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42 Academy Street #2

New Haven, Connecticut 06511

COMING SOON - NEW$595,000
Beds
2
Baths
2
SqFt
1,524
Year Built
1857
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,777

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Cheryl Szczarba

(203) 996-8328

Seabury Hill REALTORS

(203) 562-1220

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.