77 Round Hill Rd · Fairfield, CT 06824

$800,000

4 bd · 2.5 ba · 1,420 sqft · SingleFamily public records · 32 Days on market

Built 1940 9,147 sqft lot $563/sqft · 22% above area Est $960k · 17% under

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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).

• ARV discount +15.0/15.0
• Cash flow +7.2/30.0
• Schools +6.3/10.0
• Rent growth +5.0/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• 1% rule +1.5/10.0
• DSCR +1.4/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Walk to downtown Fairfield Restaurants and shopping from this well maintained and affordable Cape located close to award winning schools. Short walk (less than 10 minutes) to Metro North Train and less than 1 mile from Fairfield Beach! Main level features hardwood floors, spacious living room with wood burning fireplace, formal dining room, 4th bedroom and half bath. Bonus room currently used as kids play room leads to deck and patio of fenced in yard. Upper level consists of 3 additional bedrooms and full bath. Lower level is partially finished for additional living space along with full bath. Following have been completed within the last 5 years; Roof, Siding, Retaining Wall, Front Steps, Fence, Central Air, Deck, Patio, Garage Door and Driveway! Don't wait, come check this out and enjoy all Fairfield has to offer.

Key facts

• 9,147 sq ft lot
• Garage
• Built 1940

Property features AI

Exterior

• Parking: Attached garage (1-car)
• Utilities: Public water connected; Public sewer connected; Domestic hot water via oil
• Home design: Single-family home
• Construction: Frame construction; Asphalt shingle roof; Concrete foundation; Shingle siding; Built area recorded as 1420 (public record)
• Exterior features: Sidewalk; Deck; Patio; Fully fenced lot; Beach rights and membership in a water community

Interior

• Kitchen: Electric range; Refrigerator; Dishwasher
• Bedrooms: Four bedrooms
• Bathrooms: Two full bathrooms; One half bathroom
• Heating & cooling: Hot water heating (oil-fired) with fuel tank in basement; Central air and ductless cooling
• Interior features: Eight total rooms; One fireplace; Full finished basement with storage, interior access and garage access; Attic with pull-down stairs
• Laundry & utility: Washer and dryer; Laundry located on lower level

What this means for you Summary

Snapshot

• This is a 4-bed/2.5-bath single-family listed at $800k.

Deal economics

• At list price, monthly cash flow is $-1k ($-13k/yr) — negative.
• To cash-flow at today's rent, offer at most $607k (24.2% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $516k (35.5% below list).
• Recommended offer: $516k (35.5% below list) — sets the bar for 1% rule.

Location & tenants

• Location reads: area grade D — affects rentability + tenant quality, not the cash-flow math above.
• Fairfield School District (suburban): math 61% / reading 72% proficiency, ranked #21 of 153 in CT (top 14%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 7% free/reduced lunch — higher-income household profile.
• Zoned schools: Riverfield School (math 82% / reading 82%, grade A+, #11 of 553 statewide, top 3%, 391 students, 4% FRL); Roger Ludlowe Middle School (math 66% / reading 74%, grade A, #16 of 175 statewide, top 9%, 771 students, 8% FRL); Fairfield Ludlowe High School (math 69% / reading 85%, grade A-, #9 of 194 statewide, top 4%, 1,498 students, 15% FRL) — zoned schools at 9% FRL track the district average.
• Market conditions: Rents rising fast (+12.4%/yr); 152 active listings in the ZIP; 23 comparable units currently listed for rent nearby; rentals lingering (median 46d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 61% of comp listings sitting > 30 days — soft ceiling on asking rent; high-income renter base; 852 units permitted in Greater Bridgeport Planning Region in 2024 (698 in 5+ unit buildings).
• This rent runs 32% of the median local income ($193k/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 $6k of loan paydown is wiped out by about $24k of value loss. Plan a longer hold.

Negotiation context

• It's been on market 32 days — a 3% lower offer ($776k) is reasonable based on typical stale-listing flexibility.
• 5 sale attempts since 34y 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 $375k; list at $800k implies a 113% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: built in 1940 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: major wind risk, 66% chance of damaging wind over 30y; extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $516,358 (35.5% 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. It's been on market 32 days. Have you received any prior offers? Is the seller open to a 35% concession, seller financing, or rate buy-down credit?
3. Built in 1940 — 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. 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?
6. 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.
7. 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.
8. 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.

Investment metrics

• 1% rule: 0.65% ✗
• Cap rate: 4.65%
• Cash-on-cash: -5.86%
• DSCR: 0.74
• GRM: 12.9

CMA / ARV

• ARV (median comp): $959,699
• List price: $800,000
• Delta: -16.64%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 12 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
855 Riverside Dr	0.56mi	4/2.0	1,482 (+4%)	2mo	$980,000	$661	63
98 Cambridge St	0.64mi	4/2.0	1,552 (+9%)	3mo	$1,200,000	$773	50
174 Blaine St	0.74mi	3/1.5 (-1)	1,404 (-1%)	10mo	$1,100,000	$783	46
59 Fairview Ave	0.61mi	4/2.0	1,357 (-4%)	20mo	$440,819	$325	46
20 Benson Pl	0.66mi	4/2.0	1,243 (-12%)	2mo	$960,000	$772	45
158 Fairview Ave	0.68mi	3/2.0 (-1)	1,511 (+6%)	9mo	$875,000	$579	43
277 Meadowbrook Rd	0.75mi	3/1.5 (-1)	1,460 (+3%)	13mo	$625,000	$428	40
172 Nichols St	0.59mi	3/2.0 (-1)	1,298 (-9%)	14mo	$885,000	$682	39
58 Smith St	0.53mi	3/1.5 (-1)	1,254 (-12%)	10mo	$1,000,000	$797	38
558 Riverside Dr	0.74mi	3/1.5 (-1)	1,296 (-9%)	8mo	$975,000	$752	35
196 Catherine Ter	0.69mi	3/1.5 (-1)	1,224 (-14%)	6mo	$800,000	$654	31
122 Colony St	0.71mi	3/1.0 (-1)	1,217 (-14%)	6mo	$411,000	$338	27

Match score weights: distance 35% · size 25% · config 20% · recency 20%. Top-matched comps best support the ARV.

Projected returns pro-forma

-3.0% appreciation · 8.0% rent growth · sell at horizon

5-year hold

• IRR: -21.4%
• Equity multiple: 0.23×
• Total profit: $-172,204
• Equity at exit: $119,283

10-year hold

• IRR: -6.8%
• Equity multiple: 0.48×
• Total profit: $-116,095
• Equity at exit: $69,169

Cash invested: $224,000 (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 06824

• Rents YoY: 12.4%
• Active inventory: 152
• Price-to-rent: 12.9×

Monthly cashflow live

• Estimated rent: $5,164 high
• Mortgage (P&I): −$4,195
• Tax from tax record: −$645 /mo · $7,743/yr
• Insurance: −$333
• HOA: −$0
• Vacancy / Maint / Mgmt: −$1,084
• Net cashflow: $-1,095

Break-even live

Break-even rent $6,549

Max offer price $606,627

Occupancy floor —

Sensitivity live

Price	-10% $-642	-5% $-868	+0% $-1,095	+5% $-1,321	+10% $-1,548
Rent	-10% $-1,503	-5% $-1,299	+0% $-1,095	+5% $-891	+10% $-687
Rate	-1.0pp $-692	-0.5pp $-891	base $-1,095	+0.5pp $-1,302	+1.0pp $-1,513

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: $200,000
• Closing costs: $24,000
• Reserves months: —
• Total cash needed: —

Rent comps 23 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
46 Parkway Fairfield, CT	3.0	2.0	1831	$5,450	$2.98	16d	1	0.44mi
258 Ruane St Fairfield, CT	3.0	1.5	1040	$3,100	$2.98	5d	1	0.73mi
503 Reef Rd Fairfield, CT	5.0	2.5	1632	$18,000	$11.03	45d	1	0.74mi
50 Craig Pl Fairfield, CT	3.0	2.0	1004	$8,500	$8.47	45d	1	0.77mi
27 Reef Ct Fairfield, CT	4.0	1.0	1267	$6,000	$4.74	45d	1	0.82mi
123 Longview Ave Fairfield, CT	3.0	1.5	1107	$3,500	$3.16	45d	1	0.83mi
109 Churchill St Unit 2nd Fl Fairfield, CT	3.0	1.0	1387	$3,500	$2.52	45d	1	0.84mi
109 Churchill St Unit 2nd Fl Fairfield, CT	3.0	1.0	1387	$3,300	$2.38	25d	1	0.84mi
74 Oldfield Dr Fairfield, CT	5.0	2.0	1188	$7,250	$6.10	45d	1	0.96mi
58 Post Rd Fairfield, CT	4.0	1.5	1200	$3,200	$2.67	45d	1	0.97mi
788 Reef Rd Fairfield, CT	3.0	2.0	1770	$4,500	$2.54	25d	1	0.97mi
161 Mona Ter Fairfield, CT	4.0	1.0	1075	$4,540	$4.22	45d	1	1.03mi
892 Reef Rd Fairfield, CT	3.0	2.0	1488	$5,200	$3.49	45d	1	1.06mi
25 Penfield Pl Fairfield, CT	3.0	3.0	1600	$14,000	$8.75	16d	1	1.06mi
96 Kenwood Ave Unit Labs Fairfield, CT	3.0	2.0	1300	$3,200	$2.46	45d	1	1.09mi
799 Rowland Rd Fairfield, CT	3.0	2.0	1056	$8,000	$7.58	45d	1	1.11mi
969 Reef Rd Fairfield, CT	3.0	2.0	1566	$6,000	$3.83	25d	1	1.11mi
664 Fairfield Beach Rd Fairfield, CT	3.0	2.0	1514	$8,000	$5.28	25d	1	1.19mi
116 College Pl Fairfield, CT	5.0	2.0	1500	$7,000	$4.67	45d	1	1.26mi
172 College Pl Fairfield, CT	3.0	1.5	1188	$85,000	$71.55	45d	1	1.28mi
918 Fairfield Beach Rd Fairfield, CT	4.0	1.5	1220	$5,500	$4.51	16d	1	1.30mi
1140 Fairfield Beach Rd Fairfield, CT	3.0	2.0	1277	$5,000	$3.92	45d	1	1.32mi
1235 Fairfield Beach Rd Fairfield, CT	3.0	1.5	1188	$12,000	$10.10	25d	1	1.38mi

Listing history 29 events

1. 2026-06-22
   days on market $800,000 Active 32 DOM
2. 2026-06-18
   days on market $800,000 Active 29 DOM
3. 2026-06-17
   days on market $800,000 Active 28 DOM
4. 2026-06-16
   days on market $800,000 Active 27 DOM
5. 2026-06-15
   days on market $800,000 Active 26 DOM
6. 2026-06-13
   days on market $800,000 Active 24 DOM
7. 2026-06-10
   days on market $800,000 Active 21 DOM
8. 2026-06-09
   days on market $800,000 Active 20 DOM
9. 2026-06-08
   days on market $800,000 Active 19 DOM
10. 2026-06-07
    days on market $800,000 Active 18 DOM
11. 2026-06-05
    days on market $800,000 Active 15 DOM
12. 2026-06-03
    days on market $800,000 Active 14 DOM
13. 2026-06-03
    days on market $800,000 Active 13 DOM
14. 2026-06-01
    days on market $800,000 Active 12 DOM
15. 2026-05-31
    days on market $800,000 Active 11 DOM
16. 2026-05-14
    historical $800,000 1418-char remark
17. 2019-07-02
    soldstatus $375,000
18. 2019-07-01
    soldstatus $375,000 Closed 828-char remark

    Show marketing remark (828 chars)

    Walk to downtown Fairfield Restaurants and shopping from this well maintained and affordable Cape located close to award winning schools. Short walk (less than 10 minutes) to Metro North Train and less than 1 mile from Fairfield Beach! Main level features hardwood floors, spacious living room with wood burning fireplace, formal dining room, 4th bedroom and half bath. Bonus room currently used as kids play room leads to deck and patio of fenced in yard. Upper level consists of 3 additional bedrooms and full bath. Lower level is partially finished for additional living space along with full bath. Following have been completed within the last 5 years; Roof, Siding, Retaining Wall, Front Steps, Fence, Central Air, Deck, Patio, Garage Door and Driveway! Don't wait, come check this out and enjoy all Fairfield has to offer.

19. 2019-06-27
    historical 828-char remark

    Show marketing remark (828 chars)

    Walk to downtown Fairfield Restaurants and shopping from this well maintained and affordable Cape located close to award winning schools. Short walk (less than 10 minutes) to Metro North Train and less than 1 mile from Fairfield Beach! Main level features hardwood floors, spacious living room with wood burning fireplace, formal dining room, 4th bedroom and half bath. Bonus room currently used as kids play room leads to deck and patio of fenced in yard. Upper level consists of 3 additional bedrooms and full bath. Lower level is partially finished for additional living space along with full bath. Following have been completed within the last 5 years; Roof, Siding, Retaining Wall, Front Steps, Fence, Central Air, Deck, Patio, Garage Door and Driveway! Don't wait, come check this out and enjoy all Fairfield has to offer.

20. 2019-05-05
    historical Under Contract - Continue to Show 828-char remark

    Show marketing remark (828 chars)

    Walk to downtown Fairfield Restaurants and shopping from this well maintained and affordable Cape located close to award winning schools. Short walk (less than 10 minutes) to Metro North Train and less than 1 mile from Fairfield Beach! Main level features hardwood floors, spacious living room with wood burning fireplace, formal dining room, 4th bedroom and half bath. Bonus room currently used as kids play room leads to deck and patio of fenced in yard. Upper level consists of 3 additional bedrooms and full bath. Lower level is partially finished for additional living space along with full bath. Following have been completed within the last 5 years; Roof, Siding, Retaining Wall, Front Steps, Fence, Central Air, Deck, Patio, Garage Door and Driveway! Don't wait, come check this out and enjoy all Fairfield has to offer.

21. 2019-05-01
    listed $369,900 Active 828-char remark

    Show marketing remark (828 chars)

    Walk to downtown Fairfield Restaurants and shopping from this well maintained and affordable Cape located close to award winning schools. Short walk (less than 10 minutes) to Metro North Train and less than 1 mile from Fairfield Beach! Main level features hardwood floors, spacious living room with wood burning fireplace, formal dining room, 4th bedroom and half bath. Bonus room currently used as kids play room leads to deck and patio of fenced in yard. Upper level consists of 3 additional bedrooms and full bath. Lower level is partially finished for additional living space along with full bath. Following have been completed within the last 5 years; Roof, Siding, Retaining Wall, Front Steps, Fence, Central Air, Deck, Patio, Garage Door and Driveway! Don't wait, come check this out and enjoy all Fairfield has to offer.

22. 2013-12-02
    soldstatus $320,000
23. 2013-11-27
    soldstatus $320,000

    Show marketing remark (419 chars)

    Walk to town & train from a fabulous condition 4 bedroom cape. Front to back living room with fireplace. Hardwood floors throughout. Formal dining room. 2 tandem bedrooms on the 1st floor with separate entrance for an option to have an in home office. 3 bedrooms & full bath on 2nd floor. Finish able lower level with full bath. Newer windows & mechanicals. Convenient location. This is a great opportunity.

24. 2011-03-03
    listed $320,000

    Show marketing remark (419 chars)

    Walk to town & train from a fabulous condition 4 bedroom cape. Front to back living room with fireplace. Hardwood floors throughout. Formal dining room. 2 tandem bedrooms on the 1st floor with separate entrance for an option to have an in home office. 3 bedrooms & full bath on 2nd floor. Finish able lower level with full bath. Newer windows & mechanicals. Convenient location. This is a great opportunity.

25. 2011-03-02
    historical
26. 2008-09-11
    listed $339,000
27. 1992-12-17
    soldstatus $128,000
28. 1992-08-10
    historical
29. 1992-04-23
    listed $159,000

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

Tax reassessment forecast CT · Partial reset (capped growth)

• Current annual tax: $7,743 · $645/mo
• Projected year-2 tax: $12,432 · $1,036/mo
• Expected delta: +$4,688/yr (+$391/mo · 60.6%)

ⓘ Screening estimate from a state-policy table — verify with the county assessor before closing.

Climate risk First Street

• 🌊 Flood 4/10 Moderate FEMA zone X (unshaded) · 13% chance over 30 yrs
• 🔥 Wildfire 1/10 Low
• 🌡 Heat 6/10 Major 7 d/yr ≥97°F today · 15 d/yr by 30 yrs out
• 💨 Wind 6/10 Major 66% chance of damaging wind over 30 yrs
• 🫁 Air quality 8/10 Severe 13 unhealthy d/yr today · 18 by 30 yrs out

Taxation est. · year 1

• Rental income: $61,963
• − Mortgage interest: −$44,812
• − Property taxes: −$7,743
• − Insurance: −$4,000
• − Repairs & maintenance: −$4,957
• − Management: −$4,957
• − Depreciation: −$23,273
• Taxable loss: −$27,779
• Est. tax savings @ 24.0%: +$6,667
• After-tax cash flow: $-6,469/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: Fairfield School District
• NCES district ID: 0901530
• Math proficiency: 61% ▼ -10.00%
• Reading proficiency: 72% ▼ -7.00%
• Median HH income: $119,139
• Composite: 63.03/100
• National rank: #650
• State rank: #21 of 153 in CT

Livability — Fairfield

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

Census & demographics

• County: Fairfield County · 765,532 people
• City population: 58,698
• Metro: Bridgeport-Stamford-Norwalk, CT
• Population (ZIP): 36,716
• Household income: $193,300
• Rent vs Own: 15.6% rent · 84.4% own
• Severe rent burden: 380.0

Population outlook (Greater Bridgeport County) Hauer SSP2

• By 2040: 365,581

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (88%)
• Race & ethnicity: White 88% Asian 5% Hispanic / Latino 5% Two or more races 5%
• Common ancestry: Romanian 7% Lithuanian 2% Scotch-Irish 2%
• Foreign-born: 11% · Canada, China
• Languages at home: 87% English-only · Other Indo-European 4% Spanish 3% Arabic 1%

Political lean MEDSL · Greater Bridgeport

• 2024 margin: Strong D (+23.3) · D 60.9% · R 37.6% · Other 1.5%
• All cycles: 2024: D+23.3

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -723.44%
• Current HPI: 178.7206
• Rent YoY: ▲ 12.37%
• 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

+403.1% since first listed

15 events — show timeline

• 2026-05-21 Listed $800,000 Smart MLS
• 2026-05-14 Coming Soon $800,000 Smart MLS
• 2019-07-02 Sold (Public Records) $375,000 Public Records
• 2019-07-01 Sold (MLS) $375,000 Smart MLS
• 2019-06-27 Listing Removed — Smart MLS
• 2019-05-05 Contingent — Smart MLS
• 2019-05-01 Listed $369,900 Smart MLS
• 2013-12-02 Sold (Public Records) $320,000 Public Records
• 2013-11-27 Sold (MLS) $320,000 Smart MLS
• 2011-03-03 Listed $320,000 Smart MLS
• 2011-03-02 Listing Removed — Smart MLS
• 2008-09-11 Listed $339,000 Smart MLS
• 1992-12-17 Sold (Public Records) $128,000 Public Records
• 1992-08-10 Listing Removed — Smart MLS
• 1992-04-23 Listed $159,000 Smart MLS

Property tax history

+3.2%/yr

Latest (2023): $7,743 · +1.0% YoY. Source: county tax records.