Homes for Sale near Keeseville Elementary School

• 

  

  

  /45

  $349,000

  • 3 Beds
  • 2 Baths
  • 1,344 Sq Ft

  1889 New York 22, Wingdale, NY 12594

  Move right into this beautifully maintained 3-bedroom, 2-bath home in Dover, NY featuring cathedral ceilings, an open-concept layout, and comfortable everyday living. Conveniently located along Route 22, the property offers easy access to outdoor recreation, local dining, shopping, and Metro-North commuting options. Nearby attractions and amenities include: Scenic hiking, waterfalls, and nature

  

  Milton Hyatt

  KFortuna All Aspects Realty

  (845) 251-3348

  1889 New York 22, Wingdale, NY 12594
• 

  

  

  /46

  $815,000

  • 4 Beds
  • 4 Baths
  • 2,234 Sq Ft

  360 Old State Route 22, Dover Plains, NY 12522

  Stunning Riverfront Retreat offers serene water views and the luxury of fishing and kayaking right in your own backyard. Beautifully renovated three-bedroom home is complemented by a one-bedroom pool house that works perfectly as a guest cottage - true resort-style living. Open-concept living and dining areas are filled with natural light, featuring two sets of French doors that lead to a

  

  Judith 'Judy' Albert

  BHHS Hudson Valley Properties

  (845) 412-9430

  360 Old State Route 22, Dover Plains, NY 12522
• 

  

  

  /34

  $3,900,000

  • 3 Beds
  • 2 Baths
  • 1,933 Sq Ft

  6 Hoyt Rd, Sherman, CT 06784

  Black Dog Farm, owned by artist Elaine Voghelle, an exceptional estate offering a refined storybook ambiance. The fully restored 1803 Antique Eyebrow Colonial Farmhouse is set on 4.6 acres of prime land along the Appalachian Trail. Renovations throughout the home are executed to the highest standard. The property includes several substantial outbuildings, including a three-level cottage, a

  

  Eric Bergers

  William Raveis Real Estate

  (860) 936-9247

  6 Hoyt Rd, Sherman, CT 06784
• 

  

  

  /8

  $169,900

  $20K PRICE DROP

  • Land
  • 3.04 Acres
  • $55,888 per Acre

  34 Front of the Mountain Rd, New Milford, CT 06776

  34 Front of The Mountain Road in New Milford is a premier parcel where you can enjoy the tranquility of Litchfield County. This scenic location offers a peaceful setting with stunning views, serving up a perfect blend of natural beauty and New England charm. Situated in New Milford, Front of the Mountain Road has a rural feel while still providing easy access to the amenities in town and nearby

  

  Sharon Watson Stokland

  List N Show LLC

  (860) 752-1571

  34 Front of the Mountain Rd, New Milford, CT 06776
• 

  

  

  /23

  $499,900

  • 3 Beds
  • 2 Baths
  • 2,050 Sq Ft

  79 Wendy Dr, Poughquag, NY 12570

  Welcome to 79 Wendy Drive, privately sited on 1.84 beautifully landscaped acres offering a peaceful oasis with mature landscaping, while still enjoying the charm of cul-de-sac living — perfect for neighborhood walks and bike rides. This is a unique opportunity to own this versatile property offering endless potential — ideal for single-family living, multi-generational living, or the opportunity

  

  Amber Thomas

  Compass Greater NY, LLC

  (845) 684-2719

  79 Wendy Dr, Poughquag, NY 12570
• 

  

  /40

  $1,463,000

  $26K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 4,884 Sq Ft

  27 Smoke Ridge Dr, Sherman, CT 06784

  A rare opportunity to own a private 3.70-acre retreat in Sherman-set back from the road down a scenic driveway, offering you seclusion. The stand out one-of-a-kind oversized six car garage easily adapts for, car collections, workspace, or recreational needs. Sherman is known for its low taxes, located just 90 minutes from NYC, this property delivers the ideal balance of privacy and convenience. A

  Ginny Gordon-O’Neill William Raveis Real Estate

  27 Smoke Ridge Dr, Sherman, CT 06784
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  /2

  $1,195,000

  New Construction

  • 4 Beds
  • 4.5 Baths
  • 3,675 Sq Ft

  60 Long River Rd, Sherman, CT 06784

  River Oaks Golf Course New Construction!! Sherman's best value. New construction 4 bedroom 4.5 bath colonial with open floorplan and 2 primary bedrooms. (main level and upper) Propane heat and Central Air. Composite decking. 9 Ft ceilings on the main level. 3 car attached garage. Hardwood floors throughout. Center island kitchen with large pantry and granite/quartz counters. All bedrooms have

  Joe Chemero Coldwell Banker Realty

  60 Long River Rd, Sherman, CT 06784
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  /45

  $600,000

  • 4 Beds
  • 2.5 Baths
  • 2,924 Sq Ft

  5 Red Tail Ct, Pawling, NY 12564

  Space, style, and convenience come together in this beautiful Squire Green home. Featuring a brand-new kitchen with granite countertops, gas stove and stainless steel appliances, spacious living areas, a cozy fireplace, and oversized bedrooms. Need space? This home delivers. The home continues to impress with a large unfinished basement offering endless potential for additional living space.

  Susan Salamone Houlihan Lawrence Inc.

  5 Red Tail Ct, Pawling, NY 12564
• 

  

  /45

  $1,299,000

  • 4 Beds
  • 3.5 Baths
  • 3,770 Sq Ft

  110 Hillside Ave, Wingdale, NY 12594

  Set on four beautiful acres with sweeping long range views of the foothills and ridges around Litchfield Hills and The Taconic Mountains, this thoughtfully designed contemporary home offers exceptional privacy, tranquility, and quality throughout. Built by the owners for their own use, no expense was spared, with high end materials and meticulous attention to detail. Incredible natural light

  Janet Myer Houlihan Lawrence Inc.

  110 Hillside Ave, Wingdale, NY 12594
• 

  

  /21

  $595,000

  • 3 Beds
  • 2.5 Baths
  • 2,636 Sq Ft

  188 N Quaker Hill Rd, Pawling, NY 12564

  Fantastic weekend getaway or full time residence, hard to find Quaker Hill, situated on 5.00 secluded acres with babbling brook running through. Master bedroom with bath, walk in closet. 2 additional bedrooms & full bath. The living room, dining area & eat in kitchen are bright & spacious with hardwood floors throughout. Finished walkout basement with powder room. This property is mostly level,

  Gillian Stewart Gillian Stewart Real Estate

  188 N Quaker Hill Rd, Pawling, NY 12564
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  /2

  $99,900

  $5K PRICE INCREASE

  • Land
  • 3.3 Acres
  • $30,273 per Acre

  Lot 7 Brookview Rd, Dover, NY 12522

  Located approximately 6.5 miles from the Village of Millbrook. Trains to New York City are available only 3.3 miles away at the Metro North Station in Dover Plains. Picturesque Stone Brook traverses the property. Ideal for your weekend or year-round dream home. Board of Health Approved and no fill required.

  Robert D Ferris R. Ferris Real Estate, LLC

  Lot 7 Brookview Rd, Dover, NY 12522
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  /9

  $140,000

  $10K PRICE DROP

  • Land
  • 20,037 Sq Ft
  • $304,348 per Acre

  20 Hickory Ln, Pawling, NY 12564

  Build your dream home on this exceptional 0.46-acre parcel, offering a rare blend of privacy, nature, and convenience. The property is BOH approved (3 bedroom residential dwelling), providing a smooth path to construction, and is landlocked at the rear, creating a peaceful, secluded setting. Enjoy access to two nearby lakes for fishing or swimming, or relax at the clubhouse. Drive into Pawling

  Tela Cook McGrath Realty Inc

  20 Hickory Ln, Pawling, NY 12564
• 

  

  /31

  $900,000

  $50K PRICE DROP

  • 4 Beds
  • 3.5 Baths
  • 3,434 Sq Ft

  128 Old Pawling Rd, Pawling, NY 12564

  You finally have the opportunity to own a home with year-round mountain views set on an expansive property. A place where you can bring your vision to life and transform the space into a true masterpiece. 128 Old Pawling Road is a beautifully positioned property in Pawling, NY, offering a rare combination of scenic views, generous land, and the potential to create a truly special home. Set back

  Juliska Martino Compass Greater NY, LLC

  128 Old Pawling Rd, Pawling, NY 12564
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  /16

  $499,999

  • 2 Beds
  • 1 Bath
  • 1,347 Sq Ft

  1141 Old Quaker Hill Rd, Pawling, NY 12564

  Welcome Home! Tucked away along storied Old Quaker Hill, this antique charmer invites you to experience a slower, richer pace of living—where history lingers in every beam and modern comfort quietly supports it. Offered fully furnished (or unfurnished) and available for immediate occupancy, this cozy retreat blends timeless character with everyday ease, making it an ideal escape for your weekend

  Chinenye Aguoji Real Broker NY LLC

  1141 Old Quaker Hill Rd, Pawling, NY 12564
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  /11

  $239,000

  • Land
  • 2.4 Acres
  • $99,583 per Acre

  0 Route 22 Unit KEY976107, Dover, NY 12594

  Just north of the Town of Pawling border, you will find this 2.4 acre parcel. Convenient location is close to schools, town library, Thomas Boyce Park, Wingdale Metro-North train station. This is a residential parcel, zoned RU.

  Lisa Liffland McGrath Realty Inc

  0 Route 22 Unit KEY976107, Dover, NY 12594
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  /39

  $599,900

  Open Sun 12PM - 3PM

  • 3 Beds
  • 2.5 Baths
  • 1,956 Sq Ft

  52 S Kent Rd, Gaylordsville, CT 06755

  Glorious in Gaylordsville! Don't miss this oversized and spacious Cape in the quiet and historic hamlet of Gaylordsville, CT. 3 bedrooms, 2.5 baths, with nearly 2,000 square feet of finished living space. Set on 1.74 level acres, this very clean and well-cared-for home has all you need to move right in and start enjoying your new digs! Hardwood flooring throughout the main and upper levels, with

  Todd Sargent Coldwell Banker Realty

  52 S Kent Rd, Gaylordsville, CT 06755
• 

  

  /40

  $2,495,000

  • 5 Beds
  • 4.5 Baths
  • 6,368 Sq Ft

  2 Pond View Ln, Sherman, CT 06784

  Custom Dream home that blends modern luxury, comfort and peaceful living. Nestled in a beautiful 18-hole golf course community, this stunning newer-construction residence offers spacious open living, abundant natural light and thoughtfully designed details throughout. From the moment you enter you'll notice the airy layout, oversized windows, 10ft ceilings and seamless flow. The heart of the home

  Joe Chemero Coldwell Banker Realty

  2 Pond View Ln, Sherman, CT 06784
• 

  

  /22

  $1,999,000

  New Construction

  • 2 Beds
  • 2 Baths
  • 2,500 Sq Ft

  8 Taber Lot 1 Rd, Sherman, CT 06784

  Taber Acres 3 lot subdivision is offering the last lot available, and this is the building lot you've been waiting for to build your dream home upon! The 7+ acre lot is mostly flat with a gentle rise, has sandy soil, 400 AMP service installed and is ready to build. With the 400 AMP service this means the lot can accommodate a pool, a 2-bedroom guest house, sport court, and more. The private

  Claudia Jiskra McGrath Realty Inc

  8 Taber Lot 1 Rd, Sherman, CT 06784
• 

  

  /33

  $619,000

  Open Sun 11:30AM - 2:30PM

  • 4 Beds
  • 2.5 Baths
  • 2,850 Sq Ft

  28 Colonial Ridge Dr, Gaylordsville, CT 06755

  Perfect for leaf-peeping season! This exceptional 4-BR Colonial offers panoramic views of the rolling Litchfield Hills right from your front door. Set back on nearly one picturesque acre, the property combines privacy, beauty, and convenience in an established, welcoming neighborhood. The home is as impressive as its surroundings, with major updates already completed for peace of mind, including

  Lisa Briscoe William Raveis Real Estate

  28 Colonial Ridge Dr, Gaylordsville, CT 06755
• 

  /2

  $599,000

  $200K PRICE INCREASE

  • Land
  • 8 Acres
  • $74,875 per Acre

  0 Route 22 Unit ONEH6222664, Dover, NY 12594

  Raw Land - Located on Route 22 in Wingdale/Dover Plains. Approximately 8 acres. The Town of Dover is progressing with a comprehensive rezoning initiative to allow multifamily dwellings to be built OR commercial use buildings IE shopping centers or other uses. Available is survey, and several documents limited topo, tax map, ariels etc. Proposal of a large box store drawings available but not

  Lydia Nioras Commerce Properties

  0 Route 22 Unit ONEH6222664, Dover, NY 12594
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  /19

  $119,900

  • Land
  • 5.86 Acres
  • $20,461 per Acre

  0 Route 39 N Unit 24179102, Sherman, CT 06784

  Escape the ordinary and build your dream retreat on this spectacular **5.86-acre canvas** in the quintessential New England town of Sherman. Perfectly positioned to offer the ultimate blend of pristine privacy and elevated living, this rare parcel of land boasts breathtaking, panoramic vistas overlooking the protected lush canopy of The Wimisink Preserve and rolling hills. The expansive acreage

  Gregg Leonard William Raveis Real Estate

  0 Route 39 N Unit 24179102, Sherman, CT 06784
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  /34

  $695,000

  $200K PRICE DROP

  • 6 Baths
  • 5,952 Sq Ft

  685 Kent Rd, Gaylordsville, CT 06755

  Church for sale! Available to be used as a new denomination, or converted to a residence. Beautiful sanctuary complete with pews with more in balcony. It has several large meeting/class rooms and an office, with two restrooms. Could be converted into a very cool house! There is also a 2931 sf 3BR antique rectory house on the property, part of which has been rented as a residence and part of which

  Richard Pomerantz William Pitt Sotheby's Int'l

  685 Kent Rd, Gaylordsville, CT 06755
• 

  

  /25

  $2,250,000

  New Construction

  • 4 Beds
  • 5 Baths
  • 4,900 Sq Ft

  8 Taber Rd, Sherman, CT 06784

  TABER ACRES -This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 7.4 acres means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both full time or weekend! Wetlands in back to remain in conservation,

  Kathleen Harrison Coldwell Banker Realty

  8 Taber Rd, Sherman, CT 06784
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  /2

  $45,000

  • Land
  • 27,878 Sq Ft
  • $70,312 per Acre

  0 Aldrich Rd, Wingdale, NY 12594

  This 0.64-acre parcel on Aldrich Road in Wingdale, NY is offered at $45,000. This property presents a unique opportunity for an investor or a visionary builder looking to create a custom residence in a quiet, rural setting.Property HighlightsAcreage: 0.64 acres of land in a serene, off-the-beaten-path location.Price: Competitive entry-point pricing at $45,000, reflecting the current

  Mark Snyder eXp Realty

  0 Aldrich Rd, Wingdale, NY 12594
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  /10

  $369,000

  • Land
  • 7.4 Acres
  • $49,865 per Acre

  8A Taber Rd, Sherman, CT 06784

  TABER ACRES-last lot in 3 lot subdivision. This is the building lot you've been waiting for! Flat lot, sandy soil, and ready to build! 400 AMP ELECTRIC SERVICE INSTALLED. 7.4 ACRES means this lot can accommodate a pool, a 2 bedroom guest house, sport court, and more! Private setting on Taber Road near a working farm with tons of curb appeal and less than 1 M to NY LINE for ease of commutes both

  Kathleen Harrison Coldwell Banker Realty

  8A Taber Rd, Sherman, CT 06784
• 

  

  /43

  $895,000

  • 3 Beds
  • 2.5 Baths
  • 3,656 Sq Ft

  212 Pleasant Ridge Rd, Poughquag, NY 12570

  Experience extraordinary at The Arboretum—more than a residence, it is a botanical sanctuary defined by a living landscape of specimen trees, perennial gardens, and the soothing sound of a year-round stream. From the moment you pass through the gated entrance framed by hydrangea-lined fencing and continue down the drive bordered by majestic Metasequoia and fragrant linden trees, you are

  Kimberly Wickes R. Ferris Real Estate, LLC

  212 Pleasant Ridge Rd, Poughquag, NY 12570
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  /49

  $460,000

  • 3 Beds
  • 2.5 Baths
  • 1,920 Sq Ft

  12 John Kane Ct, Pawling, NY 12564

  It’s the townhome in Deerfield Ponds you have been waiting for. The most sought-after layout is finally available, featuring a primary bedroom on the first floor along with the added bonus of a detached garage. Offering 3 levels, 3 bedrooms, 2.5 baths, and 1,920 finished square feet across the first and second floors, plus an additional 1,080 square feet of unfinished basement space, this home

  Claudia Jiskra McGrath Realty Inc

  12 John Kane Ct, Pawling, NY 12564
• 

  

  /46

  $1,799,000

  Open Sun 1PM - 3PM

  • 5 Beds
  • 5.5 Baths
  • 5,390 Sq Ft

  41 and 43 Meeting House Rd, Pawling, NY 12564

  Rare 5-Acre Quaker Hill Estate with Guest Cottage: Discover the ultimate sanctuary at the crest of Quaker Hill, where 43 Meeting House Road stands as a testament to refined country living. Situated on a lush 5-acre parcel and set well back from a scenic country road, this estate offers a rare degree of privacy and tranquility, surrounded by sweeping meadows, historic horse farms and prestigious

  Richard Esman Douglas Elliman Real Estate

  41 and 43 Meeting House Rd, Pawling, NY 12564
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  /56

  $3,100,000

  • 3 Beds
  • 3 Baths
  • 3,600 Sq Ft

  809 N Quaker Hill Rd, Pawling, NY 12564

  Farm Nord is a meticulously restored country estate, originally established in the 1700s as a dairy farm by the renowned Taber family of Rhode Island. The Tabers were stewards of the estate for five generations and two centuries, with only a few families since carrying on its legacy. The property's idyllic 12 acres are peppered with endless stone walls, several-hundred-year-old trees, and rolling

  Raj Kumar Four Seasons Sotheby's Int.

  809 N Quaker Hill Rd, Pawling, NY 12564
• 

  

  /13

  $335,000

  $10K PRICE DROP

  • 2 Beds
  • 2.5 Baths
  • 1,567 Sq Ft

  1 Cushing Green N, Pawling, NY 12564

  This great 2 bedroom 2.5 bath townhome is a must see. Many great amenities including attached garage, formal dining room, fireplace, rear deck and more. This is a Fannie Mae HomePath property.

  Matthew Cave Hudson Property Services, LLC

  1 Cushing Green N, Pawling, NY 12564
• 

  

  /5

  $1,350,000

  • Land
  • 110 Acres
  • $12,273 per Acre

  00 Anderson Rd, Sherman, CT 06784

  A rare 110-acre offering in Sherman, CT, where open skies and eastern-facing views create a truly peaceful setting. Whether you're envisioning a private estate, family compound, or future development, this property offers endless potential. Ideally located close to town and just a short drive to NYC, it strikes the perfect balance between seclusion and accessibility. With subdivision potential

  Carolyn Morrison William Pitt Sotheby's Int'l

  00 Anderson Rd, Sherman, CT 06784
• 

  

  /40

  $339,000

  • 2 Beds
  • 1 Bath
  • 1,825 Sq Ft

  692 Kent Rd, Gaylordsville, CT 06755

  Charming and nicely maintained antique home featuring numerous recent upgrades, including a new roof, oven/range, dishwasher, clothes dryer and hot water heater. Rich in authenticity, this 1802 residence showcases distinctive architectural details, wide-plank hardwood floors throughout, and fireplace that enhance its historic character. Step outside to a serene and private backyard oasis,

  Deborah Snopkowski Coldwell Banker Realty

  692 Kent Rd, Gaylordsville, CT 06755
• 

  

  /31

  $1,395,000

  • 4 Beds
  • 3.5 Baths
  • 3,247 Sq Ft

  73 Long River Rd, Sherman, CT 06784

  This elegant four-bedroom home, built in 2021, is perfectly sited on 1.8 acres of professionally landscaped, private grounds. Designed for effortless single-level living, it features an open-concept layout with a chef's kitchen and center island, a welcoming living room with fireplace, and a sunlit dining area that all flows seamlessly to a covered porch with views toward the Housatonic River.

  Steve Pener William Pitt Sotheby's Int'l

  73 Long River Rd, Sherman, CT 06784
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  /39

  $1,195,000

  • 2 Beds
  • 1.5 Baths
  • 1,150 Sq Ft

  131 Route 39 N, Sherman, CT 06784

  Instantly inviting this pristine circa 1940 's classic Connecticut cottage also known as Little Fox Farm is brimming with character and jewel like qualities on nearly 3 acres a wonderful mixture of meadows, light woods, and mature trees as well as stunning perennial flower gardens developed over 30 years by its owner a designer. Set back on the property the house is in mint condition with

  Karen Casey William Pitt Sotheby's Int'l

  131 Route 39 N, Sherman, CT 06784
• 

  

  /35

  $690,000

  • 2 Beds
  • 2 Baths
  • 1,892 Sq Ft

  231 Kent Rd, Kent, CT 06757

  Tucked away in a peaceful, nature-filled setting just moments from the river, this one-of-a-kind home feels like a private retreat while still being conveniently located for everyday living. Surrounded by mature trees and beautiful scenery, the property offers the kind of setting that's hard to find and even harder to leave. This approximately 1,866 square foot home offers privacy, character, and

  Mark Mermelstein eXp Realty

  231 Kent Rd, Kent, CT 06757
• 

  

  /34

  $399,000

  $26K PRICE DROP

  • 3 Beds
  • 1 Bath
  • 1,012 Sq Ft

  113 Dog Tail Corners Rd, Wingdale, NY 12594

  Located on 1.54 acres of scenic land, this charming overbuilt home has a perfect blend of comfort, privacy, and natural beauty. Enjoy open field views across the street from your living room, creating a peaceful backdrop for everyday living and relaxing evenings. The home features a warm and inviting layout, in the living room and kitchen, walls are tongue and groove knotty pine from ceiling to

  Tela Cook McGrath Realty Inc

  113 Dog Tail Corners Rd, Wingdale, NY 12594
• 

  

  /25

  $279,000

  • Land
  • 5.46 Acres
  • $51,099 per Acre

  41 Long River Rd, Sherman, CT 06784

  This exceptional 5.46-acre parcel, perfectly positioned on Long River Road, is the largest homesite in the private community of River Oaks Country Club. The lightly wooded setting offers privacy and a natural backdrop for your custom residence with potential for sweeping long views that capture the beauty of the Berkshire foothills. Club River Oaks provides access to world-class amenities,

  Donna Kennedy Compass Connecticut, LLC

  41 Long River Rd, Sherman, CT 06784
• 

  

  /29

  $525,000

  • 3 Beds
  • 1.5 Baths
  • 1,955 Sq Ft

  37 W Deer Trail, Pawling, NY 12564

  When you think about Deerfield Ponds in Pawling, this home is it.From the moment you drive up, you’re welcomed by a picture-perfect lot with breathtaking mountain views and a pond right in your backyard. Enjoy the private trails just steps away, along with kayaking in the warmer months and ice skating and ice fishing during the winter. This 3-bedroom, 1.5 bath home is packed with potential.

  Pete Rodriguez William Raveis Real Estate

  37 W Deer Trail, Pawling, NY 12564
• 

  

  /36

  $699,000

  $16K PRICE DROP

  • 3 Beds
  • 3.5 Baths
  • 3,629 Sq Ft

  921 W Dover Rd, Pawling, NY 12564

  A One-of-a-Kind Custom Ranch on Nearly 4 Private Acres. Discover exceptional space, quality, and versatility in this expansive custom-built 3+ bedroom ranch, perfectly tucked away in a serene country setting. Designed for comfort and flexibility, this home is ideal for extended family living, multi-generational needs, or a spacious mother-daughter layout. The main floor offers true single-level

  Joyce Brennan-Zolnik BHHS Hudson Valley Properties

  921 W Dover Rd, Pawling, NY 12564
• 

  

  /24

  $1,999,000

  New Construction

  • 4 Beds
  • 3.5 Baths
  • 5,900 Sq Ft

  40 Long River Rd, Sherman, CT 06784

  Craft your dream home from the ground up with this luxury built-to-suit offering set on a sprawling 5.46 acre lot on Long River Rd in River Oaks Country Club, a private gated community in Sherman, CT. This 4 bd / 3.5 bath / 3500 SF open-concept residence with main level primary suite seamlessly connects a chef's kitchen (w/ pantry) to an elegant dining area and a living room w/ cozy fireplace.

  Donna Kennedy Compass Connecticut, LLC

  40 Long River Rd, Sherman, CT 06784

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