5-Bedroom Homes for Sale in Dutchess County NY

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  /11

  $900,000

  • 5 Beds
  • 2.5 Baths
  • 2,413 Sq Ft

  2365 Route 83, Pine Plains, NY 12567

  Rare opportunity to own 160 breathtaking acres in the heart of Pine Plains, featuring rolling fields, wooded terrain, and scenic wetlands. Anchoring the property is an antique farmhouse awaiting restoration, set within a 7 plus acre residential area offering privacy and pastoral charm. Most of the property is protected under a conservation easement, preserving the natural landscape while allowing

  Richard Brenner Rich Brenner Realty, LLC

  2365 Route 83, Pine Plains, NY 12567
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• 

  

  

  /34

  $389,000

  • 5 Beds
  • 2 Baths
  • 1,800 Sq Ft

  95 Worrall Ave, Poughkeepsie, NY 12603

  Lovingly maintained by the same family for more than sixty years, find this 5 bedroom, 2 bathroom colonial situated on the City of Poughkeepsie's desirable south side. Floor plan offers tremendous potential and flexibility with large kitchen, formal dining room, living room w/fireplace, two first floor bedrooms and full bathroom plus mudroom. Second floor layout includes three bedrooms and full

  Dan Axtmann BHHS Hudson Valley Properties

  95 Worrall Ave, Poughkeepsie, NY 12603
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  /35

  $399,900

  • 5 Beds
  • 2 Baths
  • 1,628 Sq Ft

  33 Center Ave, Poughkeepsie, NY 12601

  Welcome to this spacious and timeless brick Colonial with 5 bedrooms and 2 full bathrooms, nestled in the desirable Hyde Park School District. This home offers the perfect blend of character, space, and comfort. Step into the inviting enclosed porch, a sun-filled entryway surrounded by windows—ideal for morning coffee or welcoming guests. Inside, you'll be greeted by beautiful hardwood floors

  Ronald Green KW MidHudson

  33 Center Ave, Poughkeepsie, NY 12601
• 

  

  

  /13

  $849,000

  • 7 Beds
  • 5 Baths
  • 3,848 Sq Ft

  22 Forbus St, Poughkeepsie, NY 12601

  Fully updated and ready to go, this 4-unit multifamily property at 22 Forbus Street is a great opportunity for investors looking for strong rental potential in a growing market. Each unit has been thoughtfully renovated, offering modern finishes, from a ground-up rebuild in 2023.Tenants will appreciate access to laundry in the basement and the convenience of both on-street and off-street

  Stefania Riccitelli KW MidHudson

  22 Forbus St, Poughkeepsie, NY 12601
• 

  

  

  /51

  $19,995,000

  • 7 Beds
  • 9 Baths
  • 11,970 Sq Ft

  309 Woodstock Rd, Millbrook, NY 12545

  Presenting Canoe Hill, a remarkable 63-acre estate and vineyard in the heart of Millbrook, New York. This extraordinary property stands as a testament to architectural evolution, where a storied mid-1700s colonial core has been thoughtfully expanded to create a remarkable 12,650 SF main residence that seamlessly marries Colonial, Georgian and Greek Revival influences. Two significant expansions,

  Jason Karadus Corcoran Country Living

  309 Woodstock Rd, Millbrook, NY 12545
• 

  

  /23

  $399,000

  • 6 Beds
  • 2 Baths
  • 2,806 Sq Ft

  185 Mill St, Poughkeepsie, NY 12601

  Calling all investors to this 2 family house in prime area! Both units are rented and in an excellent condition. Being sold as-is. Inquire today- before it's gone!

  Avi Samet Avion

  185 Mill St, Poughkeepsie, NY 12601
• 

  

  /26

  $725,000

  • 5 Beds
  • 3 Baths
  • 2,808 Sq Ft

  47 Main St, Wappingers Falls, NY 12590

  This beautifully renovated two-unit apartment building is situated in the charming hamlet of New Hamburg, offering a prime investment opportunity in a highly desirable location. Just a short walk from the Metro-North train station, tenants enjoy an effortless commute while benefiting from the area’s peaceful, small-town atmosphere.Apartment 1: Is a charming 2-bedroom, 2-bathroom apartment

  Daniel Staley Staley Real Estate, LLC

  47 Main St, Wappingers Falls, NY 12590
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  /47

  $890,000

  • 5 Beds
  • 3.5 Baths
  • 4,375 Sq Ft

  14 Chestnut St, Hopewell Junction, NY 12533

  Nestled in peaceful and sought-after Four Corners this stately brick-face Colonial blends comfort, style and convenience while boasting five bedrooms and three full baths on a premium, level lot. The Grand two story entry flows into a Great room with vaulted ceilings, gas fireplace and a wall of windows. The gourmet Kitchen with large center island is well equipped with high-end stainless steel

  Kathy Kane Coldwell Banker Realty

  14 Chestnut St, Hopewell Junction, NY 12533
• 

  

  /22

  $475,000

  • 10 Beds
  • 3 Baths
  • 3,052 Sq Ft

  77 Carroll St, Poughkeepsie, NY 12601

  Three family home located on a quiet street in the desirable South Side of Poughkeepsie. This home is in good condition and has been nicely maintained throughout the years. Improvements include replacement windows, exterior & interior painting, and new floors in some rooms. Gas boilers, municipal water and sewer. The heating systems and electric meters are fully separated for each unit so the

  Mark Snyder eXp Realty

  77 Carroll St, Poughkeepsie, NY 12601
• 

  

  /33

  $479,999

  • 6 Beds
  • 2 Baths
  • 5,016 Sq Ft

  89 S Cherry St, Poughkeepsie, NY 12601

  PRIME 2-FAMILY INVESTMENT offers a Epic Opportunity for passive income or leverage into commercial. This 2-Family investment opportunity is sited on a huge double lot just shy of a quarter of an acre on the south side of Poughkeepsie. Perfect for the Owner Investor who lives in one unit while the rental income pays your mortgage. Unique property features that add value include private off street

  Latanya Frazier Oxford Property Group USA

  89 S Cherry St, Poughkeepsie, NY 12601
• 

  

  /30

  $610,000

  • 6 Beds
  • 3 Baths

  27 Hooker Ave, Poughkeepsie, NY 12601

  Discover the perfect investment opportunity in the heart of Poughkeepsie's Vibrant South Side! This recently renovated 3-unit apartment building offers a turnkey experience for both tenants and investors. Each unit is designed for comfort and functionality, featuring contemporary finishes and ample light ideally located within walking distance to schools, parks, and convenient shopping

  Jennifer Martini K. Fortuna Realty, Inc.

  27 Hooker Ave, Poughkeepsie, NY 12601
• 

  

  /18

  $549,000

  • 6 Beds
  • 3 Baths
  • 3,249 Sq Ft

  86 S Hamilton St, Poughkeepsie, NY 12601

  Great find! Three family fully rented. Located on the Southside of Poughkeepsie. All tenants would like to stay. The set up is 2 Bedrooms and 1 bath on each floor. All apartments have gas stoves and refrigerators; Flooring is mixed with some hardwood and laminate. There is only 1 heating system and 1 electric meter. All apartments have baseboard /radiator hot water heat. Separation can be done

  Michelle Ayala BHHS Hudson Valley Properties

  86 S Hamilton St, Poughkeepsie, NY 12601
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  /33

  $769,000

  • 5 Beds
  • 4 Baths
  • 3,252 Sq Ft

  61 Sherwood Heights, Wappingers Falls, NY 12590

  Discover timeless elegance in this beautifully landscaped 5 bedroom custom colonial, perfectly sited in a peaceful, sought after neighborhood. The perfect home for a large or extended family. This home offers the ideal blend of classic architecture and contemporary updates, providing both space and sophistication for modern living. Stone pillars grace the entrance to the property, setting a

  Jan Kaplan BHHS Hudson Valley Properties

  61 Sherwood Heights, Wappingers Falls, NY 12590
• 

  

  /19

  $359,900

  • 7 Beds
  • 3 Baths
  • 2,200 Sq Ft

  94 South Ave, Poughkeepsie, NY 12601

  Rare opportunity to acquire this legal rooming house on the City of Poughkeepsie's desirable south side. Featuring seven rooms, shared kitchen & three full bathrooms. Natural gas for heating, hot water & cooking. Unfinished basement & walkup attic for abundant storage. Large covered front porch & huge backyard for outdoor enjoyment. Centrally located just minutes from hospitals, colleges, bus

  Dan Axtmann BHHS Hudson Valley Properties

  94 South Ave, Poughkeepsie, NY 12601
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  /24

  $399,000

  • 5 Beds
  • 1,062 Sq Ft

  215 Little Pond Rd, Pawling, NY 12564

  Private Lake House on a Private Lake!Little Whaley Lake, a serene 46-acre spring-fed, motor-free lake with only six homes offers unparalleled tranquility. This lot offers 150 feet of lake frontage and a private dock; ideal for peaceful swimming, fishing, kayaking, and reconnecting with nature. There are only 6 homes on this lake, with no public access, creating a quiet and

  Jillian Pajer Douglas Elliman Real Estate

  215 Little Pond Rd, Pawling, NY 12564
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  /36

  $699,000

  • 7 Beds
  • 5 Baths
  • 4,353 Sq Ft

  2 Hunns Lake Rd, Stanfordville, NY 12581

  Calling all investors! A great opportunity to acquire an income-producing asset with value-add potential, featuring two buildings on one parcel in the heart of Standfordville. The site is over an acre with great frontage on NYS Rt 82. This property has four units consisting of one vacant space that was used as a commercial office in years past (with potential for residential conversion), and

  Ryan Arket Compass Greater NY, LLC

  2 Hunns Lake Rd, Stanfordville, NY 12581
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  /47

  $725,000

  • 5 Beds
  • 4 Baths
  • 3,334 Sq Ft

  8 Anna D Ct, Hopewell Junction, NY 12533

  Incredible and rare opportunity to own a lovingly maintained, multi-family property in Hopewell Junction. Located on a quiet, private cul-de-sac, this expansive home features a unique layout offering the option for either the top or bottom floor units to live as a 2 or 3-bedroom unit.The upper level features a spacious, light-filled living area, formal dining room and a charming

  Veronica Monz-Martell Coldwell Banker Choice Prop.

  8 Anna D Ct, Hopewell Junction, NY 12533
• 

  

  /20

  $340,000

  • 5 Beds
  • 2 Baths
  • 2,272 Sq Ft

  320 Mansion St, Poughkeepsie, NY 12601

  Excellent investment opportunity in the City of Poughkeepsie! This legal 2-family offers a spacious 3-bedroom, 1 bath unit upstairs and a 2-bedroom, 1-bath unit on the main level. Both units are separately metered and currently leased, providing immediate income with value-add potential through future updates. Tenants pay their own utilities. Recent updates include a new roof just one year ago!

  Michael Cahill HomeSmart Homes & Estates

  320 Mansion St, Poughkeepsie, NY 12601
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  /49

  $950,000

  • 5 Beds
  • 4 Baths
  • 3,500 Sq Ft

  55 Teller Ave, Beacon, NY 12508

  Welcome to 55 Teller, where classic style meets modern potential. Nestled on a corner lot with captivating mountain views and blocks away from the bustling Main Street, this property offers a world of possibilities. Perfect for a residential transformation or exploring special permitted uses like a bed and breakfast, museum, social club, private school, nursing home, animal care facility, nursery

  William Stafford Compass Greater NY, LLC

  55 Teller Ave, Beacon, NY 12508
• 

  

  /38

  $3,000,000

  • 9 Beds
  • 5 Baths
  • 7,500 Sq Ft

  3412 Route 52, Stormville, NY 12582

  Former Mount Storm Ski Area – 88 Acres with Stunning Views & Rich History This unique property, once the site of the iconic Mount Storm Ski Area, is now available for sale. A total of 5 parcels, spanning 88 acres, it offers breathtaking 180-degree panoramic views from the mountaintop, where you can see for miles and experience the natural beauty of the region. The property features a main

  Christopher Galli Century 21 Elite Realty

  3412 Route 52, Stormville, NY 12582
• 

  

  /33

  $1,999,999

  • 5 Beds
  • 2 Baths
  • 2,618 Sq Ft

  148 Creek Rd, Staatsburg, NY 12580

  Welcome to 148 N creek, a stunning property boasting 136 acres of preserved farmland. The sale features a charming 5 bedroom 2 bath farmhouse from the 1800s, several restored and updated barns, . This property is also home to an active farm brewery and agrotourism center. The acreage is protected by the Winnakee Land Conservancy, with future upgrades in mind. Upgraded electric, septic, and well

  EUGENE VALOY BHHS Hudson Valley Properties

  148 Creek Rd, Staatsburg, NY 12580
• 

  

  /39

  $649,000

  • 6 Beds
  • 2 Baths
  • 3,100 Sq Ft

  11-13 Eldridge Ln, Red Hook, NY 12571

  Red Hook Village Compound! Once in a generation a property offering like this is available. Tucked in at the end of Eldridge lane in the village walkable to parks, shoppes, and restaurants. This is composed of a lovely four bedroom home, with 2 sunrooms, large living room with stone fireplace, massive bathroom with skylights, new roof with warranty, new skylights and carpets. The home is light

  Chelsea Pollard-Seiler Mondello Upstate Properties

  11-13 Eldridge Ln, Red Hook, NY 12571
• 

  

  /17

  $490,000

  • 6 Beds
  • 3 Baths

  39 Delafield St, Poughkeepsie, NY 12601

  3-unit triplex, Southside Poughkeepsie location! Separate utilities except for electric. 2 bedroom, 1 bath. Unit #2... 2 bedroom, 1 bath. Unit #3... 2 bedroom, 1 bath. Live in one and let the other 2 units pay your mortgage! This city of Poughkeepsie triplex is located just minutes from Vassar College, Vassar Hospital, parks, Poughkeepsie train station, restaurants and schools. Contact for

  Gregory Pikor Inspire Realty

  39 Delafield St, Poughkeepsie, NY 12601
• 

  

  /22

  $635,000

  • 5 Beds
  • 3 Baths
  • 2,524 Sq Ft

  27 Mill St, Wappingers Falls, NY 12590

  Prime Multi-Family Investment in the Heart of the Village of Wappingers Falls!Don’t miss this exceptional opportunity to own a well-maintained and income-generating three-family home in the vibrant Village of Wappingers Falls. Ideal for investors or savvy owner-occupants, this versatile property features three fully independent units—each with private entrances, separate utilities, and

  Virginia Corbett eXp Realty

  27 Mill St, Wappingers Falls, NY 12590
• 

  

  /45

  $3,750,000

  • 5 Beds
  • 7 Baths
  • 6,050 Sq Ft

  33 Pells Rd, Rhinebeck, NY 12572

  This magnificent Modern Farmhouse, sheltered in an elegant landscape of rolling hills, mature trees, colorful gardens and a 7-acre lake, is the quintessential Hudson Valley retreat on 43+ picturesque acres. Located an easy five minutes from historic, cultural-rich Rhinebeck Village, it’s the country destination for the sophisticated buyer who values privacy, property and proximity. The striking

  Peggy Santamorena Houlihan Lawrence Inc.

  33 Pells Rd, Rhinebeck, NY 12572
• 

  

  /49

  $1,200,000

  • 5 Beds
  • 3.5 Baths
  • 4,356 Sq Ft

  1035 Noxon Rd, Lagrangeville, NY 12540

  Discover timeless charm blended with modern comfort in this Classic Circa 1810 Historical Beauty, set on 7-acres in the heart of the Hudson Valley! (Also, an additional 7 acres are available!) There's space galore featuring 4,356 sq. ft. of finished living space with 5 bedrooms, 3.5 baths, and an additional 1,435 sq. ft. full, unfinished basement. All rooms are generously sized, with 3

  Susan Stevens BHHS Hudson Valley Properties

  1035 Noxon Rd, Lagrangeville, NY 12540
• 

  

  /31

  $2,875,000

  • 5 Beds
  • 6 Baths
  • 7,600 Sq Ft

  26 Mountain Farm Rd, Millerton, NY 12546

  Totally Private Top of the World Setting with Monster Catskill Views. 10-Min to the Center of Millerton NY/Sharon CT & 15-Min to Metro North Train. Graciously Scaled Rooms Throughout. 4 Fireplaces. The Ultimate Swimming Pool & Pool Area Complete with: Hot Tub; Outdoor Kitchen; Fireplace & Large Stone Terrace. Tennis Court. 3-Car+ Attached Garaging. 6 Paddocks with Run-In Sheds + Riding Ring &

  Graham Klemm GRAHAM T. KLEMM LIC. RE BROKER

  26 Mountain Farm Rd, Millerton, NY 12546
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  /44

  $4,500,000

  • 5 Beds
  • 4.5 Baths
  • 6,124 Sq Ft

  93 Mill Rd, Rhinebeck, NY 12572

  Upstate Down Interiors presents, The Mill House. Tucked into ten curated acres just outside the village of Rhinebeck, The Mill House stands as a statement of subtle luxury—where design is not dictated by trend, but by timelessness. Originally built in 1991 and now exquisitely reimagined, this 4-bedroom, 4.5-bath main residence, accompanied by a 1-bedroom guest house and an ensemble of deeply

  Delyse Berry Upstate Down

  93 Mill Rd, Rhinebeck, NY 12572
• 

  

  /18

  $380,000

  • 7 Beds
  • 3 Baths

  10 Lexington Ave, Poughkeepsie, NY 12601

  Welcome to 10 Lexington Ave, a fantastic two-family home situated on a quiet one-way street in the heart of Poughkeepsie! This versatile property features a spacious 5-bedroom, 2-bath unit and a comfortable renovated 2-bedroom, 1-bath unit, making it an excellent opportunity for investors or owner-occupants looking for additional rental income. Convenience is key—this home is located directly

  Jose Cruz Douglas Elliman Real Estate

  10 Lexington Ave, Poughkeepsie, NY 12601
• 

  

  /46

  $885,000

  • 6 Beds
  • 5 Baths
  • 4,097 Sq Ft

  32 Old Route 199, Red Hook, NY 12571

  PRICE IMPROVEMENT AND ADDITIONAL LAND! Price is now $885,000 and more land is offered at 5 acres instead of 4! Welcome to Shepard's Knoll Farm! A bucolic family farm with a legal two family dwelling, a small cabin, and barn. The 5 acre farm boasts an organic garden with 4 apple trees, fenced in area for goats and sheep, fenced in chicken coops and a barn previously used for livestock. The

  Lisa Fountain Corcoran Country Living

  32 Old Route 199, Red Hook, NY 12571
• 

  

  /34

  $935,000

  • 5 Beds
  • 3.5 Baths
  • 3,423 Sq Ft

  47 Dartmouth Dr, Poughkeepsie, NY 12603

  Check out this beautifully crafted home with well-appointed interior finishes offering 5 Bedrooms and 3.5 full Baths. The oversized kitchen island is the perfect centerpiece for entertaining. Just off the kitchen and perfect for those large gatherings is the great room, its massive size offers the perfect setting for relaxation with its cozy linear fireplace and ample natural light and vaulted

  Alicia Goldman Christie's Int. Real Estate

  47 Dartmouth Dr, Poughkeepsie, NY 12603
• 

  

  /19

  $549,999

  • 5 Beds
  • 4 Baths

  185 Creek Rd, Pleasant Valley, NY 12569

  Welcome to your own private retreat! This two-family home offers a peaceful, park-like setting with a creek right in your backyard—perfect for fishing or simply unwinding by the water. The home is set back from the road, offering privacy and serenity, with stairs leading down to the creek and multiple decks for relaxing or entertaining.Inside, you'll find an open floor plan that features eat-in

  Anthony Melella Vision Alliance Realty Inc.

  185 Creek Rd, Pleasant Valley, NY 12569
• 

  

  /27

  $849,000

  • 5 Beds
  • 5 Baths
  • 3,456 Sq Ft

  45 Manor Dr W, Poughkeepsie, NY 12603

  New construction Colonial in the city of Lagrange, and the Arlington School District and close proximity to NYC. This contemporary/Colonial home has charm and elegance, with open concept floorplan. Gourmet kitchen with quartz countertops and ample cabinets space and pantry a chef's dream is just one the many upgrades in this home. Enjoy a bright and sunlit living room, plus the vaulted ceilings

  Joseph Brown RE/MAX Real Property Group

  45 Manor Dr W, Poughkeepsie, NY 12603
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  /33

  $12,500,000

  • 5 Beds
  • 6.5 Baths
  • 6,054 Sq Ft

  129 W Meadow Ln, Millbrook, NY 12545

  Set in the hills above Millbrook, West Meadow is encircled as far as the eye can see by endless, heart-stopping views of the entire Hudson Valley. The house and pool sit on a beautifully landscaped plateau above a sloping lawn that gives way to a prolific cutting garden, rose beds, tennis court wrapped in wisteria vines, and groomed meadows. A fruit orchard and abundant vegetable garden enhance

  Candy Anderson Compass Greater NY, LLC

  129 W Meadow Ln, Millbrook, NY 12545
• 

  

  /9

  $700,000

  • 9 Beds
  • 3 Baths

  108 Winnikee Ave, Poughkeepsie, NY 12601

  Turnkey three-family investment opportunity in the heart of the City of Poughkeepsie! Each unit features three bedrooms and one bathroom, all currently rented with consistent cash flow and a solid NOI of $61,309—with room for upside, as insurance costs can be optimized. The property has been thoughtfully updated: Unit 1 was fully renovated in April 2025 with a brand-new range and fridge; Unit 2

  Savannah Miceli Century 21 Alliance Rlty Group

  108 Winnikee Ave, Poughkeepsie, NY 12601
• 

  

  /20

  $2,199,000

  • 5 Beds
  • 5.5 Baths
  • 3,314 Sq Ft

  10 Old Town Rd Unit Extension, Beacon, NY 12508

  26+ park-like acres in Beacon, NY. Surrounded by Hudson Highlands State Park Preserve, this distinctive property offers income-producing residences, a cabin, beautiful trails, magnificent views and incredible privacy. Owner financing available.

  Louise Darhansoff Douglas Elliman Real Estate

  10 Old Town Rd Unit Extension, Beacon, NY 12508
• 

  

  /40

  $430,000

  • 6 Beds
  • 2 Baths
  • 2,462 Sq Ft

  41 Lagrange Ave, Poughkeepsie, NY 12603

  Unlock the potential in this classic two-family home located in the heart of this Arlington neighborhood , just a short walk to shops, restaurants, and Vassar College. Featuring two spacious units, each offering 3 bedrooms, 1 bathroom and separate utilities, this property is perfect for investors, renovators, or owner-occupants looking to customize their space. The first-floor unit offers

  Lyra Blumenthal RE/MAX Benchmark Realty Group

  41 Lagrange Ave, Poughkeepsie, NY 12603
• 

  

  /45

  $4,950,000

  • 5 Beds
  • 5.5 Baths
  • 6,310 Sq Ft

  310 Carpenter Hill Rd, Pine Plains, NY 12567

  Nestled on top of Carpenter Hill, with unparalleled views of Stissing Mountain, the Catskills and the surrounding farmland, sits this country estate on 24.78 acres. The traditional, cedar shake 6,310 square foot home exudes elegance exhibited through the well proportioned rooms with 9’4” ceiling height, exceptional craftmanship and attention to detail found throughout the home. A dramatic double

  PAULA REDMOND Corcoran Country Living

  310 Carpenter Hill Rd, Pine Plains, NY 12567
• 

  

  /4

  $460,000

  • 6 Beds
  • 3 Baths
  • 2,475 Sq Ft

  69 Glenwood Ave, Poughkeepsie, NY 12603

  Fully rented 3-unit triplex, Southside Poughkeepsie location! Newer Roof. Unit #3 recently renovated. Unit #1... 3 bedroom, 1 bath. Unit #2... 2 bedroom, 1 bath. Unit #3... 1 bedroom, 1 bath. Live in one and let the other 2 units pay your mortgage! This city of Poughkeepsie triplex is located just minutes from Vassar College, Vassar Hospital, parks, Poughkeepsie train station, restaurants

  Gregory Pikor Inspire Realty

  69 Glenwood Ave, Poughkeepsie, NY 12603
• 

  

  /8

  $475,000

  • 9 Beds
  • 3 Baths
  • 1,716 Sq Ft

  64 Glenwood Ave, Poughkeepsie, NY 12603

  3-unit triplex, Southside Poughkeepsie location! Separate utilities. Unit #1 and Unit#2 recently renovated. Unit #1... 2 bedroom, 1 bath. Unit #2... 1 bedroom, 1 bath. Unit #3... 4 bedroom, 1 bath. Live in one and let the other 2 units pay your mortgage! This city of Poughkeepsie triplex is located just minutes from Vassar College, Vassar Hospital, parks, Poughkeepsie train station,

  Gregory Pikor Inspire Realty

  64 Glenwood Ave, Poughkeepsie, NY 12603

Showing Results 41 - 80, Page 2 of 3