161 Olive Street, New Haven, CT 06511
What's special
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 sophisticated 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.
- 117 days
- 98
- 1
Travel times
Family Room
Kitchen
Primary Bedroom
Zillow last checked:
Listing updated:
Seigel Team at RE/MAX Rise,
Marc A. Seigel (203)494-3888,
RE/MAX RISE 203-806-1435,
Co-Listing Agent: Lauren Seigel-Gross 203-530-8819,
RE/MAX RISE
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 3
- Bathrooms: 2
- Full bathrooms: 2
Primary bedroom
- Features: Full Bath, Hardwood Floor
- Level: Upper
Bedroom
- Features: Hardwood Floor
- Level: Upper
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
Den
- Features: Wall/Wall Carpet
- Level: Main
Dining room
- Features: High Ceilings, Fireplace, Hardwood Floor
- Level: Main
Kitchen
- Features: Bookcases, Breakfast Nook, Granite Counters, Tile Floor
- Level: Main
Living room
- Features: High Ceilings, Bookcases, Built-in Features, Fireplace, Hardwood Floor
- Level: Main
Study
- Features: Wide Board Floor
- Level: Other
Heating
- Forced Air, Natural Gas
Cooling
- Window Unit(s)
Appliances
- Included: Electric Cooktop, Convection Oven, Gas Water Heater
- Laundry: Lower Level
Features
- Basement: Full,Storage Space,Partially Finished,Walk-Out Access
- Attic: Walk-up
- Number of fireplaces: 2
Interior area
- Total structure area: 1,945
- Total interior livable area: 1,945 sqft
- Finished area above ground: 1,845
- Finished area below ground: 100
Property
Parking
- Total spaces: 4
- Parking features: Detached, Off Street, Driveway, Asphalt
- Garage spaces: 2
- Has uncovered spaces: Yes
Features
- Patio & porch: Porch
- Fencing: Chain Link
Lot
- Size: 3,049 Square Feet
- Features: Corner Lot
Details
- Parcel number: 1245917
- Zoning: RM2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Brick
- Foundation: Stone
- Roof: Asphalt,Flat
Condition
- New construction: No
- Year built: 1870
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Community & HOA
Community
- Features: Near Public Transport, Health Club, Medical Facilities, Park
- Subdivision: Wooster Square
HOA
- Has HOA: No
Location
- Region: New Haven
Financial & listing details
- Price per square foot: $398/sqft
- Tax assessed value: $357,910
- Annual tax amount: $14,303
- Date on market: 6/30/2026
- Exclusions: Hydrangea bush by driveway
Price history
| Date | Event | Price |
|---|---|---|
| 10/8/2026 | Pending sale | $775,000$398/sqft |
Source:  Smart MLS #24187215 Report a problem | ||
| 7/2/2026 | Listed for sale | $775,000+104.5%$398/sqft |
Source: Smart MLS #24187215 Report a problem | ||
| 5/5/2011 | Listing removed | $379,000$195/sqft |
Source: SEABURY-HILL REALTORS #N311630 Report a problem | ||
| 4/10/2011 | Price change | $379,000-5%$195/sqft |
Source: SEABURY-HILL REALTORS #N311630 Report a problem | ||
| 3/5/2011 | Listed for sale | $399,000+33.4%$205/sqft |
Source: SEABURY-HILL REALTORS #N311630 Report a problem | ||
| 8/29/2003 | Sold | $299,000+184.8%$154/sqft |
Source: Smart MLS #N204614 Report a problem | ||
| 3/14/2001 | Sold | $105,000+365.5%$54/sqft |
Source: Smart MLS #N176759 Report a problem | ||
| 6/27/2000 | Sold | $22,556-59.7%$12/sqft |
Source: Smart MLS #N170731 Report a problem | ||
| 7/7/1998 | Sold | $56,000$29/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $14,102 +2.3% | $357,910 |
| 2024 | $13,780 +3.5% | $357,910 |
| 2023 | $13,314 -6.4% | $357,910 |
| 2022 | $14,227 +35.6% | $357,910 +49.7% |
| 2021 | $10,490 | $239,050 |
| 2020 | $10,490 +2.1% | $239,050 |
| 2019 | $10,274 | $239,050 |
| 2018 | $10,274 +11.1% | $239,050 |
| 2017 | $9,246 -8.6% | $239,050 -1.8% |
| 2016 | $10,119 | $243,530 |
| 2015 | $10,119 | $243,530 |
| 2014 | $10,119 +1.8% | $243,530 |
| 2013 | $9,936 +4.9% | $243,530 |
| 2012 | $9,468 -2.3% | $243,530 +10.4% |
| 2011 | $9,686 | $220,640 |
| 2010 | $9,686 +4% | $220,640 |
| 2009 | $9,313 +70.1% | $220,640 +70.1% |
| 2007 | $5,474 +14.1% | $129,696 +21.3% |
| 2006 | $4,797 +52.2% | $106,960 +34.2% |
| 2004 | $3,152 +2.6% | $79,730 |
| 2003 | $3,072 +14.8% | $79,730 +4.1% |
| 2000 | $2,677 | $76,600 |
Monthly payment
Estimated market value
$756,000
$718,000 - $794,000
$2,704/mo
Climate risks
Explore flood, wildfire, and other predictive climate risk information for this property on First Street®️.