292 houses for sale in Horseshoe Hill, Pound Ridge town Westchester County New York

Highest and Best Monday@8PM* *PRIVATE STREET OFF LONG RIDGE* Space is one thing. Usable space is another. This North Stamford Colonial offers something buyers rarely regret: a 5th bedroom and bonus room above the garage, ready to become a playroom, gym, movie room, office, guest space, or whatever life calls for next. One of North Stamford's best-kept secrets is how convenient the Long Ridge corridor really is. Near the Merritt Pkwy, Old Long Ridge Village, restaurants and everyday conveniences, getting where you need to go is surprisingly easy. Set on a private road, this charming New England Colonial offers a layout that works for everyday living and entertaining. The updated eat-in kitchen features updated cabinetry, stainless steel appliances, island seating, a breakfast area and great sightlines into the family room with a wood-burning fireplace. The dining room opens directly to the living room, creating easy flow for entertaining, holiday gatherings and everyday life. Upstairs a

Timeless character and thoughtful, recent updates come together beautifully at this classic 1930s Colonial set on over three private acres in one of New Canaan's most serene settings. Lovingly maintained and enhanced over time, you'll find a rare combination of architectural charm, graceful living spaces, and a sense of quiet retreat surrounded by protected land. The gracious foyer introduces interiors filled with warmth and personality, where rich finishes and curated details create a home that feels both refined and deeply comfortable. The living room, anchored by a fireplace, opens seamlessly to a terrace, inviting an easy connection between indoor and outdoor living. A very generous dining room and a cozy, wood-paneled family room offer intimate spaces for gathering or unwinding, while the recently renovated kitchen is both functional and beautifully designed, with custom cabinetry, high-end appliances, and beautiful western sunlight with views across the property. Upstairs, four w

Set on a desirable 1-acre lot in a quiet neighborhood setting on the west side of town, this property offers exceptional potential to renovate, expand or reimagine the existing home to fit your lifestyle. Ideally located with easy access to town, the Merritt Parkway, shopping, dining, and top-rated schools, the property combines convenience, privacy, and enduring neighborhood appeal. A rare opportunity to create your dream home in one of New Canaan's most desirable locations. Please do not walk property without confirmed appointment

4 Bedrooms | 3.5 Bathrooms | 3,208 Square Feet Welcome to 71 Blackberry Drive, where contemporary updates meet exceptional design. While the field card lists the property as 2 bedrooms and 2.5 bathrooms, the home currently offers 4 bedrooms and 3.5 bathrooms, providing substantially more space and functionality than the public record reflects. The total gross living area, including the finished lower level, is 3,208 square feet, comprised of: 1,367 sq. ft. in the lower level, 1,486 sq. ft. on the first floor, 355 sq. ft. on the second floor. This beautifully renovated home features a dramatic open-concept floor plan with soaring vaulted ceilings, exposed wood beams, and expansive living and dining spaces filled with natural light. The custom kitchen is equipped with premium cabinetry, quartzite countertops, a large center island, a farmhouse sink, and stainless-steel appliances, making it ideal for both everyday living and entertaining. Additional highlights include stylishly updated b

Set on over four and a half acres of private, level grounds in one of New Canaan's most sought after locations, this exceptional estate offers a rare combination of scale, privacy, and close to town convenience. Originally built in 1962 and thoughtfully expanded, the property unfolds as a true compound. The main residence features five bedrooms, seven baths, and beautifully proportioned living spaces anchored by three fireplaces. A seamless connection between the chef's kitchen and family room creates the heart of the home, designed for both everyday living and effortless entertaining. The kitchen is fully equipped with a six burner Wolf gas range, second Wolf oven, Miele dishwasher, Sub Zero refrigerator and freezer, wine cooler, beverage drawers, marble island, and double sinks. Beyond the main residence, the estate continues to impress. A separate antique guest house with full kitchen, 3 bedroom and 1-1/2 bath provides ideal accommodations for extended family or guests. The heated g

Welcome to 761 Den Road, a charming and character-filled home set on a private, level lot in desirable North Stamford. Offering 3-4 bedrooms, 2 full baths, and timeless architectural details, this special property blends classic New England charm with comfortable everyday living. Custom built-ins, original millwork, and a beautiful stone fireplace create warmth and character throughout. The spacious living room flows seamlessly into the formal dining room, making entertaining easy and inviting. One of the home's standout features is the sun-filled family room with cathedral ceilings and walls of windows that bring the outdoors in. The kitchen offers ample space for casual dining and easy access to the patio and backyard. Outside, enjoy a large, flat yard with exceptional privacy, perfect for entertaining, gardening, pets, or play. A detached one-car garage and oversized driveway provide abundant parking for guests and multiple vehicles. Additional features include central air condition

Located in North Stamford, tucked away at the end of a cul-de-sac, this exceptional contemporary residence offers 3,544 sq. ft. of living space, 4 bedrooms, and 2.5 baths. It sits on 1.78 acres of professionally landscaped grounds overlooking a scenic pond. The sun-filled main level features a spacious living room that flows into a formal dining room with a wood-burning fireplace and a recreation room, all capturing serene water views. The second floor includes a primary suite with a fireplace and an en-suite bath, plus three additional bedrooms, each enjoying views of the pond. Outdoor living includes an expansive wraparound deck and a pool with a hot tub and attractive cascading waterfalls. A circular driveway, two-car garage, covered carport, and whole-house generator complete this exceptional move-in-ready residence, offering privacy and serenity in a south-after Stamford location. Exterior and interior security cameras are in use

Welcome to Windermere on the Lake, a premier, gated community in North Stamford. Situated on a private, scenic lot, this custom 5-bedroom, 5.1-bathroom home offers year-round views of the lake within a sought-after neighborhood. Upon entry, guests are greeted by a stunning foyer with soaring ceilings. The heart of the home is the gourmet eat-in kitchen, featuring brand-new quartzite countertops, a substantial center island, and plenty of counter space for meal prep. The kitchen flows seamlessly to the outdoor deck (with firepit), offering guests captivating views of the lake. From the elegant, formal dining room to the warmth of the cozy great room with custom built- ins, every corner of this home is a sanctuary. A spacious office is conveniently located just off the great room on the first floor. This spectacular home boasts new decorative lighting inside and out, a new entertainment system throughout, refinished floors, a repaved driveway (2025), and a new modern stair railing. The l

Set on one of North Stamford's most sought-after lanes, this beautifully refreshed New England Colonial blends timeless elegance with modern functionality, offering an ideal layout for today's lifestyle. A sun-filled, open floor plan welcomes you with a spacious living room that flows seamlessly into the formal dining room-perfect for both everyday living and entertaining. The eat-in kitchen features all new SS appliances, including a washer and dryer, and opens to a warm and inviting family room complete with custom built-ins and a fireplace. A separate sunroom, framed by French doors, leads to a rear deck and private flagstone patio-creating a perfect indoor-outdoor connection. Flexible spaces throughout the home offer endless possibilities for a home office, sitting room, or playroom. Upstairs, the expansive primary suite provides a true retreat, featuring an en-suite bath, a large exercise or sitting room, multiple closets, vaulted ceilings, and oversized windows that flood the spa

Nestled on nearly two acres at the end of a quiet cul-de-sac in desirable North Stamford, this lovely Colonial offers nearly 4,000 square feet of elegant living space. A welcoming foyer leads to sun-filled formal living and dining room, ideal for entertaining. The spacious eat-in kitchen features granite countertops, abundant cabinetry, and a bright breakfast area overlooking the scenic property. The adjoining family room boasts a fireplace and French doors that open to the outdoor living space, creating the perfect setting for indoor and outdoor gatherings. A first-floor bedroom offers private bathroom for guests, extended family, or a home office. Upstairs, the spacious primary suite features hardwood floors and a luxurious bath with a whirlpool tub, separate shower, and double-sink vanity. Three additional generously sized bedrooms and full bath complete the upper level. Additional highlights include hardwood floors, two wood burning fireplaces, central air, main-level laundry, a fu

Experience the beauty of North Stamford in this immaculate Cape with CITY WATER, set on a private acre with endless expansion possibilities. The main level offers comfortable living space with three bedrooms, an inviting living room with fireplace, and a formal dining room that opens to a bright, updated kitchen with granite countertops and stainless-steel appliances. The primary bedroom includes a classic bathroom with an elegant clawfoot tub and marble tile floor and a modern hall bathroom with a walk- in shower. The second floor opens to a spacious room that could serve as a fourth bedroom or playroom, along with a half-bath and unfinished area that could be finished to add more living space. Relax on the patio overlooking a gorgeous level yard with mature plantings, plus a detached two-car garage with loft for additional storage. Other highlights include central air, 200-amp service and more!

119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere. Spacious entertaining areas flow seamlessly to a tranquil terrace. The heart of the home includes a chef's kitchen that opens to a Great Room with a remarkable 35.5-foot vaulted ceiling, centered around a large quartz island with integrated audio. A formal dining room beneath another Baccarat chandelier sets the stage for memorable gatherings. The West wing hosts the primary suite, featuring a cozy retreat and a study with a hidden staircase leading to a gym and an 800-square-foot dressing room. An adjacent Junior Primary Suite has its own entrance and living area. Upstairs, four additional be

Located on one of New Canaan's most desirable streets, here's a home that immediately feels welcoming from the moment you arrive. Its sophisticated style and understated elegance create a quiet sense of calm the moment you walk through the doors. Filled with natural light and designed for both everyday living and elegant entertaining, this exceptional property offers timeless appeal in a beautifully private setting, just moments from town and perfectly positioned for both privacy and convenience. Professionally landscaped grounds with specimen trees further enhance the home's sense of beauty and privacy. Soaring ceilings and airy, light-filled rooms flow naturally from one to another, while elegant French doors open to a lushly landscaped courtyard, allowing the fountain and sparkling pool to become an extension of the living spaces. The formal living and dining rooms flow naturally into the airy eat-in kitchen with two chef's islands and dual ovens to a family room with a soaring cath

Welcome to The Benjamin Weed House, a distinguished and storied estate set across 3.5 exquisite acres-where historic provenance meets refined modern living. Expanded and meticulously curated over time, this exceptional five-bed, four-bath residence offers a rare blend of architectural integrity and contemporary sophistication. Inside, soaring ceilings, wide-plank hardwood floors, and masterful craftsmanship create an atmosphere of understated elegance. The chef's kitchen is both functional and beautiful, appointed with a Sub-Zero refrigerator, Wolf cooktop, granite countertops, and an expansive dining area designed for effortless entertaining. The grounds are nothing short of extraordinary-evoking the romance of an English country garden with fountain, mature specimen plantings, hydrangeas, and peonies woven throughout the landscape. A collection of thoughtfully designed outdoor amenities elevates the estate to a private retreat: a newly constructed post-and-beam barn in pine and cedar

Welcome to 193 Eden Road in Stamford, a spacious 4 bedroom, 3 bathroom home filled with opportunity and potential! This wonderful property offers generous living space, including an additional room on the lower level that can easily be used as a fifth bedroom, home office, gym, or flex space to fit your needs. Featuring two beautiful fireplaces, this home provides warmth, charm, and the perfect setting for relaxing or entertaining. A desirable layout, and endless possibilities to customize and add your personal touch, this is the perfect opportunity to create your dream home. Located in a sought-after Stamford neighborhood, this property offers space, character, and tremendous value. Don't miss the chance to make this amazing property your own!

An extraordinary 268-acre legacy estate spanning the New York-Connecticut border, Hillandale offers unrivaled privacy and timeless grandeur. Once owned by the Sulzberger family of the New York Times, the 15,000+ sq ft, eight-bedroom European-inspired manor has been meticulously restored and features magnificent formal entertaining rooms, 11 fireplaces, two elevators, a paneled library, sun-filled conservatory, billiard room, sauna, gym and an Olympic-sized indoor pool with spa. There is also an outdoor pool with dedicated pool house. Vast, beautifully designed grounds showcase formal gardens, a private lake, woodland trails, a hedge maze and lighted tennis court. Four separate guest houses and a separate garage apartment on the property create a truly unparalleled private compound. This is a once in a generation offering for those seeking exceptional elegance and seclusion. Total Acreage 268+ acres: 173+ in Pound Ridge, New York, 95+ in Stamford, Connecticut

Privately set at the end of a long drive and elevated to capture tranquil reservoir views, this more than 5,500 square foot Colonial offers a rare sense of serenity and scale. Designed to embrace its natural surroundings, the home features beautifully proportioned interiors and oversized windows that bathe each space in light. The grand living room with fireplace opens seamlessly to a screened porch, creating an effortless indoor-outdoor experience ideal for quiet mornings or relaxed entertaining. A spacious eat-in kitchen with SubZero, Wolf and Miele appliances, huge center island, and skylight connects to the inviting family room with fireplace. The second level offers a refined primary suite along with five additional bedrooms, including ensuite and Jack-and-Jill configurations. Surrounded by professionally landscaped grounds, with a tennis court and charming gazebo, the property offers a peaceful retreat just minutes from town

Set on 2.77 manicured acres in North Stamford, 223 Jonathan Drive is a stately red brick colonial that seamlessly blends classic elegance with modern updates. Set back from the quiet road, the timeless facade creates a grand first impression, leading to the home's gracious foyer with sweeping staircase. Offering nearly 5000 square feet of living space, this extensively renovated home features 6 bedrooms, 4 full and 1 half baths. The updated kitchen boasts all-new cabinetry and appliances, while the luxurious primary suite includes a spa-like bath with soaking tub, double vanities, glass shower, and walk-in closet. Enjoy the private, resort-like backyard with a beautiful pool - perfect for summer living and entertaining. New landscaping, walkways, and patio enhance the outdoor setting. Also included within the majestic property is a barn with two horse stalls. The basement offers great flex space and a gym. Elegant, updated, and set in a serene North Stamford location, this is a rare of

Rich in history and beautifully reimagined for modern living, this extraordinary North Stamford property began as a c.1780 Saltbox Colonial and has evolved into a gracious country estate. Set on 2.7 bucolic acres, the property artfully blends historic character with contemporary comfort. Expanded in the 1940s and meticulously renovated in 2020, the home honors its architectural heritage while accommodating today's lifestyle with ease and sophistication. Encompassing approximately 7,000 square feet, the main house showcases period details, elegant entertaining spaces, and warm, inviting interiors. Every renovation was thoughtfully executed to maintain authenticity, while introducing refined finishes and modern amenities. The idyllic grounds provide a private retreat, complete with a tranquil pond, heated gunite pool, and historic Lord and Burnham greenhouse. Mature landscaping, expansive level lawns, and serene surroundings create a timeless country setting. Complementing the main resid

Fall in love with the unmistakable character of this sun-drenched 1870 Farmhouse Colonial. Beautifully preserved on a lush, private 0.83-acre lot, this home blends timeless 19th-century architecture with modern updates, including a new roof, new septic system, and new well installed in 2020. Historic highlights include original wide-plank floors, exposed beams, and lovely built-ins. The main level features a spacious living room with a fireplace, a formal dining room with built-ins, framing the window, and a charming eat-in kitchen with new stone flooring, marble countertops, stainless steel appliances, a breakfast bar, and laundry. Relax in the glass-enclosed family room, which retains its original beams and flooring and opens effortlessly to a beautiful stone patio for outdoor entertaining. The second floor boasts the primary bedroom, a secondary bedroom, and a full hall bath. The third-floor features a versatile loft space that offers incredible potential to serve as a third bedroom

Architect designed Contemporary. Modern Serenity Meets Architectural Charm. Experience the perfect balance of architectural scale with a peaceful, zen atmosphere. This stunning light-filled residence is defined by its expansive open-concept layout, starting with a dramatic living and dining area featuring soaring cathedral ceilings. A series of sliding glass doors creates a seamless indoor-outdoor flow, opening the entire main level to one deck-ideal for tranquil afternoons or large-scale entertaining. The heart of the home features a chef's kitchen that opens directly into a comfortable family room, supported by a butler's pantry for effortless hosting. For ultimate convenience, the primary suite is located on the main level, offering a personal sanctuary complete with a full bath, closets, and another large deck. Upstairs, the airy feeling continues with two additional bedrooms, both featuring en-suite baths to ensure privacy for family or guests. The lower level adds even more flexi

Welcome to 150 Wildwood Road, an exceptional new construction residence that perfectly blends timeless colonial architecture with modern sophistication. Set on 1.12 private acres in one of Stamford's most sought-after neighborhoods, this 9,349-square-foot masterpiece showcases superior craftsmanship and thoughtful design by a respected local builder known for quality and attention to detail. This modern colonial offers four fully finished levels of luxurious living space, designed for both everyday comfort and elegant entertaining. From the moment you enter, you're greeted by a 2-story foyer, sun-filled open spaces, and exquisite mill work throughout. The main level features a grand foyer, expansive family room/EIK with custom fireplaces, formal dining rm, living room with custom fireplace and a gourmet chef's kitchen with Thermador appliances, custom cabinetry, and a generous center island - all opening to a light-filled breakfast area and spacious family room that lead to the huge de

Turn-key, 3-bedroom, 2-full bath split-level home set on a level 2+ acre property in a sought-after neighborhood, perfect for walking and bike riding. Enjoy direct access to Sackett State Park, offering miles of scenic trails for hiking and walking your dogs. The updated kitchen features quartz countertops, stainless steel appliances, and a breakfast bar that opens seamlessly to the dining area and spacious living room, creating an ideal layout for everyday living and entertaining. Two bedrooms share a full bath, while the primary suite offers a walk-in closet, raised ceiling with skylight, and a private full bath. The finished lower level includes a welcoming family room with a fireplace, built-in shelving, office, full bath, and walkout access to the backyard and deck. Hardwood floors throughout, a gracious entry foyer, and fresh interior and exterior paint add to the home's appeal. Solar panels help keep electric costs low. Conveniently located close to town, schools, and New Canaan

FrogPond Estate is a modern Scandinavian masterpiece unlike anything New Canaan has ever seen - an architecturally rare achievement set on 2.25 pristine, private acres, moments from the train and village. Spanning 11,836 plus square feet of sleek, sun-drenched living space, this 7-bedroom, nine-and-a-half-bath residence is defined by its 12-foot ceilings, bespoke millwork, and designer lighting - details that elevate every room into something memorable. Four thoughtfully placed laundry rooms, multiple fireplaces, and a fully custom build throughout speak to a level of intentionality rarely found at any price point. At the heart of the main level, a gourmet kitchen with double islands anchors an open floor plan crafted for both quiet daily living and effortless large-scale entertaining. Walls of glass dissolve the boundary between inside and out, opening to covered porches and private balconies that complete the estate's serene, Scandinavian sensibility. A separate 1,190 sq. ft. guest c

A tree -lined driveway leads you to the piece of paradise you've been waiting for. Tucked away on a private acre at the end of a quiet cul-de-sac this beautifully maintained Ranch features an open concept with sunken living room, adjoining dining room, well-proportioned kitchen with breakfast nook, granite countertops and stainless-steel appliances. Just off the kitchen is a family room with a fireplace. A sunlit media room adjacent to a bedroom and full bath has the potential to be a guest or in-law suite. The main level also includes a primary bedroom with a full bath, walk-in closet, skylights, plus two additional bedrooms, full bath, laundry room and an office or a possible 5th bedroom. The finished lower level adds flexible living space with a mudroom, game room, full bath, and a quartz countertop with a sink and refrigerator-ideal for entertaining. Enjoy a large deck overlooking an in-ground pool, gazebo and mature landscaping. Has city water, an oversized 2 car garage and much m