The Most Expensive Home Sales in New Haven, CT in May 2025

While less glamorous than a city like New York, New Haven offers something unique: old-school charm, world-class universities, and tight-knit neighborhoods. It’s also far more affordable – and competitive. 

Homes in New Haven commonly sell above their asking price – in fact, most properties on this list did. This is because New Haven has a growing housing shortage, which is putting sellers in charge and spurring bidding wars. New Haven has also seen among the steepest drops in inventory since January, further straining the market. 

So, as buyers fight over every listing in a blossoming Rust Belt metro, where did they spend the most? Here were the most expensive home sales in New Haven in May, according to data from Redfin. 

The most expensive home sales in New Haven: May 2025

1. 274 Ogden St, New Haven, CT 06511

• Sale price: $1,675,000
• List price: $1,600,000

This architect-designed Colonial in Prospect Hill spans 3,747 square feet with 6 bedrooms, 4 baths, formal living and family rooms, an office with fireplace, and a wall of glass opening to a flagstone patio. 

2. 76 Everit St, New Haven, CT 06511

• Sale price: $1,250,000
• List price: $1,525,000

Nestled in New Haven’s East Rock, this 8,105-square-foot Tudor‑Revival estate (built 1909) offers 9 bedrooms, 7.5 baths, original wood paneling and nine fireplaces, plus a four‑car garage and terraced garden.

3. 130 Westwood Rd, New Haven, CT 06515

• Sale price: $950,000
• List price: $852,500

This 3,842-square-foot brick Colonial in New Haven features 6 bedrooms, 3.5 baths, and a blend of 1920s charm and modern updates. It was recently renovated but still includes period details throughout.

4. 567 Orange St, New Haven, CT 06511

• Sale price: $850,765
• List price: $750,000

This 4-bedroom, 3.5-bath home offers 2,205 square feet of updated living space with a modern open layout and three finished levels.

5. 63-1/2 Canner St, New Haven, CT 06511

• Sale price: $725,000
• List price: $675,000

A home with a unique ½ address, it features 3 beds and 2 baths across 1,405 square feet. It was recently renovated with classic charm and modern flair, and contains an open living area with bay window, California-style kitchen, more.

6. 1695 Ella T Grasso Blvd, New Haven, CT 06511

• Sale price: $665,000
• List price: $665,000

This 2,746 sq ft home features 4 bedrooms, 2.5 baths, and a two-car garage. Built in 1935, it combines classic character with thoughtful updates.

7. 155 Stevenson Rd, New Haven, CT 06515

• Sale price: $620,000
• List price: $665,000

This 4-bedroom home includes two bonus rooms, four full baths, and a large renovated eat-in kitchen. It also offers a two-car garage, central air, and a finished lower level.

8. 114 Whittier Rd, New Haven, CT 06515

• Sale price: $565,000
• List price: $475,000

This 3-bedroom, 2½‑bath ranch offers 2,609 square feet, with a screened sunroom, eat-in quartz kitchen, and bonus room. The finished lower level walks out to the yard, and it includes a two-car garage.

9. 120 Stevenson Rd, New Haven, CT 06515

• Sale price: $535,000
• List price: $535,000

This split-level home spans 2,412 square feet and includes 3 bedrooms, 3 baths, and a two-car garage. A modern kitchen with updated appliances is the highlight.

10. 70 Wood Ter, East Haven, CT 06513

• Sale price: $490,000
• List price: $450,000

This well-maintained 3-bedroom, 2.5-bath home sits on a 0.72-acre lot at the end of a quiet cul‑de‑sac and includes a 2-car garage and soaring cathedral ceilings in the living room and kitchen.

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