Dutchess County NY Homes under $300,000

/44
$275,000
- 2 Beds
- 2 Baths
- 1,836 Sq Ft
3465 Route 22, Dover Plains, NY 12522

Experience serene country living at 3465 Route 22, Dover Plains, NY 12522! This spacious, well-maintained ranch-style home offers the perfect blend of comfort and style, set back from the road for privacy and boasting breathtaking panoramic views of the surrounding Hudson Valley landscape. Step inside to discover a bright and inviting living room, complete with a cozy fireplace—perfect for

Omar Harper

Epique Realty

(845) 599-0147

3465 Route 22, Dover Plains, NY 12522
/24
$225,000
- 2 Beds
- 1 Bath
- 1,396 Sq Ft
79 Powder House Rd, Amenia, NY 12501

Step back in time to the 1860s with this charming, well-preserved home, lovingly cared for by the current owners for the past 39 years. Key updates include a durable metal roof and a new furnace, both installed in 2018, and a recently added hot water heater from 2022.The original two-story structure boasts spacious rooms, and a thoughtfully designed living room addition (21x13) was incorporated

Larry Havens

Havens Real Estate

(845) 482-0516

79 Powder House Rd, Amenia, NY 12501
/28
$279,500 Open Sun 3PM - 6PM
- 2 Beds
- 2.5 Baths
- 1,356 Sq Ft
1807 Holly Walk, Poughkeepsie, NY 12603

Welcome to this 2 bedroom 2.5 bath townhome in the Fox Hill community! This charming two-story home offers both comfort and convenience, with prime off street parking located just outside your private rear gate. Spacious two-level living with a half bath on the main floor, the formal living with a dining area boast a sliding glass door that opens onto a private patio—perfect for enjoying your

Neeta Gupta

Fathom Realty NY LLC

(845) 599-1232

1807 Holly Walk, Poughkeepsie, NY 12603
/15
$215,000
- Land
- 9 Acres
- $23,395 per Acre
0 Kent Rd Unit 20252538, Amenia, NY 12592

Welcome to 9.19 acres of rolling meadow, offering breathtaking vistas of the Eastern Dutchess County countryside. Tucked away from the road, this peaceful and private setting provides the perfect canvas for your dream home.Whether you're envisioning a simple retreat, a working farm, or a lush garden oasis, this land supports a wide range of possibilities.Enjoy easy access to Metro-North,

Larry Havens

Havens Real Estate

(845) 442-1853

0 Kent Rd Unit 20252538, Amenia, NY 12592
/11
$215,000
- Land
- 9 Acres
- $23,395 per Acre
0 Kent Rd Unit KEY882325, Amenia, NY 12592

9.19 versatile acres with remarkable vistas of the gorgeous Eastern Dutchess County countryside. At the moment you will have the ability to select a site for your dream home on this open rolling open meadow. Offering privacy and set well off the road the ideal homesite welcomes your vision and ingenuity.This parcel is currently being used as a hayfield; however, your horticultural and

Larry Havens

Havens Real Estate

(845) 439-2876

0 Kent Rd Unit KEY882325, Amenia, NY 12592
/7
$229,000
- Land
- 5.00 Acres
- $45,800 per Acre
Lot # 5 Smithfield Rd, Millerton, NY 12546

Welcome to Smithfield Road—where open meadows, gentle woodlands, and sweeping pastoral views create the perfect setting for your dream home. With BOHA approval already in place on this 5-acre parcel, you're one step closer to building your own Hudson Valley retreat.A bit of strategic clearing will unlock even more beauty and possibility. This peaceful location feels worlds away, yet it's just

Larry Havens

Havens Real Estate

(518) 656-0343

Lot # 5 Smithfield Rd, Millerton, NY 12546
/7
$229,000
- Land
- 5.00 Acres
- $45,800 per Acre
0 Smithfield Rd Unit KEY879008, North East, NY 12546

An exceptional location! This Smithfield Road setting is a combination of open meadow, with extraordinary vistas of the splendid pastoral countryside, light woodland and a patch that is overgrown. The potential increases enormously with a careful thinning of the excessive weeds etc. With 5 acres that is BOHA your dream home is much closer to a reality. This place is heaven on earth.Away from the

Larry Havens

Havens Real Estate

(518) 594-8105

0 Smithfield Rd Unit KEY879008, North East, NY 12546
/8
$225,000
- Land
- 24 Acres
- $9,418 per Acre
710 Smithfield Rd, Millerton, NY 12546

Expansive 23.89 Parcel in Millerton, NY! Prime Location with Endless Potential. Discover a rare opportunity to own 23.89 acres of raw, wooded land nestled in the scenic hills of Millerton, NY. This private and peaceful property offers a true escape with a mix of mature trees, rolling terrain, and the potential for a long-range view from the upper elevations. Perfect for building your dream home,

Rebecca Doh

W. Raveis Lifestyles Realty

(518) 667-9706

710 Smithfield Rd, Millerton, NY 12546
/28
$269,900
- 3 Beds
- 1.5 Baths
- 1,262 Sq Ft
164 Thompson St, Poughkeepsie, NY 12601

House is now Rented: No Showings. Affordable And Freshly Painted, With New Kitchen, Updated Bathrooms And New Engineered Flooring, Is This Three Bedroom, Two Bath Home. The First Floor Displays A Dual Entry Kitchen And Formal Living And Dining Rooms While The Upper Level Features Three Bedrooms. This Two Story Home Grants A Bathroom On Each Level. There's A Fenced In Backyard Allowing A Healthy

Joyce Stanton

Century 21 Hudson Valley Rlty.

(845) 581-3471

164 Thompson St, Poughkeepsie, NY 12601
/32
$299,900
- 3 Beds
- 1.5 Baths
- 2,068 Sq Ft
107 Garden St, Poughkeepsie, NY 12601

House is now Rented: No Showings. Price Reduced! Affordable, Multi Level Brick Home For Sale Offering Three Bedrooms, Two Baths, Formal Living And Dining Rooms, Eat In Kitchen With Large Pantry And Driveway With Parking Pad In Back. Needing Some TLC, This Home Is Being Sold As Is With A Combination Of Ceramic Tiled, Hardwood And Laminate Floors. There May Be A Potential For Additional Living

Joyce Stanton

Century 21 Hudson Valley Rlty.

(845) 704-4815

107 Garden St, Poughkeepsie, NY 12601
/14
$285,000
- Land
- 9 Acres
- $32,872 per Acre
3362 New York 199, Pine Plains, NY 12567

Here is an opportunity for you to build your dream home.8.67 acres of land in Pine Plain in Dutchess County, New York is for sale. This exceptional property is situated behind a 70-foot road frontage on Route 199.Key Features:Location: Pine Plains in Dutchess County, New YorkLand Size: 8.67 acresAccess: 70 feet of road frontage on Route 199Amenities: Cleared

Community Lands

3362 New York 199, Pine Plains, NY 12567
/32
$247,000
- Land
- 25 Acres
- $9,860 per Acre
00WP Rossway Rd, Pleasant Valley, NY 12569

Welcome to your idyllic escape in the beautiful Hudson Valley town of Pleasant Valley, NY! This exceptional piece of property is a hidden gem, offering unmatched privacy and an abundance of natural beauty. Spanning acres of mixed hardwood and softwood species, the land is a harmonious blend of lush greenery and scenic vistas, providing the perfect backdrop for your dream project. Whether

Mitchell Serlin WHITETAIL PROPERTIES REAL ESTATE LLC (NY)

00WP Rossway Rd, Pleasant Valley, NY 12569
/20
$299,900
- 3 Beds
- 1 Bath
- 967 Sq Ft
10 Amherst Rd, Red Hook, NY 12571

Charming 3-Bedroom Home in a Prime Red Hook LocationNestled in a well-established and desirable neighborhood, this 3-bedroom, 1-bath home offers incredible potential and a fantastic opportunity for the right buyer. While it could benefit from some TLC, its solid bones and ideal location make it well worth the effort.Inside, you'll find hardwood floors, a spacious living and dining

Jason Walch Coldwell Banker Advisor Realty

10 Amherst Rd, Red Hook, NY 12571
/17
$299,900
- 3 Beds
- 1 Bath
- 904 Sq Ft
37 Shady Creek Rd, Pleasant Valley, NY 12569

Peaceful, Polished & Move-In Ready, this charming home is tucked away in the scenic Shady Creek community within minutes of Eastdale Village. Whether you’re looking for a weekend escape or a stylish starter home, this thoughtfully renovated ranch checks all the boxes. Inside, you’ll find a bright, open layout with three freshly painted bedrooms and new flooring throughout. The kitchen shines

Zef Camaj Corcoran Country Living

37 Shady Creek Rd, Pleasant Valley, NY 12569
/23
$299,900
- 3 Beds
- 1.5 Baths
- 1,620 Sq Ft
20 Manor Rd, Rhinebeck, NY 12572

HOME IS IN NEED OF MAJOR RENOVATION ON ITS LOWER LEVEL WHERE DUE TO A WATER LEAK THERE IS A POTENTIAL MOLD CONCERN. THE LOWER LEVEL WAS ONCE HOME TO A LICENSED DAY CARE FOR CHILDREN WITH KITCHENETTE AND A HALF BATH. WITH ITS OWN ENTRANCE IT MAY LEND WELL TO A POTENTIAL MOTHER/DAUGHTER. THE HARDWOOD FLOORS COULD BE SANDED DOWN AND REFINISHED SHOWING SIGNS OF SLIGHT BUCKLING FROM THE WATER. THERE

EDWIN MCNIFF JR. McNiff Real Estate LTD

20 Manor Rd, Rhinebeck, NY 12572
/64
$285,000
- 2 Beds
- 1 Bath
- 1,235 Sq Ft
100 White Schoolhouse Rd, Temple, ME 04984

Calling All Preppers and Homesteaders: Your Off-Grid Paradise Awaits! 🌲🏡 If you're dreaming of total privacy, escaping the chaos of the world, and embracing nature without sacrificing modern comforts—this TURN KEY FURNISHED mountaintop gem in Maine is your dream come true!🛖 Surrounded by thousands of acres of pristine forest, this home offers nothing but peace,

Wendy Pelletier Meservier & Associates

100 White Schoolhouse Rd, Temple, ME 04984
/23
$299,999
- 4 Beds
- 1 Bath
- 1,292 Sq Ft
17 Henmond Blvd, Poughkeepsie, NY 12603

Welcome to 17 Henmond Blvd, a classic Hudson Valley Cape Cod-style home. When you first walk in you'll notice the hardwood floors and large living area.Two bedrooms and one full bath on the first floor, a large kitchen and dining area off the back with sliding glass doors that lead to a deck.Upstairs you have sizable bedrooms and storage spaceDownstairs, you have a full

Vincent Reda Keller Williams Realty

17 Henmond Blvd, Poughkeepsie, NY 12603
/22
$270,000
- 4 Beds
- 1.5 Baths
- 1,356 Sq Ft
16 Eastman Terrace, Poughkeepsie, NY 12601

Welcome to this inviting two-story home located on a quiet street walking distance to the park! As you enter you'll notice the original hardwood floors adding plenty of character to the home. Upstairs features 3 large sized bedrooms, and a full bathroom that has been recently updated with new tile floor. Enjoy outdoor activity In the backyard, or spending your mornings and evenings out on the

Matthew Skowronski HomeSmart Homes & Estates

16 Eastman Terrace, Poughkeepsie, NY 12601
/22
$299,000 Open Sat 12PM - 3PM
- 3 Beds
- 1 Bath
- 1,395 Sq Ft
9 Kinderhook Dr, Poughkeepsie, NY 12603

PRICE SLASHED!!! Adorable cape cod style home in desirable neighborhood in Spackenkill Schools! This has 3 bedrooms and 1 full bathroom, a full basement, an enclosed porch used as a second living room, and a spacious and private flat backyard. Public water and sewer with forced air heating and central AC. Finished attic is 3rd bedroom and has a window AC unit to keep it cool. Large back deck

Lance Pahucki RE/MAX Town & Country

9 Kinderhook Dr, Poughkeepsie, NY 12603
/27
$275,000
- 2 Beds
- 1.5 Baths
- 1,020 Sq Ft
19 Albany St, Poughkeepsie, NY 12601

Charming Two-Story in the heart of Poughkeepsie, minutes to the vibrant Waterfront district. Home features 2 beds. 1.5 baths, luxury laminate plank flooring throughout the first floor, central air, high efficiency gas fired furnace, updated kitchen with granite countertops and SS appliances, first floor laundry room and two well sized bedrooms with updated full bath. Municipal water, sewer and

Justin LaFalce KW MidHudson

19 Albany St, Poughkeepsie, NY 12601
/4
$280,000
- 3 Beds
- 1 Bath
- 1,520 Sq Ft
88 Velie Rd, Lagrangeville, NY 12540

CALLING ALL INVESTORS!!! or BUYERS looking to build their dream home. Versatile 8.4-acre property with endless possibilities and potential for subdivision. This expansive parcel caters to a range of uses. Close to parkway, shops, schools and transportation. Featuring a stream at the back and privacy. The property includes a shed, septic, well, and electrical (not on). Hard work done. Ideal for a

SUSAN GIGI RESTA Century 21 Alliance Realty Grp

88 Velie Rd, Lagrangeville, NY 12540
/9
$280,000
- 4 Beds
- 3.5 Baths
- 3,178 Sq Ft
16 Bethlehem Place, Poughkeepsie, NY 12603

Four bedroom, 3.5 Bathroom home in Hyde Park School District in the Town of Poughkeepsie on 0.58 acres! Wooded back yard. Configured with an accessory apartment building department says property is only a legal single family. Great opportunity to get in to the market and build sweat equity. Close to shopping, schools and amenities. Sold as-is. Buyer to pay NYS and any local transfer

Brian Smith River Realty Services, Inc.

16 Bethlehem Place, Poughkeepsie, NY 12603
/25
$210,000
- Land
- 14 Acres
- $14,685 per Acre
0 Medwyn Ln Unit 20253322, Red Hook, NY 12571

A rare opportunity to own premium buildable land in one of Red Hook's most desirable private communities. Multiple lots are available, with the option to purchase one or all, totaling 14 acres of scenic Hudson Valley landscape. Each lot offers access to a private lake and is set within a peaceful, natural environment just minutes from the charm of Red Hook Village. Design and build with

Charlie Brassard Mahar Real Estate, LLC

0 Medwyn Ln Unit 20253322, Red Hook, NY 12571
/13
$230,000
- Land
- 19 Acres
- $11,856 per Acre
A Skunks Misery Rd, Millerton, NY 12546

Stunning 19.4 Acres – Estate Setting on a Premier Country RoadDiscover the perfect blend of natural beauty and refined location with this 19.4-acre parcel situated on a picturesque country road, renowned for its stately homes and rural charm.With multiple elevated building sites, long road frontage, and sweeping view potential, this property offers endless opportunities. Explore

Robert Dunlop Havens Real Estate

A Skunks Misery Rd, Millerton, NY 12546
/9
$275,000
- Land
- 15 Acres
- $17,776 per Acre
0 Cricket Hill Rd, Wingdale, NY 12594

This land is ready for you to fulfill your dreams. 15.47 acres in a pastoral setting. With multiple potential hilltop building sites, choose your view from awe inspiring western sunsets to eastern mountain views overlooking the Ten Mile River. There is plenty of room up top to build your country escape and fulfill your dreams, whether it is adding a barn for a small hobby farm, avid collector,

Brian McGrath McGrath Realty Inc

0 Cricket Hill Rd, Wingdale, NY 12594
/33
$235,000
- 2 Beds
- 1 Bath
- 1,030 Sq Ft
33 Scarborough Ln Unit C, Wappingers Falls, NY 12590

Welcome to this bright and inviting 2-bedroom, 1-bath condo located in the highly desirable Pavilion Complex. This well-maintained home features a spacious living area perfect for relaxing or entertaining, and the convenience of an in-unit washer and dryer. Enjoy access to fantastic community amenities including a swimming pool, park, tennis court, and playground, ideal for both leisure and an

Jeliana Melendez Christie's Int. Real Estate

33 Scarborough Ln Unit C, Wappingers Falls, NY 12590
/20
$225,500
- 1 Bed
- 1 Bath
- 610 Sq Ft
1 Colonial Rd Unit 127, Beacon, NY 12508

Welcome to 1 Colonial Rd, Unit 127 – Beacon, NY! This freshly painted and professionally cleaned 1-bedroom, 1-bath condo is located in a highly desirable and peaceful community in Beacon. Enjoy the best of both worlds—quiet surroundings with easy access to nearby dining, shopping, and just steps from the local golf course. Conveniently located minutes from I-84 and the Beacon Metro-North

Ling Han Century 21 Alliance Rlty Group

1 Colonial Rd Unit 127, Beacon, NY 12508
/6
$285,000
- Land
- 0.81 Acre
- $351,852 per Acre
16 Kingwood Ln, Spackenkill, NY 12601

Attention all builders and end users! One of the last building lots in all of the Spackenkill School District. Situated in the highly desirable and prestigious Kingwood Park, it’s the last cul-de-sac lot on Kingwood Lane. Surrounded by $1M+ homes with access to town water and sewer on just under an acre. This lot has amazing walk-out potential. Come build your dream home today!

Justin LaFalce KW MidHudson

16 Kingwood Ln, Spackenkill, NY 12601
/4
$220,000
- Land
- 3.00 Acres
- $73,333 per Acre
301 Mountain View Rd, Clinton Corners, NY 12514

A wonderful 3 acre building lot on beautiful Mountain View Road , Cleared with driveway in and BOHA in progress . A park like setting Read to build property is 12 minutes from Rhinebeck and 10 minutes from Taconic Parkway at Slate Quarry Mountain View is a scenic road with many high end homes .Rhinebeck Schools

Thomas LeGrand LeGrand Real Estate, Inc.

301 Mountain View Rd, Clinton Corners, NY 12514
/5
$300,000
- Land
- 3.60 Acres
- $83,333 per Acre
1209 Route 9g, Hyde Park, NY 12538

Commercial opportunity in East Park Business District, Hyde Park NY. This business district is mixed with commercial and residential perfect location for your business to be a part of the community.

Jennifer LaDuca BHHS Hudson Valley Properties

1209 Route 9g, Hyde Park, NY 12538
/4
$200,000
- 2 Beds
- 1 Bath
- 840 Sq Ft
32 Givens Ln, Fishkill, NY 12524

Unleash the potential of this home, situated on a quiet street and only steps from all that Fishkill's charming Main Street has to offer. The flag property (30 Givens) is also for sale, providing you with endless opportunity to expand and create your dream home. Bring your tools and your imagination. Don't let this rare opportunity pass you by!

Kathleen Carey Joncar Realty Inc

32 Givens Ln, Fishkill, NY 12524
/4
$200,000
- 1,176 Sq Ft
52 N Center St, Millerton, NY 12546

Opportunity knocks with this 1,176 sq ft as-is village home, perfect for investors or rehab-minded buyers. The existing structure is a shell—no floors inside—offering a clean slate for your custom renovation or flip. Electric, water, and septic systems are already in place, saving you time and cost on infrastructure. Located in a quiet village setting, this property has no driveway and requires a

Arleen Shepley Elyse Harney Real Estate

52 N Center St, Millerton, NY 12546
/12
$250,000
- Land
- 5 Acres
- $46,642 per Acre
51 Kirby Hill Rd, Pawling, NY 12564

Down a winding country road, across the street from 350 acres of hiking trails and just 10 minutes from the heart of Pawling, this 5.36-acre parcel offers a rare blend of readiness and wildness. This is the kind of place where ideas can take shape beneath a canopy of oaks and mountain laurel. The elevated, partially cleared build site holds promise for views, with a roughed-in driveway already

Donna Kennedy Keller Williams Prestige Prop

51 Kirby Hill Rd, Pawling, NY 12564
/6
$220,000
- Land
- 2.80 Acres
- $78,571 per Acre
301 Mountain View Rd, Rhinebeck, NY 12572

2.8 acre building lot on picturesque Mountain View road , Lot formerly had a large mobile home and several sheds all were removed and lot restored ,Driveway is in and plans are submitted to health department for a new septic system . Additionally I am applying to the town for a side yard variance to allow construction . The variance and the health department approval will be delivered at closing.

Thomas LeGrand LeGrand Real Estate, Inc.

301 Mountain View Rd, Rhinebeck, NY 12572
/22
$299,000
- 2 Beds
- 1.5 Baths
- 1,000 Sq Ft
95 van Vlack Rd, Hopewell Junction, NY 12533

HANDYMAN SPECIAL! Calling all investors or owner occupiers looking for some sweat equity! Step inside and explore this hidden gem in the highly sought after Wappingers school district! This ranch style home sits on a 1.8 acre lot and features 2 beds, 1 full bath, open dinning room/living room and a screened in porch. Major upgrades have already been started with brand-new windows (complete with

Justin LaFalce KW MidHudson

95 van Vlack Rd, Hopewell Junction, NY 12533
/12
$217,000
- 3 Beds
- 1.5 Baths
- 1,248 Sq Ft
47 Gifford Ave, Poughkeepsie, NY 12601

Use your imagination and do a little improving. Lacks closets but can work them in. Centrally located, close to train station and restaurant.. Vacant....Municipal services.

JOAN PEDATELLA BHHS Hudson Valley Properties

47 Gifford Ave, Poughkeepsie, NY 12601
/28
$300,000
- 3 Beds
- 1 Bath
- 875 Sq Ft
31 Peter Cooper Dr, Poughkeepsie, NY 12601

Charming and well-maintained one-level ranch located in the Hyde Park Central School District. This 3-bedroom, 1-bathroom vinyl-sided home offers comfortable single-level living with an inviting eat-in kitchen featuring newer appliances. Enjoy abundant natural light through the large bay window in the living room. Updates include replacement windows, a LeafFilter gutter guard system, and central

Gregory Pikor Inspire Realty

31 Peter Cooper Dr, Poughkeepsie, NY 12601
/37
$299,900
- 2 Beds
- 1.5 Baths
- 1,220 Sq Ft
13 Knightsbridge Unit G, Poughkeepsie, NY 12603

Beautifully renovated two-bedroom, second floor condo located at the Commons at Cedar on Poughkeepsie’s lovely, highly desirable southside. As you step inside, you are greeted by elegant crown molding, a ceramic tile entry and a pleasing open layout. Sunlight streams in through the sliding glass doors which lead to an east-facing, private balcony buffered by woods; the perfect spot to sit and

Lori Rheingold

13 Knightsbridge Unit G, Poughkeepsie, NY 12603
/9
$225,000
- 1 Bed
- 1 Bath
- 798 Sq Ft
57 van Vlack Rd, Hopewell Junction, NY 12533

Tucked away at the end of a dirt driveway you'll find this one bedroom one bath ranch/rambler home that sits on a serene and spacious 1.82 acre park-like setting. Surrounded by nature and mature trees, the property offers a peaceful retreat with room to garden or simply enjoy the tranquility of the outdoors. The home does need a good amount of love/work, but if you've been looking for a place to

Anthony DeGelormo Century 21 Alliance Rlty Group

57 van Vlack Rd, Hopewell Junction, NY 12533
/26
$299,900
- 2 Beds
- 1 Bath
- 875 Sq Ft
46 van Wyck Dr, Poughkeepsie, NY 12601

The beautiful plantings, lovely rose bushes, cozy front porch and flagstone walkway are sure to catch your eye. What great curb appeal. Adorable, affordable, one level living. As you step inside, you are welcomed into a spacious living room flooded with natural light from the west-facing picture window. From the living room, enjoy full view into the kitchen which offers loads of cabinetry,

Lori Rheingold

46 van Wyck Dr, Poughkeepsie, NY 12601

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