Bedford Homes with Detached Parking features

Welcome to Bedford, New York, a picturesque town nestled in the heart of Westchester County, where community spirit and educational excellence thrive. Known for its lush landscapes and charming neighborhoods, Bedford is not just a beautiful place to live; it’s also home to a highly regarded school district that prioritizes academic achievement and personal growth.

The Bedford Central School District is celebrated for its commitment to providing a top-notch education, with a strong emphasis on fostering a love for learning. With a variety of innovative programs and extracurricular activities, students are encouraged to explore their interests and develop their talents. The district boasts impressive graduation rates and a plethora of Advanced Placement courses, ensuring that students are well-prepared for college and beyond. Parents can take comfort in knowing that their children are receiving a quality education in a supportive environment.

In addition to its educational offerings, Bedford is known for its beautiful homes, many of which feature the convenience of detached parking. These properties not only provide ample space for your vehicles but also enhance the overall aesthetic of the neighborhood. Imagine coming home to a charming residence with a spacious yard and the added benefit of a detached garage, perfect for hobbies or additional storage.

Whether you’re drawn to the area's natural beauty, its vibrant community, or its educational opportunities, Bedford, NY, offers a perfect blend of comfort and convenience. Come discover your dream home in this idyllic town, where every day feels like a retreat!

Newest Bedford Homes with Detached Parking features

$2,250,000

4 Beds ⋅ 4 Baths ⋅ 1048139 MLS

OVER 14 PEACEFUL ACRES. Located off a quiet country lane, the perfect private refuge. Exquisite setting with level lawns, Ornamental Grasses and remarkable plantings. Incredible Weeping Cherry, Cut-leaf Maple, Dogwoods, Mountain Laurel, Lilac and Andromeda. Heated, gunite Swimming Pool surrounded by colorful perennials. Classic Country Colonial with warm and inviting living space. Beautifully scaled Living Room with fireplace. Library with extensive built-ins – the perfect spot for reading or working remotely. Comfortable Great Room with fireplace and wet bar. Skylit Sunroom, with window seat, brick floor and doors to the deck for easy indoor-outdoor entertaining. Well-designed Kitchen with center island, pantry and breakfast area. Spacious Primary Suite with fireplace and Bath. Guest Suite with Bedroom and Bath. Two additional Bedrooms. Multi-purpose Bonus Room with rear staircase. Garages for four cars. Convenient location moments to Scotts Corners, the town park, local schools and the library. Easy drive to New Canaan, Stamford and Bedford Village as well as I-684, the Merritt Parkway and Metro North trains. First time listed in over 40 years!

29 Bender Way, Pound Ridge

$1,550,000

3 Beds ⋅ 3 Baths ⋅ 1023810 MLS

A Storied Colonial. A Picturesque Pond. A Rare Piece of Pound Ridge History. Set in the heart of Pound Ridge’s historic hamlet, the Horace Reynolds House is an extraordinary 18th-century Colonial that beautifully marries the romance of the past with the elegance of today. Originally built in 1784 and later thoughtfully renovated by renowned philanthropist Hiram Halle in the 1930s, this exceptional residence is steeped in the history and character of old Pound Ridge. Today, the home has been exquisitely and thoughtfully decorated by a renowned local interior designer, creating an atmosphere that is sophisticated yet inviting, polished yet entirely at home in its historic setting. Inside, original architectural deals take center stage -- wide board floors, high ceilings, hand hewn beams, beautifully aged paneling and multiple fireplaces lend warmth and authenticity throughout. Gracious proportions, beautifully considered space for both everyday living and entertain. Large windows draw you outward to the property's most enchanting feature -- a picturesque pond of more than two acres, complete with private dock. 18 Salem Road is more than an antique home - it is a beautifully preserved slice of Pound Ridge history, reimagined with extraordinary style and surrounded by a timeless landscape.

18 Salem Road, Pound Ridge

$899,000

4 Beds ⋅ 3 Baths ⋅ 1043043 MLS

SITUATED IN BEDFORD CORNERS! Welcome to 88 Pines Bridge Road, a beautifully appointed home in the sought-after Bedford School District, privately set back from the road and offering an ideal blend of quality, comfort, and convenience. Refined throughout with crown molding, custom cabinetry, granite kitchen and bath finishes, walk-in closets, and high-end appliances, the home features fully renovated bathrooms with modern, high-end fixtures and a sophisticated design. Recent improvements include exterior re-siding (approx. 4 years ago), a new retaining wall, a hot water heater (approx. 5 years), and a forced hot-air oil furnace (approx. 10 years). A three-car garage provides excellent storage and flexibility, with approximately 1,000 square feet of additional space above offering strong future potential. Conveniently located near Metro-North, major highways, shopping, and daily amenities, yet set in a private, tranquil setting, this home delivers space, craftsmanship, and location in one compelling package. With its oversized rooms, updated interiors, and endless possibilities for customization and expansion, this property offers a rare combination of move-in-ready comfort and future value.

88 Pines Bridge Road, Mount Kisco

$2,900,000

4 Beds ⋅ 4 Baths ⋅ 1042389 MLS

The Epitome of Mid-Century Modern Architecture: Streamlined wood and glass MCM home exudes warmth and ease-of-living layout in its private , preserve-like setting. Minimalist design details and its turn-key condition will attract the mid-century modern enthusiast which includes 21st century digital updates. High-beamed ceilings and open social spaces inclusive of dining & living areas present vistas of lush, well designed grounds. The fenced outdoors has thoughtfully designed landscaping and the swimming pool is outfitted with a sun-shelf, electric cover and spa. There is a 2 car, climate controlled attached garage in addition to a newly built 2 car garage which is also climate controlled. Both have dual EV electric charging units. Offered fully furnished except for artwork.

14 Cradle Rock Road E, Pound Ridge

$2,150,000

4 Beds ⋅ 4 Baths ⋅ 1036619 MLS

Set behind private gates on bucolic, quiet property, this fully renovated 4-bedroom mid-century modern is a rare turn-key retreat. The custom kitchen anchors the home with a Wolf 6-burner gas range with griddle, 42” Sub-Zero refrigerator, and a quartzite double-waterfall island, all set atop new 7” wide-plank white oak floors with radiant heat throughout. New skylights draw natural light through freshly renovated interiors, backed by all-new HVAC, plumbing, electrical, roof, and a full-house generator. Outside, new landscaping and hand-laid stone walls frame a resort-worthy 62’ x 28’ pool with cabana. A detached barn/guest studio offers a recreation room, full bath, sleeping loft, its own new HVAC system, and a 2-car garage — ideal for guests, staff, or creative studio space.

39 Lower Shad Road, Pound Ridge

$3,200,000

4 Beds ⋅ 4 Baths ⋅ 1032314 MLS

A landmark Pound Ridge residence, this circa-1769 Amon Marshall Homestead was expanded over generations and has now been masterfully restored with remarkable sensitivity to its architectural heritage. Set on nearly four acres of lawns, gardens, woodland, stone walls and a picturesque pond, the home preserves its centuries-old character while offering exceptional modern comfort. Original hand-hewn beams, wood walls, historic doors and hearths were carefully restored and complemented by Venetian plaster, Marmorino, limewash, bespoke millwork, custom stonework and vintage European lighting. The chef’s kitchen pairs Cristallo marble with custom cabinetry, an AGA range and Sub-Zero appliances, while gracious living and dining spaces showcase wide-plank and herringbone floors, beautifully restored fireplaces and remarkable architectural detail. The four-bedroom layout includes a serene first-floor bedroom. The upper level offers a primary suite with custom closets and a luxurious marble bath with freestanding tub and restored steam shower. Outside, historic gardens and mature rhododendrons were revived, woodland reclaimed, stone walls repaired and the pond restored. A beautiful cedar-shake barn and possible pool site complete this singular setting. The result feels neither newly renovated nor frozen in the past, but as though it has evolved beautifully over generations, a rare property of authenticity, craftsmanship and enduring character.

156 Old Stone Hill Road, Pound Ridge

$2,350,000

3 Beds ⋅ 3 Baths ⋅ 1019874 MLS

Originally built in 1860 as the Samuel Parker House, this extraordinary property has been thoughtfully transformed into a one-of-a-kind luxury live/work compound featuring a main residence, a street-level showroom, and a heated, air-conditioned barn with a private studio above. Set in the heart of Pound Ridge's charming hamlet, directly across from The Inn at Pound Ridge by Jean-Georges, it offers a rare blend of historic character, modern functionality, and exceptional lifestyle appeal. Following a complete, no-compromise 2019 renovation under acclaimed New York interior designer Jenny Wolf of The Huntress, every element, infrastructure, mechanical systems, and all interiors alike - was reimagined to honor the homes history while delivering modern luxury. The result adapts effortlessly to almost any life: full time residence, weekend retreat, designer showroom, creative studio, gallery, or true live/work estate, creating a home that is as functional as it is beautiful. The beautifully finished street-level space offers remarkable flexibility and may continue as an inspiring showroom or seamlessly become part of the residence, creating expansive living and entertaining areas. The private upper-level home is filled with warmth and character, where soaring vaulted beamed ceilings, abundant natural light, and timeless architectural details create an atmosphere of understated elegance. A spacious great room anchors the residence, complemented by a beautifully appointed kitchen with soapstone countertops, a serene primary suite with a walk-in closet, two additional bedrooms, and thoughtfully designed baths that reflect the home's refined aesthetic. Adding to the property's exceptional appeal is a heated and air-conditioned barn offering endless possibilities. With an expansive first level ideal for a showroom, studio, workshop, entertaining, business use, or storage, and a spacious second-level studio or office, it is a rare complement to an already extraordinary offering. Life here extends far beyond the property itself. Spend mornings walking the picturesque hamlet, enjoy world-class dining just steps away at The Inn at Pound Ridge by Jean-Georges, explore nearby hiking trails, nature preserves, and equestrian estates, or simply embrace the quiet beauty and timeless charm that define Pound Ridge. Located within the highly regarded Katonah-Lewisboro School District and just over an hour from Manhattan, this is a rare opportunity to experience a lifestyle where history, design, creativity, and modern luxury exist in perfect harmony. Properties of this caliber rarely come to market. Rich in history, impeccably renovated, and genuinely unlike anything else available today, this is a singular opportunity to own one of Pound Ridge's most distinctive homes.

259 Westchester Avenue, Pound Ridge

$695,000

3 Beds ⋅ 2 Baths ⋅ 1020037 MLS

Welcome to this charming and beautifully maintained 3-bedroom, 2-bath ranch nestled on 1.21 private, wooded acres in desirable Bedford, NY. Offering the ease and convenience of true one-level living, this warm and inviting home features a thoughtfully designed layout, spacious living areas, and a peaceful natural setting that provides the perfect blend of comfort, privacy, and tranquility. The bright and welcoming living room is highlighted by an oversized picture window that fills the space with natural light and showcases views of the picturesque property. The well-appointed eat-in kitchen offers a functional and inviting space for everyday living, while the spacious formal dining room creates an elegant setting for entertaining family and friends. The sun-filled family room provides a cozy retreat overlooking the serene, wooded surroundings. The generous floor plan features two spacious bedrooms with a beautifully renovated hall bathroom, while the private primary suite is thoughtfully positioned on the opposite side of the home for added privacy and includes a stylish en-suite bath. Rich hardwood floors extend throughout the home, adding warmth and timeless character. The full basement offers abundant storage space and exciting potential for future expansion. Outside, enjoy the peaceful beauty of mature trees, lush natural landscaping, and a private backyard oasis perfect for relaxing, gardening, or enjoying the changing seasons. The detached one-car garage provides convenient parking, additional storage, or a versatile workshop space. Ideally located just minutes from charming Bedford Village, highly regarded schools, scenic parks, local shopping, exceptional dining, and major commuting routes, this delightful property offers the rare combination of peaceful country living and everyday convenience. Experience the privacy, charm, and timeless appeal that make Bedford one of Westchester’s most coveted communities.

136 Pound Ridge Road, Bedford

$15,000,000

5 Beds ⋅ 6 Baths ⋅ 1007263 MLS

EASTLAKE. Nearly 39 serene acres offering the ultimate in privacy. Long, gated drive over rushing stream and through manicured grounds. Remarkable estate compound owned for years by renowned fashion designer as a family residence. Impressive architect-designed Stone and Country House positioned to overlook a private eight-acre lake. Striking and sophisticated Contemporary with elements of a Mid-Century Modern. Impressive rooms with natural finishes of fine woods and hand-cut stone. 5500 square feet of airy, loft-like living space positioned to capture views of the water. Beautifully scaled main rooms with vaulted ceilings, finished in warm woods, stone and hardwood floors and walls of glass. Striking Living Room with stone fireplace and vaulted ceiling lit by a modern cupola. Doors to wrap-around porch for fantastic indoor-outdoor living. Open-concept Dining Area also with water view, perfectly scaled for entertaining. Sleek Kitchen designed for the consummate chef. Private Office with conference area and wet bar. Lower Level Family Room for more casual everyday living. Spacious first floor Primary Suite with ample closets and private Bath. Four additional Bedrooms, most with en-suite Baths. Breathtaking grounds amid dramatic rock outcroppings with stone walls and terraces, an incredible array of flowering plantings, rare and specimen trees and rolling lawns down to the water. Fenced garden for flowers and seasonal produce. Lakefront dock, heated Swimming Pool with Pool House and privately sited Tennis Court make for an incredible sporting lifestyle. Separate building complex with a Three-Bedroom, fully equipped Guest House, Garages for six-plus cars and equipment storage. The perfect, peaceful refuge.

164 Eastwoods Road, Pound Ridge

$6,400,000

6 Beds ⋅ 5 Baths ⋅ 992131 MLS

WOLSEY FARM. One of Bedford’s most iconic estate properties—first time offered in nearly 100 years. Remarkable Colonial Estate dating to 1810. Grand main rooms with incredibly preserved period detailing. Stunning interior with graciously proportioned rooms, high ceilings, period millwork, intricate moldings and spectacular quarter-sawn oak floors with black walnut inlays. Impressive Portico supported by massive Corinthian columns. Center Entrance Hall. Living Room with fireplace and doors to covered porch for alfresco entertaining. Formal Dining Room for entertaining. Country Kitchen with breakfast area. Family Room with doors to terrace. Library and Office for working remotely. Six Bedrooms including Primary Suites. Spectacular terrace and covered porch for alfresco entertaining. Heated Pool with Spa. Over eighteen spectacular acres with incredible trees and flowering plantings in the heart of Bedford. Gate House with fireplace-the ideal artists’s or writer’s studio. Two Bedroom Guest Cottage. Second “Superintendent’s” Cottage with two Bedrooms. Numerous barns and farm buildings including large Chicken Coop. Six fenced paddocks, an orchard, a spring-fed pond and open meadows. A once in a lifetime opportunity!

345 McLain Street, Bedford Hills

$2,795,000

5 Beds ⋅ 5 Baths ⋅ 991143 MLS

This one-of-a-kind 5 bedroom, 5 full bathroom rustic California inspired residence on one of the toniest roads in Pound Ridge sits on 6.5 private acres, complete with a pool, tennis court and treehouse. Situated in a resort like setting, the home's exquisite indoor-outdoor flow and abundant natural materials, you'll feel worlds away, but is just 3 minutes from town and an hour from NYC. Once owned by Ted Sorenson, JFK's speechwriter, the unique estate is ideal as a year-round home, weekend retreat or secluded hideaway with Belgian block and chestnut floors, stone columns (the stone of which was excavated from the site), tongue-in-groove cedar walls, soaring beamed ceilings, 22 skylights and custom windows. Custom stair railings designed by renowned rustic artist, Daniel Mack. Enjoy lavish entertaining in impressive living spaces with floor-to-ceiling fireplace and windows. The rustic dining room seats 16, the masterful kitchen with original copper bar counter, accommodates gatherings of any size. Upper-level primary suite, main-floor two-bedroom suite, home gym, media room, sauna and office with custom desk made of one solid piece of hundreds of years old Baobab tree. The lower level en suite bunk room provides ample accommodations, with private entrance. Resort-like grounds and a bucolic location make this an exceptional country estate. Custom, high level properties like this don't come up very often.

217 Trinity Pass, Pound Ridge

$3,825,000

5 Beds ⋅ 5 Baths ⋅ 987844 MLS

Refined and timeless, this gracious residence has been meticulously preserved and maintained for over a century. Approached by a gated, tree-lined gravel drive, the house is a distinguished example of early 20th-century Georgian architecture, offering exceptional privacy and a profound sense of tranquility. Set on over five acres in the heart of Bedford Hills, surrounded by majestic specimen trees and beautifully curated perennial gardens, the property embodies the essence of a classic country estate. Amenities include a heated pool, an enchanting guest cottage, a greenhouse, a caretaker’s residence, a detached two-car garage, and dedicated maintenance buildings. Inside, the house reflects the signature elegance and proportion associated with Delano & Aldrich; high ceilings, expansive openings between principal rooms, and refined architectural detailing create a seamless flow for both formal entertaining and relaxed living. Fireplaces anchor the generously scaled living and dining rooms, while framed-glass French doors open to a grand sunroom. This light-filled space extends to a stone terrace overlooking the gardens—ideal for summer gatherings or sunlit winter afternoons. The kitchen, complemented by an adjoining sitting room, offers an inviting setting for intimate meals and everyday living. Upstairs, the primary suite provides a serene retreat, complete with its own fireplace and a luxurious ensuite bath designed for quiet indulgence. A former sleeping porch has been thoughtfully reimagined as a charming playroom with adjoining guest quarters, accompanied by an additional spacious bedroom and hall bath. Each bedroom features its own distinctive fireplace and enjoys picturesque garden views through large casement windows. The third floor offers two substantial bedrooms, a classic bath, and a skylit artist’s studio filled with natural light, along with an adjoining atelier and generous storage. More land available.

328 McLain Street, Bedford Hills

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