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$679,000

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

4 Beds ⋅ 4 Baths ⋅ 1046418 MLS

Custom-built by renowned builder Lou Tedaldi, this one-owner Center Hall Colonial offers nearly 3,000 sq. ft. of exceptionally crafted living space nestled on 6.2 pristine, park-like acres. Set on an exclusive private road shared by only 9 homes, this sanctuary delivers total privacy and tranquility while remaining in the highly sought after Monroe-Woodbury School District and close to all local amenities, major routes, and shopping. Inside, beautiful hardwood floors, custom crown and chair rail moldings, and oversized windows with screens bring continuous natural light throughout. The main level features a welcoming foyer with two coat closets, a formal living room with a cozy brick fireplace, and a family room also featuring its own brick fireplace. The gourmet eat-in kitchen boasts granite countertops, a double electric oven, abundant cabinet space, surplus counters, and Tiffany-style lighting, opening via sliders directly onto the back deck. Enjoy formal meals in the dining room, which features sliders out to a spacious, light-filled screened back porch with ceiling fan, perfect for effortless outdoor entertaining. A major highlight of the main level is a versatile 16x24 bonus addition featuring custom woodworking, a beamed ceiling, a bay window, and an ADA-accessible level including a full bathroom, ideal for a luxurious main floor primary suite, guest wing, or private office. Main floor laundry and a half bath add extra convenience. Upstairs, discover four generously sized bedrooms, including an expansive primary suite with hardwood flooring, a spacious walk-in closet, and an en-suite full bath with double vanity. The second bedroom is exceptionally large, easily serving as an alternate primary, while the remaining bedrooms offer ample closet space and bright, oversized windows.The property continues to impress with incredible functional spaces: Two Basements: Main walk-out basement with shelving, a dedicated workshop area, and a sound-proof room (perfect for a media room or studio). Plus a second insulated basement under the addition with separate exterior access. Property Grounds: Stone-faced concrete foundation, iconic Hudson Valley stone walls, manicured lawn, mature landscaping, storage shed, and surrounding private woods. Modern Comforts & Accessibility: ADA-accessible 2-car garage with ramp entry, full-house propane automatic generator, whole-house alarm system, 4-zone oil heating, attic fan, and 30-year shingle roof. An extraordinary property combining top-tier craftsmanship, flexible living spaces, and unmatched outdoor beauty!

5 Red Fox Run, Chester

$635,999

If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of finished living space, offering room for everyone and every lifestyle. Set on approximately 2 acres and conveniently located near schools, shopping, and transportation, this home delivers the perfect combination of space, flexibility, privacy, and convenience! Step inside to a bright, open-concept main level with soaring vaulted ceilings, a welcoming living room with fireplace, and a dining area featuring custom lighting. The beautifully appointed kitchen offers granite countertops, breakfast island, stainless steel appliances, and direct access to the spacious back deck—perfect for effortless indoor/outdoor entertaining. Three bedrooms are located on the main level, including a spacious primary suite with vaulted ceiling, wall-to-ceiling closets, hardwood floors, and abundant natural light. Two additional bedrooms and convenient main-level laundry complete the first floor. The fully finished lower level is a true bonus, offering endless possibilities with LVP flooring, custom built-in shelving, walk-out access, entertainment space, family room/den, and a bonus room currently used as an office that could easily serve as a guest room or additional sleeping space. A full bath with custom vanity and tiled shower makes this level ideal for guests, extended living, hobbies, or working from home. Outside, enjoy a sprawling yard, mature landscaping, circular driveway, and plenty of room to play, relax, and entertain. The spacious back deck and hot tub create the perfect private retreat. Space, style, flexibility, and location—all in one exceptional property. This is the one you’ve been waiting for!

3 Beds ⋅ 3 Baths ⋅ 1041906 MLS

If open concept and bountiful space is what you are looking for, STOP right here—you have found it! Spectacular contemporary-designed ranch with nearly 3,000 sq ft of finished living space, offering room for everyone and every lifestyle. Set on approximately 2 acres and conveniently located near schools, shopping, and transportation, this home delivers the perfect combination of space, flexibility, privacy, and convenience! Step inside to a bright, open-concept main level with soaring vaulted ceilings, a welcoming living room with fireplace, and a dining area featuring custom lighting. The beautifully appointed kitchen offers granite countertops, breakfast island, stainless steel appliances, and direct access to the spacious back deck—perfect for effortless indoor/outdoor entertaining. Three bedrooms are located on the main level, including a spacious primary suite with vaulted ceiling, wall-to-ceiling closets, hardwood floors, and abundant natural light. Two additional bedrooms and convenient main-level laundry complete the first floor. The fully finished lower level is a true bonus, offering endless possibilities with LVP flooring, custom built-in shelving, walk-out access, entertainment space, family room/den, and a bonus room currently used as an office that could easily serve as a guest room or additional sleeping space. A full bath with custom vanity and tiled shower makes this level ideal for guests, extended living, hobbies, or working from home. Outside, enjoy a sprawling yard, mature landscaping, circular driveway, and plenty of room to play, relax, and entertain. The spacious back deck and hot tub create the perfect private retreat. Space, style, flexibility, and location—all in one exceptional property. This is the one you’ve been waiting for!

3561 Rte 94, Chester

$1,195,000

Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

4 Beds ⋅ 4 Baths ⋅ 1010585 MLS

Welcome to a one-of-a-kind Arts and Crafts style sanctuary where timeless craftsmanship meets modern luxury. Tailored for the discerning buyer or avid automotive enthusiast, this exceptional property features an expansive multi-car garage designed to accommodate prized vehicle collections, a workshop, or custom storage needs. Located in the Town of Chester, this 4,281-square-foot estate masterfully blends timeless architectural detail, rich natural textures, and modern sophistication. Exceptional artistry is on display throughout, highlighted by solid wood doors, dual staircases, striking red oak flooring with Mahogany inlays, and radiant-heated floors across the entire main level. Formal living and dining spaces framed by soaring floor-to-ceiling windows flow effortlessly onto a sweeping bluestone patio, while the chef's kitchen and sunken family room with a rustic wood-burning fireplace lead to a covered outdoor patio and private fire pit area. The main-level primary suite offers a peaceful sanctuary with a gas fireplace, wrap-around covered Trex deck, and a spa-inspired bath with a vintage cast iron clawfoot tub. Upstairs, 3 oversized bedrooms—two with private en-suite baths—are complemented by a full walk-up attic and a bonus loft accessed via a spiral staircase. Enjoy the perfect mix of local charm and seamless transit. Located just minutes from the historic Village of Goshen, you’ll have quick access to boutique shopping, famed local dining, craft breweries, local wineries, and the scenic Orange Heritage Trail. Just 10 miles from Woodbury Common Premium Outlets and 60 miles from NYC, with immediate access to Route 17 (I-86), the NYS Thruway, Chester Park & Ride, and Harriman Train Station.

22 Goshen Road, Chester

$1,145,000

Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of one of the most significant equestrian properties in history. Gracefully set atop a scenic knoll on nearly three private acres in the heart of Chester, New York, the estate offers exceptional privacy while remaining just 40 miles from Manhattan. From the moment you arrive, the home's commanding presence, timeless architecture, and beautifully maintained grounds create an unforgettable first impression. The stately main residence features seven bedrooms and four-and-a-half bathrooms, where authentic Victorian craftsmanship has been meticulously preserved. Soaring ceilings, original hardwood floors, intricate millwork, marble fireplaces, elegant pocket doors, and exquisite architectural details reflect the grandeur of a bygone era, while thoughtful modern updates provide today's expected comforts. Designed for both elegant entertainment and everyday living, the home's expansive gathering spaces flow effortlessly to the surrounding grounds, creating an ideal setting for celebrations, family gatherings, or quiet evenings enjoying the beauty of the property. Adding to the estate's resort-style appeal is a separate pool house, complete with a full bathroom and private sauna, offering the perfect retreat for relaxation, wellness, or entertaining guests throughout the seasons. One of the property's most compelling features is its detached second residence, offering a beautifully appointed two-bedroom apartment with exceptional flexibility. Beyond providing luxurious accommodation for guests or extended family, this separate living space creates an outstanding opportunity for additional income. Whether utilized as a premium long-term rental, short-term vacation rental, executive housing, caretaker's residence, or owner's quarters while operating the main home as a hospitality property, it provides the versatility today's buyers are seeking. Beyond its architectural beauty, the property presents an exceptional opportunity to offset ownership costs through multiple revenue streams. This rare combination of a landmark residence and an income-producing secondary dwelling makes the estate equally attractive to homeowners, investors, and entrepreneurs. With its iconic history, breathtaking setting, and expansive layout, The Hambletonian House is ideally suited as a luxury bed and breakfast, boutique inn, private event venue, executive retreat, or premier destination rental—offering limitless possibilities for both lifestyle and investment. The current owner has invested extensively in preserving the estate's historic integrity while making significant improvements to major mechanical systems and the roof, ensuring modern reliability without compromising its timeless character. This careful stewardship allows the next owner to enjoy the confidence of updated infrastructure while preserving a truly irreplaceable piece of history. Ideally located near the shops, restaurants, and conveniences of the Village of Chester, with easy access to major highways and the best of the Hudson Valley, the property offers the perfect balance of peaceful country living and metropolitan accessibility. Properties of this significance rarely become available. Combining rich history, exceptional architecture, income-producing potential, and an irreplaceable legacy, The Hambletonian House represents a once-in-a-generation opportunity to own one of the most celebrated equestrian landmarks. Some homes are purchased. Others become part of history. This is one of them.

9 Beds ⋅ 7 Baths ⋅ 995148 MLS

Own One of America's Great Equestrian Landmarks Steeped in history and unlike anything else on the market, The Hambletonian House is a magnificent Victorian estate built in the 19th century by William Rysdyk, owner of the legendary Hambletonian 10—the foundation sire of nearly every modern Standardbred racehorse. More than a remarkable home, this is an opportunity to become the next steward of one of the most significant equestrian properties in history. Gracefully set atop a scenic knoll on nearly three private acres in the heart of Chester, New York, the estate offers exceptional privacy while remaining just 40 miles from Manhattan. From the moment you arrive, the home's commanding presence, timeless architecture, and beautifully maintained grounds create an unforgettable first impression. The stately main residence features seven bedrooms and four-and-a-half bathrooms, where authentic Victorian craftsmanship has been meticulously preserved. Soaring ceilings, original hardwood floors, intricate millwork, marble fireplaces, elegant pocket doors, and exquisite architectural details reflect the grandeur of a bygone era, while thoughtful modern updates provide today's expected comforts. Designed for both elegant entertainment and everyday living, the home's expansive gathering spaces flow effortlessly to the surrounding grounds, creating an ideal setting for celebrations, family gatherings, or quiet evenings enjoying the beauty of the property. Adding to the estate's resort-style appeal is a separate pool house, complete with a full bathroom and private sauna, offering the perfect retreat for relaxation, wellness, or entertaining guests throughout the seasons. One of the property's most compelling features is its detached second residence, offering a beautifully appointed two-bedroom apartment with exceptional flexibility. Beyond providing luxurious accommodation for guests or extended family, this separate living space creates an outstanding opportunity for additional income. Whether utilized as a premium long-term rental, short-term vacation rental, executive housing, caretaker's residence, or owner's quarters while operating the main home as a hospitality property, it provides the versatility today's buyers are seeking. Beyond its architectural beauty, the property presents an exceptional opportunity to offset ownership costs through multiple revenue streams. This rare combination of a landmark residence and an income-producing secondary dwelling makes the estate equally attractive to homeowners, investors, and entrepreneurs. With its iconic history, breathtaking setting, and expansive layout, The Hambletonian House is ideally suited as a luxury bed and breakfast, boutique inn, private event venue, executive retreat, or premier destination rental—offering limitless possibilities for both lifestyle and investment. The current owner has invested extensively in preserving the estate's historic integrity while making significant improvements to major mechanical systems and the roof, ensuring modern reliability without compromising its timeless character. This careful stewardship allows the next owner to enjoy the confidence of updated infrastructure while preserving a truly irreplaceable piece of history. Ideally located near the shops, restaurants, and conveniences of the Village of Chester, with easy access to major highways and the best of the Hudson Valley, the property offers the perfect balance of peaceful country living and metropolitan accessibility. Properties of this significance rarely become available. Combining rich history, exceptional architecture, income-producing potential, and an irreplaceable legacy, The Hambletonian House represents a once-in-a-generation opportunity to own one of the most celebrated equestrian landmarks. Some homes are purchased. Others become part of history. This is one of them.

19 High Street, Chester

$379,900

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.

2 Beds ⋅ 1 Baths ⋅ 964090 MLS

Great new price! Come take a look at this 2 bedroom charmer with additional room offers potential 3+ bedrooms. Larger than it looks - need to see. Discover the timeless charm and surprising spaciousness of this delightful carriage house, set on a property rich with character and possibility. Step inside to a generous living room where a wood burning fireplace, hardwood floors, and a large bay window create a bright, welcoming atmosphere. Wall sconces add a soft glow, and a wall A/C unit ensures comfort throughout the warmer months. The eat in kitchen blends practicality with charm, offering tile floors, a newer refrigerator, a handy island, abundant cabinetry, and a pantry for extra storage. Another bay window brings in natural light and enhances the home’s cozy appeal. A full bathroom with a classic pedestal sink and tub completes the main living space. The primary bedroom features hardwood floors, newer windows, two closets, and its own wall A/C unit. A second bedroom—equally charming—also offers hardwood floors and plenty of natural light. Throughout the home, you’ll find generous storage options, including ample closets and a pull down attic. The property is thoughtfully equipped with a natural gas generator, a paved driveway, and multiple outbuildings that expand its functionality. The main house includes an attached two car garage, while a separate two car detached garage showcases original carriage house doors that add a touch of historic character. A small shed provides additional storage, and an oversized outbuilding—with an 8' garage door, separate electric and gas meter, and gas boiler heat—offers exceptional versatility. Above it sits a caretaker’s apartment, ideal for guests, extended family, or workspace needs. All structures are being sold as is. This property blends charm, practicality, and potential in a way that’s increasingly rare—inviting you to imagine the many ways it can fit your lifestyle.

7 Hambletonian Avenue, Chester

$28,000,000

BUILDING FEATURES: • Building Size: 270,000 sq. ft. • Smaller sections available: 60,000-270,000 sq.ft. • Lot size: 33.40 acres • Ceiling Heights: 14.7' clear height. • Column Spacing: 48’ x 25’ • Office Space: 13,000 sq. ft. (Includes: several sizes of private offices, open space, conference room, kitchenette, bathrooms) • Loading Access: Eight 8'x10' tailgate loading docks with levelers + 7 Drive-in doors. (Possible to add many more loading docks or drive-in doors) • Utilities: Heavy electric power (4x 3000 amps, 3 phase, 480 volt), natural gas, municipal sewer and water. • Sprinkler: Fully sprinklered, wet system. • Heat: Full heating system in the warehouse area. • Parking & Storage: 2 acre of fenced and paved lot for parking or storage. • New roof installed 3/2022 with a 20 year warranty. • Many opportunities for building expansion. LOCATION & ACCESS: The property is strategically located within short distance of major highways; Right off I-86/Route 17 - Exit 126, NYS Thruway (I-87) - Exit 16, I-84 - Exit 19, 20 minutes from Stewart International Airport and 45 Minutes to NYC. Location is stationed within close proximity of the Chester Industrial Park, Orange County's largest industrial park. Location has easy access to public transportation by bus or train and has a large amount of amenities including restaurants, department stores, hotels and shopping outlet.

949886 MLS

BUILDING FEATURES: • Building Size: 270,000 sq. ft. • Smaller sections available: 60,000-270,000 sq.ft. • Lot size: 33.40 acres • Ceiling Heights: 14.7' clear height. • Column Spacing: 48’ x 25’ • Office Space: 13,000 sq. ft. (Includes: several sizes of private offices, open space, conference room, kitchenette, bathrooms) • Loading Access: Eight 8'x10' tailgate loading docks with levelers + 7 Drive-in doors. (Possible to add many more loading docks or drive-in doors) • Utilities: Heavy electric power (4x 3000 amps, 3 phase, 480 volt), natural gas, municipal sewer and water. • Sprinkler: Fully sprinklered, wet system. • Heat: Full heating system in the warehouse area. • Parking & Storage: 2 acre of fenced and paved lot for parking or storage. • New roof installed 3/2022 with a 20 year warranty. • Many opportunities for building expansion. LOCATION & ACCESS: The property is strategically located within short distance of major highways; Right off I-86/Route 17 - Exit 126, NYS Thruway (I-87) - Exit 16, I-84 - Exit 19, 20 minutes from Stewart International Airport and 45 Minutes to NYC. Location is stationed within close proximity of the Chester Industrial Park, Orange County's largest industrial park. Location has easy access to public transportation by bus or train and has a large amount of amenities including restaurants, department stores, hotels and shopping outlet.

25 Oakland Avenue, Chester