Most expensive homes for sale in Connecticut
Written by:
October 23, 2025
scarp577 // 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:
The Brine Boom: Pickles are popping off in grocery aisles in Connecticut
#30. 14 Owenoke Park, Westport
- Price: $11,795,000
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,050
- Price per square foot: $1,949
- Lot size: 0.8 acres
- Days on market: 29 days
- View listing on realtor.com
- 5 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 6,050
- Price per square foot: $1,949
- Lot size: 0.8 acres
- Days on market: 29 days
- View listing on realtor.com
#29. 260 Willow St, Fairfield
- Price: $12,000,000
- 7 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 8,119
- Price per square foot: $1,478
- Lot size: 1.3 acres
- Days on market: 156 days
- View listing on realtor.com
- 7 bedrooms, 6 full bathrooms, 1 half bathroom
- Square feet: 8,119
- Price per square foot: $1,478
- Lot size: 1.3 acres
- Days on market: 156 days
- View listing on realtor.com
#28. 39 Compo Pkwy, Westport
- Price: $12,950,000
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 11,150
- Price per square foot: $1,161
- Lot size: 2.1 acres
- Days on market: 68 days
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 11,150
- Price per square foot: $1,161
- Lot size: 2.1 acres
- Days on market: 68 days
- View listing on realtor.com
#27. 52 Carriglea Dr, Greenwich
- Price: $13,750,000
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,418
- Price per square foot: $1,459
- Lot size: 1.1 acres
- Days on market: 82 days
- View listing on realtor.com
- 6 bedrooms, 5 full bathrooms, 2 half bathrooms
- Square feet: 9,418
- Price per square foot: $1,459
- Lot size: 1.1 acres
- Days on market: 82 days
- View listing on realtor.com
#26. 52 Carriglea Dr, Call Listing Agent
- 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: 203 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: 203 days (-$500,000 price reduction since listing)
- View listing on realtor.com
#25. 411 Stanwich Rd, Greenwich
- Price: $13,750,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,189
- Price per square foot: $1,496
- Lot size: 6.0 acres
- Days on market: 30 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 9,189
- Price per square foot: $1,496
- Lot size: 6.0 acres
- Days on market: 30 days
- View listing on realtor.com
#24. 537 North St, Greenwich
- Price: $13,950,000
- 6 bedrooms, 7 full bathrooms, 4 half bathrooms
- Square feet: 15,171
- Price per square foot: $919
- Lot size: 3.0 acres
- Days on market: 282 days (-$950,000 price reduction since listing)
- View listing on realtor.com
- 6 bedrooms, 7 full bathrooms, 4 half bathrooms
- Square feet: 15,171
- Price per square foot: $919
- Lot size: 3.0 acres
- Days on market: 282 days (-$950,000 price reduction since listing)
- View listing on realtor.com
#23. 7 Parsonage Rd, Greenwich
- Price: $13,995,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 10,286
- Price per square foot: $1,360
- Lot size: 1.1 acres
- Days on market: 93 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 10,286
- Price per square foot: $1,360
- Lot size: 1.1 acres
- Days on market: 93 days
- View listing on realtor.com
#22. 16 Windrose Way, Greenwich
- Price: $15,000,000
- 8 bedrooms, 10 full bathrooms, 1 half bathroom
- Square feet: 10,171
- Price per square foot: $1,474
- Lot size: 2.0 acres
- Days on market: 81 days
- View listing on realtor.com
- 8 bedrooms, 10 full bathrooms, 1 half bathroom
- Square feet: 10,171
- Price per square foot: $1,474
- Lot size: 2.0 acres
- Days on market: 81 days
- View listing on realtor.com
#21. 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: 168 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: 168 days
- View listing on realtor.com
You may also like:
Fastest-growing jobs in Connecticut
#20. 550 Round Hill Rd, Greenwich
- Price: $15,900,000
- 8 bedrooms, 9 full bathrooms, 4 half bathrooms
- Square feet: 13,268
- Price per square foot: $1,198
- Lot size: 4.1 acres
- Days on market: 71 days
- View listing on realtor.com
- 8 bedrooms, 9 full bathrooms, 4 half bathrooms
- Square feet: 13,268
- Price per square foot: $1,198
- Lot size: 4.1 acres
- Days on market: 71 days
- View listing on realtor.com
#19. 71 N Porchuck Rd, Greenwich
- Price: $16,000,000
- 1 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 16,417
- Price per square foot: $974
- Lot size: 6.7 acres
- Days on market: 63 days
- View listing on realtor.com
- 1 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 16,417
- Price per square foot: $974
- Lot size: 6.7 acres
- Days on market: 63 days
- View listing on realtor.com
#18. 90 Oneida Dr, Greenwich
- Price: $16,750,000
- 8 bedrooms, 9 full bathrooms, 2 half bathrooms
- Square feet: 16,300
- Price per square foot: $1,027
- Lot size: 1.3 acres
- Days on market: 95 days
- View listing on realtor.com
- 8 bedrooms, 9 full bathrooms, 2 half bathrooms
- Square feet: 16,300
- Price per square foot: $1,027
- Lot size: 1.3 acres
- Days on market: 95 days
- View listing on realtor.com
#17. 50 Dingletown Rd, Greenwich
- Price: $16,750,000
- 5 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 13,031
- Price per square foot: $1,285
- Lot size: 7.4 acres
- Days on market: 106 days
- View listing on realtor.com
- 5 bedrooms, 7 full bathrooms, 2 half bathrooms
- Square feet: 13,031
- Price per square foot: $1,285
- Lot size: 7.4 acres
- Days on market: 106 days
- View listing on realtor.com
#16. 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
- Days on market: 461 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
- Days on market: 461 days (-$2,000,000 price reduction since listing)
- View listing on realtor.com
You may also like:
Counties with the most pre-war homes in Connecticut
#15. 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: 140 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: 140 days
- View listing on realtor.com
#14. 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: 214 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: 214 days
- View listing on realtor.com
#13. 92 Beachside Ave, Westport
- Price: $19,800,000
- 8 bedrooms, 8 full bathrooms, 1 half bathroom
- Square feet: 9,995
- Price per square foot: $1,980
- Lot size: 3.5 acres
- Days on market: 61 days
- View listing on realtor.com
- 8 bedrooms, 8 full bathrooms, 1 half bathroom
- Square feet: 9,995
- Price per square foot: $1,980
- Lot size: 3.5 acres
- Days on market: 61 days
- View listing on realtor.com
#12. 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: 175 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: 175 days
- View listing on realtor.com
#11. 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: 552 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: 552 days (-$3,000,000 price reduction since listing)
- View listing on realtor.com
You may also like:
Most popular diamond shapes in the Northeast
#10. 5 and 7 John St, Greenwich
- Price: $24,000,000
- 10 bedrooms, 12 full bathrooms, 4 half bathrooms
- Square feet: 15,820
- Price per square foot: $1,517
- Lot size: 14.9 acres
- Days on market: 1 day
- View listing on realtor.com
- 10 bedrooms, 12 full bathrooms, 4 half bathrooms
- Square feet: 15,820
- Price per square foot: $1,517
- Lot size: 14.9 acres
- Days on market: 1 day
- View listing on realtor.com
#9. 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: 65 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: 65 days
- View listing on realtor.com
#8. 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: 244 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: 244 days
- View listing on realtor.com
#7. 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: 156 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: 156 days
- View listing on realtor.com
#6. 276 Otter Rock Dr, Greenwich
- Price: $27,500,000
- 8 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 11,536
- Price per square foot: $2,383
- Lot size: 1.7 acres
- Days on market: 24 days
- View listing on realtor.com
- 8 bedrooms, 5 full bathrooms, 3 half bathrooms
- Square feet: 11,536
- Price per square foot: $2,383
- Lot size: 1.7 acres
- Days on market: 24 days
- View listing on realtor.com
You may also like:
Coldest Decembers in Connecticut since 1895
#5. 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: 212 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: 212 days
- View listing on realtor.com
#4. 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: 582 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: 582 days
- View listing on realtor.com
#3. 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: 461 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: 461 days
- View listing on realtor.com
#2. 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: 501 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: 501 days
- View listing on realtor.com
#1. 545 Indian Field Rd, Greenwich
- Price: $45,000,000
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 12,492
- Price per square foot: $3,602
- Lot size: 1.6 acres
- Days on market: 26 days
- View listing on realtor.com
- 6 bedrooms, 6 full bathrooms, 2 half bathrooms
- Square feet: 12,492
- Price per square foot: $3,602
- Lot size: 1.6 acres
- Days on market: 26 days
- View listing on realtor.com
You may also like:
The scoop on Connecticut's ice cream preferences, according to Instacart
