Most expensive homes for sale in New Haven County, CT

$35,000,000

6 beds • 4.5 baths • 5,354 sqft

215 Uncas Point Rd, Guilford, CT 06437

#24034137, Joseph Piscitelli, Listing office: Coldwell Banker Realty

Tour

$29,995,000

10 beds • 7 baths • 10,662 sqft

Rogers Is, Branford, CT 06405

#24086938, Joseph Barbieri, Listing office: Sotheby's International Realty

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$5,700,000

3 beds • 3.5 baths • 4,236 sqft

66 High St Unit 56-57, Guilford, CT 06437

#24057270, Margaret Muir, Listing office: William Pitt Sotheby's Int'l

$4,750,000

4 beds • 4.5 baths • 4,325 sqft

250 Joshua Point Rd, Guilford, CT 06437

#24093717, Jane Von Holzhausen, Listing office: Coldwell Banker Realty

$4,000,000

3 beds • 4 baths • 6,216 sqft

405 Whitfield St Unit 2, Guilford, CT 06437

#24065215, Rose Ciardiello, Listing office: William Raveis Real Estate

Coming soon

$4,000,000

5 beds • 6.5 baths • 4,450 sqft

77 E Wharf Rd, Madison, CT 06443

#24104754, Meig Walz, Listing office: Coldwell Banker Realty

6 days on Rocket

$3,975,000

5 beds • 4.5 baths • 4,062 sqft

218 Kuhne Rd, Call Listing Agent, CT 06488

#876889, Listing office: Showcase Realty Tristate

Room to negotiate?

Median Sold Price

$370.5K

Based on our May 2025 Market Report.

$3,975,000

5 beds • 4.5 baths • 5,183 sqft

218 Kuhne Rd, Southbury, CT 06488

#24097826, John Donato Jr, Listing office: Showcase Realty, Inc.

Tour

$3,250,000

3 beds • 2.5 baths • 2,571 sqft

66 High St Unit 40, Guilford, CT 06437

#24095541, Nicole White, Listing office: William Raveis Real Estate

$3,100,000

6 beds • 5 baths • 3,948 sqft

48 Andrews Rd, Guilford, CT 06437

#24074214, Joseph Piscitelli, Listing office: Coldwell Banker Realty

$3,000,000

6 beds • 4.5 baths • 6,300 sqft

37 Lantern Hill Rd, Madison, CT 06443

#24094658, Cathy Lynch, Listing office: Coldwell Banker Realty

$2,975,000

4 beds • 5 baths • 7,314 sqft

65 Morningside Dr, Milford, CT 06460

#24071194, Frank D'Ostilio, Listing office: Houlihan Lawrence WD

Tour

$2,950,000

3 beds • 2.5 baths • 3,024 sqft

66 High St Unit 17, Guilford, CT 06437

#24100593, Barbara Goetsch, Listing office: William Pitt Sotheby's Int'l

Tour

$2,950,000

6 beds • 4.5 baths • 4,262 sqft

10 Island View Ave, Branford, CT 06405

#24057044, Vicky Welch, Listing office: William Raveis Real Estate

$2,900,000

5 beds • 4 baths • 3,397 sqft

25 Seaview Ave, Madison, CT 06443

#24087649, Alison Gould, Listing office: Gould Group LLC

$2,900,000

7 beds • 5.5 baths • 6,110 sqft

113 Linden Ave, Branford, CT 06405

#24083831, Michelle Wininger, Listing office: William Pitt Sotheby's Int'l

Tour

$2,875,000

4 beds • 4.5 baths • 6,194 sqft

24 Indigo Trl, Madison, CT 06443

#24083085, Ron Stewart, Listing office: Houlihan Lawrence WD

$2,799,000

7 beds • 5.5 baths • 6,000 sqft

127 Hillside Ave, Milford, CT 06460

#24052219, Peggy Jorgensen, Listing office: Compass Connecticut, LLC

$2,750,000

4 beds • 2 baths • 2,038 sqft

Belden Is, Branford, CT 06405

#24090225, Kiara Rusconi, Listing office: William Raveis Real Estate

$2,650,000

5 beds • 7.5 baths • 8,476 sqft

75 Half Mile Rd, Guilford, CT 06437

#24076393, Cathy Lynch, Listing office: Coldwell Banker Realty

$10,000 Closing Credit¹

$2,495,000

5 beds • 4.5 baths • 4,430 sqft

590 Gulf St, Milford, CT 06460

#24089596, Richard Higgins, Listing office: Higgins Group Bedford Square

$10,000 Closing Credit¹

$2,200,000

5 beds • 4.5 baths • 3,174 sqft

630 Cook Hill Rd, Cheshire, CT 06410

#170617954, Kelsey Oddo, Listing office: Kelsey & Co. Real Estate

Backup offers

$10,000 Closing Credit¹

$2,195,000

3 beds • 4 baths • 3,973 sqft

405 Whitfield St Unit 3, Guilford, CT 06437

#24049984, Rose Ciardiello, Listing office: William Raveis Real Estate

$10,000 Closing Credit¹

$2,150,000

6 beds • 7 baths • 8,430 sqft

6 Prospect Ct, Hamden, CT 06517

#24054098, Eric Bergers, Listing office: William Raveis Real Estate

$10,000 Closing Credit¹

$2,150,000

4 beds • 4.5 baths • 4,000 sqft

412 Tanner Marsh Rd, Guilford, CT 06437

#24079789, Diane Dupont, Listing office: William Pitt Sotheby's Int'l

Tour

$10,000 Closing Credit¹

$2,150,000

4 beds • 5.5 baths • 6,572 sqft

139 Rogers Ave, Milford, CT 06460

#24089629, Laurie Quatrella, Listing office: Higgins Group Real Estate

$10,000 Closing Credit¹

$2,000,000

5 beds • 4.5 baths • 4,682 sqft

224 Tepi Dr, Southbury, CT 06488

#24083811, Deborah Bette, Listing office: Joseph Bette REALTORS Inc

$10,000 Closing Credit¹

$1,995,000

5 beds • 3.5 baths • 3,912 sqft

30 Meeting House Ln, Madison, CT 06443

#24097336, Cathy Lynch, Listing office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,975,000

5 beds • 6 baths • 5,795 sqft

584 Boston Post Rd, Madison, CT 06443

#24083244, Kate Jasko, Listing office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,975,000

4 beds • 3.5 baths • 3,869 sqft

91 Shelter Cove Rd, Milford, CT 06460

#24079942, Luke Porto, Listing office: William Raveis Real Estate

$10,000 Closing Credit¹

$1,950,000

4 beds • 3 baths • 2,864 sqft

917 Boston Post Rd, Madison, CT 06443

#24083074, Meig Walz, Listing office: Coldwell Banker Realty

$10,000 Closing Credit¹

$1,950,000

5 beds • 7 baths • 5,414 sqft

173 Highwoods Dr, Guilford, CT 06437

#24093734, Kiara Rusconi, Listing office: William Raveis Real Estate

$10,000 Closing Credit¹

$1,900,000

4 beds • 3 baths • 3,033 sqft

55-69 Sawmill Rd, Branford, CT 06405

#24090401, Nancy Bullis, Listing office: Great Estates, CT

$10,000 Closing Credit¹

$1,880,000

2 beds • 2 baths • 8,704 sqft

380 Main Street 3, 4, 6, 7, 12, 13, 14 &, Wallingford, CT 06492

#24083077, E. Tyler Della Valle, Listing office: Dow Della Valle

$10,000 Closing Credit¹

$1,875,000

3 beds • 2.5 baths • 2,194 sqft

66 High St Unit 36, Guilford, CT 06437

#24102720, Kirsten Adams, Listing office: William Pitt Sotheby's Int'l

$10,000 Closing Credit¹

$1,850,000

4 beds • 3 baths • 1,931 sqft

43 Melba St, Milford, CT 06460

#24099663, Luke Porto, Listing office: William Raveis Real Estate

Tour

$10,000 Closing Credit¹

$1,825,000

4 beds • 6.5 baths • 12,088 sqft

114 Cove St, New Haven, CT 06512

#24083475, Ariel Tortora, Listing office: William Raveis Real Estate

$10,000 Closing Credit¹

$1,800,000

3 beds • 4 baths • 4,804 sqft

2 Woods Way Unit 2, Guilford, CT 06437

#24072872, John Campbell, Listing office: Compass Connecticut, LLC

$10,000 Closing Credit¹

$1,799,000

4 beds • 4.5 baths • 4,567 sqft

415 Northwood Dr, Orange, CT 06477

#24073421, Jake Forchetti, Listing office: Houlihan Lawrence WD

764 Bethany Mountain Rd, Cheshire, CT 06410 - drone / aerial view

$10,000 Closing Credit¹

$1,759,900

5 beds • 4.5 baths • 7,762 sqft

764 Bethany Mountain Rd, Cheshire, CT 06410

#24085738, Joel Matson, Listing office: Divine Realty, LLC

New Haven County, CT Real Estate Market Overview

There are 1,651 most expensive homes for sale in New Haven County, CT. The following market insights reflect all property types in the New Haven County, CT real estate market. The inventory of homes for sale in New Haven County, CT between April 2025 and May 2025 increased by 8.2%. In May 2025, listings were on the market for 0 days. During the same period, the median list price in this real estate market was $370,507. In May 2025, from all listings sold in New Haven County, CT there were more than 418 sold above asking price, over 213 sold below and more than 64 were sold right at the asked price.

From Rocket Homes Real Estate and based on county public records data

Schools near New Haven County, CT

Elementary Schools

Oxford Center School
50 Great Oak Rd
Public District 3-5
Mary R. Tisko Elementary School
118 Damascus Rd
Public District PK-4
Irving School
9 Garden Pl
Public District KG-5

Middle Schools

Newtown Middle School
11 Queen St
Public District 7-8
Woodbury Middle School
67 Washington Ave
Public District 6-8
Mauro - Sheridan Interdistrict Magnet School
191 Fountain St
Public Magnet PK-8

High Schools

Kennedy High School
422 Highland Ave
Public District 9-12
Masuk High School
1014 Monroe Tpke
Public District 9-12
Southington High School
720 Pleasant St
Public District 9-12

Data provided by Great Schools

Most expensive homes for sale in New Haven County, CT

New Haven County, CT Real Estate Market Overview

Schools near New Haven County, CT

Housing market reports in New Haven County

Homes for sale near New Haven County, CT

Top real estate cities in Connecticut