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225 Lakeside Drive, South Salem
$349,000
1 Baths ⋅ 1059419 MLS
Imagine coming home to a beautifully updated studio loft in Oakridge Condos. From the moment you enter, soaring cathedral ceilings, rich hardwood floors, and abundant natural light create an inviting sense of space. The stunning living room is anchored by a Carrara marble fireplace with a custom mantel, complemented by elegant chair rail and picture frame moldings. Just beyond, a private balcony offers a peaceful retreat. The spacious kitchen is designed to impress, featuring stainless steel appliances, diamond quartz countertops, and pendant lighting above a welcoming peninsula dining area. Above the main living space, an expansive loft with picturesque lake/pond views offers endless possibilities for relaxation, creativity, or a home office. The beautifully finished bathroom features travertine tile, while an oversized in-unit washer and dryer provide everyday convenience. Three double closets and two additional main level closets offer exceptional storage. Ideally situated near New Canaan and Ridgefield, CT, with convenient access to the New Canaan train station, this home places recreation and entertainment within easy reach. Explore the scenic hiking trails of Leon Levy Preserve, approximately 3.5 miles away, enjoy the ball fields and community garden at Onatru Park. More than a place to call home, this is a lifestyle that brings comfort and convenience together.

225 Lakeside Drive, South Salem
196 Smith Ridge Road, South Salem
$1,498,000
4 Beds ⋅ 4 Baths ⋅ 1057559 MLS
This Farmhouse Homestead has it all; inviting, spacious and well-proportioned rooms that flow seamlessly from one to the next, offering places to gather, spaces to unwind, and spots to reflect. As the outside beckons from every window, step through the veranda inspired screened-in porch or traipse onto the back deck and the whimsical magic of this property quickly unfolds. Mature plantings, meandering pathways, perennial gardens, and a field of dreams makeup these park like grounds. Offering 4 Bedrooms and 3.5 Baths, Office and Bonus Room, on over 2 acres, situated within the Katonah-Lewisboro School District with easy access to New Canaan CT, Ridgefield CT, minutes to Onatru Farm and an easy commute to NYC, this peaceful sanctuary is a fairy-tale awaiting its next chapter.

196 Smith Ridge Road, South Salem
72 East Street, South Salem
$1,050,000
2 Beds ⋅ 2 Baths ⋅ 1060291 MLS
Welcome to 72 East Street, South Salem! Discover the perfect blend of comfort, charm, and convenience in this spacious 2-bedroom, 1.5-bath home, offering 2,059 square feet of inviting living space. Nestled along a peaceful street in the highly desirable Katonah-Lewisboro School District, this lovely residence offers a tranquil setting while keeping you just minutes from I-684, the Merritt Parkway, and the shopping, dining, and everyday conveniences of Oakridge Common. Thoughtfully updated, this home combines modern touches with warmth and character, creating an inviting atmosphere perfect for comfortable everyday living and effortless entertaining. Enjoy the serenity of South Salem while benefiting from easy access to major commuting routes and nearby amenities. A wonderful opportunity to enjoy the best of South Salem living!

72 East Street, South Salem
29 Hoyt Street, South Salem
$1,175,000
3 Beds ⋅ 3 Baths ⋅ 1059751 MLS
Enjoy the best of Lake Truesdale lifestyle from this beautifully updated contemporary, privately perched on an elevated setting with seasonal lake views and deeded lake rights. Vaulted ceilings, exposed beams and hardwood floors create an airy, inviting interior designed for both everyday living and entertaining. The flexible floor plan lives like a four-bedroom and includes two dedicated offices, multiple gathering spaces, a cozy fireside den and additional finished space on the lower level. Thoughtfully updated throughout, the home features renovated baths, newer appliances, stylish wallpaper and finishes, fresh interior and exterior paint, Serena and Lily lighting and a custom mudroom for easy trips to/from the lake. Outside, a large fenced backyard is framed by mature landscaping, hydrangeas and natural stonework, with plenty of room to play, entertain or simply unwind. Best of all, Lake Truesdale is just moments away, offering swimming, kayaking, paddling and a private association beach with picnic areas and kayak storage. Enjoy the relaxed feel of a lake retreat while remaining convenient to Katonah, Cross River and Ridgefield for shopping, dining, theater and everyday necessities. Located in the Katonah-Lewisboro School District, this is a home that makes every season feel like a getaway. Showings start Thursday 10/15

29 Hoyt Street, South Salem
137 Stone Meadow Unit #137, South Salem
$585,000
2 Beds ⋅ 2 Baths ⋅ 1059000 MLS
Welcome to one-level living in Oakridge! This private and spacious two bedroom/two full bath corner unit welcomes you with new flooring and fresh paint. The entry with coat closet leads to the large inviting living room which features a wood-burning fireplace. The dining area with views to the surrounding green space has plenty of room for dining table, buffet, etc. A sunny kitchen with updated stainless appliances features plentiful cabinetry, utility closet and pantry. Adjacent to the kitchen (with opening which could be made into a convenient coffee/breakfast bar) is a multi-use family room with built-in work space and sliders out to the generously-sized, newly-refinished private deck. The hallway laundry has a brand-new washer/dryer. Inside the spacious ensuite primary bedroom is a private hallway with double closets on each side, and a full bath with a tub shower. The second large bedroom has a door to a full bath with shower and door to the hallway. An outdoor storage unit on the side of the building and an assigned parking space just outside the door add to the convenience. Amenities such as tennis and basketball courts, playground two pools and spa, clubhouse, and walking paths surrounding a peaceful private sparkling lake round out the relaxation and enjoyment of Oakridge. Enjoy the best of both worlds in the vibrant community of South Salem, with access to thousands of acres of parks and preserves with miles of hiking trails and activities, museums, shops, restaurants, entertainment, highways, and train. Oakridge is minutes from Ridgefield and New Canaan, Connecticut, 14 miles from the charming village of Katonah, 1 hour to NYC, with award-winning Katonah-Lewisboro schools. STAR tax rebate of $1,496 available for those who qualify. Upcoming 2-year assessment for road repaving will be additional $124/month for two years beginning January. $225 move-in/move-out fee and $100 contribution to capital fund.

137 Stone Meadow Unit #137, South Salem
195 Kitchawan Road, South Salem
$1,495,000
5 Beds ⋅ 5 Baths ⋅ 1041208 MLS
Set high on 2.94 landscaped acres in South Salem, This home is a distinctive Yates Colonial that feels equally suited to everyday life as it does to a weekend country getaway. Freshly painted inside and out, the home retains the unique architectural character that makes it memorable. A cedar shingle multidimensional roofline, custom copper-topped turret, shaker shingle siding and a welcoming covered front porch. The dramatic two-story foyer sets the tone with a guest closet & half bath. A graceful staircase with newly installed runner & landing carpeting ascends within the turret with large windows leading to a large open second-floor landing overlooking the entry. This space creates a quiet sitting area, reading nook or game table spot. From the foyer the home flows naturally into the formal living room and dining room, connected by a double-sided wood burning fireplace and framed by large windows and french door with side glass panels that open to a balcony. The spacious chef’s kitchen looks out toward the pool and landscaped grounds. With an abundance of cabinetry, a large center island and a generous eat-in area that leads to the patio & pool, this kitchen can easily accommodate a large gathering. Directly off the kitchen is the cozy family room featuring custom built-ins, high ceilings, large windows overlooking the front grounds and the third wood burning fireplace. A first-floor bedroom ensuite with its own entrance from the pool area offers flexibility for guests, or a private office, while the adjoining full bath and first-floor laundry add everyday convenience. Upstairs the primary bedroom ensuite is privately positioned, with vaulted beamed ceiling, walk in closet, separate shower & soaking tub, double vanities. Three additional bedrooms are naturally separated and share a renovated hall bath. The home continues downstairs with approximately 1,425 square feet of space, multiple large walk-in closets, a half bath, full walkout access to the property, offering additional room to work, play or simply spread out. Outside is where your next summer experience begins. A freeform Gunite pool and stone patio create a private setting for swimming, dining and lingering into the evening, surrounded by mature landscaping and the natural beauty of the property. The pond that is on the property had been part of the owner’s lifestyle with everyone enjoying time out on the water. It has not been used lately and the stone path can easily be cleared back again. The attached two-car garage and thoughtfully placed storage throughout the home add to its practicality. The setting provides a true Northern Westchester country experience without giving up convenience. Close to restaurants, shops and daily amenities, with easy access to Ridgefield and Katonah. Leon Levy Preserve and Onatru farm park are both conveniently less than 2 miles away. A true move-in ready home.

195 Kitchawan Road, South Salem
257 Smith Ridge Road, South Salem
$700,000
3 Beds ⋅ 3 Baths ⋅ 1051757 MLS
Offered for sale for the first time, this three-bedroom, two-and-a-half-bath home is set back from the road on two private acres. Beautifully cared for throughout, the kitchen and baths have a fresh, updated feel, complementing the home's comfortable proportions and easy floor plan. Outside, mature trees and open lawn create a peaceful setting with plenty of room to garden, gather or simply enjoy the outdoors. An exceptionally well-kept home in South Salem, with easy access to the nearby hamlet of Vista and just over the border from Ridgefield, Connecticut.

257 Smith Ridge Road, South Salem
46 Truesdale Lake Drive, South Salem
$899,000
4 Beds ⋅ 4 Baths ⋅ 1045301 MLS
Lake days. Dinner reservations. The best of both worlds. This updated 4-bedroom, 3.1-bath Colonial offers 2,924 square feet and the relaxed rhythm of Truesdale Lake, just minutes from the restaurants, shopping, theater and acclaimed arts and entertainment venues in Ridgefield, Katonah and Danbury. Set on .47 acres of level property with lake views, TEA membership for private beach access and recreation, and a legal accessory apartment, this is a home that gives you plenty of ways to enjoy every day. A covered front porch welcomes you inside, where a tiled entry connects the kitchen, dining room and living room. Spacious rooms set the stage for easy entertaining, while hardwood floors, built-in bookshelves and a fireplace make the living room an inviting spot to settle in. The separate dining room is ready for casual dinners, holiday gatherings and evenings that call for a second bottle. Upstairs, the primary suite delivers room to truly spread out, with three walk-in closets and a generous alcove with built-in bookshelves—perfect for a reading lounge, home office or exercise space. A renovated marble-tiled primary bath features a spacious walk-in shower. Three additional bedrooms and a full hall bath complete the second floor. With its own entrance around back, the legal accessory apartment adds valuable flexibility for housing relatives, guests, a caregiver or potential rental use*. Outside, a level, partially-fenced backyard and stone patio offer space to play, entertain or simply enjoy a quiet evening at home. An attached two-car garage, storage and an on-demand generator with an automatic transfer switch round out the practical perks. Spend the afternoon at the private beach, head into town for dinner or a show, and enjoy HART shuttle service to the train from the area. More room, more options, and a lake lifestyle that keeps you close to everything you love.

46 Truesdale Lake Drive, South Salem
230 Lakeside Drive, South Salem
$599,000
2 Beds ⋅ 2 Baths ⋅ 1032550 MLS
Gorgeous, updated, two bedroom townhome that lives like a three bedroom! The light-filled, living area features a wood-burning fireplace and flows seamlessly into the recently renovated large eat-in kitchen. Perfect for entertaining, the kitchen boasts stainless steel appliances, an oversized center island, and sliders to the deck. The main level also includes a spacious primary suite with an en-suite bath, a second bedroom, a full hall bath, and laundry. A newly installed main staircase leads to the upper level, where you'll find a versatile loft/den space and a skylit office with a door and a closet, providing flexible space for work or guests. Updates completed within the past few years include the hot water heater, HVAC system, windows, flooring, bathroom vanities, and kitchen appliances. Residents of the Oakridge Community enjoy two recently refurbished outdoor pools, new tennis and basketball courts, and a playground. This property also includes two assigned parking spaces. A Detached One Car Garage, right next to the unit, is available separately. Walking distance to shopping and dining at Oakridge Commons and just minutes from New Canaan, Ridgefield, and Katonah. Part of the award winning Katonah Lewisboro School District.

230 Lakeside Drive, South Salem
9 Laurel Road, South Salem
$894,999
4 Beds ⋅ 2 Baths ⋅ 1036838 MLS
Welcome to 9 Laurel Road, a spacious home set on 1.5 acres along a quiet residential street in the desirable South Salem area. Surrounded by mature trees and wooded views, the property offers a peaceful setting with plenty of privacy, a generous lawn, and expansive backyard space. The home features 4 bedrooms, hardwood floors, a spacious living room, dining area, eat-in kitchen, and a comfortable family room. The flexible layout on the second floor offers many additional options, including a home office, study, or guest room. The lower level offers ample space for storage, recreation, a workshop, or future use. The attached two-car garage comfortably accommodates two vehicles with plenty of additional space. Conveniently located with local restaurants, grocery shopping, and everyday amenities just down the road, you can enjoy the privacy of a quiet, wooded setting while remaining close to everything you need.

9 Laurel Road, South Salem
32 Boutonville Road, South Salem
$250,000
1 Beds ⋅ 1 Baths ⋅ 1034248 MLS
Built in 1933, this 630 SF, 3 room cabin features a living room with original stone hearth, small kitchen, bathroom with shower, and bedroom. Private, paved uphill drive to house with rear deck and and level, usable, large yard. Septic was redone in 2018 and is rated for 2 BR. Occupied by the current owner for more than 20 years. Owner pays share of mtc (plowing etc) for Truesdale Woods Rd, where there is additional access and parking for this home.

32 Boutonville Road, South Salem
2 Tommys Lane, South Salem
$1,398,000
4 Beds ⋅ 4 Baths ⋅ 1035007 MLS
2 Tommy’s Lane in South Salem, New York, is a fully renovated four-bedroom transitional Colonial set on just shy of two flat, sun-drenched private acres with a large swimming pool. Completed in 2025, an extensive top-to-bottom renovation combines custom millwork, designer lighting, luxurious bathrooms, and a chef’s kitchen with an open floor plan designed for comfortable everyday living and entertaining. Custom black glass front doors open to a dramatic two-story foyer, introducing interiors that blend the warmth of Restoration Hardware with the sophistication of a boutique luxury hotel. Rich hardwood floors flow throughout the main living spaces. The family room features a wood-burning fireplace and a custom rich wood bar with brass mesh detailing, creating an inviting setting for quiet evenings and gatherings. The chef’s kitchen features Sub-Zero refrigeration, a professional gas range, custom cabinetry, and two-inch-thick quartz countertops. Thoughtfully selected materials and finishes bring together practical function and distinctive design. The second-floor principal suite includes a beautifully designed walk-in closet and a newly completed marble bathroom with brass fixtures, mosaic marble flooring with brass inlay, a seamless glass shower, and a soaking tub. Three additional bedrooms share a beautifully renovated hall bathroom with the same refined finishes found throughout the home. The finished lower level offers a spacious game room with a pool table, a dedicated media lounge with theater seating, a full wet bar, and a full bathroom. Windows provide natural light, while direct access to the garage adds everyday convenience. Outside, the expansive private backyard and large swimming pool create a resort-like setting for summer entertaining, outdoor relaxation, and time with family and friends. Nearly two acres of flat grounds offer space to enjoy the property’s sunshine and privacy. Located in South Salem in Northern Westchester County, 2 Tommy’s Lane offers convenient access to the Merritt Parkway. Approximate driving times are 10 minutes to New Canaan, Connecticut, 15 minutes to Ridgefield, Connecticut, and 15 minutes to downtown Katonah, New York, providing access to shopping, dining, and commuting options. With its 2025 renovation, four bedrooms, designer interiors, finished entertainment level, private acreage, and swimming pool, 2 Tommy’s Lane delivers thoughtfully finished living inside and out. More than move-in ready, this home is walk-in stylish.

2 Tommys Lane, South Salem
1 Sabbathday Hill Road, South Salem
$965,000
4 Beds ⋅ 3 Baths ⋅ 1026664 MLS
Nestled on a picturesque road in the heart of South Salem, this beautifully maintained 4-bedroom, 3-full-bath home offers the perfect balance of privacy, comfort, and convenience. Lovingly cared for by only its second owner, this exceptional home has been thoughtfully updated over the years while maintaining its warmth and charm. Set amid mature woodlands, the hilltop retreat offers a peaceful backdrop with exceptional privacy while remaining just minutes from everything you need. Designed for both everyday living and entertaining, the light-filled interior features a spacious, flowing layout with oversized windows that fill the home with natural light. The inviting living room is anchored by a cozy fireplace, creating the perfect gathering space, while the generous living areas seamlessly connect to an expansive oversized deck for effortless indoor-outdoor living. Whether hosting friends and family or enjoying a quiet morning surrounded by nature, the outdoor spaces are equally inviting. As the day winds down, unwind on the charming front porch and take in spectacular sunset views. Numerous improvements have been made throughout the years, including a beautifully renovated spa-inspired primary bathroom, an updated first-floor full bathroom, significant mechanical upgrades and many other thoughtful enhancements that provide peace of mind for years to come. The versatile lower level, currently configured as a recording studio, offers endless possibilities and can easily be transformed into a home office, recreation room, fitness studio, playroom, or creative space to fit your lifestyle. Ideally located just minutes from the charming hamlets of South Salem, Ridgefield and Katonah, you'll enjoy convenient access to boutique shopping, award-winning restaurants, wellness studios, parks, golf courses, hiking trails, and year-round recreation. Commuters will appreciate the nearby Katonah Metro-North Station with direct service to Grand Central Terminal, as well as easy access to I-684, I-84, and the Saw Mill River Parkway. Westchester County Airport is approximately 30 minutes away, making business and leisure travel effortless. The home is also conveniently located near highly regarded public schools. Whether you're seeking peaceful country living, an easy commute, or convenient access to vibrant town centers, this exceptional South Salem home offers the best of Westchester County living in one of its most desirable locations.

1 Sabbathday Hill Road, South Salem
42 Gilbert Street, South Salem
$1,150,000
3 Beds ⋅ 2 Baths ⋅ 978344 MLS
A special opportunity to own a piece of Westchester's sought after private lake communities! Beautifully sited on 83 acre Lake Truesdale. It has a large deck and dock overlooking the water, along with a private driveway. This 1930 antique colonial is full of character - beamed ceilings, a fireplace and glass doors opening to a deck built for lakeside living. The spacious living room with fireplace/dining room combo offers a wonderful layout to reimagine. Bring your vision and updates to transform this classic retreat into your dream home. Residents enjoy swimming, fishing, boating (electric motors only), sailing, paddle boarding and kayaking in warmer months, and ice skating and ice fishing in winter. All this and a private beach! Convenient to schools, shopping and town park. Ideal for full time living or a weekend getaway, this is a canvas ready for it's next chapter.

42 Gilbert Street, South Salem
9 Stewart Road, South Salem
$575,000
4 Beds ⋅ 2 Baths ⋅ 1016167 MLS
Significant price reduction. Located on a quiet cul-de-sac, this expanded four-bedroom Cape Cod-style home has great potential for the homeowner willing to invest in updating this home. It has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. The original Cape includes four bedrooms, two full bathrooms, a living room and a kitchen. A past expansion added a two-car garage on the lower level, as well as a dining room, expanded family room, and home office/den on the main level. A large walk-in attic offers lots of storage and may offer future expansion potential. The lot has a level backyard, and a large outdoor deck, with a fenced area, old stone walls, mature trees, a concrete pad/patio with a basketball hoop, and plenty of room for a garden.

9 Stewart Road, South Salem
1203 OLD POST RD RTE 35, South Salem
$569,000
3 Beds ⋅ 3 Baths ⋅ 936604 MLS
Looking for a great opportunity? Look no more! This property has tons of potential and is average in living space size for the neighborhood. It is located close to main roads with easy access to local amenities, such as shopping, banking, schools, and various eateries. Per our Appraisal describe the property as a SFR (colonial) built in 1980. It has a GLA of approx. 2100 and has 3 bedrooms and 3baths, Full/Unfinished basement and 2- ATT Garage. The property is on 27,007 sq ft lot *** Seller cannot guarantee access at any given time. Offers may be made sight unseen ***

1203 OLD POST RD RTE 35, South Salem

Listings courtesy of OneKey® MLS as distributed by MLS GRID. Based on information submitted to the MLS GRID as of . All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information.