5 bedroom homes for sale in Dutchess County, NY

dining space with stairs, plenty of natural light, light wood-style flooring, and crown molding

living area featuring a stone fireplace, wood finished floors, crown molding, and a decorative wall

living area featuring beam ceiling, baseboard heating, and wood finished floors

12 hours on Rocket

$10,000 Closing Credit¹

$1,750,000

5 beds • 4.5 baths • 3,325 sqft

26 Curry Ln, Hyde Park NY 12538

#834893, Listing Office: Atelier WM LLC

ranch-style home with a front lawn, aphalt driveway, a chimney, a garage, and a carport

single story home with aphalt driveway, a carport, a chimney, and a front lawn

1 day on Rocket

$6,888 Closing Credit¹

$580,000

5 beds • 3 baths • 2,950 sqft

7 Hujay Ter, Wappingers Falls NY 12590

#834678, Listing Office: eXp Realty

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colonial house featuring a fenced front yard and a chimney

view of front facade featuring a fenced front yard and a chimney

doorway featuring a notable chandelier, stairs, and ornamental molding

5 days on Rocket

$10,000 Closing Credit¹

$1,650,000

5 beds • 2.5 baths • 3,802 sqft

460 Silvernails Rd, Gallatin NY 12567

#156109, Annabel Taylor, Listing Office: Four Seasons Sothebys International Realty - Hudson

colonial-style house featuring a front yard

colonial house featuring a chimney and a front yard

5 days on Rocket

$6,472 Closing Credit¹

$545,000

5 beds • 3 baths • 2,830 sqft

222 Oriole Mills Rd, Rhinebeck NY 12572

#832720, Listing Office: HomeSmart Homes & Estates

view of front of property with a shingled roof and a chimney

view of front of home with a chimney and roof with shingles

7 days on Rocket

$5,344 Closing Credit¹

$450,000

5 beds • 2 baths

122 Garden St, Poughkeepsie NY 12601

#832016, Listing Office: Clarke Realty & Associates LLC

view of front of house featuring a garage, a shingled roof, a gambrel roof, a chimney, and a front yard

$10,000 Closing Credit¹

$2,395,000

5 beds • 4.5 baths • 3,530 sqft

43 Meeting House Rd, Pawling NY 12564

#H6335603, Listing Office: Compass Greater NY, LLC

view of front facade with a chimney and a wooden deck

$8,301 Closing Credit¹

$699,000

5 beds • 3 baths • 3,045 sqft

239 Rokeby Rd, Red Hook NY 12571

#830122, Listing Office: BHHS Hudson Valley Properties

Room to negotiate?

Median Sold Price

$452K

Avg. Sale Time

70 Days

Based on our February 2025 Market Report.

$5,641 Closing Credit¹

$475,000

5 beds • 3 baths • 3,360 sqft

85 Round Hill Rd, Poughkeepsie NY 12603

#829716, Listing Office: K. Fortuna Realty, Inc.

colonial home featuring a fenced front yard and a chimney

view of front of property with a fenced front yard and a chimney

doorway to outside featuring a notable chandelier, stairway, and crown molding

$10,000 Closing Credit¹

$1,650,000

5 beds • 2.5 baths • 3,802 sqft

460 Silvernails Rd, Pine Plains NY 12567

#245620, Annabel Taylor, Listing Office: Four Seasons Sothebys International Realty

colonial-style house with a chimney and a fenced front yard

view of front of house featuring a fenced front yard and a chimney

entryway with stairs, ornamental molding, and a notable chandelier

$10,000 Closing Credit¹

$1,650,000

5 beds • 2.5 baths • 3,802 sqft

460 Silvernails Rd, Pine Plains NY 12567

#827960, Listing Office: Four Seasons Sothebys Intl

view of front of home with a porch and a balcony

property entrance featuring covered porch and fence

$4,691 Closing Credit¹

$395,000

5 beds • 2 baths

10 Lexington Ave, Poughkeepsie NY 12601

#823232, Listing Office: Douglas Elliman Real Estate

view of front of property featuring brick siding

snow covered property entrance featuring a balcony and brick siding

interior space featuring crown molding, a decorative wall, a towering ceiling, a stone fireplace, and wood finished floors

$10,000 Closing Credit¹

$1,329,000

5 beds • 5.5 baths • 6,902 sqft

11 Huber Rd, Wappingers Falls NY 12590

#827313, Listing Office: K. Fortuna Realty, Inc.

kitchen with light countertops, a baseboard heating unit, white cabinets, white appliances, and under cabinet range hood

kitchen with white appliances, lofted ceiling, a baseboard radiator, light countertops, and a sink

$8,906 Closing Credit¹

$750,000

5 beds • 3 baths

47 Main St, Wappingers Falls NY 12590

#825191, Listing Office: Staley Real Estate, LLC

$10,000 Closing Credit¹

$2,250,000

5 beds • 3.5 baths • 4,696 sqft

98 Verbank Rd, Millbrook NY 12545

#824808, Listing Office: Houlihan Lawrence Inc.

view of front of home featuring covered porch

unfurnished room featuring light wood-type flooring and a baseboard heating unit

bathroom with hardwood / wood-style flooring, toilet, and wood walls

$5,344 Closing Credit¹

$450,000

5 beds • 2 baths • 1,758 sqft

49 Woodlawn Ave, Poughkeepsie NY 12601

#820043, Listing Office: RMB & Associates

view of front of house featuring a porch and a front yard

unfurnished living room with wooden ceiling, radiator heating unit, a fireplace, and wood walls

foyer featuring ceiling fan, hardwood / wood-style floors, wood ceiling, and wooden walls

$8,313 Closing Credit¹

$700,000

5 beds • 3.5 baths • 5,880 sqft

135 Sisters Hill Rd, Stanfordville NY 12581

#814994, Listing Office: Giner Real Estate Inc.

view of front of house featuring a garage

back of property featuring a wooden deck, a sunroom, and a yard

$6,650 Closing Credit¹

$560,000

5 beds • 2.5 baths • 2,593 sqft

24 Country Club Rd, Hopewell Junction NY 12533

#811484, Listing Office: Guardian Realty Center, LLC

$4,453 Closing Credit¹

$375,000

5 beds • 2 baths

328 Church St, Poughkeepsie NY 12601

#812146, Listing Office: Douglas Elliman Real Estate

view of front of property featuring a front lawn

$10,000 Closing Credit¹

$1,150,000

5 beds • 3.5 baths • 3,500 sqft

51 Estate Dr, Pawling NY 12564

#814566, Listing Office: Coldwell Banker Realty

living room with wooden walls, a water view, and a high ceiling

$11,250,000

5 beds • 7.5 baths • 17,200 sqft

46 Ledgerock Ln, Hyde Park NY 12538

#20250078, Jason Karadus, Richard Vizzini, Listing Office: Corcoran Country Living

living room with a high ceiling, a water view, and wood walls

Video tour

$11,250,000

5 beds • 7.5 baths • 14,800 sqft

46 Ledgerock Ln, Hyde Park NY 12538

#810504, Listing Office: Corcoran Country Living

view of building exterior featuring cooling unit

$10,000 Closing Credit¹

$995,000

5 beds • 5 baths

337 Main St, Poughkeepsie NY 12601

#803995, Listing Office: KW MidHudson

$3,500,000

5 beds • 5.5 baths • 8,925 sqft

0 Rowe Rd, Milan NY 12571

#20242387, Joseph Briggs, Listing Office: William Pitt Sothebys Intl

view of property exterior with a garage and an outdoor structure

view of side of property featuring a garage and an outbuilding

$10,000 Closing Credit¹

$975,000

5 beds • 3 baths • 4,100 sqft

7 Ferris Ln, Poughkeepsie NY 12601

#800363, Listing Office: BHHS Hudson Valley Properties

view of home's exterior featuring an outdoor structure and a garage

stairway featuring hardwood / wood-style floors and crown molding

$10,000 Closing Credit¹

$849,000

5 beds • 4.5 baths • 3,820 sqft

67 Myers Corners Rd, Wappingers Falls NY 12590

#H6330284, Listing Office: OXM Realty Group LLC

$10,000 Closing Credit¹

$1,200,000

5 beds • 3.5 baths • 3,664 sqft

3715 Rte 44, Millbrook NY 12545

#H6329108, Listing Office: Compass Greater NY, LLC

birds eye view of property featuring a rural view

drone / aerial view featuring a rural view

$6,785,000

5 beds • 5.5 baths • 5,162 sqft

47-49 Crescent Rd, Millbrook NY 12545

#H6328863, Listing Office: Elyse Harney Real Estate

32 Gristmill Ln, Pawling NY, 12564, 5 bedrooms, 4 baths house for sale

Listing photo 2 for 32 Gristmill Ln, Pawling NY 12564

Listing photo 3 for 32 Gristmill Ln, Pawling NY 12564

$7,897 Closing Credit¹

$665,000

5 beds • 4 baths • 3,732 sqft

32 Gristmill Ln, Pawling NY 12564

#H6315301, Listing Office: Houlihan Lawrence Inc.

sunroom / solarium with vaulted ceiling with beams, indoor wet bar, and a wealth of natural light

living room featuring a high end fireplace, light wood-type flooring, high vaulted ceiling, and ceiling fan

view of patio featuring outdoor lounge area and a water view

$11,500,000

5 beds • 5.5 baths • 5,170 sqft

292 Wood Duck Rd, Amenia NY 12501

#H6314006, Listing Office: Douglas Elliman Real Estate

$5,878 Closing Credit¹

$495,000

5 beds • 3.5 baths

19 Bennett Rd, Poughkeepsie NY 12601

#H6312021, Listing Office: Century 21 Alliance Rlty Group

view of yard featuring an outdoor structure

$7,719 Closing Credit¹

$650,000

5 beds • 2 baths • 2,304 sqft

22 Hunns Lake Rd, Stanfordville NY 12581

#H6280956, Listing Office: Hudson Valley Home Connection

view of front of house with a front lawn

view of front of home featuring a balcony and a front lawn

$10,000 Closing Credit¹

$1,500,000

5 beds • 7.5 baths • 5,470 sqft

604 N Quaker Hill Rd, Pawling NY 12564

#H6143742, Listing Office: Ellis Sothebys Intl Realty

view of front of property with a front yard

birds eye view of property with a water view

$3,500,000

5 beds • 5.5 baths • 8,925 sqft

0 Rowe Rd, Milan NY 12571

#202414706, Joseph Briggs, Listing Office: William Pitt Sotheby's

$3,500,000

5 beds • 6 baths • 8,925 sqft

0 Rowe Rd, Red Hook NY 12571

#H6299139, Listing Office: William Pitt Sothebys Int Rlty

$5,225 Closing Credit¹

$440,000

5 beds • 1.5 baths • 2,996 sqft

926 Smithfield Rd, Millerton NY 12546

#M417294, Listing Office: HAVENS REAL ESTATE AM

log-style house featuring a yard and a balcony

$11,950,000

5 beds • 5.5 baths • 11,500 sqft

521 Stanford Rd, Millbrook NY 12545

#M410339, Listing Office: CORCORAN COUNTRY LIVING ML

Dutchess County, NY Real Estate Market Overview

Find your perfect 5 bedroom home in Dutchess County, NY. Browse 5 in Dutchess County, NY and connect with a Rocket Homes agent to get your dream home. The number of homes for sale in Dutchess County, NY decreased by 15.6% between January 2025 and February 2025. The median list price of listings available in February 2025 was $452,086, while the average time on the real estate market was 70 days. While more than 54 listings in Dutchess County, NY in February 2025 were sold above asking price, there were more than 22 listings sold at asking price, and more than 66 were sold below.