The most expensive neighborhoods in Bridgeport
Homebuyers and sellers are navigating a slow and expensive housing market, with rising prices and stagnant demand keeping many on the sidelines. This comes amid rising economic uncertainty and growing wealth concentration. But luxury homes—multimillion-dollar estates, sleek penthouses, and one-of-a-kind custom builds—are still selling, even as most buyers pull back.
Most people can't afford high-end homes, although they're still fun to dream about. So, to highlight where luxury real estate is commanding the highest prices, Redfin analyzed the most expensive neighborhoods in the Bridgeport metro area—and showcased a few of the area's standout listings (when possible).
Note: Redfin's analysis focused on metro areas, meaning some neighborhoods fell within smaller nearby cities. Listings and data were gathered on October 15, 2025.
#1. Mid Country West (Greenwich, CT)
Median sale price: $7,350,000 | Median days on market: 70 days41 Baldwin Farms S, Greenwich, CT 06831
- List price: $7,900,000
- Beds: 6 | Baths: 9 | Square feet: 9,042
- See 41 Baldwin Farms S, Greenwich, CT 06831 on Redfin.com
52 Round Hill Rd, Greenwich, CT 06831
- List price: $4,500,000
- Beds: 4 | Baths: 3.5 | Square feet: 4,810
- See 52 Round Hill Rd, Greenwich, CT 06831 on Redfin.com
546 Lake Ave, Greenwich, CT 06830
- List price: $10,500,000
- Beds: 6 | Baths: 6.5 | Square feet: 7,456
- See 546 Lake Ave, Greenwich, CT 06830 on Redfin.com
97 Pecksland Rd, Greenwich, CT 06831
- List price: $24,950,000
- Beds: 10 | Baths: 16.5 | Square feet: 17,878
- See 97 Pecksland Rd, Greenwich, CT 06831 on Redfin.com
#2. Mid Country East (Greenwich, CT)
Median sale price: $4,155,000 | Median days on market: 16 days10 Carissa Ln, Greenwich, CT 06830
- List price: $2,650,000
- Beds: 4 | Baths: 4.5 | Square feet: 3,948
- See 10 Carissa Ln, Greenwich, CT 06830 on Redfin.com
11 Winterset Rd, Greenwich, CT 06830
- List price: $8,750,000
- Beds: 6 | Baths: 7.5 | Square feet: 10,400
- See 11 Winterset Rd, Greenwich, CT 06830 on Redfin.com
50 Dingletown Rd, Greenwich, CT 06830
- List price: $16,750,000
- Beds: 5 | Baths: 8 | Square feet: 13,031
- See 50 Dingletown Rd, Greenwich, CT 06830 on Redfin.com
78 Londonderry Dr, Greenwich, CT 06830
- List price: $3,100,000
- Beds: 4 | Baths: 4.5 | Square feet: 3,668
- See 78 Londonderry Dr, Greenwich, CT 06830 on Redfin.com
#3. South Riverside (Greenwich, CT)
Median sale price: $3,850,000 | Median days on market: 48 days203 Riverside Ave, Riverside, CT 06878
- List price: $5,000,000
- Beds: 6 | Baths: 4 | Square feet: 5,021
- See 203 Riverside Ave, Riverside, CT 06878 on Redfin.com
258 Riverside Ave, Riverside, CT 06878
- List price: $3,895,000
- Beds: 5 | Baths: 3.5 | Square feet: 3,647
- See 258 Riverside Ave, Riverside, CT 06878 on Redfin.com
37 Miltiades Ave, Riverside, CT 06878
- List price: $1,999,000
- Beds: 4 | Baths: 2.5 | Square feet: 2,540
- See 37 Miltiades Ave, Riverside, CT 06878 on Redfin.com
7 Jones Park Dr, Riverside, CT 06878
- List price: $5,795,000
- Beds: 6 | Baths: 6 | Square feet: 6,673
- See 7 Jones Park Dr, Riverside, CT 06878 on Redfin.com
#4. Millbrook (Greenwich, CT)
Median sale price: $3,702,000 | Median days on market: 83 days105 Woodside Dr, Greenwich, CT 06830
- List price: $7,950,000
- Beds: 6 | Baths: 7.5 | Square feet: 8,970
- See 105 Woodside Dr, Greenwich, CT 06830 on Redfin.com
88 Indian Field Rd, Greenwich, CT 06830
- List price: $1,399,000
- Beds: 3 | Baths: 3 | Square feet: 2,175
- See 88 Indian Field Rd, Greenwich, CT 06830 on Redfin.com
#5. Deer Park (Greenwich, CT)
Median sale price: $3,528,980 | Median days on market: 24 days9 Carleton St, Greenwich, CT 06830
- List price: $2,000,000
- Beds: 3 | Baths: 3 | Square feet: 1,683
- See 9 Carleton St, Greenwich, CT 06830 on Redfin.com
