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Explore Similar Apartments Within 2 Miles of Highland, NY

  • /29

    $465,000

    • 6 Beds
    • 2 Baths
    • 2,112 Sq Ft

    57 Smith St, Poughkeepsie, NY 12601

    Excellent 2 Family Investment Opportunity! Live in one unit and rent the other, or rent out both for maximum income potential. Recent exterior upgrades include a new roof, vinyl siding, and renovated front and back porches. Interior improvements feature a new heating system and hot water heaters.The first unit offers 2 bedrooms, a spacious living and dining room and 1 full bathroom.

    Agent Photo

    YOLANDA MENDOZA

    Century 21 Hudson Valley Rlty.

    (845) 576-9945

    57 Smith St, Poughkeepsie, NY 12601
  • /40

    $424,000

    • 6 Beds
    • 2 Baths

    52 Catharine St, Poughkeepsie, NY 12601

    Two Family Home Consisting Of Three Bedroom, One Bath Apartments With Separate Utilities (Gas And Electric.). Each Unit Has A Combination Of Ceramic Tiled And Laminate Floors. Updates Include New Electric, New Furnaces, New Plumbing, New Roof And Updated Windows Throughout. There Is A Walkup Attic, Basement With Interior And Exterior Access Plus A Driveway Allowing Off The Street Parking. There

    Agent Photo

    Joyce Stanton

    Century 21 Hudson Valley Rlty.

    (845) 402-2134

    52 Catharine St, Poughkeepsie, NY 12601
  • /47

    $549,000

    • 6 Beds
    • 4 Baths

    29 Lake St, Poughkeepsie, NY 12601

    Prime Investment Opportunity!! Spacious 3-Family in High-Demand Location. This is your chance to own a versatile, income generating multi-family property in one of the area’s most sought after neighborhoods! Whether you’re a seasoned investor looking to expand your portfolio or a buyer seeking to live in one unit while renting the others, this solid 3-family home offers the perfect blend of

    Marie Savage Curasi Realty, Inc.

    29 Lake St, Poughkeepsie, NY 12601
  • /33

    $399,900 Open Sun 11AM - 1PM

    • 6 Beds
    • 2 Baths
    • 3,222 Sq Ft

    26 Balding Ave, Poughkeepsie, NY 12601

    Welcome to 26 Balding Avenue! a well-maintained duplex offering two spacious 3-bedroom units, each designed for comfort and convenience. This property comes with a bonus attic space with limitless Potential! Both units feature in-unit washer/dryers, generous living space, and functional layouts ideal for long-term tenancy. Whether you're an investor seeking immediate cash flow or an

    Kason Fearon Serhant LLC

    26 Balding Ave, Poughkeepsie, NY 12601
  • /13

    $390,000

    • 6 Beds
    • 2 Baths

    28 Hammersley Ave, Poughkeepsie, NY 12601

    Calling all investors... 2 large 3 bedroom units, with a very large walk up attic that has the potential to be converted into a 3rd unit if City permits. 1st floor with 3 bedrooms with newer kitchen cabinets, counter tops, backsplash, flooring & appliances, newer vanity, sink, toilet & floor in bathroom. 2nd floor has 3 bedrooms, Rents are $1700 per unit, newer kitchen cabinets, countertop, floor

    Mark Snyder eXp Realty

    28 Hammersley Ave, Poughkeepsie, NY 12601
  • /8

    $249,900

    • 2 Beds
    • 2 Baths
    • 1,405 Sq Ft

    45 Delafield St, Poughkeepsie, NY 12601

    Two family duplex located in the City of Poughkeepsie, separate utilities. This brick structure has a one car garage with a cute rear yard and plenty of parking which is a big deal in this area. Come see this multi-family home. Please be kind to the tenants.

    Kimberlee Markarian BHHS Hudson Valley Properties

    45 Delafield St, Poughkeepsie, NY 12601
  • /2

    $525,000

    • 1 Bed
    • 1 Bath
    • 4,650 Sq Ft

    61 Franklin St, Poughkeepsie, NY 12601

    Four family frame building with adjoining lot with garage and off-street parking. Corner location on South Avenue and Franklin Streets. Four one-bedroom apartments 750 sf each. Listing broker is owner of the property.

    Mark Raphael River Realty Services, Inc.

    61 Franklin St, Poughkeepsie, NY 12601
  • /2

    $385,000

    • 4 Beds
    • 2 Baths
    • 2,200 Sq Ft

    69 Delafield St, Poughkeepsie, NY 12601

    **MULTIPLE OFFER SITUATION, SELLER REQUESTING HIGHEST AND BEST OFFERS DUE BY FRIDAY, 7/25/25 AT 5 PM** Large two-family house with 650 sq ft. two car garage in desirable area close to Marist University, Route 9 and Railroad Bridge. Rents under market--room to increase. Large front deck and separate den off kitchen on 2nd floor. Full basement and attic. Listing broker is owner of the property.

    Mark Raphael River Realty Services, Inc.

    69 Delafield St, Poughkeepsie, NY 12601
  • /13

    $375,000

    • 7 Beds
    • 2 Baths
    • 2,000 Sq Ft

    117 Talmadge St, Poughkeepsie, NY 12601

    Duplex in the heart of Poughkeepsie on a quiet street. Unit 1 renovated in 2018 with stainless steel appliances. Unit 2 is newly renovated with new kitchen cabinets, quartz countertops, new bathroom, vynl flooring and carpet in the bedrooms. Property line goes down the middle of the shared driveway. The backyard could be used as private parking if needed. Unit 1 has direct access to backyard but

    Maritza Soto eXp Realty

    117 Talmadge St, Poughkeepsie, NY 12601
  • /17

    $565,000

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

    5 Jefferson St, Poughkeepsie, NY 12601

    Historic Union Street neighborhood 3-unit investment property. This exquisite multifamily property, originally built in 1890, presents an opportunity for multi-family investors. Approximately 2,200 SF with three units, the property stands as an epitome of historic charm at the entrance of the City of Poughkeepsie just over the Mid Hudson Bridge. This gem in the heart of Poughkeepsie is a

    Brian Mossey BHHS Hudson Valley Properties

    5 Jefferson St, Poughkeepsie, NY 12601
  • /17

    $450,000

    • 4 Beds
    • 2 Baths
    • 2,080 Sq Ft

    190 Union St, Poughkeepsie, NY 12601

    Historic Union Street brick 2-unit investment property. This charming multifamily property, originally built in 1870, offers a fantastic investment opportunity in the sought-after Poughkeepsie neighborhood. With 2,080 SF, the building features two units on three levels. This fully leased gem is an attractive prospect for multi-family investors. The property boasts a long-standing history and a

    Brian Mossey BHHS Hudson Valley Properties

    190 Union St, Poughkeepsie, NY 12601
  • /37

    $575,000

    • 6 Beds
    • 4 Baths
    • 2,665 Sq Ft

    15 Albany St, Poughkeepsie, NY 12601

    CALLING ALL INVESTORS OR OWNER OCCUPIERS! Amazing opportunity to own a legal 4-Family in the heart of Poughkeepsie, just outside of the Waterfront District. Home consists of (2) 1 bedroom/1 bath units and (2) 2 bedroom/1 bath units. Potential gross income of almost $77K a year, all separate utilities, 4 gas meters and 5 electric meters. Most deferred maintenance has been handled over the years

    Justin LaFalce KW MidHudson

    15 Albany St, 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
  • /12

    $399,900

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

    34 High St, Poughkeepsie, NY 12601

    This beautiful 2 family home is located on a quiet street in the heart of Poughkeepsie. Both units have been very nicely updated. Stainless steel appliances, granite countertops, freshly painted, lots of recessed lighting, new roof, new flooring, too many updates to list. Tenants pay the seperated utilities. Both apartments are 2 bedrooms but the upstairs apartment has a bonus, office/nursery off

    JEFFREY COLTON Jeff S. Colton

    34 High St, Poughkeepsie, NY 12601
  • /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
  • /18

    $309,000

    • 2 Beds
    • 2 Baths

    13 Hooker Ave, Poughkeepsie, NY 12601

    Charming duplex located on Poughkeepsie's South Side, this home is just steps from parks, schools, and local shops. Easy access to Route 9, I-84, and Metro-North for commuters.Perfect for rental income or off set your mortgage by living in one unit while renting the other!

    Kali Markowski K. Fortuna Realty, Inc.

    13 Hooker Ave, Poughkeepsie, NY 12601
  • /22

    $490,000

    • 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

    $560,000

    • 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
  • /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
  • /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
  • /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
  • /40

    $415,000

    • 4 Beds
    • 2 Baths
    • 1,672 Sq Ft

    125 South Ave, Poughkeepsie, NY 12601

    AO-7/1/2025. Welcome to this well-maintained 2-family townhome style, side by side offering exceptional space, comfort, and convenience. Each unit features 2 generously sized bedrooms and 1 full bath, with a bright and airy layout perfect for modern living. Enjoy the convenience of separate utilities and private laundry setups, ensuring maximum privacy and flexibility for owners and tenants

    CHRISTOPHER HARDISTY Sams Realty

    125 South Ave, Poughkeepsie, NY 12601
  • /13

    $449,900

    • 4 Beds
    • 2 Baths
    • 2,400 Sq Ft

    10 Fox Terrace, Poughkeepsie, NY 12603

    Excellent investment! Reduced and Turn key! Legal 2 Family home. Many Possibilities-Live in and rent 2nd unit for monthly income- Perfect for In-law living, Or rent out both units as full investment property and have double the monthly income! Excellent condition and mechanicals, totally renovated interior and exterior, top to bottom. Nice back yard. Large covered front porch. Appliances all

    Lynn Simmons Dixon Smith Realty

    10 Fox Terrace, Poughkeepsie, NY 12603
  • /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
  • /7

    $510,000

    • 4 Beds
    • 2 Baths

    9 Lawrence Rd, Poughkeepsie, NY 12601

    Well maintained multi-family duplex fully rented in the City of Poughkeepsie. Property was totally renovated in 2007. Each unit has gleaming hardwood floors in living room and dinning room. Each unit has two average size bedrooms, nice size Kitchen w/granite counter tops and stainless steel appliances. Second floor unit features enclosed porch. Detached single car garage for off street

    Tijuana Vann Century 21 Alliance Rlty Group

    9 Lawrence Rd, Poughkeepsie, NY 12601
  • /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
  • /18

    $349,000

    • 2 Beds
    • 2 Baths
    • 992 Sq Ft

    451 New Paltz Rd, Highland, NY 12528

    INVESTMENT PROPERTYThis 2 family property is conveniently located in Highland. Less than 10 minutes to the Village of New Paltz, and 15 minutes to the Mid-Hudson bridge.The location is just steps away from the Hudson Valley Rail Trail, which is a 7 mile paved trail from the Walkway over the Hudson to New Paltz.Each unit is a one bedroom one bath apartment. Private parking lot has ample space for

    Jaynie Aristeo Ridgeline Realty

    451 New Paltz Rd, Highland, NY 12528
  • /22

    $385,000

    • 6 Beds
    • 2 Baths
    • 2,452 Sq Ft

    1 Gray St, Poughkeepsie, NY 12603

    PERFECT CHOICE FOR OWNER OR INVESTOR! GROUND FLOOR APARTMENT IS VACANT, MOVE IN AND COLLECT THE RENT ON THE UPSTAIRS LEASED UNIT.BOTH UNITS FEATURE 3 NICE SIZE BEDROOMS, AN EAT IN KITCHEN, LIVING ROOM AND FULL BATH. SECOND STAIRCASE IN THE BACK GIVES DIRECT ACCESS TO A FENCED IN BACKYARD. AMPLE PARKING IN THE DRIVEWAY PLUS ONE CAR GARAGE. HOUSE HAS FULL WALK-OUT BASEMENT AND A WALK-UP ATTIC.

    Hana Kogan Mark One Real Estate

    1 Gray St, Poughkeepsie, NY 12603
  • /4

    $550,000

    • 9 Beds
    • 3 Baths
    • 3,576 Sq Ft

    58 Lincoln Ave, Poughkeepsie, NY 12601

    High-Yield 3-Unit Investment Property Near Vassar Brothers Medical Center. *1031 Exchange Buyers - ask about our 13 Door Package deal with this property. Investors, take advantage of this prime multi-family opportunity at 58 Lincoln Avenue, Poughkeepsie, NY 12601. This fully occupied 3-unit property features three spacious 3-bedroom apartments, currently generating $57,000 in gross annual

    Curtis Darragh Legacy Land & Homes LLC

    58 Lincoln Ave, Poughkeepsie, NY 12601
  • /33

    $549,000

    • 6 Beds
    • 4 Baths
    • 6,418 Sq Ft

    25 Dwight St, Poughkeepsie, NY 12601

    This Circa 1900 Grand Lady, Original Schwartz Brothers Mansion is the epitome of historical and architectural detail. Majestically set on a stately corner lot in the heart of the prime south side Historic District, featuring historical street markers and boasting notable mentions on the Walkway Over The Hudson as well as the Poughkeepsie Library. This fabulous investor opportunity or

    Andi Berisha BHHS Hudson Valley Properties

    25 Dwight St, Poughkeepsie, NY 12601
  • /16

    $400,000

    • 3 Beds
    • 1 Bath
    • 3,976 Sq Ft

    59 Montgomery St, Poughkeepsie, NY 12601

    Fantastic Opportunity for business and/or residential! Multiple possibilities abound with great space and off street parking. 3 floors, 2 car detached garage, 3+ BR, living room, dining room, kitchen, Current use business first level with residential above. Architect, private practice, daycare are just a few of the permitted uses. Close to route 9, trains and hospitals. Great visibility in

    Candice Ryu BHHS Hudson Valley Properties

    59 Montgomery St, Poughkeepsie, NY 12601
  • /19

    $425,000

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

    94 Academy St, Poughkeepsie, NY 12601

    Centrally located City of Poughkeepsie multi-family featuring two spacious 3 bedroom units. Second floor unit includes renovated kitchen & bathroom, new flooring throughout & new furnace. Separate utilities w/gas furnaces & electric water heaters. Front porches and fenced backyard for outdoor enjoyment. Located just minutes from schools, shopping, dining, commuter routes, Poughkeepsie waterfront

    Dan Axtmann BHHS Hudson Valley Properties

    94 Academy St, Poughkeepsie, NY 12601
  • /6

    $480,000

    • 2 Beds
    • 2 Baths
    • 2,112 Sq Ft

    55 Smith St, Poughkeepsie, NY 12601

    City of Poughkeepsie multi-family with two well proportioned 2 bedroom units. Units feature hardwood floors, spacious kitchens w/walk-in pantry & tile bathrooms. Separate utilities. Newer gas boiler & furnace. Fully fenced backyard for outdoor enjoyment plus large screened porches on front. Centrally located just minutes from schools, shopping, dining, commuter routes, Poughkeepsie waterfront &

    Dan Axtmann BHHS Hudson Valley Properties

    55 Smith St, Poughkeepsie, NY 12601

Why Live in Highland

Highland, a hamlet in Ulster County, is nestled between the Shawangunk Mountains and the Hudson River, offering a blend of rural and suburban living. Founded in 1754, it features the world’s longest pedestrian bridge, The Walkway Over the Hudson, providing stunning river views and hosting events like summer music series and the Hudson Valley Marathon. The area is known for its vibrant community, with a bustling main street along Vineyard Avenue, and is a popular spot for those seeking a small-town lifestyle with easy access to New York City via a 2.5-hour train ride from Poughkeepsie. Highland offers numerous things to do, including exploring the Hudson Valley Rail Trail, visiting the Caboose Gallery, and enjoying riverside parks like Highland Landing and Berean Park, which offers swimming, a playground, and sports courts. The hamlet is surrounded by farmland and mountains, providing seasonal activities such as apple picking at Dubois Farms and wine tastings at local vineyards. The Highland Central School District serves the community, with Highland Primary School and Highland High School both receiving high ratings. Housing options range from condos and townhouses to historic Victorians and modern custom-built homes, with some properties prone to flooding near Twaalfskill Creek. Local amenities include mom-and-pop shops, cafes like Underground Coffee & Ales, and the Knaus Gallery & Wine Bar. For larger shopping needs, residents can visit Bridgeview Plaza or the Poughkeepsie Galleria. Highland is safer than the national average, and while many residents rely on personal vehicles, the area is bike-friendly with access to public transit.

Home Trends in Highland, NY

Housing Trends

Median Sale Price
$380,000
Median Single Family Sale Price
$413,000
Median Townhouse Sale Price
$340,000
Median 2 Bedroom Sale Price
$292,000
Average Price Per Sq Ft
$275
Number of Homes for Sale
12
Last 12 months Home Sales
63
Months of Supply
2.30
Median List Price
$399,000
Median Change From 1st List Price
1%
Median Home Sale Price YoY Change
14%
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