Most expensive homes for sale in Connecticut
Written by:
August 21, 2025
Konstantin L // Shutterstock
Most expensive homes for sale in Connecticut
Stacker compiled a list of the most expensive homes in Connecticut listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
You may also like:
Cities with the most expensive homes in Connecticut
#30. 52 Carriglea Dr, Riverside
- Price: $13,750,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,418
- Price per square foot: $1,459
- Lot size: 1.4 acres
- Days on market: 118 days (-$500,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,418
- Price per square foot: $1,459
- Lot size: 1.4 acres
- Days on market: 118 days (-$500,000 price reduction since listing)
- View listing on realtor.com
#29. 190 North St, Greenwich
- Price: $13,995,000
- 5 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 10,431
- Price per square foot: $1,341
- Lot size: 3.4 acres
- Days on market: 79 days
- View listing on realtor.com
- 5 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 10,431
- Price per square foot: $1,341
- Lot size: 3.4 acres
- Days on market: 79 days
- View listing on realtor.com
#28. 220-226 Tinker Hill Rd, Washington
- Price: $14,000,000
- 5 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 10,203
- Price per square foot: $1,372
- Lot size: 18.4 acres
- Days on market: 138 days (-$5,900,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 10,203
- Price per square foot: $1,372
- Lot size: 18.4 acres
- Days on market: 138 days (-$5,900,000 price reduction since listing)
- View listing on realtor.com
#27. 537 North St, Greenwich
- Price: $14,900,000
- 6 bedrooms, 8 full bathrooms, 4 half bathrooms
- Square feet: 15,171
- Price per square foot: $982
- Lot size: 3.0 acres
- Days on market: 149 days (-$595,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 8 full bathrooms, 4 half bathrooms
- Square feet: 15,171
- Price per square foot: $982
- Lot size: 3.0 acres
- Days on market: 149 days (-$595,000 price reduction since listing)
- View listing on realtor.com
#26. 4800 Congress St, Fairfield
- Price: $15,000,000
- 7 bedrooms, 7 full bathrooms, 3 half bathrooms
- Square feet: 9,129
- Price per square foot: $1,643
- Lot size: 38.9 acres
- Days on market: 35 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 3 half bathrooms
- Square feet: 9,129
- Price per square foot: $1,643
- Lot size: 38.9 acres
- Days on market: 35 days
- View listing on realtor.com
You may also like:
What the ongoing worker shortage looks like in Connecticut
#25. 865 Hollow Tree Ridge Rd, Darien
- Price: $17,000,000
- 6 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 10,197
- Price per square foot: $1,667
- Lot size: 4.2 acres
- Days on market: 328 days (-$2,000,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 10,197
- Price per square foot: $1,667
- Lot size: 4.2 acres
- Days on market: 328 days (-$2,000,000 price reduction since listing)
- View listing on realtor.com
#24. 11 Conyers Farm Dr, Greenwich
- Price: $17,500,000
- 7 bedrooms, 11 full bathrooms, 2 half bathrooms
- Square feet: 16,597
- Price per square foot: $1,054
- Lot size: 19.7 acres
- Days on market: 114 days (-$2,495,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 11 full bathrooms, 2 half bathrooms
- Square feet: 16,597
- Price per square foot: $1,054
- Lot size: 19.7 acres
- Days on market: 114 days (-$2,495,000 price reduction since listing)
- View listing on realtor.com
#23. 382 North St, Greenwich
- Price: $17,875,000
- 6 bedrooms, 9 full bathrooms, 3 half bathrooms
- Square feet: 14,126
- Price per square foot: $1,265
- Lot size: 2.4 acres
- Days on market: 7 days
- View listing on realtor.com
- 6 bedrooms, 9 full bathrooms, 3 half bathrooms
- Square feet: 14,126
- Price per square foot: $1,265
- Lot size: 2.4 acres
- Days on market: 7 days
- View listing on realtor.com
#22. 41 Meadow Wood Dr, Greenwich
- Price: $18,500,000
- 6 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 10,275
- Price per square foot: $1,800
- Lot size: 4.9 acres
- Days on market: 81 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 3 half bathrooms
- Square feet: 10,275
- Price per square foot: $1,800
- Lot size: 4.9 acres
- Days on market: 81 days
- View listing on realtor.com
#21. 11 Langhorne Ln, Greenwich
- Price: $19,500,000
- 8 bedrooms, 12 full bathrooms, 5 half bathrooms
- Square feet: 26,454
- Price per square foot: $737
- Lot size: 8.8 acres
- Days on market: 63 days
- View listing on realtor.com
- 8 bedrooms, 12 full bathrooms, 5 half bathrooms
- Square feet: 26,454
- Price per square foot: $737
- Lot size: 8.8 acres
- Days on market: 63 days
- View listing on realtor.com
You may also like:
Average Connecticut mortgage debt increased to $256,627 in 2024
#20. 37 Burying Hill Rd, Greenwich
- Price: $19,900,000
- 7 bedrooms, 7 full bathrooms, 3 half bathrooms
- Square feet: 18,000
- Price per square foot: $1,105
- Lot size: 9.0 acres
- Days on market: 56 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 3 half bathrooms
- Square feet: 18,000
- Price per square foot: $1,105
- Lot size: 9.0 acres
- Days on market: 56 days
- View listing on realtor.com
#19. 457 Field Point Rd, Greenwich
- Price: $19,999,000
- 8 bedrooms, 10 full bathrooms, 3 half bathrooms
- Square feet: 20,020
- Price per square foot: $998
- Lot size: 0.8 acres
- Days on market: 144 days
- View listing on realtor.com
- 8 bedrooms, 10 full bathrooms, 3 half bathrooms
- Square feet: 20,020
- Price per square foot: $998
- Lot size: 0.8 acres
- Days on market: 144 days
- View listing on realtor.com
#18. 198 Shore Rd, Old Greenwich
- Price: $21,900,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,323
- Price per square foot: $2,990
- Lot size: 0.7 acres
- Days on market: 36 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 7,323
- Price per square foot: $2,990
- Lot size: 0.7 acres
- Days on market: 36 days
- View listing on realtor.com
#17. 8 Fox Run Ln, Greenwich
- Price: $22,000,000
- 8 bedrooms, 9 full bathrooms, 3 half bathrooms
- Square feet: 14,071
- Price per square foot: $1,563
- Lot size: 5.4 acres
- Days on market: 42 days
- View listing on realtor.com
- 8 bedrooms, 9 full bathrooms, 3 half bathrooms
- Square feet: 14,071
- Price per square foot: $1,563
- Lot size: 5.4 acres
- Days on market: 42 days
- View listing on realtor.com
#16. 0 Game Cock Road, Greenwich
- Price: $22,000,000
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,166
- Price per square foot: $3,567
- Lot size: 1.1 acres
- Days on market: 419 days (-$3,000,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 6,166
- Price per square foot: $3,567
- Lot size: 1.1 acres
- Days on market: 419 days (-$3,000,000 price reduction since listing)
- View listing on realtor.com
You may also like:
Top 5 uniquely popular potato chip brands in Connecticut
#15. 97 Pecksland Rd, Greenwich
- Price: $24,950,000
- 10 bedrooms, 14 full bathrooms, 5 half bathrooms
- Square feet: 17,878
- Price per square foot: $1,395
- Lot size: 19.1 acres
- Days on market: 177 days
- View listing on realtor.com
- 10 bedrooms, 14 full bathrooms, 5 half bathrooms
- Square feet: 17,878
- Price per square foot: $1,395
- Lot size: 19.1 acres
- Days on market: 177 days
- View listing on realtor.com
#14. 1131 Sasco Hill Rd, Fairfield
- Price: $25,000,000
- 6 bedrooms, 7 full bathrooms, 4 half bathrooms
- Square feet: 19,569
- Price per square foot: $1,277
- Lot size: 11.1 acres
- Days on market: 111 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 4 half bathrooms
- Square feet: 19,569
- Price per square foot: $1,277
- Lot size: 11.1 acres
- Days on market: 111 days
- View listing on realtor.com
#13. 24 Conyers Farm Dr, Greenwich
- Price: $25,000,000
- 6 bedrooms, 6 full bathrooms, 6 half bathrooms
- Square feet: 12,312
- Price per square foot: $2,030
- Lot size: 25.5 acres
- Days on market: 125 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 6 half bathrooms
- Square feet: 12,312
- Price per square foot: $2,030
- Lot size: 25.5 acres
- Days on market: 125 days
- View listing on realtor.com
#12. 122 Beachside Ave, Westport
- Price: $25,000,000
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 11,450
- Price per square foot: $2,183
- Lot size: 6.6 acres
- Days on market: 205 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 1 half bathroom
- Square feet: 11,450
- Price per square foot: $2,183
- Lot size: 6.6 acres
- Days on market: 205 days
- View listing on realtor.com
#11. 104 Dans Hwy, New Canaan
- Price: $25,500,000
- 9 bedrooms, 10 full bathrooms, 4 half bathrooms
- Square feet: 14,266
- Price per square foot: $1,787
- Lot size: 51.9 acres
- Days on market: 23 days
- View listing on realtor.com
- 9 bedrooms, 10 full bathrooms, 4 half bathrooms
- Square feet: 14,266
- Price per square foot: $1,787
- Lot size: 51.9 acres
- Days on market: 23 days
- View listing on realtor.com
You may also like:
How Connecticut is spending federal infrastructure dollars
#10. 45 Binney Ln, Old Greenwich
- Price: $27,950,000
- 8 bedrooms, 11 full bathrooms, 1 half bathroom
- Square feet: 13,428
- Price per square foot: $2,081
- Lot size: 1.1 acres
- Days on market: 96 days
- View listing on realtor.com
- 8 bedrooms, 11 full bathrooms, 1 half bathroom
- Square feet: 13,428
- Price per square foot: $2,081
- Lot size: 1.1 acres
- Days on market: 96 days
- View listing on realtor.com
#9. Hay Is, Darien
- Price: $29,500,000
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,684
- Price per square foot: $3,397
- Lot size: 18.1 acres
- Days on market: 140 days (-$5,500,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,684
- Price per square foot: $3,397
- Lot size: 18.1 acres
- Days on market: 140 days (-$5,500,000 price reduction since listing)
- View listing on realtor.com
#8. 157 Long Neck Point Rd, Darien
- Price: $29,500,000
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,684
- Price per square foot: $3,397
- Lot size: 18.1 acres
- Days on market: 140 days (-$5,500,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 8,684
- Price per square foot: $3,397
- Lot size: 18.1 acres
- Days on market: 140 days (-$5,500,000 price reduction since listing)
- View listing on realtor.com
#7. Rogers Is, Branford
- Price: $29,995,000
- 10 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 8,746
- Price per square foot: $3,429
- Lot size: 7.7 acres
- Days on market: 79 days
- View listing on realtor.com
- 10 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 8,746
- Price per square foot: $3,429
- Lot size: 7.7 acres
- Days on market: 79 days
- View listing on realtor.com
#6. 555 Lake Ave, Greenwich
- Price: $33,000,000
- 8 bedrooms, 9 full bathrooms, 5 half bathrooms
- Square feet: 18,954
- Price per square foot: $1,741
- Lot size: 8.2 acres
- Days on market: 124 days
- View listing on realtor.com
- 8 bedrooms, 9 full bathrooms, 5 half bathrooms
- Square feet: 18,954
- Price per square foot: $1,741
- Lot size: 8.2 acres
- Days on market: 124 days
- View listing on realtor.com
You may also like:
How cybercrime losses in Connecticut compare
#5. 7 John St, Greenwich
- Price: $34,500,000
- 10 bedrooms, 12 full bathrooms, 4 half bathrooms
- Square feet: 15,820
- Price per square foot: $2,180
- Lot size: 22.0 acres
- Days on market: 449 days
- View listing on realtor.com
- 10 bedrooms, 12 full bathrooms, 4 half bathrooms
- Square feet: 15,820
- Price per square foot: $2,180
- Lot size: 22.0 acres
- Days on market: 449 days
- View listing on realtor.com
#4. 10 Cliffdale Rd, Greenwich
- Price: $35,000,000
- 8 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 9,300
- Price per square foot: $3,763
- Lot size: 66.0 acres
- Days on market: 328 days
- View listing on realtor.com
- 8 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 9,300
- Price per square foot: $3,763
- Lot size: 66.0 acres
- Days on market: 328 days
- View listing on realtor.com
#3. 215 Uncas Point Rd, Guilford
- Price: $35,000,000
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,354
- Price per square foot: $6,537
- Lot size: 13.0 acres
- Days on market: 368 days
- View listing on realtor.com
- 6 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 5,354
- Price per square foot: $6,537
- Lot size: 13.0 acres
- Days on market: 368 days
- View listing on realtor.com
#2. 579 Indian Field Rd, Greenwich
- Price: $43,000,000
- 6 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 11,500
- Price per square foot: $3,739
- Lot size: 2.7 acres
- Days on market: 110 days
- View listing on realtor.com
- 6 bedrooms, 8 full bathrooms, 3 half bathrooms
- Square feet: 11,500
- Price per square foot: $3,739
- Lot size: 2.7 acres
- Days on market: 110 days
- View listing on realtor.com
#1. 545 Indian Field Rd, Greenwich
- Price: $44,600,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 12,492
- Price per square foot: $3,570
- Lot size: 1.6 acres
- Days on market: 323 days (-$4,900,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 12,492
- Price per square foot: $3,570
- Lot size: 1.6 acres
- Days on market: 323 days (-$4,900,000 price reduction since listing)
- View listing on realtor.com
You may also like:
How enrollment of students with disabilities compares in Connecticut
