2744 W Main St · Wappingers Falls, NY 12590

$299,999

2 bd · 1.0 ba · 816 sqft · SingleFamily public records · 63 Days on market

Built 1900 2,178 sqft lot $368/sqft · 6% above area Est $403k · 26% 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 +7.9/30.0
• Schools +5.3/10.0
• Livability +3.8/5.0
• 1% rule +2.7/10.0
• Condition / age +2.5/5.0
• Rent growth +2.2/5.0
• DSCR +2.0/10.0
• Appreciation +0.0/10.0

Listing remarks MLS

Welcome to 2744 West Main Street in Wappingers Falls, a beautifully fully renovated home inside and out that perfectly blends modern updates with an unbeatable Hudson Valley lifestyle. This comprehensive renovation includes brand-new windows, roof, siding, and flooring throughout, offering peace of mind and a truly move-in-ready experience. The home features a brand-new rear deck overlooking scenic Wappingers Lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing while taking in peaceful water views. A finished ground-floor recreation room with walkout access to the backyard provides flexible living space—ideal for a family room, home office, gym, or guest area. The updated kitchen is equipped with stainless steel appliances, complementing the home’s modern finishes and design. Every detail has been thoughtfully upgraded for today’s lifestyle. The property also offers the opportunity for the new owner to create a private walking trail leading down to Wappingers Lake, enhancing the connection to the outdoors and lakeside setting. Ideally located, this home offers sidewalk access to the Village of Wappingers Falls, making it easy to enjoy local restaurants, cafe's and boutique shops just minutes from your door. Commuters will appreciate the close proximity to the New Hamburg Metro-North train station, providing convenient access to New York City. Enjoy everything the Hudson Valley has to offer, including nearby parks, waterfront activities, historic sites, and popular destinations such as the Walkway Over the Hudson. With dining, recreation, transportation, and nature all within reach, this home offers an exceptional combination of location, lifestyle, and modern living. A rare opportunity to own a fully renovated lakeside retreat in one of Dutchess County’s most desirable areas. NOTE: There is a leased parking spot for this home at 2745 Main St across the street that will convey with the sale.

Key facts

• New siding
• Fully renovated home
• New flooring

Tags

• FULLY RENOVATED HOME
• NEW WINDOWS
• NEW ROOF
• NEW SIDING
• NEW FLOORING
• REAR DECK

What this means for you Summary

Snapshot

• This is a 2-bed/1.0-bath single-family listed at $300k.

Deal economics

• At list price, monthly cash flow is $-313 ($-4k/yr) — negative.
• To cash-flow at today's rent, offer at most $245k (18.4% below list).
• To meet the 1% rule (rent ≥ 1% of price), the offer needs to be $231k (22.9% below list).
• Recommended offer: $231k (22.9% below list) — sets the bar for 1% rule.
• Cap rate 5.0% vs local median 3.5% in Wappingers Falls — 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 76/100 on livability (#225 in NY, #3,541 nationally) — a middle-class / working-renter tenant base. Strengths: health & safety A+, commute A-, housing A-; Watch: crime C-, amenities C-, employment D.
• Wappingers Central School District (suburban): math 53% / reading 65% proficiency, ranked #207 of 590 in NY (top 35%) — acceptable for families but not a draw, mixed tenant base, ~2y average lease; only 15% free/reduced lunch — higher-income household profile.
• Zoned schools: Myers Corners School (math 41% / reading 64%, grade C-, #984 of 2,108 statewide, top 47%, 825 students, 24% FRL); Wappingers Junior High School (math 30% / reading 54%, grade D-, #379 of 729 statewide, top 54%, 735 students, 36% FRL); Roy C Ketcham Senior High School (math 90% / reading 92%, grade A+, #203 of 1,100 statewide, top 20%, 1,612 students, 31% FRL) — zoned schools average 31% FRL vs 15% district-wide (16 pts higher); higher-poverty schools than district average — tighter screening recommended.
• Market conditions: Rents soft (-1.1%/yr); 206 active listings in the ZIP; 14 comparable units currently listed for rent nearby; rentals lingering (median 46d on market — plan ~5-8 weeks vacancy on turnover, expect pricing pressure); 50% of comp listings sitting > 30 days — soft ceiling on asking rent; solid renter incomes; 620 units permitted in Dutchess County in 2024 (242 in 5+ unit buildings).

Forward outlook

• Local home prices are declining (-3.0%/yr); year-one equity from $2k of loan paydown is wiped out by about $9k of value loss. Plan a longer hold.
• Dutchess County population projected at -11% by 2050 — secular population decline; favor cash flow + early exit over multi-decade hold.

Negotiation context

• It's been on market 63 days — a 6% lower offer ($282k) is reasonable based on typical stale-listing flexibility.
• 3 sale attempts since 14y ago; this cycle's ask has dropped $50k (14%) from the opening price — seller is motivated, your offer sets the floor, not the list.
• Current owner paid $200k; 50% above their basis — modest negotiation headroom, anchor on the comps not their cost.

Risks & watch-outs

• Watch-outs: built in 1900 — expect roof / HVAC / electrical / plumbing capex.
• Climate carrying-cost: extreme-heat days projected 7→15/yr by 2055 (HVAC capex compounding) — expect insurance premiums to compound above CPI over the hold.

Recommended offer $231,298 (22.9% 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 63 days. Have you received any prior offers? Is the seller open to a 23% concession, seller financing, or rate buy-down credit?
3. Built in 1900 — when were the roof, HVAC, electrical panel, plumbing, and water heater last replaced?
4. Why hasn't it sold? Are there any deal-killer items the seller is aware of (foundation, flood, title, zoning, code violations)?
5. Is there a deadline driving the sale (1031 exchange, divorce, estate, relocation)? That informs how much negotiation room exists.
6. Schools are D-rated, which usually means shorter tenancies and higher turnover. Who's the typical renter profile here, and what's been the actual vacancy rate?
7. 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?
8. 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.
9. 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.
10. 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: 0.77% ✗
• Cap rate: 5.04%
• Cash-on-cash: -4.48%
• DSCR: 0.80
• GRM: 10.8

CMA / ARV

• ARV (median comp): $403,154
• List price: $299,999
• Delta: -25.59%
• Verdict: UNDERPRICED
• Comps: 20 within 1.0 mi

Show comp detail 3 sales within ~0.75 mi

Address	Dist	Beds/Ba	Sqft	Sold	Price	$/sf	Match
1782 South Rd Lot 83	0.74mi	2/1.0	784 (-4%)	17mo	$132,000	$168	44
41 Swenson Dr	0.62mi	3/1.0 (+1)	936 (+15%)	4mo	$400,000	$427	38
38 Mill St	0.30mi	3/2.0 (+1)	936 (+15%)	22mo	$319,000	$341	35

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 · 0.0% rent growth · sell at horizon

5-year hold

• IRR: -27.4%
• Equity multiple: 0.10×
• Total profit: $-75,270
• Equity at exit: $44,731

10-year hold

• IRR: -42.0%
• Equity multiple: -0.39×
• Total profit: $-117,125
• Equity at exit: $25,938

Cash invested: $84,000 (down + closing). Projections, not guarantees.

Landlord ↔ Tenant lean methodology

• Overall (STATE): 15 Strongly Tenant-Friendly
• State New York: 15 Strongly Tenant-Friendly · D+10
• County: — inherits STATE
• City: — inherits STATE

NYC rent stabilization (~1M units); 2019 HSTPA strengthened tenant rights; courts deeply backlogged.

Methodology + full state rankings →

ZIP-level market 12590

• Rents YoY: -1.1%
• Active inventory: 206
• Price-to-rent: 10.8×

Monthly cashflow live

• Estimated rent: $2,313 high
• Mortgage (P&I): −$1,573
• Tax from tax record: −$442 /mo · $5,308/yr
• Insurance: −$125
• HOA: −$0
• Vacancy / Maint / Mgmt: −$486
• Net cashflow: $-313

Break-even live

Break-even rent $2,710

Max offer price $244,651

Occupancy floor —

Sensitivity live

Price	-10% $-143	-5% $-228	+0% $-313	+5% $-398	+10% $-483
Rent	-10% $-496	-5% $-405	+0% $-313	+5% $-222	+10% $-131
Rate	-1.0pp $-162	-0.5pp $-237	base $-313	+0.5pp $-391	+1.0pp $-470

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: $75,000
• Closing costs: $9,000
• Reserves months: —
• Total cash needed: —

Rent comps 14 comps

Address	Beds	Baths	Sqft	Rent	$/sqft	DOM	Units	Dist
10 Market St Wappingers Falls, NY	1.0	1.0	600	$2,150	$3.58	45d	1	0.40mi
10 Market St Unit D Wappingers Falls, NY	1.0	1.0	605	$2,175	$3.60	45d	1	0.40mi
10 Market St Unit C Wappingers Falls, NY	2.0	2.0	935	$2,650	$2.83	45d	1	0.40mi
10 Market St Unit B Wappingers Falls, NY	2.0	2.0	1000	$2,700	$2.70	16d	1	0.40mi
81 Market St Unit 3 Wappingers Falls, NY	2.0	1.0	1065	$2,500	$2.35	16d	1	0.55mi
9 Colonial Dr Unit D4 Wappingers Falls, NY	1.0	1.0	645	$1,600	$2.48	25d	1	0.62mi
1668 Route 9 Unit 4F Wappingers Falls, NY	2.0	1.0	876	$2,300	$2.63	45d	1	0.64mi
1668 Route 9 Unit 5M Wappingers Falls, NY	2.0	1.0	911	$2,200	$2.41	45d	1	0.64mi
14 Franklindale Ave Unit B Wappingers Falls, NY	1.0	1.0	815	$1,900	$2.33	25d	1	0.81mi
799 Sergeant Palmateer Way Unit C12 Wappingers Falls, NY	2.0	1.0	741	$2,300	$3.10	16d	1	0.93mi
46 N Gilmore Blvd Wappingers Falls, NY	2.0	1.5	864	$2,800	$3.24	45d	1	0.95mi
5118 Princess Cir Unit Two Bedroom Wappingers Falls, NY	2.0	2.0	1020	$2,250	$2.21	25d	1	1.11mi
5118 Princess Cir Unit Two Bedroom / One Bath Wappingers Falls, NY	2.0	1.0	880	$1,800	$2.05	25d	1	1.11mi
5 Wildwood Dr Unit 12C Wappingers Falls, NY	2.0	1.0	840	$2,250	$2.68	45d	1	1.33mi

Listing history 22 events

1. 2026-06-14
   statusdays on market $299,999 Pending 63 DOM
2. 2026-06-10
   days on market $299,999 Active 62 DOM
3. 2026-06-09
   days on market $299,999 Active 61 DOM
4. 2026-06-08
   days on market $299,999 Active 60 DOM
5. 2026-06-07
   days on market $299,999 Active 59 DOM
6. 2026-06-03
   days on market $299,999 Active 55 DOM
7. 2026-06-02
   days on market $299,999 Active 54 DOM
8. 2026-06-01
   days on market $299,999 Active 53 DOM
9. 2026-05-31
   days on market $299,999 Active 52 DOM
10. 2026-05-30
    days on market $299,999 Active 51 DOM
11. 2026-05-18
    price $339,000 1987-char remark

    Show marketing remark (1987 chars)

    Welcome to 2744 West Main Street in Wappingers Falls, a beautifully fully renovated home inside and out that perfectly blends modern updates with an unbeatable Hudson Valley lifestyle. This comprehensive renovation includes brand-new windows, roof, siding, and flooring throughout, offering peace of mind and a truly move-in-ready experience. The home features a brand-new rear deck overlooking scenic Wappingers Lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing while taking in peaceful water views. A finished ground-floor recreation room with walkout access to the backyard provides flexible living space—ideal for a family room, home office, gym, or guest area. The updated kitchen is equipped with stainless steel appliances, complementing the home’s modern finishes and design. Every detail has been thoughtfully upgraded for today’s lifestyle. The property also offers the opportunity for the new owner to create a private walking trail leading down to Wappingers Lake, enhancing the connection to the outdoors and lakeside setting. Ideally located, this home offers sidewalk access to the Village of Wappingers Falls, making it easy to enjoy local restaurants, cafe's and boutique shops just minutes from your door. Commuters will appreciate the close proximity to the New Hamburg Metro-North train station, providing convenient access to New York City. Enjoy everything the Hudson Valley has to offer, including nearby parks, waterfront activities, historic sites, and popular destinations such as the Walkway Over the Hudson. With dining, recreation, transportation, and nature all within reach, this home offers an exceptional combination of location, lifestyle, and modern living. A rare opportunity to own a fully renovated lakeside retreat in one of Dutchess County’s most desirable areas. NOTE: There is a leased parking spot for this home at 2745 Main St across the street that will convey with the sale.

12. 2026-05-04
    price $345,000 1987-char remark

    Show marketing remark (1987 chars)

    Welcome to 2744 West Main Street in Wappingers Falls, a beautifully fully renovated home inside and out that perfectly blends modern updates with an unbeatable Hudson Valley lifestyle. This comprehensive renovation includes brand-new windows, roof, siding, and flooring throughout, offering peace of mind and a truly move-in-ready experience. The home features a brand-new rear deck overlooking scenic Wappingers Lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing while taking in peaceful water views. A finished ground-floor recreation room with walkout access to the backyard provides flexible living space—ideal for a family room, home office, gym, or guest area. The updated kitchen is equipped with stainless steel appliances, complementing the home’s modern finishes and design. Every detail has been thoughtfully upgraded for today’s lifestyle. The property also offers the opportunity for the new owner to create a private walking trail leading down to Wappingers Lake, enhancing the connection to the outdoors and lakeside setting. Ideally located, this home offers sidewalk access to the Village of Wappingers Falls, making it easy to enjoy local restaurants, cafe's and boutique shops just minutes from your door. Commuters will appreciate the close proximity to the New Hamburg Metro-North train station, providing convenient access to New York City. Enjoy everything the Hudson Valley has to offer, including nearby parks, waterfront activities, historic sites, and popular destinations such as the Walkway Over the Hudson. With dining, recreation, transportation, and nature all within reach, this home offers an exceptional combination of location, lifestyle, and modern living. A rare opportunity to own a fully renovated lakeside retreat in one of Dutchess County’s most desirable areas. NOTE: There is a leased parking spot for this home at 2745 Main St across the street that will convey with the sale.

13. 2026-04-09
    listed $350,000 Active 1987-char remark

    Show marketing remark (1987 chars)

    Welcome to 2744 West Main Street in Wappingers Falls, a beautifully fully renovated home inside and out that perfectly blends modern updates with an unbeatable Hudson Valley lifestyle. This comprehensive renovation includes brand-new windows, roof, siding, and flooring throughout, offering peace of mind and a truly move-in-ready experience. The home features a brand-new rear deck overlooking scenic Wappingers Lake, creating the perfect setting for morning coffee, outdoor dining, or simply relaxing while taking in peaceful water views. A finished ground-floor recreation room with walkout access to the backyard provides flexible living space—ideal for a family room, home office, gym, or guest area. The updated kitchen is equipped with stainless steel appliances, complementing the home’s modern finishes and design. Every detail has been thoughtfully upgraded for today’s lifestyle. The property also offers the opportunity for the new owner to create a private walking trail leading down to Wappingers Lake, enhancing the connection to the outdoors and lakeside setting. Ideally located, this home offers sidewalk access to the Village of Wappingers Falls, making it easy to enjoy local restaurants, cafe's and boutique shops just minutes from your door. Commuters will appreciate the close proximity to the New Hamburg Metro-North train station, providing convenient access to New York City. Enjoy everything the Hudson Valley has to offer, including nearby parks, waterfront activities, historic sites, and popular destinations such as the Walkway Over the Hudson. With dining, recreation, transportation, and nature all within reach, this home offers an exceptional combination of location, lifestyle, and modern living. A rare opportunity to own a fully renovated lakeside retreat in one of Dutchess County’s most desirable areas. NOTE: There is a leased parking spot for this home at 2745 Main St across the street that will convey with the sale.

14. 2026-01-25
    historical
15. 2025-12-11
    soldstatus $200,000
16. 2024-02-02
    historical
17. 2024-02-02
    historical
18. 2013-04-15
    soldstatus $70,000
19. 2012-05-31
    listed $79,900
20. 2012-04-14
    listed $99,995
21. 2003-06-06
    soldstatus $75,000
22. 1994-12-22
    soldstatus $20,000

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

Tax reassessment forecast NY · Partial reset (capped growth)

• Current annual tax: $5,308 · $442/mo
• Projected year-2 tax: $5,308 · $442/mo
• Expected delta: $0/yr ($0/mo · 0.0%)

ⓘ 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 1/10 Low
• 🌡 Heat 5/10 Major 7 d/yr ≥100°F today · 15 d/yr by 30 yrs out
• 💨 Wind 4/10 Moderate 11% chance of damaging wind over 30 yrs
• 🫁 Air quality 3/10 Moderate 2 unhealthy d/yr today · 3 by 30 yrs out

Taxation est. · year 1

• Rental income: $27,756
• − Mortgage interest: −$16,805
• − Property taxes: −$5,308
• − Insurance: −$1,500
• − Repairs & maintenance: −$2,220
• − Management: −$2,220
• − Depreciation: −$8,727
• Taxable loss: −$9,025
• Est. tax savings @ 24.0%: +$2,166
• After-tax cash flow: $-1,594/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: Wappingers Central School District
• NCES district ID: 3629880
• Math proficiency: 53% ▼ -4.00%
• Reading proficiency: 65% ▲ 10.00%
• Median HH income: $83,184
• Composite: 53.38/100
• National rank: #1474
• State rank: #207 of 590 in NY

Livability — Wappingers Falls

• Score: 76/100
• State rank: #225
• US rank: #3541

Category grades

Amenities C- Commute A- Cost of living D Crime C- Employment D Housing A- Health & safety A+ User ratings A

Schools grade is shown separately in the Schools card above.

Census & demographics

• Census place: Wappingers Falls, NY
• County: Dutchess County · 188,048 people
• City population: 35,712
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• Population (ZIP): 35,712
• Household income: $102,285
• Rent vs Own: 30.5% rent · 69.5% own
• Severe rent burden: 786.0

Population outlook (Dutchess County) Hauer SSP2

• Today (2025): 291,768 people
• By 2030: 287,131 · -1.6%
• By 2040: 274,881 · -5.8%
• By 2050: 259,971 · -10.9%
• By 2075: 235,366 · -19.3%
• By 2100: 208,786 · -28.4%

Race, ethnicity, and origin ACS 2023

• Neighborhood character: Predominantly White (66%)
• Race & ethnicity: White 66% Hispanic / Latino 18% Two or more races 8% Black 8% Asian 4%
• Hispanic origin (detail): Mexican 3% Puerto Rican 7% Dominican 1%
• Common ancestry: Romanian 3% Italian 1% Lithuanian 1%
• Foreign-born: 12% · Canada, Jamaica, China
• Languages at home: 81% English-only · Spanish 12% Other Indo-European 3% Chinese 1%

Political lean MEDSL · Dutchess

• 2024 margin: Lean D (+5.4) · D 52.7% · R 47.3%
• 2008→2024 swing: -3.2pp toward R · 2008: 8.6pp · 2024: 5.4pp
• All cycles: 2024: D+5.4 2020: D+9.6 2016: R+1.1 2012: D+6.6 2008: D+8.6

Not yet ingested

• Civics: —

Market trends

• HPI YoY: ▼ -411.49%
• Current HPI: 255.2764
• Rent YoY: ▼ -1.08%
• Metro: Poughkeepsie-Newburgh-Middletown, NY
• State GDP YoY: ▲ 2.60%
• F500 in state: 92

Industry mix (Fortune 500 HQ in NY)

Industry	F500 HQs	Revenue
▸Financial Services	10	$950B
▸Consumer Goods	9	$162B
▸Insurance	4	$225B
▸Telecommunications	2	$144B
▸Pharmaceuticals	2	$112B
▸Media / Entertainment	2	$69B

Price history

+1595.0% since first listed

12 events — show timeline

• 2026-05-18 Price Changed $339,000 OneKey® MLS as Distributed by MLS Grid
• 2026-05-04 Price Changed $345,000 OneKey® MLS as Distributed by MLS Grid
• 2026-04-09 Listed $350,000 OneKey® MLS as Distributed by MLS Grid
• 2026-01-25 Coming Soon — OneKey® MLS as Distributed by MLS Grid
• 2025-12-11 Sold (Public Records) $200,000 Public Records
• 2024-02-02 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2024-02-02 Listing Removed — OneKey® MLS as Distributed by MLS Grid
• 2013-04-15 Sold (Public Records) $70,000 Public Records
• 2012-05-31 Listed $79,900 OneKey® MLS as Distributed by MLS Grid
• 2012-04-14 Listed $99,995 OneKey® MLS as Distributed by MLS Grid
• 2003-06-06 Sold (Public Records) $75,000 Public Records
• 1994-12-22 Sold (Public Records) $20,000 Public Records

Property tax history

+3.3%/yr

Latest (2025): $5,308 · -0.6% YoY. Source: county tax records.