42 Academy Street #2
New Haven, Connecticut 06511
- Beds
- 2
- Baths
- 2
- SqFt
- 1,524
- Year Built
- 1857
- Neighborhood
- Wooster Square
- Property Type
- Condo

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Wooster Square condo living with direct park views and historic character. This twolevel, 2 bedroom, 2 bath home offers oversized windows overlooking the cherrytreelined square, 11+ ft ceilings, exposed brick, and hardwood floors. The main level includes a bright living area with dramatic 8 ft windows, an office nook ideal for remote work, and a kitchen with granite counters, an island, and gas cooking. A full bath with walkin shower and a flexible second bedroom-complete with Murphy bed and access to a shared back deck-round out this floor. The lower level features a spacious primary suite with a walkin closet, full bath, and inunit laundry, creating a quiet, comfortable retreat. The association offers a common patio for grilling, relaxing, and outdoor dining. Additional basement storage, updated mechanicals, and central A/C add everyday convenience. Located on a quiet block in one of New Haven's most beloved neighborhoods, you're steps from worldfamous Apizza, downtown, the Wooster Square Farmers Market, and major highways. Pets allowed (with restrictions). Onstreet parking. A rare chance to live directly on Wooster Square with character, comfort, and unbeatable walkability.
Key Facts
- City/Town
- New Haven
- Neighborhood
- Wooster Square
- Property / Style
- Condo · Townhouse
- Year Built
- 1857
- Days on Market
- 0 days
- Beds
- 2
- Baths
- 2 full
- Living Area
- 1,524 sq ft
- Property Taxes
- $12,540 / Annually
- HOA Fee
- $500 / Monthly
Market Snapshot
The New Haven Market
Condo · trailing 12 months
Active Listings
44
30 under contract
Median List Price
$262,500
44 active listings
Median Closed Price
$266,250
146 sales
Median Days on Market
64
44 active listings
Median $ / Sq Ft
$244
44 active listings
Sale-to-List Ratio
100.0%
146 sales
How this home compares
List Price
$595,000
vs $262,500 median
2.3× the median
Price / Sq Ft
$390
vs $244 median
59.8% above median
Days on Market
0 days
vs 64 days median
64 days fresher than median
Based on 44 active and 146 closed sales (trailing 12 mo) of condo in New Haven. Source: SmartMLS · As of July 29, 2026.
Location
42 Academy Street #2, New Haven, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$3,034
- Property Taxes$1,045
- Insurance$198
- HOA$500
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Haven
- Neighborhood
- Wooster Square
- County
- New Haven
Residence
- Property Type
- Condo
- Subtype
- Condominium
- Style
- Townhouse
- Year Built
- 1857
- New Construction
- No/Resale
- Living Area
- 1,524 sq ft
Schools
- Elementary
- East Rock
- High
- Wilbur Cross
Interior
- Heating
- Hot Air
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Laundry
- Lower Level
- Appliances
- Oven/RangeRange HoodRefrigeratorDishwasherDisposalWasherDryer
- Basement
- PartialSump PumpStoragePartially FinishedLiveable SpacePartial With Walk-Out
- Interior Features
- Cable - Pre-wiredOpen Floor Plan
Exterior & Lot
- Zoning
- RM2
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- StuccoOther
- Exterior Features
- DeckGarden AreaPatio
- Lot Description
- Historic District
HOA / Association
- Fee
- $500 / Monthly
Listing & Financials
- Property Taxes
- $12,540 / Annually
- Days on Market
- 0
- MLS #
- 24194029
- MLS Status
- Coming Soon
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/29/2026 at 5:16 PM UTC.