299 Redding Rd · Redding Center, CT 06896

$899,000

4 bd · 3.0 ba · 2,482 sqft · SingleFamily public records · 13 Days on market

Built 1979 2.00 ac lot $362/sqft · 37% above area Est $1118k · 20% under

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Why this score? — see what drove the A- 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
• ARV discount +15.0/15.0
• 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
• Appreciation +0.0/10.0

Listing remarks MLS

Here’s your opportunity to be in beautiful Redding with its award-winning schools and the perfect blank slate to create your dream home! Built by the only owners this home has ever had, this 4 bedroom, 3 bathroom center hall colonial has endless potential, plus an opportunity to expand the living space significantly. Excellent option on the main level for a first floor primary or au pair suite. Upstairs features three bedrooms including the existing primary, a massive walk-in closet and an additional 1100+ square feet of unfinished space that could be used to create additional living on either end of the second floor. With ample living space as it is, this home also has a full, unfinished walk-out basement with ceilings ranging from 8-10 feet and another 2000 square feet of unlimited potential for finishing as well. Sited on two wooded acres, this home is only 3 miles to Georgetown, Caraluzzi’s and Route 7, for an easy commute down county. Redding boasts over 60 miles of hiking trails, two state parks, a town park and the notable Mark Twain Library. Have all of this in the “Vermont of Connecticut” and still be less than 60 miles to Midtown Manhattan!

Key facts

• Brick fireplace
• Walk-in closet
• Custom built-ins

Tags

• GOURMET CHEF'S KITCHEN
• BRICK FIREPLACE
• CUSTOM BUILT-INS
• WALK-IN CLOSET
• SPA-LIKE BATHROOM
• DEEP SOAKING TUB

Property features AI

Exterior

• Parking: Attached garage plus driveway; Two garage spaces; Total of six parking spaces
• Utilities: Private well water; Septic sewer system; Electric power (standard); Oil heat with tank in basement; 80-gallon hot water tank
• Home design: Single-family home; White exterior
• Construction: Frame construction; Shingle exterior siding; Asphalt shingle roof; Block foundation
• Exterior features: Some wetlands on the lot; Lightly wooded and treed parcel; Paved driveway; Radon mitigation (air system)

Interior

• Kitchen: Oven/Range; Microwave; Range hood; Refrigerator; Dishwasher
• Bedrooms: Four bedrooms
• Bathrooms: Three full bathrooms; One half bathroom
• Heating & cooling: Hot air heating (oil-fired) with fuel tank in the basement; Split system cooling; Ceiling fans; 80-gallon hot water tank
• Interior features: Eight total rooms; Two fireplaces; Full basement that's heated, cooled, partially finished and includes a walk-out; Has an attic that is partially finished, floored, with pull-down stairs; Ceiling fans and a split system for cooling
• Laundry & utility: Washer and Dryer located on the main level

What this means for you Summary

Snapshot

• This is a 4-bed/3.0-bath single-family listed at $899k.

Deal economics

• At list price, monthly cash flow is $10k ($117k/yr) — positive.
• The deal already cash-flows at list — no discount required.
• Meets the 1% rule at list price ($20k rent vs $899k).

Location & tenants

• Location reads: area grade A — 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: 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 (-13 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 $6k of loan paydown is wiped out by about $27k of value loss. Plan a longer hold.
• At projected returns (-3.0% appreciation + 3.0% rent growth), your $252k cash investment doubles in ~3 years — after that, you're playing with house money.

Negotiation context

• Only 13 days on market — expect competitive offers; lowballing is unlikely to land.
• 5 sale attempts since 4y 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 $220k; list at $899k implies a 309% gain — meaningful room to come down on a strong offer.

Risks & watch-outs

• Watch-outs: flood insurance adds $56/mo.
• Climate carrying-cost: severe flood risk; moderate wind risk, 26% chance of damaging wind over 30y — expect insurance premiums to compound above CPI over the hold.

Recommended offer $899,000

Questions for the listing agent

1. Built in 1979 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
2. What's the actual annual flood-insurance premium (NFIP or private), and is the property in a SFHA with mandatory coverage?
3. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
4. 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.
5. 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.
6. 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: 2.22% ✓
• Cap rate: 19.42%
• Cash-on-cash: 46.89%
• DSCR: 3.09
• GRM: 3.7

CMA / ARV

• ARV (median comp): $1,118,263
• List price: $899,000
• Delta: -15.14%
• Verdict: UNDERPRICED
• Comps: 18 within 1.0 mi

Show comp detail 4 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
34 Dorethy Rd	0.55mi	3/2.5 (-1)	2,500 (+1%)	1mo	$500,000	$200	65
4 Ledgewood Rd	0.43mi	4/3.0	2,619 (+6%)	11mo	$942,000	$360	61
343 Redding Rd	0.47mi	4/2.5	2,688 (+8%)	12mo	$755,000	$281	52
32 Beeholm Rd	0.72mi	5/4.0 (+1)	2,452 (-1%)	5mo	$1,799,000	$734	51

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: 43.9%
• Equity multiple: 2.90×
• Total profit: $477,442
• Equity at exit: $134,044

10-year hold

• IRR: 49.9%
• Equity multiple: 5.84×
• Total profit: $1,218,621
• Equity at exit: $77,729

Cash invested: $251,720 (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: 3.7×

Monthly cashflow live

• Estimated rent: $20,000 medium
• Mortgage (P&I): −$4,714
• Tax from tax record: −$875 /mo · $10,497/yr
• Insurance: −$375
• Flood insurance flood zone: −$56 /mo · $666/yr
• HOA: −$0
• Vacancy / Maint / Mgmt: −$4,200
• Net cashflow: $9,781

Break-even live

Break-even rent $7,619

Max offer price $899,000

Occupancy floor 46%

Sensitivity live

Price	-10% $10,290	-5% $10,035	+0% $9,781	+5% $9,526	+10% $9,272
Rent	-10% $8,201	-5% $8,991	+0% $9,781	+5% $10,571	+10% $11,361
Rate	-1.0pp $10,233	-0.5pp $10,009	base $9,781	+0.5pp $9,548	+1.0pp $9,311

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: $224,750
• Closing costs: $26,970
• 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	3d	1	0.91mi

Listing history 23 events

1. 2026-06-21
   days on market $899,000 Active 13 DOM
2. 2026-06-18
   days on market $899,000 Active 10 DOM
3. 2026-06-17
   days on market $899,000 Active 9 DOM
4. 2026-06-16
   days on market $899,000 Active 8 DOM
5. 2026-06-15
   days on market $899,000 Active 7 DOM
6. 2026-06-13
   days on market $899,000 Active 5 DOM
7. 2026-06-10
   days on market $899,000 Active 2 DOM
8. 2026-06-08
   pricedays on marketlisting id $899,000 Active 1 DOM
9. 2026-06-05
   days on market $949,000 Active 130 DOM
10. 2026-06-03
    days on market $949,000 Active 129 DOM
11. 2026-06-03
    days on market $949,000 Active 128 DOM
12. 2026-06-01
    days on market $949,000 Active 127 DOM
13. 2026-05-31
    days on market $949,000 Active 126 DOM
14. 2026-04-29
    price $949,000 1419-char remark
15. 2026-04-13
    status Active 1419-char remark
16. 2026-03-24
    historical 1419-char remark
17. 2026-01-05
    listed $979,000 Active 1419-char remark
18. 2022-09-26
    soldstatus $220,000
19. 2022-09-19
    soldstatus $440,000 Closed 1192-char remark

    Show marketing remark (1192 chars)

    Here’s your opportunity to be in beautiful Redding with its award-winning schools and the perfect blank slate to create your dream home! Built by the only owners this home has ever had, this 4 bedroom, 3 bathroom center hall colonial has endless potential, plus an opportunity to expand the living space significantly. Excellent option on the main level for a first floor primary or au pair suite. Upstairs features three bedrooms including the existing primary, a massive walk-in closet and an additional 1100+ square feet of unfinished space that could be used to create additional living on either end of the second floor. With ample living space as it is, this home also has a full, unfinished walk-out basement with ceilings ranging from 8-10 feet and another 2000 square feet of unlimited potential for finishing as well. Sited on two wooded acres, this home is only 3 miles to Georgetown, Caraluzzi’s and Route 7, for an easy commute down county. Redding boasts over 60 miles of hiking trails, two state parks, a town park and the notable Mark Twain Library. Have all of this in the “Vermont of Connecticut” and still be less than 60 miles to Midtown Manhattan!

20. 2022-09-08
    status Under Contract 1192-char remark

    Show marketing remark (1192 chars)

    Here’s your opportunity to be in beautiful Redding with its award-winning schools and the perfect blank slate to create your dream home! Built by the only owners this home has ever had, this 4 bedroom, 3 bathroom center hall colonial has endless potential, plus an opportunity to expand the living space significantly. Excellent option on the main level for a first floor primary or au pair suite. Upstairs features three bedrooms including the existing primary, a massive walk-in closet and an additional 1100+ square feet of unfinished space that could be used to create additional living on either end of the second floor. With ample living space as it is, this home also has a full, unfinished walk-out basement with ceilings ranging from 8-10 feet and another 2000 square feet of unlimited potential for finishing as well. Sited on two wooded acres, this home is only 3 miles to Georgetown, Caraluzzi’s and Route 7, for an easy commute down county. Redding boasts over 60 miles of hiking trails, two state parks, a town park and the notable Mark Twain Library. Have all of this in the “Vermont of Connecticut” and still be less than 60 miles to Midtown Manhattan!

21. 2022-08-09
    historical Under Contract - Continue to Show 1192-char remark

    Show marketing remark (1192 chars)

    Here’s your opportunity to be in beautiful Redding with its award-winning schools and the perfect blank slate to create your dream home! Built by the only owners this home has ever had, this 4 bedroom, 3 bathroom center hall colonial has endless potential, plus an opportunity to expand the living space significantly. Excellent option on the main level for a first floor primary or au pair suite. Upstairs features three bedrooms including the existing primary, a massive walk-in closet and an additional 1100+ square feet of unfinished space that could be used to create additional living on either end of the second floor. With ample living space as it is, this home also has a full, unfinished walk-out basement with ceilings ranging from 8-10 feet and another 2000 square feet of unlimited potential for finishing as well. Sited on two wooded acres, this home is only 3 miles to Georgetown, Caraluzzi’s and Route 7, for an easy commute down county. Redding boasts over 60 miles of hiking trails, two state parks, a town park and the notable Mark Twain Library. Have all of this in the “Vermont of Connecticut” and still be less than 60 miles to Midtown Manhattan!

22. 2022-07-12
    price $449,000 1192-char remark

    Show marketing remark (1192 chars)

    Here’s your opportunity to be in beautiful Redding with its award-winning schools and the perfect blank slate to create your dream home! Built by the only owners this home has ever had, this 4 bedroom, 3 bathroom center hall colonial has endless potential, plus an opportunity to expand the living space significantly. Excellent option on the main level for a first floor primary or au pair suite. Upstairs features three bedrooms including the existing primary, a massive walk-in closet and an additional 1100+ square feet of unfinished space that could be used to create additional living on either end of the second floor. With ample living space as it is, this home also has a full, unfinished walk-out basement with ceilings ranging from 8-10 feet and another 2000 square feet of unlimited potential for finishing as well. Sited on two wooded acres, this home is only 3 miles to Georgetown, Caraluzzi’s and Route 7, for an easy commute down county. Redding boasts over 60 miles of hiking trails, two state parks, a town park and the notable Mark Twain Library. Have all of this in the “Vermont of Connecticut” and still be less than 60 miles to Midtown Manhattan!

23. 2022-06-23
    listed $499,000 Active 1192-char remark

    Show marketing remark (1192 chars)

    Here’s your opportunity to be in beautiful Redding with its award-winning schools and the perfect blank slate to create your dream home! Built by the only owners this home has ever had, this 4 bedroom, 3 bathroom center hall colonial has endless potential, plus an opportunity to expand the living space significantly. Excellent option on the main level for a first floor primary or au pair suite. Upstairs features three bedrooms including the existing primary, a massive walk-in closet and an additional 1100+ square feet of unfinished space that could be used to create additional living on either end of the second floor. With ample living space as it is, this home also has a full, unfinished walk-out basement with ceilings ranging from 8-10 feet and another 2000 square feet of unlimited potential for finishing as well. Sited on two wooded acres, this home is only 3 miles to Georgetown, Caraluzzi’s and Route 7, for an easy commute down county. Redding boasts over 60 miles of hiking trails, two state parks, a town park and the notable Mark Twain Library. Have all of this in the “Vermont of Connecticut” and still be less than 60 miles to Midtown Manhattan!

ⓘ 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: $10,497 · $875/mo
• Projected year-2 tax: $14,868 · $1,239/mo
• Expected delta: +$4,371/yr (+$364/mo · 41.6%)

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

Climate risk First Street

• 🌊 Flood 9/10 Extreme FEMA zone X (unshaded) · 99% 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: −$50,358
• − Property taxes: −$10,497
• − Insurance: −$5,162
• − Repairs & maintenance: −$19,200
• − Management: −$19,200
• − Depreciation: −$26,153
• Taxable income: $109,431
• Est. tax owed @ 24.0%: −$26,263
• After-tax cash flow: $91,105/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 — Redding Center

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

+80.2% since first listed

14 events — show timeline

• 2026-06-08 Listed $899,000 Smart MLS
• 2026-06-05 Listing Removed — Smart MLS
• 2026-06-05 Relisted — Smart MLS
• 2026-06-05 Listing Removed — Smart MLS
• 2026-04-29 Price Changed $949,000 Smart MLS
• 2026-04-13 Relisted — Smart MLS
• 2026-03-24 Listing Removed — Smart MLS
• 2026-01-05 Listed $979,000 Smart MLS
• 2022-09-26 Sold (Public Records) $220,000 Public Records
• 2022-09-19 Sold (MLS) $440,000 Smart MLS
• 2022-09-08 Pending — Smart MLS
• 2022-08-09 Contingent — Smart MLS
• 2022-07-12 Price Changed $449,000 Smart MLS
• 2022-06-23 Listed $499,000 Smart MLS

Property tax history

+1.2%/yr

Latest (2023): $10,497 · +0.6% YoY. Source: county tax records.