Homes for Sale near Poughkeepsie Middle School

• 

  

  

  /31

  $500,000

  • Land
  • 97.1 Acres
  • $5,149 per Acre

  TBD Lily Lake Rd, Highland, NY 12528

  A rare opportunity to own a breathtaking 97-acre property featuring the very lake that gives Lily Lake Road its name. Tucked away in the beautiful countryside of Highland, New York, this one-of-a-kind parcel offers unmatched privacy, natural beauty, and endless potential for your dream retreat or legacy estate.At the heart of the property lies Lily Lake — a serene, private body of water

  John Quinn Quinn Realty Group Inc.

  TBD Lily Lake Rd, Highland, NY 12528
• 

  

  /2

  $49,000

  • Land
  • 1.28 Acres
  • $38,281 per Acre

  161 E Dorsey Ln, Hyde Park, NY 12601

  Flag lot, with old BOHA, may be able to be updated by the buyer. Home was sited in the rear of the property on the original plan. 159 E Dorsey is on the market--home in need of repair, cash or rehab 203k loan. Seller prefers to sell the two together.

  Diane Crittenden Diane E. Crittenden

  161 E Dorsey Ln, Hyde Park, NY 12601
• 

  

  

  /3

  $2,500,000

  • Land
  • 14.9 Acres
  • $167,785 per Acre

  0 MacGhee Rd Unit KEY964415, Red Oaks Mill, NY 12603

  14.9 Acres with large pond zoned Alternative Senior Citizen Housing District.

  Robert Vitanza Rand Commercial

  0 MacGhee Rd Unit KEY964415, Red Oaks Mill, NY 12603
• 

  

  

  /22

  $445,000

  7 Gray St, Poughkeepsie, NY 12603

  Welcome to 7 Gray Street - a versatile duplex offering strong income potential and flexible living options in the heart of Poughkeepsie. This well-configured multi-family property features two spacious units, each offering 2 bedrooms, a full kitchen, and comfortable living space designed for everyday functionality. The thoughtful layout makes this property ideal for owner-occupants seeking rental

  Mizan Ayers THE AYERS GROUP LLC

  7 Gray St, Poughkeepsie, NY 12603
• 

  

  

  /25

  $397,000

  • 3 Beds
  • 3 Baths
  • 1,661 Sq Ft

  7 River Rd, Highland, NY 12528

  UNIQUE FLOOR PLAN in this updated eyebrow colonial creates an ideal setup for a bed-and-breakfast use of this property. Each bedroom features it's own full bath, offering comfort and privacy for all. The spacious living area includes a formal dining room and updated kitchen. A first- floor bedroom and convenient laundry add to the home's flexibility. Enjoy a short walk to the Hamlet of Highland

  Elizabeth Decker Hudson Dwellings Realty

  7 River Rd, Highland, NY 12528
• 

  

  /16

  $475,000

  • 4 Beds
  • 2 Baths
  • 2,181 Sq Ft

  7 Brookland Farms Rd, Poughkeepsie, NY 12601

  Welcome home to this well-appointed four bedroom, two and-half bath residence offering comfort, space, and everyday convenience. The main level features a welcoming living room, a nice dining room, and nicely designed kitchen. Step out of the dining room onto a large deck with privacy. With four nice size bedrooms there is plenty of room for work and play. Ideally located just three minutes to

  JOAN PEDATELLA K. Fortuna Realty, Inc.

  7 Brookland Farms Rd, Poughkeepsie, NY 12601
• 

  

  /5

  $115,000

  • Land
  • 5.1 Acres
  • $22,549 per Acre

  TBD Evy Chestnut Ln, Milton, NY 12547

  5.1 Acres Land for Sale – Milton, NY (BOHA Approved) Build your dream home on this beautiful 5.1-acre parcel located in Milton, NY, within the Marlboro School District. BOHA approved for a 2-bedroom home (potential for 3-bedroom approval) 2.5 acres are buildable — plenty of room for your home and outdoor living Underground electric available Approved for above-ground septic system Centrally

  Angela Chenery Century 21 Alliance Rlty Group

  TBD Evy Chestnut Ln, Milton, NY 12547
• 

  

  /16

  $390,000

  • 4 Beds
  • 1.5 Baths
  • 1,525 Sq Ft

  10 Lori St, Poughkeepsie, NY 12603

  3 Level 4 Bedroom 1.5 bath Split Level home on .32 acre lot in Town of Poughkeepsie! Huge Bow Window Illuminates 1st floor with plenty of natural light. Primary bedroom on 1st floor with plenty of closet space & door leading out to rear deck overlooking your private fenced in backyard. 2nd level includes 3 bedrooms & full bath. Lower level with family room & half bath. Conveniently located near

  Ernie Acampora River Realty Services, Inc.

  10 Lori St, Poughkeepsie, NY 12603
• 

  

  /7

  $174,900

  • Land
  • 2.33 Acres
  • $75,064 per Acre

  0 Gentry Bend Unit ONEH6332533, Poughkeepsie, NY 12603

  BOH approved! Excellent cul de sac location to build you luxury Hudson Valley home on 2.33 acres. High-end neighboring homes on a tree lined street with classic light posts. Municipal water and septic system.

  Arij Kurzum

  0 Gentry Bend Unit ONEH6332533, Poughkeepsie, NY 12603
• 

  

  /34

  $305,000

  • 2 Beds
  • 1 Bath
  • 946 Sq Ft

  791 Gregory Ct Unit 706, Highland, NY 12528

  Immaculate first-floor two bedroom end-unit condominium in Highland, NY. located in the sought-after Woods at Bridgeview Community. Enjoy the French-door study and covered patio off the living room with wooded views into Franny Reese Park. A quick three minute car ride brings you to the Hudson Valley Rail Trail, that connects to the Walkway of the Hudson. Highlights of this well-maintained home

  Barbara Carter Century 21 Alliance Rlty Group

  791 Gregory Ct Unit 706, Highland, NY 12528
• 

  /2

  $150,000

  • Land
  • 5.45 Acres
  • $27,548 per Acre

  Maloney Rd, Poughkeepsie, NY 12603

  8.3 Acres of Private Poughkeepsie Land: Build Your Hudson Valley Dream Discover the perfect blend of rural tranquility and urban convenience with this unique offering of 8.3 acres on Maloney Road. Sold together as one expansive lot (split into 5.4 acres and 2.9 acres), this parcel provides unparalleled privacy and elbow room for a custom, luxury estate or a secluded, multi-generational compound.

  Michael Jenney Keller Williams Realty

  Maloney Rd, Poughkeepsie, NY 12603
• 

  

  /22

  $2,100,000

  • Land
  • 70.5 Acres
  • $29,787 per Acre

  243 Vineyard Ave Unit 251, Highland, NY 12528

  Spectacular 70 acre parcel located right outside the village of Highland. May be used as a farm or subdivided. Parcel has 3 rentals located on it in addition to 1 vacant house. Also on this property is a very large steel building with high ceilings and oversized garage doors as well as a barn! Close commuter location - Metro North, NYS Thruway, Mohonk Mountains and Hudson Valley Rail Trail.

  John Quinn Quinn Realty Group Inc

  243 Vineyard Ave Unit 251, Highland, NY 12528
• 

  /2

  $75,000

  • Land
  • 1.2 Acres
  • $62,500 per Acre

  534 Violet Ave, Hyde Park, NY 12538

  Embrace the convenience this prime 1.2 acre lot has to offer. Located just moments away from thriving shopping centers, a variety of dining choices, excellent health care facilities and local schools including Marist College, The Culinary Institute Of America and DCC. This central location not only enhances your daily life with effortless access to essential amenities but also fosters a vibrant

  MATTHEW DOHERTY McNiff Real Estate LTD

  534 Violet Ave, Hyde Park, NY 12538
• 

  

  /11

  $265,000

  • 1 Bed
  • 1 Bath
  • 730 Sq Ft

  128 Vineyard Ave Unit 206, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. Thoughtfully designed 1 and 2 bedroom residences range from 730 to 1,230 SF, blending smart design, comfort, and easy outdoor access—ideal for active living without sacrificing style. The open layouts feature large windows and a seamless flow throughout.

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 206, Highland, NY 12528
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  /37

  $439,000 Open Sun 12PM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,500 Sq Ft

  88 Innis Ave, Poughkeepsie, NY 12601

  Charming and like new! Fully renovated 2 story in and out. 3 bedrooms, 2 full baths and half bath. 2 bonus rooms. Beautiful Family Room with 2 Sky Lights and lots of windows that overlook the manicured back yard. Ceramic tile floors and wood floors through out. All New flooring and lighting. New Bathrooms, kitchen and plumbing. Recently new new windows through out. Recently new Central Air Lenox

  Lynn Simmons Dixon Smith Realty

  88 Innis Ave, Poughkeepsie, NY 12601
• 

  

  /46

  $415,000

  • 4 Beds
  • 1.5 Baths
  • 1,895 Sq Ft

  111 S Hamilton St, Poughkeepsie, NY 12601

  Located in Poughkeepsie’s desirable South Side within the Dwight-Hooker Avenue Historic District, this beautifully maintained duplex residence captures the charm of classic NYC brownstones with the comfort of modern updates. Thoughtfully preserved period details, original moldings, staircase, butlers pantry and vintage woodwork—blend seamlessly with a renovated kitchen, restored and updated

  Angela Ingham BHHS Hudson Valley Properties

  111 S Hamilton St, Poughkeepsie, NY 12601
• 

  

  /38

  $637,000

  • 3 Beds
  • 3 Baths
  • 2,652 Sq Ft

  12 Nob Hill, Poughkeepsie, NY 12603

  Beautifully updated colonial at 12 Nob Hill in the Town of Poughkeepsie, offering over 2,600 square feet of finished living space and a layout that lives like a four bedroom. This home features a formal living room with fireplace and master suite with full bathroom and walk-in closet, two additional bedrooms, two additional full bathrooms, plus a dedicated office, ideal for today’s flexible

  Ernest Smajlaj RE/MAX Town & Country

  12 Nob Hill, Poughkeepsie, NY 12603
• 

  

  /41

  $539,000

  • 4 Beds
  • 2.5 Baths
  • 1,863 Sq Ft

  5 Larch Ct, Poughkeepsie, NY 12603

  Welcome to The Larch House — a beautifully updated, light-filled home tucked on a quiet cul-de-sac, offering the perfect blend of warmth, character, and modern living. Thoughtfully designed and exceptionally maintained, this home delivers a lifestyle that feels both stylish and effortless from the moment you arrive. A charming covered front porch sets the tone, inviting you into the bright and

  Nicole Biello Compass Greater NY, LLC

  5 Larch Ct, Poughkeepsie, NY 12603
• 

  

  /34

  $467,500

  • 4 Beds
  • 3 Baths
  • 2,517 Sq Ft

  3 Pond Rd, Poughkeepsie, NY 12601

  This charming, recently updated home is ideally situated on a quiet dead-end street, offering a serene escape without sacrificing convenience. The location provides easy access to local amenities and transportation options. Step inside to discover a freshly revitalized interior featuring new flooring and paint throughout, creating a bright and welcoming atmosphere. The spacious living area is

  Samantha McCrory Exit Realty Connections

  3 Pond Rd, Poughkeepsie, NY 12601
• 

  

  /26

  $475,000

  • 3 Beds
  • 1.5 Baths
  • 1,701 Sq Ft

  29 Mcallister Dr, Pleasant Valley, NY 12569

  Town of Lagrange oversized ranch featuring hardwood floors throughout, large eat-in kitchen, formal dining room w/cork floor & living room w/fireplace. Three well proportioned bedrooms. Laundry conveniently located on main level. Sunroom leads to massive two car garage ideal for auto enthusiast, hobbyist or contractor. Expansive level backyard, which backs up to 60 acre ecological preserve, never

  Dan Axtmann BHHS Hudson Valley Properties

  29 Mcallister Dr, Pleasant Valley, NY 12569
• 

  

  /16

  $240,000

  • Land
  • 12.9 Acres
  • $18,605 per Acre

  67 Jackson Rd, Poughkeepsie, NY 12603

  Don’t miss this exceptional 12.9-acre opportunity in the heart of the Hudson Valley. Comprising three contiguous parcels, this level and partially wooded land offers ample road frontage and direct access to the serene Wappinger Creek which is perfect for kayaking, fishing, or simply enjoying the peaceful waterfront setting. Located across from Stanley Still Park and just minutes from Hudson

  Howard Payson RE/MAX Town & Country

  67 Jackson Rd, Poughkeepsie, NY 12603
• 

  

  /34

  $450,000

  • 4 Beds
  • 2.5 Baths
  • 1,988 Sq Ft

  4 Mcallister Dr, Pleasant Valley, NY 12569

  Proud ownership shines throughout this well-maintained Dutch Colonial , nestled on over 1.1 acres of picturesque land in town of Lagrange, NY with Arlington central schools. With an easy commute to New York City in under two hours, you can enjoy the serenity of the Hudson Valley while remaining conveniently connected to the bustling urban lifestyle. Step inside to discover over 1,610 square feet

  Kaye Saglibene

  4 Mcallister Dr, Pleasant Valley, NY 12569
• 

  

  /17

  $50,000

  • Land
  • 1.36 Acres
  • $36,765 per Acre

  0 White St, Highland, NY 12528

  Looking for the perfect lot for your new home? This lovely 1.36-acre wooded lot is situated on a gentle rise above an established community in historic Highland. It offers the best of both worlds; peace, privacy, and appealing elevated views, with convenient access to all amenities and the security of having neighbors nearby. Easy access to the Walkway Over the Hudson, Empire State Rail

  Carolyn Michelle KW MidHudson

  0 White St, Highland, NY 12528
• 

  

  /26

  $389,000

  • 6 Beds
  • 2 Baths

  185 Mill St, Poughkeepsie, NY 12601

  Welcome to 185 Mill Street, Poughkeepsie, NY 12601, a classic red-brick two-family in an unbeatable, commuter-friendly downtown location, just a few blocks from the Poughkeepsie Metro-North/Amtrak Station (ideal for NYC and Hudson Valley access). This versatile property offers two spacious 3-bedroom / 1-bath units (a total of 6 bedrooms / 2 bathrooms) with separate electric meters, making it a

  Hamar Clarke Clarke Realty & Associates LLC

  185 Mill St, Poughkeepsie, NY 12601
• 

  

  /12

  $295,000

  • 3 Beds
  • 2 Baths
  • 1,708 Sq Ft

  39 Spruce St, Poughkeepsie, NY 12601

  Three-bedroom, two-bath home located in the City of Poughkeepsie. Functional layout with ample living space and strong rental or owner-occupant potential. The location is the highlight. Just minutes to the Walkway Over the Hudson ( local waterfront attractions, restaurants, and shops. Easy access to the Metro-North Railroad ( Poughkeepsie station, making it ideal for commuters traveling to NYC.

  JOSE SANTOS K Fortuna Lighthouse Realty

  39 Spruce St, Poughkeepsie, NY 12601
• 

  

  /7

  $820,000

  • 4 Beds
  • 3.5 Baths
  • 2,813 Sq Ft

  34 Dartmouth Dr, Poughkeepsie, NY 12603

  This stunning four-bedroom home blends luxury, comfort, and thoughtful design. The first-floor master suite offers a private retreat, featuring generous space and a spa-like bath—perfect for convenient single-level living. At the heart of the home is an expansive, upscale kitchen with premium finishes, seamlessly flowing into a large great room ideal for both everyday living and entertaining.

  David Bartolone Christie's Int. Real Estate

  34 Dartmouth Dr, Poughkeepsie, NY 12603
• 

  

  /11

  $649,000

  • Land
  • 22.68 Acres
  • $28,616 per Acre

  24 Villa Ln, Lagrange, NY 12603

  Follow the long meandering driveway to your future build site. An amazing opportunity to own almost 23 acres in the heart of LaGrange with stunning Hudson Valley Mountain Views! BOHA for a 5 bedroom home with all utilities and site work complete. Driveway sub base is down, electric, water and natural gas are ran and fully approved 5 bedroom septic system is in. Fully approved site plan with

  Justin LaFalce KW MidHudson

  24 Villa Ln, Lagrange, NY 12603
• 

  

  /47

  $459,000

  • 4 Beds
  • 2 Baths

  21 Lent St, Poughkeepsie, NY 12601

  Welcome to 21 Lent Street, a beautifully renovated two-family home in Poughkeepsie’s College Hill neighborhood offering turnkey living and excellent investment potential. Each spacious unit features two bedrooms and a full bath, brand-new kitchens, updated flooring, and modern finishes throughout. Recent upgrades include all-new siding, a new roof, updated plumbing and electric with separate

  Hamar Clarke Clarke Realty & Associates LLC

  21 Lent St, Poughkeepsie, NY 12601
• 

  

  /18

  $449,900

  • 4 Beds
  • 3 Baths
  • 3,156 Sq Ft

  22 Old Mill Rd, Poughkeepsie, NY 12603

  A Rare Find! 24 hour notice, tenants, need confirmation. This large brick home needs work and is being sold "as-is"! Overlooking Wappingers Creek this wonderful brick cape has over 3100 sq ft of living space. Wonderful floor plan with large rooms, two kitchens, 2 living rooms one with fireplace, 3 baths plus family room. Possible accessory apartment, tax records include the apartment. Price

  ANITA CHESTER BHHS Hudson Valley Properties

  22 Old Mill Rd, Poughkeepsie, NY 12603
• 

  

  /12

  $270,000

  • 1 Bed
  • 1 Bath
  • 803 Sq Ft

  128 Vineyard Ave Unit 104, Highland, NY 12528

  Welcome to Highbridge Crossing, a modern condominium building with direct access to the Hudson Valley Rail Trail in the heart of Highland, NY. Thoughtfully designed 1 and 2 bedroom residences range from 730 to 1,230 SF, blending smart design, comfort, and easy outdoor access—ideal for active living without sacrificing style. The open layouts feature large windows and a seamless flow throughout.

  Vitaly Isaacs Magic Of Great Neck Realty Inc

  128 Vineyard Ave Unit 104, Highland, NY 12528
• 

  

  /14

  $199,000

  • 3 Beds
  • 1.5 Baths
  • 1,531 Sq Ft

  25 Woodcliff Ave, Poughkeepsie, NY 12603

  Opportunity knocks at 25 Woodcliff Ave! This 3-bedroom, 1.5-bath home offers strong upside potential for investors, contractors, or savvy buyers looking for their next renovation project. With a functional layout and solid footprint, this property is ready for a full rehab and value-add improvements. This is a true handyman special. Ideal for cash buyers or those utilizing renovation financing.

  Jasper Newman Charles Rutenberg Realty Inc

  25 Woodcliff Ave, Poughkeepsie, NY 12603
• 

  

  /50

  $699,000

  • 4 Beds
  • 3.5 Baths
  • 4,208 Sq Ft

  19 Ridgeview Rd, Poughkeepsie, NY 12603

  Nestled in complete privacy on 3.25 acres and surrounded by nature, this extraordinary mid-century modern home offers some of the most spectacular views you’ll find anywhere in the Hudson Valley. Designed to embrace light, space, and scenery, this 4 bedroom, 3.5 bath retreat perfectly blends timeless architecture with modern comfort. Gleaming hardwood floors and beamed ceilings highlight the

  Jennifer Amicucci

  19 Ridgeview Rd, Poughkeepsie, NY 12603
• 

  

  /40

  $650,000

  • 4 Beds
  • 4 Baths
  • 4,160 Sq Ft

  303 Freedom Rd, Pleasant Valley, NY 12569

  Custom 4 bedroom, 2 full bath, 2 half bath contemporary privately set on 5 acre parcel. Surrounded by wooded buffers for privacy, this nature lover's paradise is the perfect venue for entertaining. Attractive floor plan includes huge eat-in kitchen complete with center island & stainless appliances. Living room w/fireplace provides easy access to deck overlooking expansive yard. First floor

  Dan Axtmann BHHS Hudson Valley Properties

  303 Freedom Rd, Pleasant Valley, NY 12569
• 

  

  /33

  $349,990

  • 4 Beds
  • 1.5 Baths
  • 1,716 Sq Ft

  35 Shady Creek Rd, Pleasant Valley, NY 12569

  Nestled near a peaceful creek, 35 Shady Creek Dr offers a wonderful opportunity to own a solidly built Colonial home in the Arlington School District. This four-bedroom, one-and-a-half-bath home is full of character and potential, offering great bones and a comfortable layout that’s ready for your personal touch. Inside, a welcoming formal dining room centers around a charming stone fireplace,

  Helene Goodworth eXp Realty

  35 Shady Creek Rd, Pleasant Valley, NY 12569
• 

  

  /27

  $495,000

  • 3 Beds
  • 2 Baths
  • 1,596 Sq Ft

  34 Raker Rd, Poughkeepsie, NY 12603

  Welcome to this well-maintained 3 bedroom, 2 full bath raised ranch nestled in a quiet neighborhood in Poughkeepsie’s desirable Spackenkill School District. This move-in ready home offers a perfect blend of comfort, space, and convenience ideal for families, first-time buyers, or anyone looking for a peaceful retreat with easy access to amenities.Upstairs, you’ll find a bright and airy living

  Ashley Bou KW MidHudson

  34 Raker Rd, Poughkeepsie, NY 12603
• 

  

  /60

  $599,500

  • 4 Beds
  • 2 Baths
  • 2,110 Sq Ft

  122 Vineyard Ave, Highland, NY 12528

  This1900's old style spacious 2-unit home with old charm and completely gutted with new upgraded modern conveniences, is situated in the quaint village of Highland. Detailed original woodwork staircase, arched entryways, and hardwood floors are throughout. The backyard has a patio to gather for a barbeque, lounge on a chair reading a book or listening to the sound of the babbling brook passing

  Maria Ferguson Hudson River Valley Properties

  122 Vineyard Ave, Highland, NY 12528
• 

  

  /38

  $469,000

  • 2 Beds
  • 2 Baths
  • 852 Sq Ft

  15 E Dogwood Dr, Poughkeepsie, NY 12601

  Don’t miss your chance to own this charming home in the desirable Town of Poughkeepsie, nestled within the top-rated Spackenkill School District. Perfectly updated and move-in ready, this home combines cozy living with modern conveniences — making it ideal for both relaxation and entertaining.Step inside to a bright and airy living room that flows effortlessly into the newly remodeled

  Lisa DiMarzio BHHS Hudson Valley Properties

  15 E Dogwood Dr, Poughkeepsie, NY 12601
• 

  

  /26

  $549,000

  • 4 Beds
  • 2 Baths
  • 2,510 Sq Ft

  340 Vineyard Ave, Highland, NY 12528

  Step back in time with this spacious Victorian home full of original charm and character. Nestled on 41.10 acres of scenic land with mountain views. This property features a detached barn, 2 car garage and a classic summer kitchen. This property offers endless potential for restoration or creative retreat spaces. Inside you will find hardwood floors, birch cabinets with amazing stainless retro

  Ronnie Rebis Grist Mill Real Estate

  340 Vineyard Ave, Highland, NY 12528
• 

  

  /31

  $549,000

  • 4 Beds
  • 3 Baths
  • 2,148 Sq Ft

  5 3rd St, Milton, NY 12547

  Set on 1.47 acres in Ulster County within the Marlboro School District, this 4-bedroom, 3-bath raised ranch offers a flexible layout, modern finishes, and room to live both indoors and out. Built in 2021, the home features hardwood floors, abundant natural light, and a thoughtful floor plan designed for everyday living and hosting alike. The main level includes a stunning kitchen with white

  Virginia Corbett eXp Realty

  5 3rd St, Milton, NY 12547
• 

  /2

  $70,000

  • Land
  • 0.11 Acre
  • $636,364 per Acre

  83 N Bridge St, Poughkeepsie, NY 12601

  Vacant Land, Can build a 3 family. Can possibly put in an application (variance) prior to building for main street zoning and build a four family plus a store.

  Rita White Keller Williams Realty Partner

  83 N Bridge St, Poughkeepsie, NY 12601

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