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$5,750,000
4 Beds 3 Baths 1048609 MLS
In a premier location on a quiet road in Millbrook Hunt country, this unique property of 100 acres has been in the same family for 44 years. Proudly maintained, protected and in conservation, Shooter’s Hill is an exceptional offering and an unparalleled opportunity to own and enjoy the tranquility of this magical sanctuary, yet only minutes from Millbrook Village, clubs, schools and other amenities. Nestled on a hillside, this four bedroom, three bath home overlooks beautiful meadows, farm fields, three masterly designed stepping ponds, and protected woodlands laced with extensive trails. Completing the homestead is a two story barn with an artist studio and a two-room office building with a three-car garage. Contiguous to Bontecou Wildlife Conservation Preserve of 1258 acres. *Some photos AI edited

81-85 Fraleigh Hill Road, Millbrook

$199,900
3 Beds 2 Baths 1049221 MLS
Nestled against NYS Taconic Park land, this older single-family home offers unlimited potential in an irreplaceable setting. Surrounded by 1.4 acres of lush, mature landscaping, the backyard borders a scenic trail linking the historic Ogden Mills Estate to the Norrie Point Environmental Center and Marina. Whether you are looking to create a lucrative short-term rental or craft a private retreat for buyers who appreciate nature and historic Hyde Park, the possibilities are endless. Enjoy year-round outdoor recreation right from your doorstep. Located in the quaint hamlet of Staatsburg—featuring a vibrant local library, basketball and pickleball courts, a renowned golf course, local dining, and a 10-minute drive to the train station. Unique location. Property is being sold as-is and awaits your vision!

10 Cedar Street, Staatsburg

$475,000
3 Beds 1 Baths 1048856 MLS
Welcome home to this charming 3-bedroom, 1-bath Cape, offering a wonderful blend of classic character and everyday comfort. The updated kitchen has plenty of cabinets and features a wall-mounted pot-filler faucet above the range so you can fill pots directly on the cooktop without carrying them from the sink. The six-burner range is heated by propane. The living room and bedrooms all have hardwood flooring. A full unfinished basement offers plenty of storage and potential for future use. Enjoy additional living space in the inviting enclosed porch—perfect for morning coffee, relaxing, or enjoying the seasons. Outside, a level yard provides plenty of room for gardening, play, or outdoor gatherings, while the detached garage offers convenient parking and additional storage. A delightful home in a welcoming setting—come see all it has to offer!

3 Kinderhook Drive, Poughkeepsie

$1,375,000
3 Beds 2 Baths 1049518 MLS
Built in 1787, this wonderfully preserved Hudson Valley farmhouse carries more than two centuries of history with an ease that feels remarkably livable today. Original details remain at the heart of the three-bedroom, two-bath home, set on just shy of 5 acres: wood floors, period hardware, a Dutch door with distinctive patty-pan hinges, exposed structural elements and a generous fireplace anchoring the main living space. These early details are complemented by a thoughtfully updated kitchen that feels clean and understated while remaining sympathetic to the architecture. Light moves beautifully through the house, while a generous screened porch extends the living space outdoors—a relaxed place for summer dinners, morning coffee and long afternoons overlooking the surrounding landscape. Outside, mature trees and established plantings frame the farmhouse, while an impressive original three-bay barn adds another layer of history, character and possibility. And while the setting feels wonderfully removed, it is anything but remote. Bard College and the center of Red Hook are just minutes away, with Rhinebeck and Hudson both within easy reach and Amtrak service from Rhinecliff providing a convenient connection to New York City. What makes this property particularly compelling is what hasn’t been erased. The craftsmanship, patina and wonderful irregularities of an 18th-century farmhouse remain, balanced by the comfort and simplicity of a home meant to be lived in now. A rare opportunity to become the next steward of a Hudson Valley farmhouse dating to 1787—Dutch door, patty-pan hinges, original barn and all.

101 Spring Lake Road, Red Hook

$289,000
3 Beds 2 Baths 1049009 MLS
Brand-New 2026 Living in Pleasant Valley. Welcome to 9 Odell Lane, a brand-new 2026 model offering modern finishes, generous living space, and effortless low-maintenance living. The bright, open-concept interior features a spacious kitchen with center island, contemporary cabinetry, recessed lighting, new appliances, and a clean, neutral design throughout. Outside, enjoy a generous yard framed by mature trees, providing plenty of space to relax, entertain, garden, or simply enjoy the outdoors. A spacious rear deck extends your living space outside, while the detached garage offers valuable additional parking, storage, or workspace. Located in a well-maintained community, the $838/month lot fee includes snow removal, garbage pickup, water & taxes, all while keeping you minutes from Pleasant Valley, Millbrook & LaGrange. New construction, modern comfort, and outdoor space—all without the maintenance of a traditional property. Schedule your private tour of 9 Odell Lane today!

9 Odell, Pleasant Valley

$895,000
3 Beds 2 Baths 1047613 MLS
Situated along Millbrook’s main avenue, this 1900s traditional home offers character and comfort, in an exceptional location. The first floor features a spacious kitchen, a light-filled living room with fireplace and an inviting dining room. A mudroom with laundry and a full bathroom completes this main level. Upstairs, you’ll find three bedrooms and a full bathroom. A walk-up attic and full basement provide abundant space for storage. Outside, a wonderful wraparound porch offers the perfect vantage point for enjoying the energy and charm of village life, including seasonal events and community gatherings. A rear deck overlooks the beautifully landscaped yard and gardens, creating a lovely setting for relaxing or entertaining. A detached garage and additional parking are conveniently accessed from a service road at the rear of the property, preserving the home’s pristine curb appeal along Franklin Avenue. Located just steps from the best of Millbrook, this home is an easy stroll to outdoor summer concerts, the Farmers’ Market, library, public tennis courts, parks, shops and restaurants. With convenient access to the nearby Metro-North station and Taconic Parkway, this could be the perfect weekend getaway or full time residence.

3315 Franklin Avenue, Millbrook

$695,000
4 Beds 2 Baths 1047901 MLS
Situated in the prestigious, historic hamlet of Quaker Hill, this exceptional property offers a rare blend of scale, privacy, & scenic beauty. Set well back from the road at the end of a long, sweeping driveway, the 6.57-acre setting borders the picturesque, rolling pastures of Akindale Thoroughbred Rescue. Offered for the first time in nearly 76 years, this is a rare opportunity to own a distinctive piece of Quaker Hill. The grounds feature soaring mature trees, a well-maintained lawn, & a stream running through the property, creating a beautiful pastoral setting & a truly tranquil retreat. For those seeking greater scale or additional investment potential, the adjacent 4.9-acre lot is also available, offering the opportunity to significantly expand the property’s footprint. Spanning 2,160 square feet, the classic 1950 Colonial features a four-bedroom, two-bath layout centered around a warm fireplace. An established vegetable garden sits just outside the door, ready for farm-to-table living, while a detached garage provides convenient parking & equipment storage. Pawling Village offers a walkable small-town center with local restaurants, shops, & community events just minutes away. Outdoor pursuits are equally close at hand, with Appalachian Trail access, local hiking, & the Harlem Valley Rail Trail all nearby. Metro-North service into New York City provides convenient access for commuters & weekend trips alike. Whether taking in quiet views of the resident rescue horses, tending the garden, or enjoying the stream, this home captures the character of the Hudson Valley—pairing serene country living with easy access to the village and surrounding amenities.

264 Quaker Hill Road, Pawling

$680,000
3 Beds 2 Baths 1047398 MLS
A little bit of magic lives at 16 Carlson Road. Built in 1850, this charming home feels like something out of a fairytale, surrounded by nearly nine acres of mature gardens and old-growth trees. Walking paths wind through the acreage, and the beautifully established landscape gives the property a character all its own. While the history of the home is felt throughout, recent thoughtful updates have been made, creating comfortable, beautifully considered spaces while preserving the character that makes it so special. Inside, natural light fills the rooms, with skylights overhead and windows framing views of the surrounding gardens. The main level unfolds through a series of inviting spaces, including a sunroom, formal and informal dining rooms, and a living room anchored by a wood-burning stove. A deck just off the dining room sits beneath an extraordinary mature hydrangea, creating a natural canopy for long summer lunches and dinners outside. The primary suite is on the main level, with radiant floor heating extending through both the bedroom and spacious bathroom. Two generously sized walk-in closets provide ample storage, while French doors open directly onto a bluestone patio. Just off the bedroom, a charming home office with built-ins makes working from home feel decidedly less like work. Upstairs, two sun-filled bedrooms share a bathroom with a clawfoot tub, with ample storage throughout. The property also includes two outbuildings: a one-car garage and a separate garage/workshop with a loft above, ready for projects, studio space, or whatever creative pursuits the property inspires. Just five minutes from the Harlem Valley Metro-North station, the property offers easy access to New York City, with Grand Central just over two hours away. Wassaic Metro-North is 20 minutes away, with Kent, Connecticut just 10 minutes away and Millbrook approximately 25 minutes. It’s a rare kind of Hudson Valley retreat, where beautiful gardens, a sense of history, and just a little everyday magic come together.

16 Carlson Road, Wingdale

$519,990
4 Beds 3 Baths 1047097 MLS
This beautiful Victorian is located in the sought after Hamlet of Staatsburg. It has been completely updated and has all its original charm along with many modern updates. The home features its original hardwood floors throughout. The whole house has been freshly painted inside and out. Gorgeous updated kitchen with granite countertops and center island. All 3 bathrooms have been beautifully renovated. All new energy efficient windows in every room. Each and every bedroom is nicely sized. Fantastic 2 car detached garage behind the home. Full unfinished basement. Large deck off of the kitchen is great for entertaining your guests. You can walk to restaurants, the library, Dinsmore Golf Course, and the historic site at Mills Mansion. You will not find a true Victorian home for this price anywhere in Dutchess County and especially not in the Hamlet of Staatsburg.

46 Old Post Road, Staatsburg

$575,000
6 Beds 6 Baths 1036859 MLS
Welcome to a truly special piece of Poughkeepsie history. Built in 1877 and set within the Historic District, this striking Victorian residence offers an exceptional opportunity to restore and reimagine a grand historic home while preserving its remarkable architectural character. From the gracious curved staircase and soaring ceilings to original hardwood floors, intricate moldings, pocket and French doors, multiple fireplaces, and a distinctive glass-enclosed cupola, the craftsmanship and scale of this home are rarely found today. With approximately 4,831 square feet, three levels, 8 plus bedrooms (tax indicate 6), 6 baths (3 full 3 half), a spacious kitchen with cherry cabinetry, granite countertops and multiple work areas, plus a butler's pantry, the possibilities are extensive. A full basement, detached garage, private yard, and rooftop garden area with views add even more potential. Recent improvements provide a foundation for the next chapter, while the property's historic details invite thoughtful restoration. Whether envisioned as a magnificent private residence, a thoughtfully restored historic property, or another permitted use subject to municipal approval, 8 Garfield Place is an extraordinary opportunity to bring a landmark-quality home back to its full glory.

8 Garfield Place, Poughkeepsie

$650,000
3 Beds 3 Baths 1044510 MLS
Set beautifully near the center of almost 8 private acres, this cherished home has been owned by the same family for nearly 50 years and offers a setting that invites you to slow down and enjoy the natural beauty that surrounds you. A picturesque pond, meandering stream and waterfalls create a peaceful backdrop, while thoughtfully positioned gardens and mature landscaping offer something beautiful to enjoy in every season. Spend quiet mornings listening to the sounds of the water, relax on the screened-in porch with your morning coffee or evening cocktail, or gather with family and friends on the stone patio. Inside, warmth and character continue with hardwood floors throughout, two wood-burning stoves and distinctive wood details that give the home its inviting feel. The kitchen is appointed with quartz countertops and a custom island with seating, while the dining room provides the perfect setting for everything from intimate dinners to holiday gatherings and entertaining. Designed for the ease of one-level living, the home offers three bedrooms and two full baths on the main level, including a primary bedroom with private en-suite bath, along with additional rooms offering flexibility for a den, home office, in-law space, guest accommodations or whatever best suits your lifestyle. A conveniently located laundry area just off the kitchen leads directly to the stone patio, making indoor-outdoor living easy. The lower level provides convenient access to the two-car garage, while an additional carport is ideal for storing equipment and machinery or providing a dedicated exterior workspace. Located in the Millbrook School District and just five minutes from the Taconic State Parkway, this special property offers a rare combination of privacy, natural beauty, character and convenience. After nearly five decades with one family, this much-loved home and property are ready for their next chapter.

2800 Route 82, Pleasant Valley

$800,000
5 Beds 4 Baths 1044978 MLS
Looking for a Dutchess County home with acreage, mountain views, guest accommodations, and flexible living space? Set on 5.16 acres in Stanfordville, this one of a kind property offers nearly 2600 square feet of living space along with an expansive outdoor oasis, multiple outbuildings, and separate accommodations currently used as an Airbnb. Inside the 4 bedroom, 2.5 bath main home, a spacious kitchen offers abundant cabinetry, generous counter space, stainless steel appliances, and a large peninsula. Multiple living and dining areas and a dedicated home office provide room to spread out, while a wood-burning stove framed by an exposed brick wall creates a distinctive gathering space with direct access to the expansive back deck. Upstairs you will find 4 spacious bedrooms, including a primary suite with a private bath and balcony. The apartment is above the detached 2 car garage, with a separate exterior entrance, separate utilities and dedicated elevated deck, creating added separation and flexibility for guests. Inside are comfortable living and dining areas, a kitchen with ample cabinetry and counter space, a bath, and bedroom space with generous closet storage. The private deck with pergola provides an additional outdoor sitting area overlooking the surrounding greenery. Currently used for short-term accommodations, this portion of the property may appeal to buyers searching for a home with guest quarters, separate living space, or potential income. Buyers should verify applicable permits, approvals, and requirements for continued short-term rental use. Beyond the home, more than five acres of park-like landscaped and open grounds create an impressive outdoor setting framed by mountain and countryside views. The property features a large multi-level back deck with space for dining, grilling, and entertaining, along with a landscaped fire pit area, backyard irrigation system, a fountain water feature, barn, shed, an additional outbuilding and expansive open lawn areas. The property also has riparian rights on Wappingers Creek and the Buttercup Farm Audubon Sanctuary is next door, adding even more splendor to this nature lover’s paradise. On the more practical side, heating and cooling is well covered, with mini-splits in the main home on the 1st floor that provide AC and heat as well as 8 zones of oil-fired hydronic baseboads. The apartment has mini-split heat and air conditioning in addition to the electric baseboard heat. The leased solar panels at $212/month cover the main house electric usage, owners currently only pay a $48 delivery fee. The accessory apartment is on a separate meter and runs $85-$100/month. A portable generator and transfer switch adds peace of mind. Located in the Pine Plains School District, this property offers an uncommon combination of exquisite property, flexible accommodations, outdoor entertaining space, and 360-degree Hudson Valley scenery.

6725 - 6727 Route 82 Unit #6725, Stanfordville

$1,575,000
5 Beds 2 Baths 1045445 MLS
Discover the timeless character of this distinctive property at 148 Creek Rd in Staatsburg, offering the charm and craftsmanship associated with an 1800s-era home. Rich in historic appeal, the residence blends period character with the opportunity to make it your own. Set on a spacious property, the land is well-suited for a variety of agricultural, farming, or livestock uses, offering flexibility for those seeking a rural lifestyle, hobby farm, or equestrian potential, subject to local zoning and permitted uses. Enjoy the peaceful surroundings, open space, and scenic Hudson Valley setting while remaining conveniently located near parks, trails, the Hudson River, shopping, dining, and major commuter routes. A rare opportunity to own a property that celebrates history, character, and country living. Up until last year this property hosted weddings and a variety of other events. Grow hops and brew your own beer. Licenses and permits are either available or reneable. Petting zoo, Horse stables, and with 136 acres you can do just about anything. Several Utility Upgrades have been installed as well.

148 N Creek Road, Staatsburg

$395,000
3 Beds 2 Baths 1045740 MLS
This charming Cape Cod offers 3 bedrooms and 2 baths, blending 1935 character with comfortable, flexible living space. Set on a quiet residential street just minutes from shopping, dining, and everything happening in the growing Poughkeepsie area. Being move in ready, this is the perfect kind of starter home that gives you room to grow. Step inside to a bright and airy living room filled with natural light, flowing into the kitchen, and then the main level bedroom with a stylish plank ceiling. Upstairs you'll find two additional bedrooms with fresh carpet, plus side access to the attic for extra storage. The finished lower level adds real everyday value, with a full bathroom, two separate living spaces perfect for a den, office, gym, or rec room, and a dedicated laundry room tucked away from the main living areas. Outside, the fully fenced backyard is ideal for entertaining, gardening, or just relaxing, and the detached garage offers even more storage or workshop potential. Peckham Road sits within the Arlighnton school district, close by to the popular new EastDale Village, the Poughkeepsie Galleria, and the Mid Hudson Bridge, putting shops, restaurants, and daily errands within easy reach. Outdoor lovers will appreciate being just steps from the Dutchess Rail Trail, ideal for walking, jogging, or biking right from home. Conveniently positioned for easy access to NYC, the NY Thruway is about 25 minutes away, and Metro North service from the Poughkeepsie station is just around the corner. Drivers heading south can expect about a 90 minute trip down to the George Washington Bridge, making this a realistic option for anyone splitting time between the Hudson Valley and NYC.

36 Peckham Road, Poughkeepsie

$499,930
3 Beds 3 Baths 1044696 MLS
Priced to sell is this rare opportunity to bring your vision to life and enjoy fantastic views overlooking the Hudson Valley right from your own wrap around deck! This home has so much to offer! Before stepping inside you will notice an oversized 2 car garage with a massive heated bonus area above for gym equipment or a hangout area. Step inside and the main level has the open concept throughout the kitchen, living room, and dining room. You can't miss the floor to ceiling windows in the main area that gives you beautiful views overlooking your big back yard and the Hudson Valley area. In the sunk in living room you will notice custom stone all around the pellet stove for those cozy evenings. the stove also heats the main level and loft area! This home also offers two bedrooms and a full bath on the main level. Walk upstairs to the open overlooking loft area and the views get even better! Upstairs in the loft also has another fireplace to use while watching snow fall across the Hudson Valley. The second floor has an area to make a small home office, an oversized third bedroom, and another full bath. The home doesn't stop there, it continues when you go downstairs into the finished walkout basement that has another living room with a beautiful pellet stove surrounded by brick, an additional storage room, full bathroom, and kitchen area. Endless possibilities for extended visitors in this home! A commuters dream being so close to I-84 and taconic parkway. Close to the Dutchess County rail trail and Appalachian trail, making weekend fun easy to do! This home has great potential to be your Hudson Valley retreat. Book your private showing before it's too late!

123 Stagecoach Pass, Stormville

$1,475,000
3 Beds 2 Baths 1043883 MLS
Fallkill, a late 18th-century, thoughtfully renovated farmhouse, sits on six magical acres with stone walls, an artist studio, an antique barn, and a beautiful cedar sauna tucked in the woods, all overlooking idyllic rolling meadows, a meandering creek, and forest. The setting is quintessential Hudson Valley countryside, with the house sitting on one of the prettiest roads in Dutchess County, and the home has been artfully updated, with abundant historic charm intact. The Home: The home perfectly balances moodier, historic interiors with bright, modern spaces. The main level has a new addition with enormous windows, which is home to an open-plan kitchen outfitted with top-quality appliances and a sun-drenched dining area. Moving into the original circa 1700s part of the house, the living room centers around the beautiful fireplace and is framed by wood beams and the most exquisite original wood floors. A full bathroom completes the first floor, with the three bedrooms and another full bath on the second floor. The finished basement is expansive, with a laundry/utility room, office, and extensive storage space. Every tile, piece of hardware, lighting, and finishings throughout the home have been hand-picked for their quality, longevity, and unique style. The Grounds: The exterior feels very private, with a split-rail fence running along the property line and exceptionally charming landscaping. A stone patio with a gas outdoor fireplace and an outdoor shower blend in perfectly with the exterior. A stone path through a meadow leads to the artist studio, bathed in light and tucked away from the main house. Amidst the woods is a 10-person Cedar & Stone sauna with a changing room and deck. The picture windows in both the sauna and the artist studio look out onto exceptionally verdant landscapes. A historic barn could easily become a future workshop, and restored stone walls are peppered throughout the property. The Surroundings: Fallkill sits amidst a peaceful neighborhood, where weekends can be enjoyed visiting Mills Mansion and its grounds, dropping by the farmer's market in Rhinebeck or the MPO farmstand, grabbing lunch at Golden Russet, and taking long walks and bike rides near the property. The home is less than 15 minutes from Rhinebeck, under 20 minutes from Rhinecliff Amtrak Station, and an hour and a half from New York City.

234 E Fallkill Road, Hyde Park

$423,000
3 Beds 1 Baths 1035129 MLS
Charming 3-Bedroom Home with Peaceful Backyard & Classic Front Porch Welcome to 9 Garden Street in Hyde Park, a charming 3-bedroom, 1-bath home offering comfort, character, and a wonderful outdoor setting. Enjoy your morning coffee or relax at the end of the day on the inviting front porch, or head to the beautiful, peaceful backyard—a great space for entertaining, gardening, or simply enjoying the outdoors. Inside, you’ll find a comfortable layout with three bedrooms and a full bath, providing plenty of opportunity to make this home your own. The location is a standout, with convenient access to shopping, restaurants, local events, and the Dutchess County Fairgrounds, making it easy to enjoy everything Hyde Park and the surrounding Hudson Valley have to offer. A wonderful opportunity for a buyer looking for a home with charm, outdoor space, and a convenient Hyde Park location.

9 Garden Street, Hyde Park

$599,000
3 Beds 2 Baths 1042803 MLS
Set on over an acre and a half of pure enchantment, this charming predominantly one-level ranch-style home offers thoughtfully designed living space in a private and whimsical setting. A long paved driveway leads to the home, which sits high and well back from the road, creating a sense of seclusion from the moment you arrive. The backyard is truly an oasis, surrounded by lush landscaping, vibrant perennial gardens framed by a stone wall, and a recently renovated Lazy L heated inground pool. Whether envisioned as a weekend getaway or year-round sanctuary, this property offers outdoor living and relaxation at its finest. While the home presents a modest profile from the outside, the interior reveals a stylishly renovated kitchen featuring a center island with seating, crisp white cabinetry, quartz countertops, stainless steel gas range, refrigerator, dishwasher and microwave, subway tile backsplash, abundant storage, floating shelves, and a charming picture window with bench seating and storage below. The view of the pool from the kitchen is so picturesque, it feels like a living work of art. A wide hallway leads to an intimate dining room and a dramatic living room with vaulted ceiling and corner fireplace surrounded by stone. Another hallway leads to two bedrooms, including a comfortable second bedroom with pool views and a serene primary suite. The primary bedroom features French doors opening to a private deck, a bath with potential to expand by incorporating space from the adjacent walk-in closet, and three additional closets. A recently renovated hall bath with walk-in shower, full-size stacked washer and dryer tucked into a convenient laundry closet, and five additional closets of varying sizes complete the main level. From the living room, steps lead to a private third bedroom with charming sloped ceilings. Outside, the magic truly unfolds. The deck off the kitchen is an inviting spot for morning coffee, al fresco dining, or sunset cocktails. The heated inground pool is surrounded by a spacious patio finished with an exceptional concrete coating system, offering plenty of room for lounge chairs and patio furnishings. A stone patio provides the perfect setting for the gazebo, furnished for relaxing and entertaining. Beyond the gate, a custom circular fire pit creates a wonderful gathering place beneath the stars. The pool area is thoughtfully fenced, while a detached one-car garage and separate shed provide additional storage for gardening tools and equipment. Just under four miles from the charming Village of Pawling, you'll have easy access to fine dining, casual eateries, boutique shops, pubs, and the seasonal farmers market. Outdoor enthusiasts will appreciate nearby Lakeside Park, Pawling's town park, the Appalachian Trail, and the Dutchess Rail Trail, now conveniently accessible via the newly completed connector. Golf enthusiasts can choose between the public Dutcher Golf Course and the private Quaker Hill Country Club. For commuters, the Pawling Metro-North station is less than 10 minutes away, providing an approximately 90-minute train ride to New York City. A captivating private retreat with exceptional outdoor living, this enchanting property offers the perfect blend of tranquility, style, and convenience. Be sure to click the virtual tour icon and use your mouse to experience a full 360-degree tour of the sensational backyard and pool area.

140 Hurds Corners Road, Pawling

$339,000
2 Beds 2 Baths 1038481 MLS
This charming 1920s home combines character with comfortable one-level living in a highly walkable location. The inviting interior features two bedrooms, a home office, an efficient kitchen, a welcoming living room, a sun-filled dining room, one-and-a-half baths, and a mudroom with laundry. While the second floor creates flexibility for additional living space, the full basement provides generous storage. Enjoy outdoor living on the rear deck, in the thoughtfully landscaped yard, or from the front porch. The oversized two-car garage affords ample space for parking, storage, or hobbies. Conveniently located just moments from Pleasant Valley’s Main Street, this home offers easy access to the grocery store, restaurants, and shops. For the commuter, the location is easily accessible to Route 44, the Taconic Parkway, and about a 15 minute drive to Poughkeepsie Metro North/Amtrak train station.

33 North Avenue, Pleasant Valley

$1,999,000
3 Beds 3 Baths 1041154 MLS
Spectacular 100+ Acre Equestrian Estate | Premier Horse Farm Opportunity Within Approximately 90 Minutes of NYC A truly exceptional 100+ acre equestrian estate offering a rare combination of historic character, modern amenities, exceptional equestrian facilities, and expansive acreage. This remarkable property presents an outstanding opportunity for a private equestrian estate, professional training operation, boarding facility, equestrian center, or other income-producing use, all within approximately 90 minutes of New York City. At the heart of the property is an iconic 1720s cattle barn masterfully transformed into a stunning residence. The beautifully renovated open-concept home features 3 bedrooms and 2.5 baths, dramatic cathedral ceilings accented by rough-sawn chestnut, hand-scraped oak floors, and a custom staircase crafted from chestnut wood harvested on the property. The residence beautifully blends historic character with modern luxury. The expansive kitchen features high-end finishes, a center island, pantry, and wet bar, while three decks overlook the spectacular grounds and surrounding countryside. The equestrian facilities are equally impressive. A custom 13-stall modern barn features 12' x 12' matted stalls, a dedicated wash and grooming stall, approximately 24' x 12' tack room/kitchen/break room, laundry/feed room, and bathroom. The upper level includes a spacious hay loft, fully functioning office, partially finished caretaker's apartment, and large great room, offering tremendous flexibility for equestrian and residential uses. Additional facilities include an 8-stall shed row, four oversized paddocks with Nelson automatic waterers that can be divided into as many as eight individual turnout areas, and a separate barn providing extensive storage for equipment, vehicles, trailers, and farm necessities. Approximately 4–6 wells provide substantial water infrastructure throughout the property. The expansive acreage offers privacy, room for additional improvements, and extensive opportunities for riding, turnout, recreation, and continued development of the equestrian operation. Rare Opportunity to Expand to Nearly 125 Acres An extraordinary opportunity exists for a buyer to acquire this property together with the contiguous equestrian facility at 5 McCarthy Road, Listing #1003257. Purchased together, the two properties would create a nearly 125-acre equestrian compound with an exceptional collection of facilities. The combined properties would offer two residences, two exceptional barns, approximately 31 stalls, an indoor riding arena, an outdoor riding arena with ESI footing, extensive paddocks and turnout, miles of riding trails, and a large pond—creating an exceptional foundation for a professional training and boarding operation, multi-disciplinary equestrian center, horseman's estate, or premier private equestrian compound. The ability to combine two contiguous, established equestrian properties of this caliber is extraordinarily rare. For the serious equestrian buyer, the combined offering provides remarkable scale, infrastructure, and flexibility while maintaining the privacy and character of a spectacular Hudson Valley estate. Whether purchased individually or together with 5 McCarthy Road, this is a once-in-a-generation opportunity to acquire a substantial equestrian property with the acreage, facilities, and infrastructure to support virtually limitless possibilities. Note: The owner would consider selling the home with a few acres without the barn should someone be interested in the home only.

42-45 Blackstone Ridge, Holmes

$459,000
6 Beds 3 Baths 1032737 MLS
This home is located within a Historic residential corridor known for its prominent Victorian Architecture. George Corlies was responsible for mapping out and building many of the Victorian homes on South Hamilton Street. These special second Empire and Italian Villa designs give the block a Historic Charm. In the 1930's Many estates in the Hudson Valley f were retro fit internally to transition from a grand estate to a multi-Family. Today this building operates as a successful Triplex. It contains three distinct 2-bedroom apartments while preserving its defining Mansard roofline and distinctive second -empire framing. There is 1 gas meter and 1 electric meter. Seller will credit buyer $10,000 towards the conversion of the electric with acceptable offer. Theres a private off-street parking area and a detached Garage with loft. Th seller has plans drawn up of for another apartment. future plan designs for possible basement conversion. Survey has been completed. Property has a CO and has done BOH inspection.

86 S Hamilton, Poughkeepsie

$655,000
3 Beds 3 Baths 1041481 MLS
Set on nearly two acres just a few miles from the village of Pawling, this log home offers space, privacy, and real potential for the right buyer. The in-ground concrete pool and detached three-car garage add value rarely found together at this price point. Inside, the open kitchen and vaulted wood ceilings give the home a warm, cabin-like character that is hard to find in newer construction. This home is being sold as is and priced to reflect its current condition and status. The space above the garage is finished but is permitted and approved for storage use only. It is not being represented as legal living space, and any potential alternate use should be independently verified by the buyer with the Town of Pawling. The lower level is currently the subject of an active permit application to be finished, and its status should also be verified directly with the Town prior to closing. A solar panel system is installed on the property but is not currently connected to the grid. Reinstallation and reconnection through Tesla is scheduled, and buyers should confirm current status and any associated costs or timelines directly with Tesla. Given the acreage, the pool, and the bones of this home, there is a lot here for a buyer willing to do some homework. Priced at $655,000 to reflect the property's current condition and open items.

12 Rebecca Drive, Pawling

$589,000
3 Beds 3 Baths 1037637 MLS
Discover this spacious 3-bedroom, 2.5-bath home ideally located just minutes from the train and downtown Pawling, offering the perfect combination of privacy, convenience, and room to grow. Step inside to an inviting open floor plan designed for comfortable everyday living and entertaining. The first-floor primary suite is a standout feature, offering a generously sized bedroom, private bath, and two large closets for plenty of storage. Enclosed Bonus Porch area with a pellet stove with wall-to-wall windows for endless natural light. The fully finished walk-out basement provides an incredible amount of additional living and entertainment space, complete with a bar area, wood burning stove and direct outdoor access. With plenty of room to customize and enhance, the possibilities are endless for creating a game room, home theater, gym, recreation area, or the ultimate gathering space. Situated on 1.86 acres surrounded by mature trees, the property offers wonderful outdoor space to relax and entertain. Enjoy evenings on the patio or deck while taking in the sunset and peaceful surroundings. Car enthusiasts, hobbyists, or anyone needing extra storage will appreciate the impressive 1,260-square-foot detached garage, in addition to an oversized attached 2-car garage. With abundant parking and storage, there's room for vehicles, equipment, a workshop, and more. Minutes from the train and downtown yet offering nearly two acres of space, multiple garages, a first-floor primary suite, and a finished walk-out basement—this property offers a rare combination of location, versatility, and potential. Schedule your private showing today!

46 Harmony Hill Road, Pawling

$339,000
3 Beds 2 Baths 1039832 MLS
Welcome to 5112 Route 22 in Amenia, a classic Cape Cod-I’m style single-family home set on approximately 1.2 acres in Dutchess County. Built in 1954, this charming 3-bedroom, 2-bath residence offers about 1,298 square feet of living space, a comfortable 1.5-story layout, and timeless character with practical updates throughout. The home features a fireplace, hot water/steam heat, a partial basement, and a large sunporch that provides inviting additional space to relax, gather, or enjoy views of the property. In addition to the home, there’s an oversized detached 2-car garage, and a large garden shed. There are new roofs on both the house and garage that add convenience and peace of mind. Conveniently located along Route 22, the property offers easy access to local amenities, nearby schools, and the broader Harlem Valley region. A great opportunity for buyers seeking a manageable home, usable acreage, and the charm of Amenia living. Locals love the close access to the Harlem Valley Rail Trail and the Metro-North rail station, both just minutes away.

5112 Route 22, Amenia

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