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Back 99 Olive Street
Off Market

99 Olive Street

New Haven CT 06511

5
3
2885 sq. ft.
0.07 ac.
Duplex
Last sold for $950,000
John DaikusJohn Daikus, last sold this property on 05 December 2025 after 38 days on market.

Overview

Step into timeless elegance at 99 Olive Street, a rare Queen Anne Victorian style three-family in the heart of Wooster Square! This striking brick home showcases the best of 19th-century craftsmanship, with its intricate detailing, patterned facade, and beautifully preserved historic character. This lovingly maintained, legal 3 family with a bonus office space, has been thoughtfully updated. The property features a newer roof, rebuilt chimney, updated mechanicals, and recent repointing of the whole brick exterior, preserving its beauty and ensuring long-term integrity! Inside, each spacious unit offers high ceilings, hardwood floors, fireplaces, and large windows that fill the rooms with natural light. Private backyard with garden boxes and community grill is great for entertaining and relaxing in the heart of the city. Separate utilities and flexible layouts make it ideal for both investors and owner-occupants. Enjoy everything Wooster Square has to offer right outside your door- the park, weekend farmers market, cafes, and the legendary Sally's and Pepe's Apizza. Just minutes to Yale, downtown, and Union Station, this home perfectly blends Queen Anne elegance with modern reliability and city convenience. A true Wooster Square gem, full of charm, character, and opportunity.

Features

5 bedrooms
3 bathrooms
2885 sq. ft. floor area
0.07 ac. lot size
Duplex

Estimated Value

Based on this property and similar 5 bedroom duplexes sold in New Haven over the last 12 months, the estimated median property value of 99 Olive Street is $460k.

Median value
$460k
Estimated value range
$215k - $950k
Median days on market
13
Estimated value trend
14%
increase over the last 12 months
Average days on market is based on recent, comparable sales in New Haven. It is only an indication of the time a property is actively listed and should not be relied upon as an accurate representation of how soon a property will be sold.

Property history for 99 Olive Street

2025
Sold
$950,000
05 Dec 2025 by John Daikus

Happy sellers in New Haven

~%

We have insufficient information to provide an overview of customer satisfaction for New Haven. Viewing the agent profiles, reviews and sales for New Haven can provide insights for this location.

Local market activity for 5 bedroom duplexes in New Haven

In the last 12 months, 16 five-bedroom duplexes similar to 99 Olive Street, have been sold.

This represents a 16% increase in five-bedroom duplexes sales when compared to the previous 12 months.

Nearby agents

Compare and contact these top performing agents who’ve delivered exception customer service for their clients in New Haven

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Betsy Grauer

Betsy Grauer is a recommended agent for New Haven.  They have 14 local sales and collected 1 local review across the last 12 months.

  •   5   (1 review)
  •  1 Review in New Haven
  •  14 Sales in New Haven
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Jennifer D'Amato

Jennifer D'Amato is a recommended agent for New Haven.  They have 5 local sales and collected 1 local review across the last 12 months.

  •   5   (2 reviews)
  •  1 Review in New Haven
  •  5 Sales in New Haven
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Eric Schuell

Sellers who recommend Eric Schuell have praised them for being local expert, responsive, supportive, friendly, honest, reliable, and clear communication

  •   5   (53 reviews)
  •  1 Review in New Haven
  •  1 Sale in New Haven
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Arcy Khan

Arcy Khan is a recommended agent for New Haven.  They have 1 local sale and collected 1 local review across the last 12 months.

  •   5   (20 reviews)
  •  1 Review in New Haven
  •  1 Sale in New Haven
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