161 Olive Street, New Haven, CT 06511

• 3 beds |
• 2 baths |
• 1,945 sqft

Property Description

Rare historic Wooster Square compound featuring a detached carriage house and private garden retreat. Opportunities like this seldom come to market in New Haven's iconic Wooster Square Historic District. Built in 1870, this distinguished brick residence offers 3 BR, 2 full baths, and a rare blend of architectural character, flexible living space, and private outdoor living. Behind the historic brick facade, soaring ceilings, original details, and two decorative fireplaces evoke the craftsmanship & charm of a bygone era, while thoughtful updates provide modern comfort, including a remod 2nd bath. The unfinished third floor offers expansion potential and a lookout perch overlooking the neighborhood. The walk-out lower level has been transformed into a cozy cabin-inspired retreat, ideal for entertaining or relaxing, with abundant storage. Set on a fenced corner lot, the property lives like a private compound with mature landscaping, intimate garden spaces, and off-street parking-an unexpected retreat in the heart of the city. The detached carriage house has been extensively upgraded into a cigar lounge-inspired home office & fitness studio, offering flexibility and potential Yale Homebuyer Program eligibility, with the option to convert back to a 2-car gar. Just moments from Wooster Square's cherry blossoms, farmers market, world-famous pizza, Union Station,Yale,Yale NH Hospital, downtown, restaurants, and major highways. Historic. Private. Flexible. Walkable.

Listing Status:

Active

Date Added:

June 30, 2026

Data Last Updated:

July 4, 2026 at 4:50PM

Listing Office:

RE/MAX RISE : (203) 806-1435

Listing Agent:

Marc Seigel : (203) 494-3888

MLS ID:

24187215

Interior

• Appliances: Electric CooktopConvection Oven
• Laundry: Lower Level
• Basement: FullStoragePartially FinishedWalk-out
• A/C: Window Unit
• Heating: Hot AirNatural Gas
• Fireplace: Fireplaces: 2

Exterior

• General: Porch
• Style: Colonial
• Parking: Parking spaces: 4

Construction

• Roofing: Asphalt ShingleFlat

Location

• County: New Haven

Lot

• Driveway: Asphalt
• Zoning: RM21245917

Utilities

• Water: Public Water Connected
• Sewer: Public Sewer Connected

Financial

• Exclusions: Hydrangea bush by driveway