5-Bedroom Homes for Sale in Dutchess County NY

/31
$2,425,000
- 5 Beds
- 3.5 Baths
- 7,524 Sq Ft
12 Monell Place, Beacon, NY 12508

Historic Charm Meets Modern Luxury. Welcome to this brick home known as Eustatia (Greek for "good place to stay") which is a rare example of a Victorian Gothic-style cottage that has survived in Beacon, situated on Monell Place in the northwest corner of the city. It was constructed in 1867 according to Frederick Clarke Withers' plans for his friend John Monell, a state judge in New York (who is

Neeta Gupta

Fathom Realty NY LLC

(845) 498-1909

12 Monell Place, Beacon, NY 12508
/37
$1,799,000
- 5 Beds
- 4.5 Baths
- 5,490 Sq Ft
161 Whalesback Rd, Red Hook, NY 12571

Don’t miss this rare opportunity to own a breathtaking, fully renovated 5,500 sq ft converted barn in the heart of the Hudson Valley. Nestled on 15 private, picturesque acres in the safety and tranquility of Red Hook, NY, this extraordinary 5-bedroom, 4.5-bathroom home seamlessly blends historic charm with modern luxury.Originally built in 1900, the barn has been thoughtfully transformed to

Ann Stettner

Neil Charles Real Estate, LLC

(845) 448-2559

161 Whalesback Rd, Red Hook, NY 12571
/49
$3,000,000
- 5 Beds
- 4.5 Baths
- 2,304 Sq Ft
20 Paye Ave, Beacon, NY 12508

Perched above the meeting point of Fishkill Creek and the Hudson River, this home offers unobstructed sightlines that stretch all the way to the mountains of Cornwall. Sunsets are vibrant, nights sparkle—this is one of the most breathtaking vistas in Beacon.Originally built in 1920 and cherished by the same family for a century, this extraordinary home was completely reimagined in 2021–2022.

Diana Polack

Compass Greater NY, LLC

(845) 377-4620

20 Paye Ave, Beacon, NY 12508
/16
$329,900
- 5 Beds
- 2 Baths
- 2,208 Sq Ft
257 Church St, Poughkeepsie, NY 12601

Spacious Five Bedroom, Two Full Bath Home For Sale Displaying Hardwood And Ceramic Tiles Floors, Kitchen With Range, Refrigerator And Washer/Dryer Hookups, Full/Unfinished Basement Driveway And Parking In Back Of Building. This Two Story Home Is Located Nearby Shopping, Restaurants, On Bus Route And Not Far From Colleges, Hospitals And Train Station. Property To Be Sold "As Is" With Present

Joyce Stanton

Century 21 Hudson Valley Rlty.

(845) 493-2490

257 Church 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

Joyce Stanton

Century 21 Hudson Valley Rlty.

(845) 402-2134

52 Catharine St, Poughkeepsie, NY 12601
/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.

YOLANDA MENDOZA

Century 21 Hudson Valley Rlty.

(845) 576-9945

57 Smith St, Poughkeepsie, NY 12601
/36
$1,449,999
- 6 Beds
- 3.5 Baths
- 3,750 Sq Ft
9 Belleford Ln, Beacon, NY 12508

Welcome to 9 Belleford Lane! One of a kind custom built Colonial home nestled between the Hudson River and Mount Beacon. Be amazed by the beautiful sunsets and river views from this stunning home. The sweeping driveway leads to the welcoming mahogany front porch with lovely mountain views, surrounded by Japanese maple, weeping cherry and blue spruce trees. This home boasts a charming foyer, with

Claire Browne Compass Greater NY, LLC

9 Belleford Ln, Beacon, NY 12508
/37
$3,500,000
- 8 Beds
- 4.5 Baths
- 3,010 Sq Ft
2039 Salt Point Turnpike, Salt Point, NY 12578

Welcome to This Hudson Farm – a distinctive 157+ acre estate spanning 2039–2105 Salt Point Turnpike, where the beauty of the Hudson Valley meets the ultimate opportunity to enjoy as much—or as little—of the farming lifestyle as you desire. Positioned between Rhinebeck and Millbrook, and just minutes from the Taconic State Parkway, this remarkable offering blends historic charm with modern

Lindsay Rothman Compass Greater NY LLC

2039 Salt Point Turnpike, Salt Point, NY 12578
/28
$1,495,000
- 5 Beds
- 2 Baths
- 2,012 Sq Ft
77 Old Post Rd, Rhinebeck, NY 12572

Introducing the Huber Farm, being offered for the first time in over 70 years, this picturesque Rhinebeck property offers a rare opportunity to own a special piece of the Hudson Valley. Set on over 16 acres across two adjoining parcels, the land is graced with a 1930’s farmhouse and 2 antique barns. The house has 5 bedrooms, 2 full baths, and over 2,000 square feet of living space. The home is

TRACY DOBER Rouse + Co Real Estate LLC

77 Old Post Rd, Rhinebeck, NY 12572
/36
$3,500,000
- 5 Beds
- 4.5 Baths
- 4,972 Sq Ft
97 Wing Rd Unit 101, Millbrook, NY 12545

The artistry of Coole Park is in the way it unfolds from the center. Two gracious wings on either side of the original 1888 house create an architectural triptych that conveys elegance and comfort in equal measure. Warm wide board floors, soaring French doors, six working fireplaces, and numerous demi-lune windows create a sense of space and style as well as history. To the right of the entryway,

Candy Anderson Compass Greater NY, LLC

97 Wing Rd Unit 101, Millbrook, NY 12545
/50
$2,275,000
- 7 Beds
- 7.5 Baths
- 7,720 Sq Ft
143 Bedell Rd, Poughkeepsie, NY 12603

Hilltop Retreat, built in the Millenium Mansion style, provides an incomparable experience of country living. This gracious residence is approached via a meandering driveway past stone walls and a pond and is secluded within 66 acres of curated lawns w/ majestic trees, a shimmering pond, old growth forest, and year-round Catskill mountain views. Casually formal, w/over 7,000sqft of living space

Eliane Abramoff Four Seasons Sothebys Intl

143 Bedell Rd, Poughkeepsie, NY 12603
/42
$1,699,000
- 7 Beds
- 7 Baths
- 8,033 Sq Ft
125 Bedell Rd, Poughkeepsie, NY 12603

Timeless Elegance Meets Modern Comfort in the Heart of the Hudson Valley. Step into a world of refined charm and historic grandeur with this magnificent estate, originally constructed in 1867 and meticulously restored to preserve its legacy. Lovingly maintained over generations, the property blends classic architectural detail with the comforts of contemporary living, offering an unparalleled

Jillian Pajer Douglas Elliman Real Estate

125 Bedell Rd, Poughkeepsie, NY 12603
/45
$1,550,000
- 6 Beds
- 4 Baths
- 5,439 Sq Ft
3 Route 216, Hopewell Junction, NY 12533

Offered at $1,550,000, 3 Route 216, Hopewell Junction, NY is a truly exceptional offering—a Historic Colonial Homestead farmhouse built circa 1790, set on 4 picturesque acres in the heart of the Hudson Valley. With 6 bedrooms, 4 bathrooms, and 5,439 square feet of interior living space, this post-Revolutionary War Federal-style estate masterfully blends preserved early American craftsmanship with

Joan St. Aubyn BHHS Hudson Valley Properties

3 Route 216, Hopewell Junction, NY 12533
/50
$2,200,000
- 7 Beds
- 7 Baths
- 11,222 Sq Ft
3893 Route 82, Millbrook, NY 12545

Set on 11.1 private acres in the heart of Millbrook, this stately brick Colonial estate offers over 11,222 square feet of refined living space, combining timeless elegance with exceptional versatility. A true legacy property, it delivers the scale, design, and amenities expected by the most discerning buyers.A dramatic two-story granite foyer welcomes you with a sweeping double staircase and a

Howard Payson RE/MAX Town & Country

3893 Route 82, Millbrook, NY 12545
/50
$1,699,000
- 7 Beds
- 7 Baths
- 8,033 Sq Ft
125-127 Bedell Rd, Poughkeepsie, NY 12603

Timeless Elegance Meets Modern Comfort in the Heart of the Hudson Valley. Step into a world of refined charm and historic grandeur with this magnificent estate, originally constructed in 1867 and meticulously restored to preserve its legacy. Lovingly maintained over generations, the property blends classic architectural detail with the comforts of contemporary living, offering an unparalleled

Jillian Pajer Douglas Elliman Real Estate

125-127 Bedell Rd, Poughkeepsie, NY 12603
/32
$1,900,000
- 5 Beds
- 4 Baths
- 4,410 Sq Ft
645 Tyrrel Rd, Millbrook, NY 12545

This historic home was originally built in Millbrook, New York in 1733 by one of the nine partners of the early English land grant. The carefully maintained original architectural features reflect its heritage. On 10 ½ acres the property is a mixture of meadows and woods and bordered on 2 sides by a year round running stream. Clipped lawns surround the house and a privately situated

HEATHER CRONER William Pitt Sothebys Int Rlty

645 Tyrrel Rd, Millbrook, NY 12545
/43
$1,345,000
- 5 Beds
- 7 Baths
- 6,318 Sq Ft
88 Hunns Lake Rd, Stanfordville, NY 12581

This is Bullis Hall, the circa 1800’s Greek Revival landmark in the picturesque and historic hamlet of Bangall in Stanford, NY. The Hudson Valley, Dutchess County property is situated with excellent street frontage on Hunns Lake Road just off Route 82. With over 6,000 square feet, the building is ready for its next steward; a blank canvas for future use. Bangall is one of many hamlets in the

Steve Bruman Corcoran Country Living

88 Hunns Lake Rd, Stanfordville, NY 12581
/50
$1,495,000
- 5 Beds
- 3.5 Baths
- 2,772 Sq Ft
78 Schultz Hill Rd, Staatsburg, NY 12580

Private 39.9 Acres and Luxurious Turn Key Country House minutes away from Rhinebeck Village.This property perches on a beautiful mountain and is flanked by double gates with two long driveways. Trails allow residents to wander their own secluded forested refuge while viewing across the Hudson River at the Catskill Mountains; the property is one of the highest areas in town. The

Geovanna Lim PAIP

78 Schultz Hill Rd, Staatsburg, NY 12580
/35
$1,695,000
- 5 Beds
- 5.5 Baths
- 5,238 Sq Ft
15 Old Farm Rd, Rhinebeck, NY 12572

Tucked on a quiet private road under ten minutes from Rhinebeck Village, this 5-bedroom custom craftsman estate offers beautiful, high quality art-deco style for those seeking a break from the sea of sterile new builds and stark modernism. Built with the utmost quality, oak floors, premium custom windows and doors, and brass hardware throughout. A bevy of high technology make the home energy

Zev Eisenberg Hudson Modern Co

15 Old Farm Rd, Rhinebeck, NY 12572
/50
$1,690,000
- 6 Beds
- 2 Baths
- 4,265 Sq Ft
831 Wolcott Ave, Beacon, NY 12508

Elegant Circa 1900 Dutch Colonial Revival in Prime Beacon LocationSituated within walking distance of Beacon’s vibrant Main Street, this distinguished circa 1900 Dutch Colonial Revival residence offers timeless charm and modern luxury. A gracious front entrance, complete with a stately covered porch, welcomes you into this historic brick home, which features six bedrooms and two full

Charlotte Guernsey Compass Greater NY, LLC

831 Wolcott Ave, Beacon, NY 12508
/47
$1,485,000
- 5 Beds
- 7.5 Baths
- 5,470 Sq Ft
604 N Quaker Hill Rd, Pawling, NY 12564

Exceptional living awaits in this stately Georgian manor house sitting on 7 acres at the top of prestigious North Quaker Hill Road. This mostly original home offers 9’ ceilings, radiant heating and ownership that has changed hands only once. A Belgian cobblestone driveway has a center focal point awaiting your personal touch.The Living room opens to an elegant wraparound terrace, perfect for the

Leigh Tripathi Ellis Sotheby's Intl Realty

604 N Quaker Hill Rd, Pawling, NY 12564
/36
$1,499,000
- 5 Beds
- 3.5 Baths
- 4,176 Sq Ft
1598 Jackson Corners Rd, Red Hook, NY 12571

Welcome to Fallkill Farm, an incredible 37 acre oasis with expansive meadows, wooded buffers, mountain backdrop and Roeliff Jansen Kill frontage. Historic significance and modern amenities converge with the impeccably restored circa 1800 farmhouse featuring updated kitchen w/center island, designer cabinetry, Subzero refrigerator, Wolfe range and soapstone counters. Loaded with period features

Dan Axtmann BHHS Hudson Valley Properties

1598 Jackson Corners Rd, Red Hook, NY 12571
/42
$1,495,000
- 5 Beds
- 4.5 Baths
- 3,325 Sq Ft
26 Curry Ln, Hyde Park, NY 12538

Nestled in one of Hyde Park’s most coveted locations, this beautifully renovated, immaculately maintained 1920s cottage offers breathtaking, panoramic views of the Hudson River. Tucked away for ultimate privacy, this home beautifully melds historic bones with chic design and charm.Upon entering, you're immediately greeted by the expansive river views through its buttery-sunbathed living

Wendy Maitland Atelier WM LLC

26 Curry Ln, Hyde Park, NY 12538
/47
$2,900,000
- 7 Beds
- 6.5 Baths
- 5,486 Sq Ft
20 Orchard Hill Dr, Millbrook, NY 12545

Modern Country Retreat with Iconic Hudson Valley Views Proven Investment or Private Escape Seconds from MillbrookExperience refined country life in this beautifully updated Hudson Valley home, nestled on 12+ private acres with sweeping views of the Catskill Mountains. Surrounded by lush lawns, open meadows and a fenced paddock, the property offers a sense of serenity, space, and

Kathryn Johnson William Pitt Sothebys Int Rlty

20 Orchard Hill Dr, Millbrook, NY 12545
/36
$1,495,000
- 6 Beds
- 4.5 Baths
- 4,110 Sq Ft
57 Cedar Berry Ln, Dover Plains, NY 12522

Just 90 miles north of NYC, this stunning Hudson Valley property offers the ultimate live, work, play lifestyle. Nestled on 4.08 private acres, this custom-built log home captures the vibrant essence of the area, known for its booming art and music scene, farm-to-table eateries, outdoor adventures, and local wineries. Generating over $80,000 in VRBO rental income in 2022, this turnkey estate is

Lindsay Stevens eXp Realty

57 Cedar Berry Ln, Dover Plains, NY 12522
/9
$980,000
- 5 Beds
- 3 Baths
- 3,684 Sq Ft
38 Dartmouth Dr, Poughkeepsie, NY 12603

The Harley boasts an impressive first floor featuring a stunning open floor plan that offers enchanting views of the spacious great room and the inviting casual dining area, seamlessly extending to a desirable 16x20 TREX Deck—perfect for outdoor living. The well-appointed kitchen is a culinary dream, complete with a large center island and a breakfast bar that invites gatherings and casual meals.

David Bartolone Christie's Int. Real Estate

38 Dartmouth Dr, Poughkeepsie, NY 12603
/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
/17
$799,900
- 5 Beds
- 3 Baths
5 Douglas Dr, Wappingers Falls, NY 12590

Endless Opportunities Await at This Unique 9-Acre Estate!Check out this sprawling 9-acre property offering **endless opportunities** for living, income, and whatever else you can dream up. This multi-family home, all on one level, features two separate units: a 2-bedroom, 1-bath and a larger **3-bedroom, 2-bath with an updated kitchen**. It's set up for multi-generational living, rental

Lynn Fronckowiak K. Fortuna Realty, Inc.

5 Douglas Dr, Wappingers Falls, NY 12590
/31
$550,000
- 5 Beds
- 4.5 Baths
- 3,225 Sq Ft
8 Rock Garden Way, Poughkeepsie, NY 12603

A rare opportunity for someone with vision to transform this expansive property into something truly special. Nestled in the heart of the Spackenkill School District, this home offers over 4,000 total square feet, including a legal accessory apartment, ideal for multi-generational living, guests, or future rental potential. Located on a quiet cul-de-sac, the property also features a detached

DAVID DEBERARDINIS Serhant LLC

8 Rock Garden Way, Poughkeepsie, NY 12603
/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
/40
$485,000
- 6 Beds
- 2 Baths
- 4,026 Sq Ft
788 788 Dutchess Turnpike, Poughkeepsie, NY 12603

Welcome to 788 Dutchess Turnpike – a high-visibility property located in the heart of Poughkeepsie with 200 feet of road frontage in a bustling commercial and residential corridor. This versatile property offers outstanding potential for investors and entrepreneurs looking to possibly live and work in one central location. This converted residence is now a Commercial building with town permission

Ann Scarano Realty Center Hudson Valley

788 788 Dutchess Turnpike, Poughkeepsie, NY 12603
/43
$599,000 Open Sun 12PM - 2PM
- 5 Beds
- 3.5 Baths
- 3,634 Sq Ft
24 Wild Turkey Run, Wappingers Falls, NY 12590

Don't Miss This Beautiful & Spacious Home — Offering room for Everyone! Nestled on nearly 4.5 acres of peaceful, park-like land on a quiet private road, this stunning 6-bedroom, 3-bathroom home offers a unique layout ideal for multi-generational living or simply spreading out in comfort and style. Thoughtfully expanded, the home boasts a massive primary suite addition featuring an oversized

Sandra Spector Howard Hanna Rand Realty

24 Wild Turkey Run, Wappingers Falls, NY 12590
/33
$750,000
- 5 Beds
- 3 Baths
- 4,124 Sq Ft
49 Flower Rd, Hopewell Junction, NY 12533

Spacious contemporary nestled in a peaceful cul-de-sac within one of the area's most desirable neighborhoods, this expansive 4,200 sq ft open concept residence offers room to grow and endless potential. Featuring 5 generous bedrooms and 3 full baths, this home is perfect for multi-generational living or those seeking extra space for work and play. House also offer outdoor speakers in the family

Zuzana Dankova HomeSmart Homes & Estates

49 Flower Rd, Hopewell Junction, NY 12533
/48
$11,750,000
- 5 Beds
- 6 Baths
- 9,684 Sq Ft
Unlisted Address

Exquisite Shekomeko Estate with Panoramic Catskill Mountain views. Nestled on 50 private acres in the heart of the Hudson Valley, this country estate offers timeless sophistication, refined comfort, and breathtaking views of the Catskills. Designed by architect Jimmy Crisp and completed in 2004, the residence spans over 9,684 finished square feet of thoughtfully curated living space. A tree-lined

PAULA REDMOND Corcoran Country Living

Unlisted Address
/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
/36
$1,250,000
- 6 Beds
- 3.5 Baths
- 4,248 Sq Ft
11 Brown Rd, Pleasant Valley, NY 12569

Step back in time without sacrificing modern comforts in this rare, historic brick farmhouse estate, originally built in the 1760s by early settler Sarah Tobias Newcomb. Rich in Revolutionary War-era history, this extraordinary property tells a story few homes can: while Sarah's husband, Zaccheus, fought for the Loyalists, she famously sent cheese from her dairy to George Washington's encampment

Daniel Colomban Skyler Realty LLC

11 Brown Rd, Pleasant Valley, NY 12569
/36
$857,500
- 5 Beds
- 5 Baths
- 2,942 Sq Ft
15 E Salem Rd, Fishkill, NY 12524

This house can save you money! You'll never have to plan a summer vacation again as you and the entire family enjoy your own Mountain Pond salt water heated in-ground pool. With 5 bedrooms and 5 full bathrooms (1 on the 1st floor) there's never a chance of kids fighting over bathroom time or space. There's even room for expansion if needed as the walkout basement has 6 foot double wide walkout

Rik Brescia Compass Greater NY, LLC

15 E Salem Rd, Fishkill, NY 12524
/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
/11
$900,000
- 5 Beds
- 2.5 Baths
- 2,413 Sq Ft
2365 Route 83, Pine Plains, NY 12567

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

Richard Brenner Rich Brenner Realty, LLC

2365 Route 83, Pine Plains, NY 12567

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