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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.

Source: Smart MLS, MLS#: 24187215

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  • Property Type
    Residential
  • Lot
    0.07 acres

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Craig Milton

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Owning this Home

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* All calculations are estimates and provided by Reliance Network, for informational purposes only. Actual amounts may vary. ** Assumes 6.50% APR, 20% down payment, and conventional 30-year fixed rate first mortgage. Rates cited are for instructional purposes only; current rates are subject to change at any time without notice. You should not make any decisions based simply on the information provided. Additional required amounts such as taxes, insurance, homeowner association dues, assessments, mortgage insurance premiums, flood insurance or other such required payments should also be considered. Contact your mortgage company for current rates and additional information. Any mortgage broker or insurance agent that may appear is independent and is not affiliated with, endorsed by, or provided by the MLS.

Life at 161 Olive Street


Schools


School data courtesy of LiveBy, Inc.
Ratings are based on a scale of 1-5, with 5 being the highest rating and 1 being the lowest rating. The schools displayed on this website are for informational purposes only and may not represent a complete or up-to-date list. School assignments are subject to change and should be verified directly with the local school district. Please contact the appropriate school district to confirm school zoning and enrollment eligibility for this property.

History

Date Event Value Agent
6/30/2026Source: Smart MLS Added to Database
June 30, 2026
Listing provided courtesy of RE/MAX RISE- MLS# 24187215MLS ProviderContact Information: (203) 494-3888