33 E Hills Dr #33 · New Canaan, CT 06840

$699,990

3 bd · 1.5 ba · 1,554 sqft · Condo · 15 Days on market

Built 1968 $320/mo HOA · 5% of rent

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Why this score? — see what drove the D 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 +12.6/30.0
• Schools +8.1/10.0
• ARV discount +7.5/15.0
• 1% rule +4.2/10.0
• DSCR +3.7/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• Appreciation +0.0/10.0

Listing remarks MLS

Wonderfully private sanctuary steps from town with beautiful views of the Five Mile River. Updated and spacious three bedroom,1.5 bath townhouse nested at the end of a cul de sac. Sophisticated and tastefully updated interior with hardwood floors throughout, granite counters in the kitchen and over-sized deck off of the dining room. Finished walk out lower level with playroom and separate laundry room. Enjoy nationally recognized public school system. Newly Installed Central Air and Hot Water Heater. Simply the best value in New Canaan! OWNER WILL ENTERTAIN ALL OFFERS.

Key facts

• $320 HOA
• 3 parking spots
• Built 1968

Property features AI

Finance

• Other: Radon mitigation (air system); Unit owners association manages the property
• HOA & community: Homeowners association with monthly fee; HOA fee includes grounds maintenance, snow removal, and insurance; Pets allowed with no restrictions

Exterior

• Parking: Paved off-street parking; Three parking spaces
• Utilities: Public water connected; Public sewer connected; Electric service for heat and hot water
• Home design: Condominium; Unit in a 6-unit building; Three levels in unit; Part of the East Hills complex
• Construction: Frame construction
• Exterior features: Vinyl siding; Located on a cul-de-sac; Direct river frontage

Interior

• Kitchen: Electric range; Range hood; Refrigerator
• Bedrooms: Three bedrooms
• Bathrooms: One full bathroom; One half bathroom
• Heating & cooling: Electric baseboard heat; Central air; 50-gallon electric hot water tank
• Interior features: Five total rooms; End unit; Full, fully finished basement with walk-out; Attic with pull-down stairs; Central air
• Laundry & utility: Private laundry in the basement (lower level)

What this means for you Summary

Snapshot

• This is a 3-bed/1.5-bath condo listed at $700k.

Deal economics

• At list price, monthly cash flow is $-93 ($-1k/yr) — negative.
• To cash-flow at today's rent, offer at most $687k (1.9% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $641k (8.4% below list).
• Recommended offer: $641k (8.4% below list) — sets the bar for 1% rule.
• Cap rate 6.1% vs local median 1.5% in New Canaan — 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.

Location & tenants

• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• New Canaan School District (suburban): math 81% / reading 86% proficiency, ranked #1 of 153 in CT (top 1%) — strong family-tenant draw, lease renewals of 3-5y typical; only 6% free/reduced lunch — higher-income household profile.
• Zoned schools: East School (math 84% / reading 84%, grade A+, #7 of 553 statewide, top 1%, 550 students, 0% FRL); Saxe Middle School (math 79% / reading 85%, grade A+, #1 of 175 statewide, top 0%, 1,315 students, 0% FRL); New Canaan High School (math 77% / reading 92%, grade A, #1 of 194 statewide, top 1%, 1,294 students, 0% FRL).
• Market conditions: 165 active listings in the ZIP; 12 comparable units currently listed for rent nearby; rentals at typical pace (median 26d on market — plan ~3-4 weeks tenant-placement turnaround); 42% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).
• This rent runs 31% of the median local income ($250k/yr) — at the standard rent-burdened threshold; future hikes will face affordability resistance.

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $5k of loan paydown is wiped out by about $21k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 15 days — a 2% lower offer ($689k) is reasonable based on typical stale-listing flexibility.
• 4 sale attempts since 11y 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 $430k; list at $700k implies a 63% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Climate carrying-cost: major wind risk, 59% 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.

Recommended offer $641,084 (8.4% 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. Built in 1968 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
3. What does the HOA fee cover, when was the last increase, and are there any pending special assessments or reserve-fund shortfalls?
4. 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?
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 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: 0.92% ✗
• Cap rate: 6.13%
• Cash-on-cash: -0.57%
• DSCR: 0.97
• GRM: 9.1

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: -17.2%
• Equity multiple: 0.39×
• Total profit: $-119,053
• Equity at exit: $104,371

10-year hold

• IRR: -9.1%
• Equity multiple: 0.44×
• Total profit: $-110,097
• Equity at exit: $60,522

Cash invested: $195,997 (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 06840

• Active inventory: 165
• Price-to-rent: 9.1×

Monthly cashflow live

• Estimated rent: $6,411 high
• Mortgage (P&I): −$3,671
• Tax est. 1.5%: −$875 /mo · $10,500/yr
• Insurance: −$292
• HOA: −$320
• Vacancy / Maint / Mgmt: −$1,346
• Net cashflow: $-93

Break-even live

Break-even rent $6,528

Max offer price $686,546

Occupancy floor 96%

Sensitivity live

Price	-10% $391	-5% $149	+0% $-93	+5% $-335	+10% $-577
Rent	-10% $-599	-5% $-346	+0% $-93	+5% $160	+10% $414
Rate	-1.0pp $260	-0.5pp $85	base $-93	+0.5pp $-274	+1.0pp $-459

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: $174,998
• Closing costs: $21,000
• Reserves months: —
• Total cash needed: —

Rent comps 12 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
126 East Ave New Canaan, CT	3.0	1.5	2124	$4,500	$2.12	45d	1	0.09mi
172 East Ave #174 New Canaan, CT	2.0	1.0	1162	$4,100	$3.53	5d	1	0.12mi
100 Lakeview Ave New Canaan, CT	2.0–3.0	2.0	1255	$6,257	$4.99	4d	8	0.30mi
44 Hillside Ave New Canaan, CT	3.0	1.5	1200	$5,200	$4.33	45d	1	0.34mi
54 Main St New Canaan, CT	2.0	2.5	1347	$7,350	$5.46	25d	1	0.41mi
135 Millport Ave New Canaan, CT	3.0	1.5	1576	$5,300	$3.36	25d	1	0.41mi
138 Millport Ave New Canaan, CT	3.0	1.5	1750	$5,300	$3.03	45d	1	0.41mi
8 Husted Ln Unit 1D New Canaan, CT	2.0	2.0	1050	$5,975	$5.69	25d	1	0.42mi
37 Maple St New Canaan, CT	2.0	2.5	1506	$6,500	$4.32	45d	1	0.48mi
70 Seminary St Unit 1 New Canaan, CT	3.0	4.0	2100	$9,500	$4.52	45d	1	0.68mi
244 Park St #244 New Canaan, CT	3.0	2.0	1521	$7,500	$4.93	25d	1	0.68mi
52 Sunrise Ave New Canaan, CT	3.0	2.0	1198	$7,500	$6.26	16d	1	0.86mi

HOA detail condo

• Monthly dues: $320 · $3,840/yr
• Likely covers: water
• Assessments: None detected in remarks — confirm with the listing agent.

Listing history 24 events

1. 2026-06-22
   statusdays on market $699,990 Under Contract 15 DOM
2. 2026-06-18
   days on market $699,990 Active 14 DOM
3. 2026-06-17
   days on market $699,990 Active 13 DOM
4. 2026-06-16
   days on market $699,990 Active 12 DOM
5. 2026-06-15
   days on market $699,990 Active 11 DOM
6. 2026-06-13
   days on market $699,990 Active 9 DOM
7. 2026-06-10
   days on market $699,990 Active 6 DOM
8. 2026-06-09
   days on market $699,990 Active 5 DOM
9. 2026-06-08
   days on market $699,990 Active 4 DOM
10. 2026-06-07
    days on market $699,990 Active 3 DOM
11. 2026-06-05
    statusdays on market $699,990 Active 1 DOM
12. 2026-06-03
    days on market $699,990 Coming Soon 13 DOM
13. 2026-06-03
    days on market $699,990 Coming Soon 12 DOM
14. 2026-06-01
    days on market $699,990 Coming Soon 11 DOM
15. 2026-05-31
    days on market $699,990 Coming Soon 10 DOM
16. 2026-05-22
    historical $699,990
17. 2020-12-04
    historical
18. 2020-11-30
    historical Under Contract - Continue to Show
19. 2020-11-04
    status Active
20. 2020-09-08
    historical Under Contract - Continue to Show
21. 2020-07-21
    listed $459,500 Active
22. 2016-02-24
    soldstatus $430,000 575-char remark

    Show marketing remark (575 chars)

    Wonderfully private sanctuary steps from town with beautiful views of the Five Mile River. Updated and spacious three bedroom,1.5 bath townhouse nested at the end of a cul de sac. Sophisticated and tastefully updated interior with hardwood floors throughout, granite counters in the kitchen and over-sized deck off of the dining room. Finished walk out lower level with playroom and separate laundry room. Enjoy nationally recognized public school system. Newly Installed Central Air and Hot Water Heater. Simply the best value in New Canaan! OWNER WILL ENTERTAIN ALL OFFERS.

23. 2016-02-05
    historical 575-char remark

    Show marketing remark (575 chars)

    Wonderfully private sanctuary steps from town with beautiful views of the Five Mile River. Updated and spacious three bedroom,1.5 bath townhouse nested at the end of a cul de sac. Sophisticated and tastefully updated interior with hardwood floors throughout, granite counters in the kitchen and over-sized deck off of the dining room. Finished walk out lower level with playroom and separate laundry room. Enjoy nationally recognized public school system. Newly Installed Central Air and Hot Water Heater. Simply the best value in New Canaan! OWNER WILL ENTERTAIN ALL OFFERS.

24. 2015-06-11
    listed $435,000 575-char remark

    Show marketing remark (575 chars)

    Wonderfully private sanctuary steps from town with beautiful views of the Five Mile River. Updated and spacious three bedroom,1.5 bath townhouse nested at the end of a cul de sac. Sophisticated and tastefully updated interior with hardwood floors throughout, granite counters in the kitchen and over-sized deck off of the dining room. Finished walk out lower level with playroom and separate laundry room. Enjoy nationally recognized public school system. Newly Installed Central Air and Hot Water Heater. Simply the best value in New Canaan! OWNER WILL ENTERTAIN ALL OFFERS.

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥99°F today · 16 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 59% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 4 unhealthy d/yr today · 6 by 30 yrs out

Taxation est. · year 1

• Rental income: $76,930
• − Mortgage interest: −$39,210
• − Property taxes: −$10,500
• − Insurance: −$3,500
• − Repairs & maintenance: −$6,154
• − Management: −$6,154
• − HOA: −$3,840
• − Depreciation: −$20,363
• Taxable loss: −$12,792
• Est. tax savings @ 24.0%: +$3,070
• After-tax cash flow: $1,955/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: New Canaan School District
• NCES district ID: 0902700
• Math proficiency: 81% ▼ -6.00%
• Reading proficiency: 86% ▼ -4.00%
• Median HH income: $164,303
• Composite: 81.47/100
• National rank: #38
• State rank: #1 of 153 in CT

Livability — New Canaan

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

Census & demographics

• Census place: New Canaan, CT
• County: Fairfield County · 765,532 people
• City population: 20,870
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 20,870
• Household income: $250,001
• Rent vs Own: 16.3% rent · 83.7% own
• Severe rent burden: 261.0

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (83%)
• Race & ethnicity: White 83% Two or more races 7% Asian 6% Hispanic / Latino 5% Black 2%
• Common ancestry: Romanian 5% Lithuanian 4% Italian 2%
• Foreign-born: 14% · Canada, China, South Korea
• Languages at home: 85% English-only · Other Indo-European 6% Chinese 2% Spanish 2%

Political lean MEDSL · Western Connecticut

• 2024 margin: D (+19.1) · D 58.8% · R 39.7% · Other 1.6%
• All cycles: 2024: D+19.1

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -480.93%
• Current HPI: 232.5667
• Rent YoY: —
• Metro: Bridgeport-Stamford-Norwalk, CT
• 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

+60.9% since first listed

12 events — show timeline

• 2026-06-20 Pending — Smart MLS
• 2026-06-19 Contingent — Smart MLS
• 2026-06-05 Listed $699,990 Smart MLS
• 2026-05-22 Coming Soon $699,990 Smart MLS
• 2020-12-04 Listing Removed — Smart MLS
• 2020-11-30 Contingent — Smart MLS
• 2020-11-04 Relisted — Smart MLS
• 2020-09-08 Contingent — Smart MLS
• 2020-07-21 Listed $459,500 Smart MLS
• 2016-02-24 Sold (MLS) $430,000 Smart MLS
• 2016-02-05 Listing Removed — Smart MLS
• 2015-06-11 Listed $435,000 Smart MLS