Rhinebeck Homes with Off Street Parking features

Welcome to the enchanting Rhinebeck School District, a cornerstone of this picturesque community located in Dutchess County, New York. Known for its rich history and vibrant culture, Rhinebeck offers an exceptional educational experience that nurtures young minds and prepares them for a bright future. The district is home to highly-rated schools that emphasize academic excellence, innovative teaching methods, and a strong sense of community. With a variety of extracurricular activities, including sports, arts, and clubs, students are encouraged to explore their interests and develop their talents in a supportive environment.

The charm of Rhinebeck extends beyond its schools. Nestled in the heart of the Hudson Valley, this area boasts a stunning natural landscape, historic architecture, and a bustling downtown filled with unique shops, cafes, and restaurants. Residents enjoy a close-knit community atmosphere, making it an ideal place for families and individuals alike.

When it comes to housing, Rhinebeck offers a variety of properties, many of which feature the convenience of off-street parking. This desirable feature not only enhances the aesthetic appeal of homes but also provides residents with the peace of mind that comes from having secure, accessible parking. Whether you’re looking for a quaint cottage or a spacious family home, Rhinebeck’s real estate market has something to suit every taste and lifestyle.

Discover the perfect blend of education, community, and comfort in Rhinebeck, where your dream home awaits amidst the beauty of the Hudson Valley!

Newest Rhinebeck Homes with Off Street Parking features

$1,150,000

3 Beds ⋅ 3 Baths ⋅ 1032296 MLS

Experience charming Rhinebeck Village in this post and beam Village home only blocks to fine dining, shops, farmer's market, etc. This 3 bedroom 2 1/2 bath home blends craftmanship with comfort. Radiant heat on the main level, spacious country kitchen and a large living room for gathering and or entertaining. Large primary bedroom with adjoining bath with skylights, shower and whirlpool tub, two vanities and double closet. Two comfortable bedrooms, each with closet, and full bath with laundry complete the upper level. Additional features include central air, propane heat, stainless steel appliances (French door refrigerator, DW, gas range, two ovens, microwave, wine frig), breakfast bar, natural wood finishes throughout. Generator. Attached heated two car garage with automatic door opener. Stone rear patio, attractively landscaped parcel with excellent screening.

5 Prospect Street, Rhinebeck

$735,000

3 Beds ⋅ 2 Baths ⋅ 1032450 MLS

Resting on 8.6 private acres just minutes from the heart of Rhinebeck Village, this exceptional three-bedroom, two-bath residence has been thoughtfully rebuilt from the ground up, offering the rare combination of timeless Hudson Valley charm and the confidence of virtually new construction. The comprehensive renovation touched nearly every aspect of the home. A new asphalt shingle roof, new siding, energy-efficient windows, spray foam insulation, new rafters, new doors, upgraded 200-amp electrical service, all-new plumbing, a new well pump, new 1,000-gallon septic system with leach field, new hot water heater, Mitsubishi two-zone heating and cooling system, and dehumidifier ensure years of low-maintenance ownership. Inside, engineered white oak floors flow throughout the home. The beautifully designed kitchen features quartzite and granite countertops, all-new appliances, and custom finishes, while both bathrooms have been completely reimagined with radiant heated floors. The exterior has been equally transformed with new siding, rebuilt stonewalls, bluestone walkway & patio, professionally engineered retaining walls with drainage systems, and thoughtfully designed outdoor living spaces overlooking the surrounding woodlands, creating a seamless connection between the home and its natural setting. Minutes to Rhinebeck Village, Rhinecliff Amtrak, acclaimed restaurants, farmers markets, and boutique shopping, this is a rare turnkey opportunity where every major improvement has already been completed—simply move in and enjoy the very best of Hudson Valley!

621 Milan Hollow Road, Rhinebeck

$725,000

4 Beds ⋅ 4 Baths ⋅ 1025736 MLS

Nestled within the sought-after lakeside community of Sepasco Village in the Town of Rhinebeck, this spacious and meticulously maintained 2,800-square-foot home offers an exceptional blend of comfort, flexibility, and Hudson Valley living. Featuring four bedrooms and three-and-one-half baths, the thoughtfully designed floor plan includes primary suites on both the main and second levels, making it ideal for a variety of living arrangements. Designed for today’s lifestyle, the home offers an abundance of versatile living space, including a kitchen, dining room, living room, den, family room, office, gym, media/game room, and four generously proportioned bedrooms. Whether working from home, entertaining guests, pursuing hobbies, or accommodating multi-generational living, this home easily adapts to your needs. Outdoor living is equally inviting, with an expansive deck that includes both open-air and beautifully screened-in areas, creating wonderful spaces for dining, relaxing, and entertaining. The fenced backyard is spacious and offers endless possibilities for recreation, gardening, and pets. Residents enjoy access to Lake Sepasco, a motor-free glacial lake that is not open to the public. Spend your days swimming, paddleboarding, kayaking, fishing, or enjoying lakeside picnics in this peaceful natural setting just minutes from the Village of Rhinebeck. Located within the Rhinebeck Central School District, the property is also convenient to highly regarded public and private schools, children’s camps, sporting and social clubs, and the region’s renowned equestrian facilities, riding trails, fox hunting, polo grounds, fly-fishing, hiking, skiing and more. Ideally situated in the heart of the Hudson Valley, the property is approximately 5 minutes to Rhinebeck, 7 minutes to Red Hook, 10 minutes to the Amtrak station in Rhinecliff, 30 minutes to Poughkeepsie and Metro-North trains to Grand Central Terminal, 20 minutes to Kingston, 25 minutes to Millbrook, 30 minutes to Hudson, and two hours from New York City by car. Don’t pass this one by. This is town and country living at its finest.

404 Sepasco Center Street, Rhinebeck

$685,000

4 Beds ⋅ 2 Baths ⋅ 1011291 MLS

On a quiet dead-end street close to Rhinebeck Village, this IMMACULATE 4 bedroom, 2 bath home with 2078 SF is move in ready for you. Taxes are low. There are oak floors, wonderful light, an open floor plan, a DR,LR, & a FR with a fireplace, plus there's a great kitchen w/quartz counters & an island. Outside is beautiful & private w/lawns front & back, stone walls, huge trees, & a WONDERFUL INGROUND POOL. Two porches, one glassed, one screened, bring the outside in & are perfect for fun & entertaining. Enjoy Rhinebeck's farmer's market, shopping, dining, & upstate films. Amtrak, BARD, & the TSP are all close by. What a great opportunity to find the perfect country home!

6 Kipsbergen Drive, Rhinebeck

$435,000

3 Beds ⋅ 2 Baths ⋅ 1005026 MLS

Lots of potential and a rare opportunity for affordable housing in historic, charming Rhinebeck. Only minutes from the village and Amtrak, this Ranch boast three bedrooms, two baths with radiant heat in the floors, very spacious living room, separate dining room, eat in kitchen and a family room/den with fireplace. Hardwood floors in LR, DR, bedrooms and hall.

155 Rhinecliff Road, Rhinebeck

$595,000

4 Beds ⋅ 2 Baths ⋅ 1005161 MLS

-A Rhinebeck Village Classic- Nestled beneath towering shade trees in the heart of Rhinebeck Village, this charming 1933 Craftsman-inspired cottage offers the increasingly rare combination of walkability, character, and opportunity. Original hardwood floors, period details, inviting covered porches, and a detached garage speak to the home's enduring charm, while four bedrooms and two baths provide generous space for modern living. Rich in authenticity and filled with potential, this beloved home invites its next steward to thoughtfully restore, reimagine, and make it their own. Just moments from Rhinebeck's vibrant Main Street—with its celebrated restaurants, boutiques, farmers market, and cultural attractions—this is a rare opportunity to own a piece of village history while creating the next chapter of its story. A true Rhinebeck Village classic, ready for its next chapter!!

79 S Parsonage Street, Rhinebeck

$2,955,000

4 Beds ⋅ 3 Baths ⋅ 1006579 MLS

This is a rare opportunity to thoughtfully steward and restore one of Rhinebeck Village’s most architecturally compelling historic residences — a property defined by provenance, scale, and enduring beauty. Set on coveted Chestnut Street, this distinguished circa-1870 Italianate villa offers 4 bedrooms and 2.5 baths and is among the few remaining historic homes in the village to retain such remarkable original detail and integrity. Soaring ceilings, grand arched openings, oversized bay windows, marble fireplaces, original plaster medallions, plaster walls, crown moldings, decorative chandeliers, and beautifully preserved original windows speak to a level of craftsmanship rarely found today. The home’s exceptional acoustics — enhanced by the original plaster walls — create a quiet richness and warmth throughout the interiors that is immediately felt upon entering. Built for local attorney and town supervisor George Esselstyn, the residence unfolds across graciously proportioned rooms filled with natural light, including a richly atmospheric library anchored by an intact soft-coal heating stove and original glass-front bookcases. Outside, the property becomes even more extraordinary. An original two-bay carriage barn with a walk-up loft offers exceptional potential for studio, guest, or creative use. The residence sits on an oversized village parcel with 100 feet of road frontage, accompanied by an additional separately deeded adjoining lot with another 50 feet of frontage — a rarity within Rhinebeck Village and an offering that creates an estate-like setting of unusual scale, privacy, and presence. A truly exceptional offering for those who value architectural authenticity, history, and the rare privilege of bringing a significant home into its next chapter.

31 Chestnut Street, Rhinebeck

$349,000

2 Beds ⋅ 1 Baths ⋅ 1002328 MLS

Charming Rhinebeck Cottage with Lake Rights & Modern Updates ?Tucked away on a peaceful, wooded hillside at 6 Woods Road, this updated 2-bedroom plus a BONUS room cottage perfectly balances tranquil country living with everyday convenience. Located just 8 minutes from downtown Rhinebeck world-class dining and shops, and a quick 11-minute drive from the Taconic State Parkway, it is an ideal weekend retreat or full-time residence. Step inside to find a beautifully refreshed interior boasting extensive modern updates. The master bedroom serves as a private sanctuary, complete with its own private deck—the absolute perfect spot to enjoy your morning coffee surrounded by nature. Outside, you'll find plenty of parking for guests and deeded access to Round Pond one of the area's most peaceful, serene pond. Enjoy the best of the Hudson Valley right from your doorstep!

6 Woods Road, Rhinebeck

$1,975,000

5 Beds ⋅ 3 Baths ⋅ 998837 MLS

Welcome to Knickerbocker Farm, an elegant circa 1790 farmhouse overlooking rolling meadows, a tranquil pond, and two antique barns, on over 12 acres, just three miles from the heart of Rhinebeck. Enter through the classic front hall with its graceful staircase and sense of history. The living, dining, and sitting rooms are graciously proportioned, each featuring 10-foot ceilings, decorative crown and base moldings, marble fireplaces, and beautifully preserved wide-board floors that flow throughout the home. Pocket doors connect the living room and sitting rooms, adding both charm and flexibility. Sunlight pours into the corner sunroom from the east and south, while the eat-in kitchen, anchored by a striking stone fireplace, offers a warm gathering space for casual dining. French doors open to a mahogany back deck, perfect for enjoying the sweeping pastoral views. A first-floor bedroom and full bath allow for guest accommodations or one-level living. Upstairs, four sunlit bedrooms include two spacious rooms, a cozy smaller bedroom, and one tucked away in its own wing, as well as two full baths. A full walk-up attic provides generous storage. The stately front porch spans the home’s facade, inviting quiet moments of relaxation and connection to the landscape. Knickerbocker Farm is both enchanting and timeless - elegantly designed yet comfortable to live in, with thoughtful details and sweet nooks throughout. A true Hudson Valley treasure.

565 Route 308, Rhinebeck

$790,000

3 Beds ⋅ 2 Baths ⋅ 1002822 MLS

This Rhinecliff gem sits on one of the best lots in the Hamlet and is ready for someone with vision. Offered as is, the home features great bones, beautiful hardwood floors, a half bath on the main level, and a full bath upstairs. A kitchen needs to be added, giving you the rare chance to design the heart of the home exactly as you want it. Close to the Rhinecliff train station and only two miles from Rhinebeck Village, the location is unbeatable. Enjoy being moments from the library, the local restaurant, and another new dining spot on the way, and a local market —everything that makes Rhinecliff so special. The property also includes a fantastic outbuilding with electric, gorgeous wood floors, and newly installed pine floors upstairs. It’s an ideal space for an office, studio, workshop, or anything you can imagine. A few virtual photos included for ideas of how it could look. A remarkable opportunity to put your stamp on a true Rhinecliff classic.

67 Kelly Street, Rhinecliff

$1,195,000

3 Beds ⋅ 3 Baths ⋅ 999816 MLS

Did someone say"I want a New House", Well its arrived... Don't miss the charming surprisingly expansive and yet still cozy cottage, As you open the front door you are greeted by an expansive open floor plan. Looking from the front door through the Great Room the lush greenbelt greets your eyes! In between the view line and the front door the magic happened. Completely renovated from the walls in, complete electrical upgrade, completely new HVAC to maximize Energy Efficiency, Re-sheetrocked walls and New Insulation, as well as Flooring, Cabinetry and Windows, just to identify the major points of upgrades. The floor plan has been reconfigured to enlarge the Great Room and completly open to encompass the kitchen and Dinning and Living areas as one delighful space. The kitchen's large Center Island and High-end Appliances complemented by Quartz Countertops. The Living Room anchors the views between a Stone Fireplace built from local stone and the wall of windows showcasing the spectacular pastural views.. The Primary Bedroom has been completly reconfigured to include a sumpuous Primary Bathroom, Spacious Closets and the designer included a Laundry area. Don't miss the sweet screened in porch off the Great Room, designed to give you restipe from the day! The second floor has 2 extremely large Bedrooms and another Gorgeous Bathroom, both Bedrooms have vaulted ceilings and private views of the pastures out to the remote treeline. We are NOT finished yet, the Lower Level is also remodeled into a Media Room, with a Wet Bar and Game room the Multi-Panel door/window completly folds into itself alowing your get togthers to flow without walls from the inside out! We are not done, the wonderful Home does have everything you need. Besides the 5 private acre lot there is a Barn. Two complete floors do what you want with the Barn, Entertain, Man-cave, store you priceless Car Collection, your possibilities are endless... You have to consider this Beautiful home on your next tour of Rhinebeck, minutes form the Village of Rhinebeck and the Taconic yet bathed in peace and quiet You just cannot go wrong here.....

334 Lake Drive, Rhinebeck

$1,250,000

2 Beds ⋅ 2 Baths ⋅ 997184 MLS

A charming farm house freshly painted and wide board floors refinished newer kitchen and a nice sun room . Park like grounds and home has a long set back from road .Mountain view is one of the most scenic roads in Clinton with many great properties and estates. Mostly local traffic and you are minutes from the Taconic Parkway and less than 10 minutes from downtown Rhinebeck . A wonderful property . The additional land can be easily cleared for animals and it is subdividable.

292 Mountain View Road, Rhinebeck

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