Most expensive homes for sale in Poughkeepsie
Written by:
July 28, 2025
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Most expensive homes for sale in Poughkeepsie
Stacker compiled a list of the most expensive homes in Poughkeepsie listed for sale on realtor.com. Homes are ranked by price with ties broken by price per square foot.
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Cities with the most expensive homes in the Poughkeepsie metro area
#30. 65 Old Field Rd, Poughkeepsie
- Price: $739,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,034
- Price per square foot: $363
- Lot size: 0.6 acres
- Days on market: 53 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,034
- Price per square foot: $363
- Lot size: 0.6 acres
- Days on market: 53 days
- View listing on realtor.com
#29. Old Field Rd Lot 19B, Poughkeepsie
- Price: $749,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,794
- Price per square foot: $268
- Days on market: 317 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,794
- Price per square foot: $268
- Days on market: 317 days
- View listing on realtor.com
#28. 42 Kensington Ln, Poughkeepsie
- Price: $749,900
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $261
- Lot size: 0.4 acres
- Days on market: 25 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,872
- Price per square foot: $261
- Lot size: 0.4 acres
- Days on market: 25 days
- View listing on realtor.com
#27. 402 Waterview Dr, Poughkeepsie
- Price: $751,000
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,588
- Price per square foot: $290
- Days on market: 44 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,588
- Price per square foot: $290
- Days on market: 44 days
- View listing on realtor.com
#26. 21 Dartmouth Dr, Poughkeepsie
- Price: $775,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,149
- Price per square foot: $246
- Lot size: 0.4 acres
- Days on market: 124 days (-$24,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,149
- Price per square foot: $246
- Lot size: 0.4 acres
- Days on market: 124 days (-$24,000 price reduction since listing)
- View listing on realtor.com
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#25. 9 Ridgeline Dr, Poughkeepsie
- Price: $789,000
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,500
- Price per square foot: $225
- Lot size: 0.4 acres
- Days on market: 99 days (-$21,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms
- Square feet: 3,500
- Price per square foot: $225
- Lot size: 0.4 acres
- Days on market: 99 days (-$21,000 price reduction since listing)
- View listing on realtor.com
#24. Old Field Rd Lot 19A, Poughkeepsie
- Price: $794,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,011
- Price per square foot: $263
- Days on market: 317 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,011
- Price per square foot: $263
- Days on market: 317 days
- View listing on realtor.com
#23. 130 Hudson Pointe Dr, Poughkeepsie
- Price: $799,000
- 3 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 3,218
- Price per square foot: $248
- Lot size: 0.0 acres
- Days on market: 324 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 2 half bathrooms
- Square feet: 3,218
- Price per square foot: $248
- Lot size: 0.0 acres
- Days on market: 324 days
- View listing on realtor.com
#22. 14 Flower Hill Rd, Poughkeepsie
- Price: $805,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,851
- Price per square foot: $209
- Lot size: 0.8 acres
- Days on market: 30 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,851
- Price per square foot: $209
- Lot size: 0.8 acres
- Days on market: 30 days
- View listing on realtor.com
#21. 45 Manor Dr W, Poughkeepsie
- Price: $849,000
- 5 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 3,456
- Price per square foot: $245
- Lot size: 1.3 acres
- Days on market: 110 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 2 half bathrooms
- Square feet: 3,456
- Price per square foot: $245
- Lot size: 1.3 acres
- Days on market: 110 days
- View listing on realtor.com
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#20. 27 Sommerset Rd, Poughkeepsie
- Price: $850,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 5,654
- Price per square foot: $150
- Lot size: 6.7 acres
- Days on market: 31 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 5,654
- Price per square foot: $150
- Lot size: 6.7 acres
- Days on market: 31 days
- View listing on realtor.com
#19. 15 Dartmouth Dr, Poughkeepsie
- Price: $850,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,233
- Price per square foot: $262
- Lot size: 0.5 acres
- Days on market: 124 days (-$40,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,233
- Price per square foot: $262
- Lot size: 0.5 acres
- Days on market: 124 days (-$40,000 price reduction since listing)
- View listing on realtor.com
#18. 51 Dartmouth Dr, Poughkeepsie
- Price: $875,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,233
- Price per square foot: $270
- Lot size: 0.5 acres
- Days on market: 124 days (-$60,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 3,233
- Price per square foot: $270
- Lot size: 0.5 acres
- Days on market: 124 days (-$60,000 price reduction since listing)
- View listing on realtor.com
#17. 114 Hudson Pointe Dr, Poughkeepsie
- Price: $879,000
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,218
- Price per square foot: $273
- Lot size: 0.0 acres
- Days on market: 4 days
- View listing on realtor.com
- 3 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,218
- Price per square foot: $273
- Lot size: 0.0 acres
- Days on market: 4 days
- View listing on realtor.com
#16. 47 Dartmouth Dr, Poughkeepsie
- Price: $895,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,423
- Price per square foot: $261
- Lot size: 0.5 acres
- Days on market: 107 days (-$40,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,423
- Price per square foot: $261
- Lot size: 0.5 acres
- Days on market: 107 days (-$40,000 price reduction since listing)
- View listing on realtor.com
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#15. 10 Todd Hill Rd, Poughkeepsie
- Price: $897,200
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,116
- Price per square foot: $217
- Days on market: 100 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,116
- Price per square foot: $217
- Days on market: 100 days
- View listing on realtor.com
#14. 109 Sleight Plass Rd, Poughkeepsie
- Price: $899,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,172
- Price per square foot: $215
- Lot size: 6.3 acres
- Days on market: 52 days (-$50,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,172
- Price per square foot: $215
- Lot size: 6.3 acres
- Days on market: 52 days (-$50,000 price reduction since listing)
- View listing on realtor.com
#13. 38 Dartmouth Dr, Poughkeepsie
- Price: $899,000
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,684
- Price per square foot: $244
- Days on market: 18 days (-$81,000 price reduction since listing)
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms
- Square feet: 3,684
- Price per square foot: $244
- Days on market: 18 days (-$81,000 price reduction since listing)
- View listing on realtor.com
#12. 25 Dartmouth Dr, Poughkeepsie
- Price: $899,000
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,423
- Price per square foot: $262
- Lot size: 0.5 acres
- Days on market: 124 days
- View listing on realtor.com
- 5 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,423
- Price per square foot: $262
- Lot size: 0.5 acres
- Days on market: 124 days
- View listing on realtor.com
#11. 150 Kingwood Park, Poughkeepsie
- Price: $915,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,976
- Price per square foot: $230
- Lot size: 1.3 acres
- Days on market: 53 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,976
- Price per square foot: $230
- Lot size: 1.3 acres
- Days on market: 53 days
- View listing on realtor.com
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#10. 79 Victor Dr, Poughkeepsie
- Price: $945,000
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,200
- Price per square foot: $225
- Lot size: 1.3 acres
- Days on market: 103 days (-$40,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 1 half bathroom
- Square feet: 4,200
- Price per square foot: $225
- Lot size: 1.3 acres
- Days on market: 103 days (-$40,000 price reduction since listing)
- View listing on realtor.com
#9. 136 Hudson Pointe Dr, Poughkeepsie
- Price: $949,000
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,450
- Price per square foot: $275
- Lot size: 0.0 acres
- Days on market: 123 days
- View listing on realtor.com
- 2 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 3,450
- Price per square foot: $275
- Lot size: 0.0 acres
- Days on market: 123 days
- View listing on realtor.com
#8. Edwin Rd Lot 54, Poughkeepsie
- Price: $1,060,000
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,064
- Price per square foot: $260
- Lot size: 1.7 acres
- Days on market: 317 days
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 4,064
- Price per square foot: $260
- Lot size: 1.7 acres
- Days on market: 317 days
- View listing on realtor.com
#7. 262 Cream St, Poughkeepsie
- Price: $1,450,000
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,295
- Price per square foot: $631
- Lot size: 2.7 acres
- Days on market: 126 days
- View listing on realtor.com
- 4 bedrooms, 2 full bathrooms, 1 half bathroom
- Square feet: 2,295
- Price per square foot: $631
- Lot size: 2.7 acres
- Days on market: 126 days
- View listing on realtor.com
#6. 36 Spruce Ln, Poughkeepsie
- Price: $1,499,999
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,674
- Price per square foot: $408
- Lot size: 9.1 acres
- Days on market: 83 days (-$100,000 price reduction since listing)
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms, 1 half bathroom
- Square feet: 3,674
- Price per square foot: $408
- Lot size: 9.1 acres
- Days on market: 83 days (-$100,000 price reduction since listing)
- View listing on realtor.com
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#5. 125 Bedell Rd, Poughkeepsie
- Price: $1,699,000
- 7 bedrooms, 7 full bathrooms
- Square feet: 8,033
- Price per square foot: $211
- Lot size: 11.0 acres
- Days on market: 44 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms
- Square feet: 8,033
- Price per square foot: $211
- Lot size: 11.0 acres
- Days on market: 44 days
- View listing on realtor.com
#4. 125-127 Bedell Rd, Poughkeepsie
- Price: $1,699,000
- 7 bedrooms, 7 full bathrooms
- Square feet: 8,033
- Price per square foot: $211
- Lot size: 11.0 acres
- Days on market: 65 days
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms
- Square feet: 8,033
- Price per square foot: $211
- Lot size: 11.0 acres
- Days on market: 65 days
- View listing on realtor.com
#3. 5 Conifer Ct, Poughkeepsie
- Price: $1,950,000
- 4 bedrooms, 3 full bathrooms
- Square feet: 6,822
- Price per square foot: $285
- Lot size: 3.2 acres
- Days on market: 1 day
- View listing on realtor.com
- 4 bedrooms, 3 full bathrooms
- Square feet: 6,822
- Price per square foot: $285
- Lot size: 3.2 acres
- Days on market: 1 day
- View listing on realtor.com
#2. 143 Bedell Rd, Poughkeepsie
- Price: $2,150,000
- 7 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 7,720
- Price per square foot: $278
- Lot size: 66.5 acres
- Days on market: 42 days (-$125,000 price reduction since listing)
- View listing on realtor.com
- 7 bedrooms, 7 full bathrooms, 1 half bathroom
- Square feet: 7,720
- Price per square foot: $278
- Lot size: 66.5 acres
- Days on market: 42 days (-$125,000 price reduction since listing)
- View listing on realtor.com
#1. 55 Daley Rd, Lagrangeville
- Price: $3,000,000
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 12,000
- Price per square foot: $250
- Lot size: 71.7 acres
- Days on market: 334 days
- View listing on realtor.com
- 4 bedrooms, 4 full bathrooms, 3 half bathrooms
- Square feet: 12,000
- Price per square foot: $250
- Lot size: 71.7 acres
- Days on market: 334 days
- View listing on realtor.com
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