8 Windy Hill Rd · Topstone, CT 06896

$1,195,000

4 bd · 3.0 ba · 3,007 sqft · SingleFamily public records · 14 Days on market

Built 1998 2.29 ac lot Est $893k · 34% over

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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
• Schools +7.7/10.0
• Rent growth +2.5/5.0
• Livability +2.5/5.0
• Condition / age +2.5/5.0
• ARV discount +0.0/15.0
• Appreciation +0.0/10.0

Listing remarks MLS

Move right in and enjoy living in this warm and inviting 4 BR colonial located in a desirable SW Redding neighborhood. This exceptional property with 2+ level acres is highlighted by a superb gunite saltwater pool, expansive travertine patio and a professional landscape design featuring flowering plants, shrubs and, as an added bonus, a veggie garden! The charming barn serves as a wonderful sheltered seating location -- perfect for relaxing after a swim. It could be a "further finished" pool house with changing rooms and entertaining space -- the possibilities are endless! This casually elegant home enjoys an open-concept Kitchen/Family Room with HW floors, FP and a wall of doors with access to --and views of -- the fabulous backyard as well a a formal Living Room with fp and spacious formal Dining Room. The Library with custom built-ins is just perfect for relaxing with a good book -- or working from home! The upper level includes a Primary Bedroom suite with walk-in closet, fully-updated bath with dual sinks, separate shower and hydro-tub, and three additional spacious bedrooms, full bath and laundry room. A large lower level with half-bath offers a multitude of uses -- playroom, media room, gym or additional "at-home" office space. This extraordinary "quintessential Connecticut" property is simply perfect -- a private, neighborhood setting yet only minutes from shopping, restaurants, commuter routes and train to NYC!

Key facts

• 2.29 acre lot
• 2 garage spots
• Pool

Property features AI

Finance

• Other: Radon mitigation for air and water

Exterior

• Parking: Attached 2-car garage
• Security: Security system
• Utilities: Private well water; Septic system
• Home design: Single family home; Taupe exterior color
• Construction: Frame construction; Concrete foundation; Asphalt shingle roof; Wood siding
• Exterior features: Barn; Deck; Garden area; Patio; Level lot; Fully fenced; Professionally landscaped; Swimming pool (gunite, heated, salt water, in-ground)

Interior

• Kitchen: Cooktop; Wall oven; Refrigerator; Dishwasher
• Bedrooms: 4 bedrooms (upper level laundry)
• Bathrooms: 2 full bathrooms; 2 half bathrooms
• Heating & cooling: Central air conditioning; Hot air heating fueled by oil; Oil hot water (domestic); fuel tank in basement
• Interior features: Audio system; Auto garage door opener; Central vacuum; Security system; Two fireplaces; Full, fully finished basement; Attic with storage space and pull-down stairs; Total of 9 rooms; Gym
• Laundry & utility: Laundry room on upper level

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $1.20M.

Deal economics

• At list price, monthly cash flow is $8k ($91k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $1.20M).

Location & tenants

• Location reads: area grade B — affects rentability + tenant quality, not the cash-flow math above.
• Regional School District 09 (rural): math 75% / reading 90% proficiency, ranked #7 of 192 in CT (top 4%) — strong family-tenant draw, lease renewals of 3-5y typical.
• Zoned schools: Redding Elementary School (math 67% / reading 72%, grade A-, #78 of 553 statewide, top 17%, 479 students, 9% FRL); John Read Middle School (math 69% / reading 76%, grade A, #6 of 175 statewide, top 3%, 350 students, 9% FRL); Joel Barlow High School (math 57% / reading 82%, grade B, #18 of 194 statewide, top 10%, 768 students, 12% FRL).
• Zoned-school proficiency averages 70% at this address vs 82% district-wide (-12 pts) — the specific schools serving this property underperform the Regional School District 09 average; the district grade overstates school quality for this exact location.
• Market conditions: 62 active listings in the ZIP; 1 comparable units currently listed for rent nearby; 1,151 units permitted in Western Connecticut Planning Region in 2024 (714 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $8k of loan paydown is wiped out by about $36k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $335k cash investment doubles in ~5 years — after that, you're playing with house money.

Negotiation context

• Only 14 days on market — expect competitive offers; lowballing is unlikely to land.
• 8 sale attempts since 30y 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 $1.02M; 17% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Climate carrying-cost: moderate wind risk, 26% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $1,195,000

Questions for the listing agent

1. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
2. 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.
3. 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.
4. 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: 1.67% ✓
• Cap rate: 13.94%
• Cash-on-cash: 27.33%
• DSCR: 2.22
• GRM: 5.0

CMA / ARV

• ARV (on-the-fly): $893,079
• Comps found: 5

Show comp detail 5 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
6 Windy Hill Rd	0.06mi	4/3.5	3,045 (+1%)	11mo	$1,199,000	$394	84
144 Seventy Acre Rd	0.40mi	4/2.5	3,005 (-0%)	20mo	$728,000	$242	62
12 Granite Ridge Rd	0.60mi	4/2.0	3,024 (+1%)	8mo	$725,000	$240	61
158 Old Redding Rd	0.27mi	4/4.5	3,200 (+6%)	12mo	$1,248,000	$390	60
18 Mine Hill Rd	0.38mi	4/2.5	2,922 (-3%)	23mo	$869,000	$297	56

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 · 3.0% rent growth · sell at horizon

5-year hold

• IRR: 21.3%
• Equity multiple: 1.87×
• Total profit: $291,900
• Equity at exit: $178,178

10-year hold

• IRR: 29.5%
• Equity multiple: 3.63×
• Total profit: $880,098
• Equity at exit: $103,322

Cash invested: $334,600 (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 06896

• Active inventory: 62
• Price-to-rent: 5.0×

Monthly cashflow live

• Estimated rent: $20,000 medium
• Mortgage (P&I): −$6,267
• Tax from tax record: −$1,416 /mo · $16,991/yr
• Insurance: −$498
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,200
• Net cashflow: $7,619

Break-even live

Break-even rent $10,355

Max offer price $1,195,000

Occupancy floor 57%

Sensitivity live

Price	-10% $8,296	-5% $7,958	+0% $7,619	+5% $7,281	+10% $6,943
Rent	-10% $6,039	-5% $6,829	+0% $7,619	+5% $8,409	+10% $9,199
Rate	-1.0pp $8,221	-0.5pp $7,923	base $7,619	+0.5pp $7,310	+1.0pp $6,995

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: $298,750
• Closing costs: $35,850
• Reserves months: —
• Total cash needed: —

Rent comps 1 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
142 Seventy Acre Rd Redding, CT	4.0	4.5	3350	$20,000	$5.97	5d	1	0.38mi

Listing history 21 events

1. 2026-05-14
   status Under Contract
2. 2026-05-05
   historical Under Contract - Continue to Show
3. 2026-05-01
   listed $1,195,000 Active
4. 2026-04-29
   historical $1,195,000
5. 2022-08-16
   soldstatus $1,025,000
6. 2022-08-15
   soldstatus $1,025,000 Closed 1474-char remark

   Show marketing remark (1474 chars)

   Move right in and enjoy living in this warm and inviting 4 BR colonial located in a desirable SW Redding neighborhood. This exceptional property with 2+ level acres is highlighted by a superb gunite saltwater pool, expansive travertine patio and a professional landscape design featuring flowering plants, shrubs and, as an added bonus, a veggie garden! The charming barn serves as a wonderful sheltered seating location -- perfect for relaxing after a swim. It could be a "further finished" pool house with changing rooms and entertaining space -- the possibilities are endless! This casually elegant home enjoys an open-concept Kitchen/Family Room with HW floors, FP and a wall of doors with access to --and views of -- the fabulous backyard as well a a formal Living Room with fp and spacious formal Dining Room. The Library with custom built-ins is just perfect for relaxing with a good book -- or working from home! The upper level includes a Primary Bedroom suite with walk-in closet, fully-updated bath with dual sinks, separate shower and hydro-tub, and three additional spacious bedrooms, full bath and laundry room. A large lower level with half-bath offers a multitude of uses -- playroom, media room, gym or additional "at-home" office space. This extraordinary "quintessential Connecticut" property is simply perfect -- a private, neighborhood setting yet only minutes from shopping, restaurants, commuter routes and train to NYC!

7. 2022-05-12
   historical Under Contract - Continue to Show 1474-char remark

   Show marketing remark (1474 chars)

   Move right in and enjoy living in this warm and inviting 4 BR colonial located in a desirable SW Redding neighborhood. This exceptional property with 2+ level acres is highlighted by a superb gunite saltwater pool, expansive travertine patio and a professional landscape design featuring flowering plants, shrubs and, as an added bonus, a veggie garden! The charming barn serves as a wonderful sheltered seating location -- perfect for relaxing after a swim. It could be a "further finished" pool house with changing rooms and entertaining space -- the possibilities are endless! This casually elegant home enjoys an open-concept Kitchen/Family Room with HW floors, FP and a wall of doors with access to --and views of -- the fabulous backyard as well a a formal Living Room with fp and spacious formal Dining Room. The Library with custom built-ins is just perfect for relaxing with a good book -- or working from home! The upper level includes a Primary Bedroom suite with walk-in closet, fully-updated bath with dual sinks, separate shower and hydro-tub, and three additional spacious bedrooms, full bath and laundry room. A large lower level with half-bath offers a multitude of uses -- playroom, media room, gym or additional "at-home" office space. This extraordinary "quintessential Connecticut" property is simply perfect -- a private, neighborhood setting yet only minutes from shopping, restaurants, commuter routes and train to NYC!

8. 2022-04-29
   listed $975,000 Active 1474-char remark

   Show marketing remark (1474 chars)

   Move right in and enjoy living in this warm and inviting 4 BR colonial located in a desirable SW Redding neighborhood. This exceptional property with 2+ level acres is highlighted by a superb gunite saltwater pool, expansive travertine patio and a professional landscape design featuring flowering plants, shrubs and, as an added bonus, a veggie garden! The charming barn serves as a wonderful sheltered seating location -- perfect for relaxing after a swim. It could be a "further finished" pool house with changing rooms and entertaining space -- the possibilities are endless! This casually elegant home enjoys an open-concept Kitchen/Family Room with HW floors, FP and a wall of doors with access to --and views of -- the fabulous backyard as well a a formal Living Room with fp and spacious formal Dining Room. The Library with custom built-ins is just perfect for relaxing with a good book -- or working from home! The upper level includes a Primary Bedroom suite with walk-in closet, fully-updated bath with dual sinks, separate shower and hydro-tub, and three additional spacious bedrooms, full bath and laundry room. A large lower level with half-bath offers a multitude of uses -- playroom, media room, gym or additional "at-home" office space. This extraordinary "quintessential Connecticut" property is simply perfect -- a private, neighborhood setting yet only minutes from shopping, restaurants, commuter routes and train to NYC!

9. 2018-11-01
   historical
10. 2018-03-25
    listed $859,000 Active
11. 2017-10-31
    historical
12. 2017-07-31
    listed $875,000
13. 2006-11-06
    soldstatus $875,000
14. 2006-11-03
    soldstatus $875,000
15. 2006-07-21
    listed $949,000
16. 1999-04-01
    soldstatus $503,600
17. 1999-02-04
    listed $513,000
18. 1999-01-31
    historical
19. 1998-01-28
    listed $498,000
20. 1997-09-30
    historical
21. 1996-06-12
    listed $485,000

ⓘ 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: $16,991 · $1,416/mo
• Projected year-2 tax: $21,282 · $1,774/mo
• Expected delta: +$4,291/yr (+$358/mo · 25.3%)

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

Climate risk First Street

• 🌊 Flood 1/10 Low FEMA zone X (unshaded) · 0% chance over 30 yrs
• 🔥 Wildfire 3/10 Moderate
• 🌡 Heat 4/10 Moderate 7 d/yr ≥98°F today · 15 d/yr by 30 yrs out
• 💨 Wind 5/10 Major 26% chance of damaging wind over 30 yrs
• 🫁 Air quality 4/10 Moderate 3 unhealthy d/yr today · 5 by 30 yrs out

Taxation est. · year 1

• Rental income: $240,000
• − Mortgage interest: −$66,939
• − Property taxes: −$16,991
• − Insurance: −$5,975
• − Repairs & maintenance: −$19,200
• − Management: −$19,200
• − Depreciation: −$34,764
• Taxable income: $76,932
• Est. tax owed @ 24.0%: −$18,464
• After-tax cash flow: $72,970/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: Regional School District 09
• NCES district ID: 0903780
• Math proficiency: 75% ▲ 3.00%
• Reading proficiency: 90% ▲ 5.00%
• Median HH income: $120,713
• Composite: 77.14/100
• National rank: #169
• State rank: #7 of 192 in CT

Livability — Topstone

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

Census & demographics

• Population (ZIP): 8,719

Population outlook (Western Connecticut County) Hauer SSP2

• By 2040: 685,031

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (81%)
• Race & ethnicity: White 81% Hispanic / Latino 9% Two or more races 9% Asian 4%
• Hispanic origin (detail): Mexican 1% Puerto Rican 1% Dominican 1%
• Common ancestry: Slovak 5% Scotch-Irish 5% Romanian 3%
• Foreign-born: 9% · Canada, China
• Languages at home: 86% English-only · Spanish 6% Other Indo-European 3% Chinese 1%

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: ▼ -236.94%
• Current HPI: 163.4307
• 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

+146.4% since first listed

21 events — show timeline

• 2026-05-14 Pending — Smart MLS
• 2026-05-05 Contingent — Smart MLS
• 2026-05-01 Listed $1,195,000 Smart MLS
• 2026-04-29 Coming Soon $1,195,000 Smart MLS
• 2022-08-16 Sold (Public Records) $1,025,000 Public Records
• 2022-08-15 Sold (MLS) $1,025,000 Smart MLS
• 2022-05-12 Contingent — Smart MLS
• 2022-04-29 Listed $975,000 Smart MLS
• 2018-11-01 Listing Removed — Smart MLS
• 2018-03-25 Listed $859,000 Smart MLS
• 2017-10-31 Listing Removed — Smart MLS
• 2017-07-31 Listed $875,000 Smart MLS
• 2006-11-06 Sold (Public Records) $875,000 Public Records
• 2006-11-03 Sold (MLS) $875,000 Smart MLS
• 2006-07-21 Listed $949,000 Smart MLS
• 1999-04-01 Sold (MLS) $503,600 Smart MLS
• 1999-02-04 Listed $513,000 Smart MLS
• 1999-01-31 Listing Removed — Smart MLS
• 1998-01-28 Listed $498,000 Smart MLS
• 1997-09-30 Listing Removed — Smart MLS
• 1996-06-12 Listed $485,000 Smart MLS

Property tax history

+3.2%/yr

Latest (2023): $16,991 · +8.7% YoY. Source: county tax records.