000/month:

At $275k: ~$350/month

At $300k: ~$510/month

(I currently pay $0 in rent living with family, so my goal is to keep my costs low while building equity.)

REHAB ESTIMATES

Big House (rent-ready):

Cleaning + paint + small fixes: $1,000–$3,500

Optional cosmetic upgrades: $2,000–$5,000

Small House (my unit):

Cosmetic repairs only: $500–$3,000

Optional improvements (done slowly): $2,000–$7,000

Major systems (worst-case ranges):

Roof: $8k–$12k

Boiler: $4k–$8k

Electrical panel: $1,500–$4,000

Plumbing repairs: $500–$2,000 typical

(Inspection will tell me more.)

CASH NEEDED TO CLOSE

With CHFA:

Down payment: $0 out of pocket

Closing costs: varies, but often reduced

Expected out-of-pocket: $1,400–$1,800

Inspection: $400–$600

Appraisal: $500–$700

MY FINANCIAL POSITION

(To give you context for risk tolerance)

Income: $5,000–$6,000/month

Monthly bills: ~$2,600

Emergency fund: $10,000

Credit: 717

Access to 0% APR business credit card (likely $8k–$12k limit)

Currently pay $0 rent (living with family)

MY QUESTIONS FOR THE COMMUNITY

1.) Does this seem like a reasonable house-hack opportunity for Southern CT?

2.) Any concerns with owning two separate houses on one lot?

3.) Do the photos suggest any major red flags I should watch for during the showing?

4.) What would YOU offer in today’s market?

5.) Anything you would approach differently given my goals and budget?

My Goal:

Reduce my cost of living, build equity, and get my first real estate foothold while keeping risk manageable.

Appreciate any insight you all can provide. Thanks in advance!