Holmes Real Estate

Welcome to Holmes, New York – a hidden gem nestled in the heart of Dutchess County. This charming hamlet is the perfect blend of serene countryside living and vibrant community spirit, making it an ideal place for those looking to escape the hustle and bustle of city life while still enjoying convenient access to urban amenities.

Holmes is characterized by its picturesque landscapes, featuring rolling hills, lush greenery, and tranquil lakes that invite residents to embrace the great outdoors. Whether you enjoy hiking, fishing, or simply taking leisurely strolls, the natural beauty of Holmes provides endless opportunities for relaxation and recreation. The nearby Appalachian Trail is a favorite among nature enthusiasts, offering breathtaking views and a chance to connect with nature.

The community in Holmes is tight-knit, with friendly neighbors and a welcoming atmosphere that makes newcomers feel right at home. Local events and seasonal festivals foster a sense of belonging, allowing residents to engage with one another and create lasting memories. The local schools are highly regarded, providing quality education and a supportive environment for families.

For those commuting to nearby cities, Holmes is conveniently located just a short drive away from Poughkeepsie and Fishkill, where you’ll find a plethora of shopping, dining, and entertainment options. With its charming rural setting and proximity to urban conveniences, Holmes offers the best of both worlds.

Whether you’re looking to buy your first home, retire in peace, or invest in a vacation property, Holmes, NY, is a delightful place to call home. Discover the charm of this enchanting hamlet and experience the tranquility and community spirit that make it truly special.

Newest Listings in Holmes

$425,000

2 Beds ⋅ 2 Baths ⋅ 1028683 MLS

Nestled on 1.49 private acres in the White Pond neighborhood, this thoughtfully updated ranch pairs classic character with modern comfort. The open concept kitchen, with white shaker cabinets, quartz counters, and a center island, flows into a family room and dining area, perfect for everyday living and entertaining. A separate light-filled living room is warmed by a brick fireplace with pellet stove insert. The first floor offers a primary bedroom, a second bedroom, and a full bathroom, and an upper bonus level in the attic, complete with a fully lined cedar closet, adds everyday flexibility. The lower level provides tons of extra space for whatever your heart desires. Step outside to a stone patio and fire pit, plus a charming outhouse tucked at the edge of the yard, ideal for an artist studio, hobbies, or whatever you can imagine, the possibilities are endless. With an attached lower-level garage, generous storage, and a location just two miles from I-84, this property offers the rare combination of storage, character, and convenience.

174 Milltown Road, Holmes

$80,000

PADE2120734 MLS

Lot for sale! Roughly .7 acre wooded lot in Ridley Township. Zoned for commercial C2 but some residential and C-1 allowed based on zoning website. Public utilities are on street (Gas, water and sewer). Irregular shaped lot, Delaware county public records has roughly 278x93 and 150x34 (about .7 acres) with wood portion and cleared portion. Buyer responsible for u&o requirements and any re-zoning wanted.

2320 Baldwin Ave, Holmes

$249,000

1 Beds ⋅ 1 Baths ⋅ 1031078 MLS

Attention investors, contractors, and DIYers looking for affordable lake living - this one may be just what you are looking for! Welcome to this charming 1-bedroom, 1-bath cottage-style home in Holmes, offering a unique opportunity to enjoy lake access and views of Whaley Lake. Located directly across the street from the lake, this 733 sq ft home provides lake rights and convenient access to the water, making it an appealing option for buyers looking for a property near Whaley Lake. Built in 1940, the home features a cozy layout with a fireplace, a sunroom, and a patio area to enjoy the outdoor setting. This property offers a chance to bring your vision and updates to a classic cottage. The basement provides potential additional space for future expansion, and the home’s location is the true highlight offering the opportunity to enjoy the Whaley Lake lifestyle from just across the road. Whether you are looking for a weekend getaway, seasonal retreat, or a smaller home with lake access in Dutchess County, this property offers a rare setting in the Pawling community. Conveniently located near local shops, dining, schools, parks, and transportation options, including access to Metro-North rail service in the surrounding area, this home combines a lake setting with accessibility to nearby amenities and commuting routes.

1555 Route 292, Holmes

$1,475,000

4 Beds ⋅ 5 Baths ⋅ 1029458 MLS

**Do not walk or go to the property without an agent**Set privately on more than 22 acres just minutes from the quaint Village of Pawling, this exceptional country estate captures the essence of Hudson Valley living with breathtaking mountain views, extraordinary privacy, and timeless elegance. Designed for both sophisticated entertaining and comfortable everyday living, this exquisite Colonial showcases refined craftsmanship and beautifully appointed living spaces throughout. A dramatic two-story foyer welcomes you with a sweeping staircase, cathedral ceiling, gleaming ceramic tile flooring, and an elegant chandelier. Bathed in natural light, the gracious living room features a tray ceiling, oversized windows, hardwood floors, and a handsome wood-burning fireplace, while the formal dining room offers rich hardwood flooring, expansive windows, and a tray ceiling, creating an elegant setting for intimate dinners and memorable celebrations. The heart of the home is the open-concept kitchen and family room. The eat-in kitchen boasts abundant cabinetry, granite countertops, stainless steel appliances, recessed lighting, hardwood floors, and a large center island, making meal preparation and casual gatherings effortless. The adjoining sunken family room impresses with soaring ceilings, a dramatic floor-to-ceiling brick fireplace, wet bar, oversized windows, and glass doors leading to a freshly painted deck overlooking beautifully landscaped grounds, mature trees, and peaceful vistas. Whether hosting or enjoying a quiet evening at home, this inviting space offers warmth, comfort, and spectacular year-round views. The first-floor primary suite offers a luxurious retreat with a spa-inspired bath featuring a soaking tub, oversized glass-enclosed shower, dual marble vanities, and generous natural light. A private home office, powder room, laundry room, and access to the oversized three-car garage complete the main level. Upstairs, a spacious bonus room provides endless possibilities as a media room, playroom, library, or additional gathering space. Three generously sized bedrooms with hardwood floors and generous closets are served by two full baths, providing comfortable accommodations for all. The walk-out lower level offers exceptional flexibility with a recreation room featuring a full bar, den with walk-in closet, sitting area, exercise space, game room, full bath, and abundant storage—ideal for multigenerational living, extended guests, or an au pair suite. Beyond the beautifully maintained lawn, the property unfolds into acres of rolling countryside where open meadows, mature trees, and sweeping mountain views create an unforgettable backdrop. The expansive acreage offers endless possibilities for a pool, cabana, gardens, equestrian pursuits, or simply preserving the serenity and remarkable natural beauty that surrounds you. Spectacular sunsets paint the western sky, providing a breathtaking finale to each day. Additional amenities include hardwood flooring, recessed lighting, a generator, brick walkway, storage shed, tray ceilings, decorative columns, transom and bow windows, and dramatic floor-to-ceiling windows that beautifully frame the surrounding landscape. Conveniently located just 90 minutes from New York City with easy access to Metro-North, Routes 22, 311, I-684 and I-84, and just minutes from Thunder Ridge Ski Area, the Harlem Valley Rail Trail, golf, parks, shopping, dining, and the charming Village of Pawling. This extraordinary estate offers a rare opportunity to enjoy refined country living where timeless architecture, breathtaking scenery, and exceptional privacy create an unforgettable Hudson Valley retreat. Whether enjoyed as a full-time residence or an exceptional weekend escape, this is a place where luxury, nature, and tranquility exist in perfect harmony.

7 Herd And Tanner Road, Holmes

$749,900

4 Beds ⋅ 4 Baths ⋅ 1029051 MLS

Nestled on 2.01 private acres, this beautifully maintained Colonial offers the perfect blend of timeless elegance, modern comfort, and exceptional convenience, just minutes from the Putnam County border, Interstate 84, and the Metro-North Railroad for an easy commute. Built in 2001, this move-in ready home features four spacious bedrooms, three full bathrooms, and one half bathroom, highlighted by soaring nine-foot and vaulted ceilings, gleaming hardwood and ceramic tile floors, crown moldings, French and pocket doors, recessed lighting, and striking Palladian windows that fill the home with natural light. The heart of the home is a spacious maple kitchen complete with a center island, abundant cabinetry, and a full suite of appliances, opening seamlessly to the home's inviting living and entertaining spaces. The luxurious primary suite offers a vaulted ceiling, a private sitting room, and a spa-inspired bathroom with a whirlpool tub, creating the perfect private retreat. The finished, walk-out lower level is at grade and offers exceptional versatility with a summer kitchen, full ADA-compliant bathroom, spacious den or recreation area, abundant storage and utility space, making it ideal for extended family living, guests, a home office, or flexible multi-generational living. Additional highlights include central air conditioning, a security system, computer networking, an attached two-car garage, and a picturesque setting with a combination of level and gently sloping land that provides privacy and room to enjoy the outdoors. Offering quality craftsmanship, thoughtful design, and an ideal commuter location, this exceptional property delivers the perfect balance of privacy, functionality, and convenience

26 E Forest Trail, Holmes

$699,000

4 Beds ⋅ 3 Baths ⋅ 991422 MLS

Situated on 2.56 acres overlooking Stump Pond, this contemporary raised ranch offers a tranquil setting while showcasing the peace of mind of completely brand-new construction. The spacious primary suite is thoughtfully positioned on its own side of the home for added privacy and features a walk-in closet and ensuite bath. Two additional bedrooms, a full bath, and open concept kitchen/dining/living complete the main level, with the anchor of it being the oversized kitchen island with quartz countertops. The lower level expands the living space with a large family room, fourth bedroom, and an additional full bath, making it an ideal space for guests or extended family. There's still time to personalize select finishes- hardware, floor stain, and kitchen appliances, to make this home your own. Conveniently located just 0.5 miles from I-84 and less than 10 minutes from both Patterson and Southeast Metro-North stations, this home offers an easy commute while enjoying the beauty of the Hudson Valley. Outdoor enthusiasts will appreciate everything Kent has to offer, including scenic hiking trails, nature preserves, and picturesque lakes, all just moments from your doorstep.

592 Ludingtonville Road, Holmes

$1,150,000

5 Beds ⋅ 4 Baths ⋅ 1024239 MLS

Introducing a stunning to-be-built farmhouse by respected local builders known for exceptional craftsmanship, thoughtful design, and quality construction. Perfectly positioned on more than 11 private acres, this custom home blends timeless farmhouse charm with modern comfort, offering a peaceful retreat in one of the Hudson Valley's most desirable settings. Designed with today's lifestyle in mind, the open-concept floor plan is filled with natural light and offers an effortless flow for both everyday living and entertaining. At the heart of the home, the dramatic vaulted family room with a gas fireplace opens to a sun-filled eat-in kitchen featuring a large center island, abundant cabinetry, and direct access to a covered porch—creating the perfect setting for seamless indoor-outdoor living. The thoughtfully designed main-level primary suite is privately situated away from the secondary bedrooms and offers a luxurious escape with a spacious walk-in closet and spa-inspired bath. Two additional bedrooms and a full bath complete the first floor, although the floor plan can easily be customized to create a second primary suite with a sitting area, accommodate multi-generational living, or provide dedicated home office space. The second level expands the home's versatility with plans for a fourth bedroom, full bath, an optional fifth bedroom or office, and a generous bonus room ideal as a media room, fitness studio, recreation room, playroom, or additional living space. The flexibility of the design allows you to tailor the home to your lifestyle. Quality finishes include hardwood flooring, high ceilings, energy-efficient insulation, central air conditioning, a welcoming Trex front porch, and an attached three-car garage. Although privately tucked away, the property is just minutes from the charming Village of Pawling, Metro-North, shopping, restaurants, major commuter routes, and the area's many hiking trails, golf courses, and cultural attractions. Whether you're searching for a full-time residence or a refined country retreat, this exceptional to-be-built home presents a rare opportunity to create a custom residence where privacy, elegance, and convenience come together. Photos include virtual renderings and images of a recently completed similar home and are for illustrative purposes only. Finishes, specifications, and features are subject to change during construction.

Lot 5 S White Rock Road, Holmes

$399,777

PADE2119064 MLS

Discover House Hacking at 2223 Amosland Road in Holmes. Live for less then renting... stop making your landlords mortgage payment... let your tenants pay your mortgage in this rare, income-producing triplex. This property is the ultimate find for a first-time homebuyer looking to build immediate wealth, a downsizer seeking easy first-floor living, or a family looking for a multi-generational setup. Why This Property is a Smart Financial Move: Built-In Income: Collect $1,729 (Below Market) every month from two reliable, long-term tenants right from day one. Offset Your Mortgage: Use the existing rental income to heavily slash your monthly housing costs. Room to Grow: Move into the vacant first floor or rent it out later for an extra $1,100 to $1,500+ per month. Low Landlord Stress: Enjoy hassle-free management with separate boilers, gas meters, and updated electric panels for every unit. Consider adding an Accessory Use Dwelling or garage for added income and value to the property. Bonus: The roof and siding were done in 2024, the basement has a French drainage system, windows were replaced in 2019.

2223 Amosland Rd, Holmes

$879,800

3 Beds ⋅ 3 Baths ⋅ 1021432 MLS

Nestled in the hamlet of Pawling, NY. This rare find in Holmes is a gorgeous Four-SQ. colonial custom & unique property is a must see. Privacy awaits in a pristine area with nearly 5 acres. Enchanting landscapes surround the property, patio and waterfall. Inside this colonial farmhouse is a beautiful blend of comfort and unique craftsmanship that is well-loved. Every single detail of the house has been meticulously selected to evoke a perfect blend of elegance and timeless design. The open-concept design connects the great room, featuring custom bookcases and granite fireplace which flows into a stunning chef’s kitchen. This chef designed kitchen encompasses a huge granite workspace which has also developed & recipe tested numerous successful cookbooks. Featuring three spacious bedrooms and a studio/office which can easily be transformed to a 4th. This charming home offers ample space for life, living and entertaining. Opportunity to own a home with this much heart and elegance rarely comes along. Additional Information: Cooling: SEER Rating 14+, Marble Bath, 2 Soaking Tubs, Storage, Heating Fuel :Oil & propane gas fireplace, 2 Car garage (oversized). New Heat system, 10/24, new Miele dishwasher racks, new gas lines for Professional Wolf 8 burner range, new kitchen sink faucet including new plumbing, new baths vanities, new shower fixtures, exterior; new gutter system 10/25, new washer, backed with warranty and much more... Home warranty, SEPARATE warranty on Lux-Care W&D. Conveniently located to Manhattan & Connecticut. Enjoy activities of the Hudson Valley, historical sites, enjoy over 450 Wineries in NYS, unique shopping and hike the Hudson Valley Trail. SURVEY AVAILABLE. Engineered to accommodate a 4th bedroom.

57 S White Rock Road, Holmes

$650,000

3 Beds ⋅ 3 Baths ⋅ 1017740 MLS

**Lakefront Living at Its Finest on Private Sunset Lake Just over an HOUR to NYC*** Newly priced at $650,000, this beautifully maintained 3-bedroom, 2.5-bath lakefront home offers four-season living on private Sunset Lake. Located in Holmes, a hamlet of Pawling, this waterfront retreat combines peaceful surroundings, inviting indoor and outdoor spaces, and convenient access to everything the Hudson Valley has to offer. Are you a runner or a walker? This house in conveniently located moments from the local rail trail as well! Inside, you’ll find gleaming hardwood floors, elegant crown molding, two fireplaces, and central air. The thoughtfully designed kitchen features concrete countertops, tile flooring, radiant heat, propane cooking, and an adjoining mudroom with radiant heat—an especially welcome feature during Hudson Valley winters. The screened-in porch is the perfect place to enjoy morning coffee or unwind while overlooking the lake. A spacious open-air deck provides even more room for barbecues, outdoor dining, and entertaining. Gather around your private fire pit or enjoy the community fire pit with neighbors and friends. Sunset Lake residents also enjoy access to a private sandy community beach and pavilion. Spend summer days swimming, fishing, kayaking, or paddleboarding, then enjoy ice skating when winter transforms the lake. The property also offers the potential for a private dock, subject to applicable community and municipal approvals. A invisible fenced yard provides a secure outdoor space for pets, while high-speed internet makes working from home easy. The attached two-car garage offers plenty of room for vehicles, kayaks, paddleboards, and other recreational equipment. Located in the Pawling School District and just minutes from the Village of Pawling, Metro-North, restaurants, shops, hiking trails, golf courses, wineries, breweries, farms, and Interstate 84. Whether you’re searching for a year-round home or a weekend escape, 45 Willow Lake offers the opportunity to enjoy lakefront living in every season.

45 Willow Lake Drive, Holmes

$389,900

5 Beds ⋅ 2 Baths ⋅ PADE2117774 MLS

Situated on a prominent corner lot in Ridley Township, this versatile home offers over 2,000 square feet of living space and a flexible floor plan ideal for those seeking additional room, multi-generational living arrangements, or a variety of work-from-home and lifestyle options. With the potential for 4 to 6 bedrooms spread across two levels, a full bathroom on each floor, a detached two-car garage, and parking for 6+ vehicles, this property offers exceptional functionality both inside and out. The main level provides the convenience of one-floor living with multiple bedroom configurations to suit your needs. A full bathroom featuring a roll-in shower enhances accessibility and makes the home especially accommodating for those requiring mobility assistance. The spacious living room flows into a large bonus room currently utilized as a bedroom, while the kitchen offers ample workspace with a convenient peninsula. A rear bedroom includes a side exterior entrance leading to the partially covered breezeway, creating an ideal setting for a home office, sitting room, or private retreat. Cedar and linen closets provide additional storage options throughout the first floor. Accessible through the laundry area with its own exterior entrance and access to a separate driveway along Hutchinson Avenue, making it well-suited for extended family, guests, or private living quarters. This space gives access to the upper level, which includes a spacious family room with existing plumbing should a future kitchenette be desired, a generous living area, a large bedroom with multiple closets, 2 additional bedrooms, a walk in closet, and a full bathroom. Outdoor amenities include the partially covered breezeway perfect for entertaining, an oversized detached two-car garage, and abundant off-street parking. Conveniently located directly across from a township playground and within walking distance to shopping and everyday conveniences, the home also offers easy access to Routes 420, MacDade Boulevard, I-95, and I-476. Philadelphia, Philadelphia International Airport, tax-free Delaware, and King of Prussia are all within approximately 30 minutes, making this a fantastic location for commuters and travelers alike.

2400 Grand Ave, Holmes

$3,400,000

1011237 MLS

Exceptional investment and development opportunity offering nearly 100 acres across two contiguous parcels with six existing single-family homes, including two waterfront residences situated on a private 5-acre lake. Owned by the same family since 2001, the property was privately occupied until 2016 and is now fully leased, providing immediate income with significant upside potential. All tenants are currently on month-to-month leases, and rents are believed to be below current market rates. The portfolio includes three 3-bedroom homes, two 5-bedroom homes, and one 6-bedroom home. Current gross rental income is approximately $16,150 per month, with rents remaining largely unchanged for many years. Additional features include shared well water and septic systems, a private dead-end road setting, and substantial undeveloped acreage. The property is currently approved for single-family residential use and presents a rare opportunity for investors, developers, builders, or end users seeking a private compound, income-producing asset, or future development potential. Buyers are encouraged to conduct their own due diligence regarding zoning, subdivision possibilities, and development opportunities.

29-35 Bowen Court, Holmes

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