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$699,000

Opportunity awaits in the heart of Katonah! Nestled on a quiet cul-de-sac in the highly sought-after Katonah-Lewisboro School District, this 4-bedroom, 2-bath Cape Cod offers the perfect opportunity to create your dream home in one of Northern Westchester's most desirable communities. Ideally located just minutes from Katonah Elementary School, Katonah Village, Metro-North, shopping, restaurants, parks, tennis courts, and town amenities, this home combines an exceptional location with outstanding potential. Features include a spacious layout, walk-out basement, and attached one-car garage. This property offers an excellent opportunity for buyers looking to renovate and customize the home to their own taste and style. Ideal for homeowners, contractors, or investors, it presents tremendous upside in a neighborhood where homes rarely become available. Improvements made to the property have the potential to significantly enhance its value. Enjoy all that Katonah has to offer, from charming boutiques and dining along Katonah Avenue to community pools, playgrounds, parks, and convenient Metro-North access for an easy commute to New York City. A rare opportunity to own in one of Westchester's most sought-after villages. Bring your vision and make this Katonah gem your own!

4 Beds ⋅ 2 Baths ⋅ 1027327 MLS

Opportunity awaits in the heart of Katonah! Nestled on a quiet cul-de-sac in the highly sought-after Katonah-Lewisboro School District, this 4-bedroom, 2-bath Cape Cod offers the perfect opportunity to create your dream home in one of Northern Westchester's most desirable communities. Ideally located just minutes from Katonah Elementary School, Katonah Village, Metro-North, shopping, restaurants, parks, tennis courts, and town amenities, this home combines an exceptional location with outstanding potential. Features include a spacious layout, walk-out basement, and attached one-car garage. This property offers an excellent opportunity for buyers looking to renovate and customize the home to their own taste and style. Ideal for homeowners, contractors, or investors, it presents tremendous upside in a neighborhood where homes rarely become available. Improvements made to the property have the potential to significantly enhance its value. Enjoy all that Katonah has to offer, from charming boutiques and dining along Katonah Avenue to community pools, playgrounds, parks, and convenient Metro-North access for an easy commute to New York City. A rare opportunity to own in one of Westchester's most sought-after villages. Bring your vision and make this Katonah gem your own!

15 Nightingale Road, Katonah

$1,150,000

Through a gated entrance framed by stone pillars awaits one of South Salem's most enchanting hidden treasures. Circa 1802, this extraordinary residence has been thoughtfully restored and impeccably maintained, blending authentic period character with the comforts of modern living. Set on a level, manicured acre, the grounds are magical, with lush lawns, specimen trees, mature hemlocks, hydrangeas, perennial gardens, a gentle stream with a charming bridge, stone patios, an arbor, white picket fencing, and exceptional privacy. Inside, the home evokes the warmth of a fine New England inn with wide-plank floors, exposed beams, granite stone fireplaces, and custom built-ins. The chef's kitchen with Viking range opens to the inviting family room with fireplace and sliding doors to the deck. A gracious office with bay window and full bath complete the main level. Upstairs, charming bedrooms, an additional full bath, and a luxurious primary suite with vaulted ceiling, fireplace, walk-in closet, spa bath with oversized steam shower, and adjacent laundry provide comfort and privacy. Complete with two-zone central air, whole-house generator, sprinkler system, detached garage, and Pella windows, this rare turnkey offering is just one minute to shopping and only ten minutes to the New Canaan train.

3 Beds ⋅ 3 Baths ⋅ 1027772 MLS

Through a gated entrance framed by stone pillars awaits one of South Salem's most enchanting hidden treasures. Circa 1802, this extraordinary residence has been thoughtfully restored and impeccably maintained, blending authentic period character with the comforts of modern living. Set on a level, manicured acre, the grounds are magical, with lush lawns, specimen trees, mature hemlocks, hydrangeas, perennial gardens, a gentle stream with a charming bridge, stone patios, an arbor, white picket fencing, and exceptional privacy. Inside, the home evokes the warmth of a fine New England inn with wide-plank floors, exposed beams, granite stone fireplaces, and custom built-ins. The chef's kitchen with Viking range opens to the inviting family room with fireplace and sliding doors to the deck. A gracious office with bay window and full bath complete the main level. Upstairs, charming bedrooms, an additional full bath, and a luxurious primary suite with vaulted ceiling, fireplace, walk-in closet, spa bath with oversized steam shower, and adjacent laundry provide comfort and privacy. Complete with two-zone central air, whole-house generator, sprinkler system, detached garage, and Pella windows, this rare turnkey offering is just one minute to shopping and only ten minutes to the New Canaan train.

336 Smith Ridge Road, South Salem

$780,000

Nestled in the charming hamlet of Katonah, this inviting four-bedroom home offers the perfect blend of comfort, privacy and natural beauty. Surrounded by mature trees and peaceful scenery, you’ll enjoy a tranquil setting that feels like a private retreat while remaining close to everything Katonah has to offer. Inside, a bright open floor plan creates an effortless flow for everyday living and entertaining. The spacious eat-in kitchen with custom wood cabinetry, granite counters and a generous center island serve as the heart of the home, opening to the dining area where sliding glass doors lead to a deck – perfect for morning coffee, outdoor dining or simply taking in the serene surroundings. The welcoming living room features a wood-burning fireplace, creating a warm gathering space throughout the seasons. A spacious primary bedroom with an en-suite bath, two additional bedrooms and a hall bath complete the main level. The walkout lower level expands the home’s living space with a large family room featuring sliding glass doors to the deck and backyard, providing an ideal setting for relaxing, entertaining, or hosting guests. This level also includes a fourth bedroom, powder room, laundry area, and direct access to the attached garage. Whether you’re looking for peaceful everyday living or a home designed for gathering with family and friends, this exceptional property delivers both. Experience the charm of Katonah, the beauty of nature, and a home you’ll love coming back to every day. The home also features hardwood floors throughout the main level, roof and furnace only 10 years old.

4 Beds ⋅ 3 Baths ⋅ 1026527 MLS

Nestled in the charming hamlet of Katonah, this inviting four-bedroom home offers the perfect blend of comfort, privacy and natural beauty. Surrounded by mature trees and peaceful scenery, you’ll enjoy a tranquil setting that feels like a private retreat while remaining close to everything Katonah has to offer. Inside, a bright open floor plan creates an effortless flow for everyday living and entertaining. The spacious eat-in kitchen with custom wood cabinetry, granite counters and a generous center island serve as the heart of the home, opening to the dining area where sliding glass doors lead to a deck – perfect for morning coffee, outdoor dining or simply taking in the serene surroundings. The welcoming living room features a wood-burning fireplace, creating a warm gathering space throughout the seasons. A spacious primary bedroom with an en-suite bath, two additional bedrooms and a hall bath complete the main level. The walkout lower level expands the home’s living space with a large family room featuring sliding glass doors to the deck and backyard, providing an ideal setting for relaxing, entertaining, or hosting guests. This level also includes a fourth bedroom, powder room, laundry area, and direct access to the attached garage. Whether you’re looking for peaceful everyday living or a home designed for gathering with family and friends, this exceptional property delivers both. Experience the charm of Katonah, the beauty of nature, and a home you’ll love coming back to every day. The home also features hardwood floors throughout the main level, roof and furnace only 10 years old.

99 Lakeside Drive, Katonah

$1,550,000

Escape to your own private waterfront retreat on Lake Oscaleta! This natural glacial lake offers peaceful scenery and year-round recreation. The updated, 2,226-square-foot lakehouse combines quiet privacy with the warmth of a welcoming lake community. A private dock and sandy shallows provide gradual water entry, creating an ideal place for summer swimming, launching a kayak, fishing or simply relaxing at the water's edge. As the seasons change, the lake becomes a backdrop for boating, brilliant fall foliage, winter ice skating, spring birdwatching, and countless opportunities to reconnect with nature. Entertain outdoors on the slate patio and spacious lawn, or enjoy the ever-changing lake views from inside the home. Life on Lake Oscaleta is more than waterfront living -- it is a rare opportunity to experience the beauty, recreation, and sense of escape that only a lake community can offer. The open-concept kitchen, dining, and living areas are designed to maximize the views, anchored by hardwood floors and a wood-burning fireplace. A primary bedroom, full bathroom, versatile den or study, and second bathroom complete the main floor. Upstairs, a second primary bedroom and adjacent sitting room offer expansive vistas in any season, while a third bedroom and another full bathroom complete the upper level. A practical breezeway connects the home and garage, offering an additional sheltered outdoor space. Downstairs, a large unfinished basement is ready for storage and calls out for a home gym or a future recreation room. Whole-house emergency generator (propane). Katonah-Lewisboro School District, Twin Lakes Village/Two Lake Club HOA. Additional photos to follow... This property will not last—come see it for yourself before it is too late!

3 Beds ⋅ 3 Baths ⋅ 1025934 MLS

Escape to your own private waterfront retreat on Lake Oscaleta! This natural glacial lake offers peaceful scenery and year-round recreation. The updated, 2,226-square-foot lakehouse combines quiet privacy with the warmth of a welcoming lake community. A private dock and sandy shallows provide gradual water entry, creating an ideal place for summer swimming, launching a kayak, fishing or simply relaxing at the water's edge. As the seasons change, the lake becomes a backdrop for boating, brilliant fall foliage, winter ice skating, spring birdwatching, and countless opportunities to reconnect with nature. Entertain outdoors on the slate patio and spacious lawn, or enjoy the ever-changing lake views from inside the home. Life on Lake Oscaleta is more than waterfront living -- it is a rare opportunity to experience the beauty, recreation, and sense of escape that only a lake community can offer. The open-concept kitchen, dining, and living areas are designed to maximize the views, anchored by hardwood floors and a wood-burning fireplace. A primary bedroom, full bathroom, versatile den or study, and second bathroom complete the main floor. Upstairs, a second primary bedroom and adjacent sitting room offer expansive vistas in any season, while a third bedroom and another full bathroom complete the upper level. A practical breezeway connects the home and garage, offering an additional sheltered outdoor space. Downstairs, a large unfinished basement is ready for storage and calls out for a home gym or a future recreation room. Whole-house emergency generator (propane). Katonah-Lewisboro School District, Twin Lakes Village/Two Lake Club HOA. Additional photos to follow... This property will not last—come see it for yourself before it is too late!

56 Twin Lakes Road, South Salem

$1,150,000

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.

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

$2,750,000

A rare opportunity to own a custom-designed home in Silvermine Preserve, an exclusive enclave of architecturally distinctive residences in South Salem. Set on 1.33 private acres at the entrance to Sachem Way, this exceptional residence was envisioned by the builder in collaboration with acclaimed architect Teo Siguenza, inspired by the enduring character of the farmhouse and reimagined through a modern-rustic architectural lens. Clean, elegant architecture is paired with earthy, natural materials—including rich stained wood siding, handcrafted stone, iron, and concrete—creating a home that is both timeless and distinctive. Expansive walls of glass fill the thoughtfully designed interiors with natural light and capture peaceful backyard views. Built for exceptional comfort, performance, and sustainability, the home features geothermal heating and cooling, rooftop solar, insulated concrete form (ICF) construction, and premium European triple-pane windows and doors. Thoughtfully designed living spaces include a dramatic great room with fireplace, a beautifully appointed kitchen with breakfast area and terrace access, a formal dining room, an expansive primary suite with dressing room and spa-inspired bath, and a walkout lower level. Located in the highly regarded Katonah-Lewisboro School District, this is a rare opportunity to own a home where inspired architecture, exceptional craftsmanship, and energy-conscious living come together.

4 Beds ⋅ 4 Baths ⋅ 1023010 MLS

A rare opportunity to own a custom-designed home in Silvermine Preserve, an exclusive enclave of architecturally distinctive residences in South Salem. Set on 1.33 private acres at the entrance to Sachem Way, this exceptional residence was envisioned by the builder in collaboration with acclaimed architect Teo Siguenza, inspired by the enduring character of the farmhouse and reimagined through a modern-rustic architectural lens. Clean, elegant architecture is paired with earthy, natural materials—including rich stained wood siding, handcrafted stone, iron, and concrete—creating a home that is both timeless and distinctive. Expansive walls of glass fill the thoughtfully designed interiors with natural light and capture peaceful backyard views. Built for exceptional comfort, performance, and sustainability, the home features geothermal heating and cooling, rooftop solar, insulated concrete form (ICF) construction, and premium European triple-pane windows and doors. Thoughtfully designed living spaces include a dramatic great room with fireplace, a beautifully appointed kitchen with breakfast area and terrace access, a formal dining room, an expansive primary suite with dressing room and spa-inspired bath, and a walkout lower level. Located in the highly regarded Katonah-Lewisboro School District, this is a rare opportunity to own a home where inspired architecture, exceptional craftsmanship, and energy-conscious living come together.

Lot 13 Sachem Way, South Salem

$2,295,000

Gracious Country Colonial! Originally built in 1932 and thoughtfully renovated, this timeless antique Colonial seamlessly blends historic character with modern updates. Offering approximately 2,800 square feet of beautifully appointed living space, the home features hardwood floors, period millwork, abundant natural light, French doors, and nicely proportioned rooms throughout. Former owner Liz Lange engaged noted designer Jonathan Adler to appoint the interior. The chef's kitchen features all Viking appliances, custom cabinetry, marble countertops, a center island with breakfast bar, and provides easy access to the outdoor terrace—ideal for everyday living and entertaining. Expansive, level lawns lead to hidden walking trails at the rear of the property, while a private in-ground pool and cabana create a peaceful outdoor retreat. This home is brimming with charm and distinctive character throughout. Additional highlights include a formal dining room, an elegant living room with a fireplace and custom built-ins, a sweet sunroom, and a versatile den/home office. The second-floor features three beautifully appointed bedrooms, an additional office, and a spacious primary suite with an ensuite bath. Professionally landscaped grounds enhance the property's setting, offering a peaceful and picturesque backdrop. Conveniently located just minutes from the Villages of Katonah and Ridgefield, with easy access to major commuting arteries. This home is located within the award-winning Katonah-Lewisboro School District. This is one you won't want to miss!

3 Beds ⋅ 5 Baths ⋅ 1018990 MLS

Gracious Country Colonial! Originally built in 1932 and thoughtfully renovated, this timeless antique Colonial seamlessly blends historic character with modern updates. Offering approximately 2,800 square feet of beautifully appointed living space, the home features hardwood floors, period millwork, abundant natural light, French doors, and nicely proportioned rooms throughout. Former owner Liz Lange engaged noted designer Jonathan Adler to appoint the interior. The chef's kitchen features all Viking appliances, custom cabinetry, marble countertops, a center island with breakfast bar, and provides easy access to the outdoor terrace—ideal for everyday living and entertaining. Expansive, level lawns lead to hidden walking trails at the rear of the property, while a private in-ground pool and cabana create a peaceful outdoor retreat. This home is brimming with charm and distinctive character throughout. Additional highlights include a formal dining room, an elegant living room with a fireplace and custom built-ins, a sweet sunroom, and a versatile den/home office. The second-floor features three beautifully appointed bedrooms, an additional office, and a spacious primary suite with an ensuite bath. Professionally landscaped grounds enhance the property's setting, offering a peaceful and picturesque backdrop. Conveniently located just minutes from the Villages of Katonah and Ridgefield, with easy access to major commuting arteries. This home is located within the award-winning Katonah-Lewisboro School District. This is one you won't want to miss!

137 Boway Road, South Salem

$2,595,000

INDOOR POOL! Primary on the main level. Set behind gates on more than 13 acres, with an indoor pool, this subdividable, thoughtfully renovated country property offers a rare combination of privacy, space, and convenience just minutes from the heart of Katonah. With over 4,000 square feet of updated living space, the home features a welcoming layout designed for comfortable everyday living and entertaining. Seasonal glimpses of the reservoir complement the property's natural setting. The home includes four bedrooms - primary on the main level; four renovated baths; an updated kitchen; expansive gathering spaces; and a heated indoor pool that provides year-round enjoyment -- an amenity rarely found in the area. Large windows bring in abundant natural light and frame views of the surrounding landscape. Recent improvements, including a new roof, energy-efficient windows, all-new plumbing, durable Hardie(R)Plank siding, and extensive interior renovations, provide the benefits of modern updates along with peace of mind. Whether as a full-time residence or a weekend retreat, this distinctive property offers generous acreage with easy access to Katonah Village, Metro-North, schools, and major commuting routes. A unique opportunity to enjoy updated country living in one of northern Westchester's most desirable locations.

4 Beds ⋅ 4 Baths ⋅ 1020428 MLS

INDOOR POOL! Primary on the main level. Set behind gates on more than 13 acres, with an indoor pool, this subdividable, thoughtfully renovated country property offers a rare combination of privacy, space, and convenience just minutes from the heart of Katonah. With over 4,000 square feet of updated living space, the home features a welcoming layout designed for comfortable everyday living and entertaining. Seasonal glimpses of the reservoir complement the property's natural setting. The home includes four bedrooms - primary on the main level; four renovated baths; an updated kitchen; expansive gathering spaces; and a heated indoor pool that provides year-round enjoyment -- an amenity rarely found in the area. Large windows bring in abundant natural light and frame views of the surrounding landscape. Recent improvements, including a new roof, energy-efficient windows, all-new plumbing, durable Hardie(R)Plank siding, and extensive interior renovations, provide the benefits of modern updates along with peace of mind. Whether as a full-time residence or a weekend retreat, this distinctive property offers generous acreage with easy access to Katonah Village, Metro-North, schools, and major commuting routes. A unique opportunity to enjoy updated country living in one of northern Westchester's most desirable locations.

380 Cross River Road, Katonah

$999,999

First time ever offered on the market! Welcome to 9 Lois Lane, a rare opportunity in one of Katonah’s most desirable settings. Located on a quiet cul-de-sac, this 5-bedroom, 4.5-bath home sits on over 2 beautiful, level acres offering privacy, space, and endless potential. The property features a spacious layout, two-car garage, in-ground pool, and an incredible flat backyard surrounded by mature trees. The home is ready for its next chapter and offers the perfect canvas for renovation, customization, or creating your dream estate. Conveniently located close to Katonah Village, Metro-North, shops, restaurants, parks, and major highways. Property, pool, deck, and all structures are being sold strictly as-is. Bring your vision and take advantage of this special opportunity to transform this property into something truly special.

5 Beds ⋅ 5 Baths ⋅ 1023189 MLS

First time ever offered on the market! Welcome to 9 Lois Lane, a rare opportunity in one of Katonah’s most desirable settings. Located on a quiet cul-de-sac, this 5-bedroom, 4.5-bath home sits on over 2 beautiful, level acres offering privacy, space, and endless potential. The property features a spacious layout, two-car garage, in-ground pool, and an incredible flat backyard surrounded by mature trees. The home is ready for its next chapter and offers the perfect canvas for renovation, customization, or creating your dream estate. Conveniently located close to Katonah Village, Metro-North, shops, restaurants, parks, and major highways. Property, pool, deck, and all structures are being sold strictly as-is. Bring your vision and take advantage of this special opportunity to transform this property into something truly special.

9 Lois Lane, Katonah

$1,695,000

Architecturally distinctive and beautifully connected to its natural surroundings, this custom cedar contemporary offers a refreshing alternative to the traditional colonial. Set on over 4 private acres in the heart of South Salem, the home blends dramatic volume, natural light, privacy, and flexible living spaces designed for modern living. The home’s layout flows easily from one inviting space to the next, creating a comfortable setting for both everyday living and entertaining. A welcoming entry opens to the formal dining room and wet bar, then leads into the heart of the home: a spacious kitchen and great room overlooking the backyard. The kitchen features a Viking range, Sub-Zero refrigerator, generous island, dining area, and an adjoining sitting area with fireplace. Walls of glass and oversized windows bring in beautiful natural light while framing views of the rolling lawn, mature trees, and charming barn beyond. The main level also includes a home office with full bath, as well as a separate guest wing with a bedroom, full bath, and laundry. Just off the entry, the formal living room is slightly elevated and offers hardwood floors, dramatic ceiling height, a wood-burning stove, and French doors to a deck overlooking the grounds. From the living room, stairs lead to the bedroom level, where the spacious primary suite feels like a private retreat with vaulted ceilings, fireplace, oversized walk-in closet, and spa-inspired bath. Three additional bedrooms complete this level, along with spiral stairs to a loft area ideal for a game room, creative space, storage, or secondary office. Above the garage, the private guest quarters offer exceptional flexibility for extended guests, multigenerational living, a refined work-from-home setup, or supplemental income potential. This space includes its own entry, living room, kitchen, two bedrooms, and a full bath. The lower level adds even more usable space with an additional bedroom and bath, home gym, storage, and walk-out access to the yard. Outside, expansive decks and patios overlook the rolling lawn and mature woodland, creating a peaceful setting for entertaining, quiet mornings, or simply enjoying the beauty of the property. A barn adds charm and function for the hobbyist, gardener, or outdoor enthusiast, and the grounds offer plenty of room for a pool. Additional highlights include a three-car attached garage, abundant storage, and numerous recent improvements, including a new roof, refinished cedar exterior, new garage doors, and meticulous maintenance throughout. Located within the Katonah-Lewisboro School District, this special South Salem retreat offers the ideal balance of privacy and convenience, just minutes from Metro-North, Ward Pound Ridge Reservation, local hamlets, shopping, dining, and major commuting routes.

5 Beds ⋅ 6 Baths ⋅ 1020960 MLS

Architecturally distinctive and beautifully connected to its natural surroundings, this custom cedar contemporary offers a refreshing alternative to the traditional colonial. Set on over 4 private acres in the heart of South Salem, the home blends dramatic volume, natural light, privacy, and flexible living spaces designed for modern living. The home’s layout flows easily from one inviting space to the next, creating a comfortable setting for both everyday living and entertaining. A welcoming entry opens to the formal dining room and wet bar, then leads into the heart of the home: a spacious kitchen and great room overlooking the backyard. The kitchen features a Viking range, Sub-Zero refrigerator, generous island, dining area, and an adjoining sitting area with fireplace. Walls of glass and oversized windows bring in beautiful natural light while framing views of the rolling lawn, mature trees, and charming barn beyond. The main level also includes a home office with full bath, as well as a separate guest wing with a bedroom, full bath, and laundry. Just off the entry, the formal living room is slightly elevated and offers hardwood floors, dramatic ceiling height, a wood-burning stove, and French doors to a deck overlooking the grounds. From the living room, stairs lead to the bedroom level, where the spacious primary suite feels like a private retreat with vaulted ceilings, fireplace, oversized walk-in closet, and spa-inspired bath. Three additional bedrooms complete this level, along with spiral stairs to a loft area ideal for a game room, creative space, storage, or secondary office. Above the garage, the private guest quarters offer exceptional flexibility for extended guests, multigenerational living, a refined work-from-home setup, or supplemental income potential. This space includes its own entry, living room, kitchen, two bedrooms, and a full bath. The lower level adds even more usable space with an additional bedroom and bath, home gym, storage, and walk-out access to the yard. Outside, expansive decks and patios overlook the rolling lawn and mature woodland, creating a peaceful setting for entertaining, quiet mornings, or simply enjoying the beauty of the property. A barn adds charm and function for the hobbyist, gardener, or outdoor enthusiast, and the grounds offer plenty of room for a pool. Additional highlights include a three-car attached garage, abundant storage, and numerous recent improvements, including a new roof, refinished cedar exterior, new garage doors, and meticulous maintenance throughout. Located within the Katonah-Lewisboro School District, this special South Salem retreat offers the ideal balance of privacy and convenience, just minutes from Metro-North, Ward Pound Ridge Reservation, local hamlets, shopping, dining, and major commuting routes.

South Salem

$1,750,000

Katonah, swim at your private oasis, this multi-functional home with in-law capacity, entertainment amenities, and office workspace is nestled on almost 3 acres of lush parklike property. Enjoy the ease of being close to town, elementary school, and Metro-North; this exceptional 3,738 sqft residence offers the perfect blend of tranquility and commuter convenience. Designed with flexible home features including an open floor plan with soaring vaulted ceilings, skylights, full office suite, and beautifully refinished hardwood floors. Offering 4 bedrooms that live like five, along with 4 full and 3 half baths, the layout includes the option of a first-floor primary suite or an equally inviting second-floor suite. The finished lower level with walkout access to patio and gated pool, adds 2,186 sqft, and includes an entertainment area with fireplace, an abundance of storage, and changing rooms. Previously used as a doctor's office with a separate entrance and a renovated waiting area. The newly created chef's kitchen features a Sub-Zero refrigerator, all-new Bosch appliances, including an induction cooktop, quartz counters, and premium finishes. Many upgrades include new HVAC system, all new pool equipment, and freshly painted interior and exterior. Surrounded by mature landscaping, this gated and fully fenced property feels like a private retreat. A rare offering that is move-in ready yet brimming with potential.

4 Beds ⋅ 7 Baths ⋅ 1014445 MLS

Katonah, swim at your private oasis, this multi-functional home with in-law capacity, entertainment amenities, and office workspace is nestled on almost 3 acres of lush parklike property. Enjoy the ease of being close to town, elementary school, and Metro-North; this exceptional 3,738 sqft residence offers the perfect blend of tranquility and commuter convenience. Designed with flexible home features including an open floor plan with soaring vaulted ceilings, skylights, full office suite, and beautifully refinished hardwood floors. Offering 4 bedrooms that live like five, along with 4 full and 3 half baths, the layout includes the option of a first-floor primary suite or an equally inviting second-floor suite. The finished lower level with walkout access to patio and gated pool, adds 2,186 sqft, and includes an entertainment area with fireplace, an abundance of storage, and changing rooms. Previously used as a doctor's office with a separate entrance and a renovated waiting area. The newly created chef's kitchen features a Sub-Zero refrigerator, all-new Bosch appliances, including an induction cooktop, quartz counters, and premium finishes. Many upgrades include new HVAC system, all new pool equipment, and freshly painted interior and exterior. Surrounded by mature landscaping, this gated and fully fenced property feels like a private retreat. A rare offering that is move-in ready yet brimming with potential.

60 Cherry Street, Katonah

$650,000

Golden Opportunity. Welcome to South Salem! Nestled on a picturesque 1.09 acre, this inviting split-level home offers the perfect combination of privacy, and everyday convenience on a spacious private lot. The main level features a bright and open design with a modern eat-in kitchen, dining area, and a living room anchored by a fireplace — creating the ideal setting for both quiet evenings and effortless entertaining. The upper level offers a comfortable primary suite with a hall full bath along with an additional bedroom. The lower level adds valuable storage space with a bedroom plus a dedicated laundry area. Beyond the home itself, enjoy the added lifestyle benefit providing opportunities to relax, explore, and enjoy the outdoors throughout the seasons. A wonderful South Salem retreat ready to welcome its next owner.

3 Beds ⋅ 2 Baths ⋅ 1016494 MLS

Golden Opportunity. Welcome to South Salem! Nestled on a picturesque 1.09 acre, this inviting split-level home offers the perfect combination of privacy, and everyday convenience on a spacious private lot. The main level features a bright and open design with a modern eat-in kitchen, dining area, and a living room anchored by a fireplace — creating the ideal setting for both quiet evenings and effortless entertaining. The upper level offers a comfortable primary suite with a hall full bath along with an additional bedroom. The lower level adds valuable storage space with a bedroom plus a dedicated laundry area. Beyond the home itself, enjoy the added lifestyle benefit providing opportunities to relax, explore, and enjoy the outdoors throughout the seasons. A wonderful South Salem retreat ready to welcome its next owner.

4 Lorraine Road, South Salem

$649,000

This lake community home has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. Located on a quiet cul-de-sac, this expanded cape cod-style home has good bones and great potential. Upon entering, a fireplace warms the front parlor and living room. Beyond, the kitchen opens to a dining room and an expanded family room with a stone fireplace, home office/den, and a large outdoor deck, forming the hub of this four-bedroom home. There are two bedrooms upstairs and two down, with a full bathroom on each floor. Extra storage is available in an attic easily accessible from the second floor as well as in a large unfinished basement. The level backyard includes a fenced area, old stone walls, mature trees, a concrete pad/patio with a basketball hoop, and plenty of room for a garden.

4 Beds ⋅ 2 Baths ⋅ 1016167 MLS

This lake community home has deeded access to Truesdale Lake and is located in the award-winning Katonah-Lewisboro School District. Located on a quiet cul-de-sac, this expanded cape cod-style home has good bones and great potential. Upon entering, a fireplace warms the front parlor and living room. Beyond, the kitchen opens to a dining room and an expanded family room with a stone fireplace, home office/den, and a large outdoor deck, forming the hub of this four-bedroom home. There are two bedrooms upstairs and two down, with a full bathroom on each floor. Extra storage is available in an attic easily accessible from the second floor as well as in a large unfinished basement. The level backyard includes 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

$1,795,000

RIVERBEND FARM. Remarkable frontage on the rushing Waccabuc River. The original Adams Dairy Farm--an absolutely breathtaking property with level lawns lined by old stone walls, specimen trees and vibrant flowering perennials. Incredible gardens of Daffodils, Tulips, Iris, wild Roses, Lilac, Wysteria, Allium, and Peonies along with fragrant and flowering Magnolia, Apple, and Viburnum. Raised bed, fenced gardens for seasonal produce. A former working farm with Craftsman restored dairy barn, hen house/chicken coop and old icehouse. Rare antique Farmstead dating to 1792. Beautifully scaled room with high ceilings, hardwood floors and vintage millwork. Formal Entrance Hall with front staircase and incredible newel post. Sun-filled front Parlor. Dining Room with fireplace, bay window and door to delightful, covered porch. Spacious Country Kitchen with new appliances and breakfast area incorporating an antique Boyton & Lakewood cooking stove. Warm and inviting Family Room. Second floor with Three Bedrooms, one with en suite Sitting Room with fireplace, Office and Nursery. Spectacular Party Barn with loft and game room, formerly a horse barn, brimming with endless possibilities. Over five spectacular acres. A remarkable offering -- own part of the past!

3 Beds ⋅ 2 Baths ⋅ 1012484 MLS

RIVERBEND FARM. Remarkable frontage on the rushing Waccabuc River. The original Adams Dairy Farm--an absolutely breathtaking property with level lawns lined by old stone walls, specimen trees and vibrant flowering perennials. Incredible gardens of Daffodils, Tulips, Iris, wild Roses, Lilac, Wysteria, Allium, and Peonies along with fragrant and flowering Magnolia, Apple, and Viburnum. Raised bed, fenced gardens for seasonal produce. A former working farm with Craftsman restored dairy barn, hen house/chicken coop and old icehouse. Rare antique Farmstead dating to 1792. Beautifully scaled room with high ceilings, hardwood floors and vintage millwork. Formal Entrance Hall with front staircase and incredible newel post. Sun-filled front Parlor. Dining Room with fireplace, bay window and door to delightful, covered porch. Spacious Country Kitchen with new appliances and breakfast area incorporating an antique Boyton & Lakewood cooking stove. Warm and inviting Family Room. Second floor with Three Bedrooms, one with en suite Sitting Room with fireplace, Office and Nursery. Spectacular Party Barn with loft and game room, formerly a horse barn, brimming with endless possibilities. Over five spectacular acres. A remarkable offering -- own part of the past!

121 Post Office Road, South Salem

$1,595,000

Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled interiors, rich wood floors, a fabulous fireplace, and an excellent floor plan for everyday living and entertaining. At the heart of the home is a classic Poggenpohl kitchen, as functional and elegant today as when it was first installed, opening seamlessly to inviting gathering spaces filled with natural light. Offering three bedrooms and three-and-a-half baths, the home lives comfortably with generous entertaining areas, excellent indoor flow, and peaceful views of the spacious deck and surrounding property. The expansive grounds provide exceptional privacy and ample room for a pool, creating the opportunity to further enhance this special setting. A rare offering in a coveted South Salem location, 78 Old Church Lane is ready to be enjoyed from day one.

3 Beds ⋅ 4 Baths ⋅ 1008473 MLS

Nestled on one of South Salem's most picturesque country lanes, 78 Old Church Lane offers a beautiful blend of privacy, comfort, and timeless style. Set on 4.6 magical, level acres surrounded by classic architecture and rolling countryside, this beautifully maintained residence is move-in-ready and designed for effortless living. Completely renovated in 2004, the home features sun-filled interiors, rich wood floors, a fabulous fireplace, and an excellent floor plan for everyday living and entertaining. At the heart of the home is a classic Poggenpohl kitchen, as functional and elegant today as when it was first installed, opening seamlessly to inviting gathering spaces filled with natural light. Offering three bedrooms and three-and-a-half baths, the home lives comfortably with generous entertaining areas, excellent indoor flow, and peaceful views of the spacious deck and surrounding property. The expansive grounds provide exceptional privacy and ample room for a pool, creating the opportunity to further enhance this special setting. A rare offering in a coveted South Salem location, 78 Old Church Lane is ready to be enjoyed from day one.

78 Old Church Lane, Pound Ridge

$849,000

Nestled on a private, picturesque 1-acre property, this move-in-ready home offers the perfect blend of comfort, convenience, and natural beauty. Freshly painted throughout, the home features newly refinished hardwood floors that shine with warmth and character. The spacious interior boasts two fireplaces, creating inviting gathering spaces for every season, while a beautiful bay window fills the home with natural light and frames peaceful views. The updated kitchen is equipped with stainless steel appliances, including a recently replaced dishwasher and microwave, making everyday living both stylish and practical. The primary suite offers a generous walk-in closet, and central air conditioning ensures year-round comfort. For added peace of mind, the home is generator-ready and includes a spacious two-car garage. Step outside and enjoy the stunning wraparound two-tier deck, perfect for entertaining, dining al fresco, or simply relaxing while taking in the seasonal water views and serene surroundings. A charming white fence enhances the property's curb appeal and sense of privacy. Ideally located just off Route 35, this exceptional home offers easy access to the Goldens Bridge Metro-North station on the Harlem Line, providing a convenient commute to New York City. The station also offers ample parking, making travel effortless. With its private setting, thoughtful updates, and desirable location, this beautifully maintained home is ready for its next owner to move right in and enjoy. Enjoy Seasonal lake views.

3 Beds ⋅ 3 Baths ⋅ 1007931 MLS

Nestled on a private, picturesque 1-acre property, this move-in-ready home offers the perfect blend of comfort, convenience, and natural beauty. Freshly painted throughout, the home features newly refinished hardwood floors that shine with warmth and character. The spacious interior boasts two fireplaces, creating inviting gathering spaces for every season, while a beautiful bay window fills the home with natural light and frames peaceful views. The updated kitchen is equipped with stainless steel appliances, including a recently replaced dishwasher and microwave, making everyday living both stylish and practical. The primary suite offers a generous walk-in closet, and central air conditioning ensures year-round comfort. For added peace of mind, the home is generator-ready and includes a spacious two-car garage. Step outside and enjoy the stunning wraparound two-tier deck, perfect for entertaining, dining al fresco, or simply relaxing while taking in the seasonal water views and serene surroundings. A charming white fence enhances the property's curb appeal and sense of privacy. Ideally located just off Route 35, this exceptional home offers easy access to the Goldens Bridge Metro-North station on the Harlem Line, providing a convenient commute to New York City. The station also offers ample parking, making travel effortless. With its private setting, thoughtful updates, and desirable location, this beautifully maintained home is ready for its next owner to move right in and enjoy. Enjoy Seasonal lake views.

58 Gilbert Street, South Salem

$2,995,000

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence. The grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature. Outdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation. The residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in. At the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chef’s kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living. The home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for today’s lifestyle. A screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property. Complete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease. Just minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

4 Beds ⋅ 5 Baths ⋅ 995187 MLS

Welcome to Brooke Hollow, a private and refined country estate set on over 8.7 acres along one of Pound Ridge’s most desirable roads. Tucked behind a gated entrance, the property unfolds into a quiet, beautifully composed landscape of rolling lawns, mature plantings, three serene ponds, and wooded walking paths that create a true sense of privacy and permanence. The grounds are thoughtfully designed to enhance both beauty and livability. The three ponds are supported by aerator systems that maintain water quality, circulation, and ecological balance, allowing them to remain vibrant and visually striking year-round. A wireless deer fence system, along with perimeter fencing, helps preserve the integrity of the landscape and plantings, ensuring the setting remains peaceful, natural, and undisturbed. The result is an environment that feels both curated and effortless, offering a true sense of calm and connection to nature. Outdoor living is elevated with an infinity-edge saltwater pool and spa positioned to overlook the property, a full tennis court, and multiple outdoor spaces designed for both entertaining and quiet relaxation. The residence, a meticulously maintained stone and shingle Country House, offers over 5,500 square feet of light-filled living space. A two-story entrance hall introduces the home, leading into a series of elegant yet comfortable interiors defined by high ceilings, custom millwork, and walls of windows that bring the outdoors in. At the center of the home, a dramatic great room with a soaring ceiling and fireplace anchors the main living level, flowing seamlessly into a chef’s kitchen with a large center island and adjoining breakfast area. Formal living and dining rooms provide a more classic setting, while the overall layout remains open and adaptable for modern living. The home offers four bedrooms, including a first-floor primary suite designed as a true private retreat. The suite features a double-sided fireplace, a spa-like en-suite bath, and custom walk-in closets, along with direct access to the grounds, creating a seamless connection between indoor comfort and the surrounding landscape. Additional spaces include a large playroom, multiple offices, and flexible bonus rooms suited for today’s lifestyle. A screened porch and expansive rear terrace extend the living spaces outdoors, creating a natural flow for entertaining or quiet evenings overlooking the property. Complete with a three-car garage and surrounded by preserved land and natural beauty, this is a home that offers both substance and ease. Just minutes to Katonah, Bedford Village, Ridgefield CT and Metro-North, yet entirely removed, this is Pound Ridge at its best: understated, private, and enduring.

127 Boutonville Road, Pound Ridge

$1,695,000

Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc and lives like four bedrooms (4 bedroom septic). Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic elegance with sophisticated comfort. The dramatic living room is anchored by vaulted ceilings, authentic rustic beams, and a wood-burning fireplace, creating a warm yet refined gathering space. For today’s remote lifestyle, a handsome den/home office with custom paneling and built-ins offers the perfect work-from-home setting. At the heart of the home is the expansive kitchen, uniquely warmed by a double-sided wood-burning fireplace. Entertain effortlessly in the character-filled formal dining room or unwind in the sun-drenched sunroom, which opens directly to the sprawling rear patio and picturesque grounds beyond. A rare and highly sought-after feature, the luxurious first-floor primary suite offers exceptional convenience and privacy, complete with two oversized walk-in closets and a spa-like bath. The second level provides incredible flexibility with two additional bedrooms, two full bathrooms, a dedicated second office, and an expansive playroom or media/recreation space. Experience the quiet luxury of Northern Westchester living in a home that truly has it all.

3 Beds ⋅ 4 Baths ⋅ 997072 MLS

Welcome to 158 Mead Street — offered for the first time, this custom-designed sanctuary is nestled in the heart of Waccabuc and lives like four bedrooms (4 bedroom septic). Privately sited on over four park-like acres, this elegant residence is surrounded by mature trees, creating a serene retreat just minutes from town, train, and everyday conveniences. Inside, the home seamlessly blends rustic elegance with sophisticated comfort. The dramatic living room is anchored by vaulted ceilings, authentic rustic beams, and a wood-burning fireplace, creating a warm yet refined gathering space. For today’s remote lifestyle, a handsome den/home office with custom paneling and built-ins offers the perfect work-from-home setting. At the heart of the home is the expansive kitchen, uniquely warmed by a double-sided wood-burning fireplace. Entertain effortlessly in the character-filled formal dining room or unwind in the sun-drenched sunroom, which opens directly to the sprawling rear patio and picturesque grounds beyond. A rare and highly sought-after feature, the luxurious first-floor primary suite offers exceptional convenience and privacy, complete with two oversized walk-in closets and a spa-like bath. The second level provides incredible flexibility with two additional bedrooms, two full bathrooms, a dedicated second office, and an expansive playroom or media/recreation space. Experience the quiet luxury of Northern Westchester living in a home that truly has it all.

158 Mead Street, Waccabuc

$835,000

A rare opportunity in the charming Truesdale Lake community of South Salem. This quaint cottage is in need of renovation and is being sold as-is, offering outstanding potential for restoration, investment, or new construction. Truesdale Lake is an 83-acre private lake community known for its peaceful setting, natural beauty, and long-established neighborhood character. Located in the Town of Lewisboro near the Connecticut border, the property offers access to the quiet appeal of Northern Westchester while remaining convenient to Ridgefield, Pound Ridge, Katonah, New Canaan, and surrounding towns. Ideal for builders, contractors, investors, or end users with vision. Buyer to verify all property details, lake rights, association membership, condition, permits, and building potential. Spend year round at one of Westchester's most coveted Lake communities. Buyer to do due diligence.

2 Beds ⋅ 2 Baths ⋅ 992940 MLS

A rare opportunity in the charming Truesdale Lake community of South Salem. This quaint cottage is in need of renovation and is being sold as-is, offering outstanding potential for restoration, investment, or new construction. Truesdale Lake is an 83-acre private lake community known for its peaceful setting, natural beauty, and long-established neighborhood character. Located in the Town of Lewisboro near the Connecticut border, the property offers access to the quiet appeal of Northern Westchester while remaining convenient to Ridgefield, Pound Ridge, Katonah, New Canaan, and surrounding towns. Ideal for builders, contractors, investors, or end users with vision. Buyer to verify all property details, lake rights, association membership, condition, permits, and building potential. Spend year round at one of Westchester's most coveted Lake communities. Buyer to do due diligence.

8 Hoyt Street, South Salem

$4,500,000

Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 4.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for both everyday living and entertaining. High ceilings, unique designer chandeliers, and a marble fireplace framed by expansive windows create a dramatic yet inviting ambiance. The primary suite is a private retreat, complete with a serene seating area, walk-in closet, and spa-inspired bath with soaking tub and his-and-hers sinks. The top-floor laundry room ensures effortless convenience, while the fully finished basement boasts a gym, media/recreation room, full bath, and direct walk-out to a covered patio with speakers and ceiling fans. Outdoors, an entertainer’s dream awaits: a stunning in-ground pool and hot tub with a glass railing, outdoor kitchen, fire pit lounge, and professionally landscaped grounds with Kentucky bluegrass sod and Thuja trees, creating your own private oasis. This home has been extensively updated with new roofing, siding, windows, flooring, systems, and high-end finishes, combining elegance with modern functionality. Every element has been thoughtfully curated to offer a posh lifestyle, flawless entertaining, and refined daily living. Nestled within the prestigious Pine Hill Estates, this home offers access to the highly rated Katonah-Lewisboro School District. Commuting is effortless, with close proximity to major highways and multiple Metro-North stations, providing convenient access to New York City and surrounding areas. Beyond the home's luxurious features, the location offers a wealth of recreational opportunities. Just a short drive away, Ward Pound Ridge Reservation, Westchester County's largest park, provides over 4,300 acres of natural beauty. Enjoy hiking, fishing, and camping amidst scenic landscapes and diverse wildlife. For shopping and dining, Ridge Hill is nearby, offering a variety of retail stores, restaurants, and entertainment options. Additionally, Untermyer Gardens Conservancy and Lenoir Preserve offer tranquil settings for nature walks and exploration. This residence is not just a home; it is an elevated lifestyle of comfort, convenience, as well as curated leisure and recreation. Seize the opportunity to make it yours today!

4 Beds ⋅ 5 Baths ⋅ 986698 MLS

Welcome to 45 Pine Hill Drive, where modern luxury meets timeless sophistication. This fully renovated 4-bedroom, 4.5-bath residence has been transformed into a true showpiece, offering every amenity for elevated living. Inside, discover a breathtaking open-concept kitchen by Leicht (Germany) with premium electric stainless steel appliances, dual sinks, and a striking oversized island—perfect for both everyday living and entertaining. High ceilings, unique designer chandeliers, and a marble fireplace framed by expansive windows create a dramatic yet inviting ambiance. The primary suite is a private retreat, complete with a serene seating area, walk-in closet, and spa-inspired bath with soaking tub and his-and-hers sinks. The top-floor laundry room ensures effortless convenience, while the fully finished basement boasts a gym, media/recreation room, full bath, and direct walk-out to a covered patio with speakers and ceiling fans. Outdoors, an entertainer’s dream awaits: a stunning in-ground pool and hot tub with a glass railing, outdoor kitchen, fire pit lounge, and professionally landscaped grounds with Kentucky bluegrass sod and Thuja trees, creating your own private oasis. This home has been extensively updated with new roofing, siding, windows, flooring, systems, and high-end finishes, combining elegance with modern functionality. Every element has been thoughtfully curated to offer a posh lifestyle, flawless entertaining, and refined daily living. Nestled within the prestigious Pine Hill Estates, this home offers access to the highly rated Katonah-Lewisboro School District. Commuting is effortless, with close proximity to major highways and multiple Metro-North stations, providing convenient access to New York City and surrounding areas. Beyond the home's luxurious features, the location offers a wealth of recreational opportunities. Just a short drive away, Ward Pound Ridge Reservation, Westchester County's largest park, provides over 4,300 acres of natural beauty. Enjoy hiking, fishing, and camping amidst scenic landscapes and diverse wildlife. For shopping and dining, Ridge Hill is nearby, offering a variety of retail stores, restaurants, and entertainment options. Additionally, Untermyer Gardens Conservancy and Lenoir Preserve offer tranquil settings for nature walks and exploration. This residence is not just a home; it is an elevated lifestyle of comfort, convenience, as well as curated leisure and recreation. Seize the opportunity to make it yours today!

45 Pine Hill Drive, South Salem

$3,250,000

The Cross Pond Residence, designed by acclaimed architect Frank Lupo, FAIA, is a rare architect-designed estate set on 3.48 private acres overlooking a large pond in Pound Ridge. Conceived as a series of interconnected structures thoughtfully positioned within the landscape, the property offers a level of design, craftsmanship, and flexibility seldom found in residential architecture. The main residence is organized around dramatic living spaces that embrace the surrounding landscape through expansive walls of glass, soaring ceilings, and carefully framed views of the water and grounds. The primary living area flows seamlessly to dining and kitchen spaces, creating an environment equally suited for everyday living and entertaining. The upper level serves as a private retreat with a spacious primary suite, while the lower level provides additional recreation and gathering space. Complementing the main residence is a fully self-contained secondary living quarters featuring its own living room, dining area, kitchen, bedroom, elevator, and private primary suite. Ideal for extended family, guests, live-in staff, or multigenerational living, it offers complete independence while remaining architecturally integrated with the overall composition. Additional structures include a substantial heated studio building with exceptional flexibility for creative work, hobbies, fitness, collector use, or additional vehicle storage, as well as a detached six-car garage with front and rear access, providing ample space for automobiles, equipment, and storage. Constructed with a level of detail and material quality rarely seen today, the residence incorporates steel framing, glulam beams, commercial-grade window systems, lead-coated copper roofing, standing-seam metal roofing, cedar siding, radiant heating, humidity control, and a hydraulic elevator. The result is a home designed not only for visual impact, but for longevity and performance. The grounds are equally compelling, with expansive lawns, mature trees, exposed rock outcroppings, gardens, and a large pond that serves as the focal point of the property. The landscape was conceived as an extension of the architecture, creating a seamless relationship between built form and nature. For buyers seeking additional outdoor amenities, the property offers attractive opportunities for a future pool installation. Conceptual plans have been prepared illustrating both a garage-side pool pavilion overlooking the pond and a more secluded pool retreat adjacent to the studio building, allowing future owners to tailor the outdoor experience to their lifestyle and entertaining preferences. Published in The New American House 2: Innovations in Residential Design and Construction, The Cross Pond Residence represents a rare opportunity to own an architecturally significant estate where design, landscape, and function exist in complete harmony.

4 Beds ⋅ 5 Baths ⋅ 979591 MLS

The Cross Pond Residence, designed by acclaimed architect Frank Lupo, FAIA, is a rare architect-designed estate set on 3.48 private acres overlooking a large pond in Pound Ridge. Conceived as a series of interconnected structures thoughtfully positioned within the landscape, the property offers a level of design, craftsmanship, and flexibility seldom found in residential architecture. The main residence is organized around dramatic living spaces that embrace the surrounding landscape through expansive walls of glass, soaring ceilings, and carefully framed views of the water and grounds. The primary living area flows seamlessly to dining and kitchen spaces, creating an environment equally suited for everyday living and entertaining. The upper level serves as a private retreat with a spacious primary suite, while the lower level provides additional recreation and gathering space. Complementing the main residence is a fully self-contained secondary living quarters featuring its own living room, dining area, kitchen, bedroom, elevator, and private primary suite. Ideal for extended family, guests, live-in staff, or multigenerational living, it offers complete independence while remaining architecturally integrated with the overall composition. Additional structures include a substantial heated studio building with exceptional flexibility for creative work, hobbies, fitness, collector use, or additional vehicle storage, as well as a detached six-car garage with front and rear access, providing ample space for automobiles, equipment, and storage. Constructed with a level of detail and material quality rarely seen today, the residence incorporates steel framing, glulam beams, commercial-grade window systems, lead-coated copper roofing, standing-seam metal roofing, cedar siding, radiant heating, humidity control, and a hydraulic elevator. The result is a home designed not only for visual impact, but for longevity and performance. The grounds are equally compelling, with expansive lawns, mature trees, exposed rock outcroppings, gardens, and a large pond that serves as the focal point of the property. The landscape was conceived as an extension of the architecture, creating a seamless relationship between built form and nature. For buyers seeking additional outdoor amenities, the property offers attractive opportunities for a future pool installation. Conceptual plans have been prepared illustrating both a garage-side pool pavilion overlooking the pond and a more secluded pool retreat adjacent to the studio building, allowing future owners to tailor the outdoor experience to their lifestyle and entertaining preferences. Published in The New American House 2: Innovations in Residential Design and Construction, The Cross Pond Residence represents a rare opportunity to own an architecturally significant estate where design, landscape, and function exist in complete harmony.

54 Cross Pond Road, Pound Ridge

$2,500,000

Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of elegance and ease. Enter through the impressive oversized foyer and immediately sense the grandeur. Sunlight pours through large windows, highlighting the home’s impeccable finishes and thoughtful design. The gourmet kitchen, appointed with granite countertops, opens seamlessly to the expansive living room which is ideal for both intimate gatherings and large celebrations. Additional main level spaces include a formal dining room, front and rear staircases, and a private home office with its own entrance. Upstairs, six spacious bedrooms offer exceptional comfort, each with oversized walk-in closets. Four bedrooms feature en-suite baths, while two share a classic Jack-and-Jill perfect for guests, or multi-generational living. Beautiful stone walls, natural rock outcroppings, lush lawns and wooded landscape frame the outdoor spaces. Relax on the expansive stone patio, unwind in the hot tub, or enjoy quiet evenings in the screened porch. There's even ample space for a pool. A semi-circular drive, 3-car garage, large recreation or game room, home gym, five fireplaces and whole-house generator complete this exceptional offering. Located minutes from Pound Ridge’s charming Scotts Corners and convenient to New Canaan, this home combines country serenity with everyday accessibility to shops and restaurants. A true retreat only 50 miles from Manhattan. Also available for rent at $20,000/month.

6 Beds ⋅ 8 Baths ⋅ 928343 MLS

Set on over two spectacular acres in a premier location in Pound Ridge, this custom built Colonial offers an extraordinary blend of scale, craftsmanship, and complete privacy. Tucked along a quiet country road, this home has exquisite architectural detail throughout that includes extensive custom millwork, gleaming hardwood floors, soaring ceilings, and spacious rooms that create an atmosphere of elegance and ease. Enter through the impressive oversized foyer and immediately sense the grandeur. Sunlight pours through large windows, highlighting the home’s impeccable finishes and thoughtful design. The gourmet kitchen, appointed with granite countertops, opens seamlessly to the expansive living room which is ideal for both intimate gatherings and large celebrations. Additional main level spaces include a formal dining room, front and rear staircases, and a private home office with its own entrance. Upstairs, six spacious bedrooms offer exceptional comfort, each with oversized walk-in closets. Four bedrooms feature en-suite baths, while two share a classic Jack-and-Jill perfect for guests, or multi-generational living. Beautiful stone walls, natural rock outcroppings, lush lawns and wooded landscape frame the outdoor spaces. Relax on the expansive stone patio, unwind in the hot tub, or enjoy quiet evenings in the screened porch. There's even ample space for a pool. A semi-circular drive, 3-car garage, large recreation or game room, home gym, five fireplaces and whole-house generator complete this exceptional offering. Located minutes from Pound Ridge’s charming Scotts Corners and convenient to New Canaan, this home combines country serenity with everyday accessibility to shops and restaurants. A true retreat only 50 miles from Manhattan. Also available for rent at $20,000/month.

11 Lost Nations Road, Pound Ridge