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

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This is a Real Estate-Owned (REO)/post-foreclosure home owned or managed by a bank. All offers are considered; however, the highest and best will most likely be accepted

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

This home is in preforeclosure, which means the homeowner is in default (missed payments). Therefore, there could be an opportunity to strike a great deal with the owner and the bank

Welcome to 231 Skymeadow Drive, a lovely and beautifully maintained ranch style home with a complete accessory dwelling/in-law suite and a flexible 4Bd floorplan set on 1.11 picturesque acres in North Stamford. Blending style, comfort, and easy one-level living, this inviting home showcases light-filled interiors, generously sized rooms, and a versatile layout ideal for today's lifestyle. The main level features spacious living and entertaining areas, an expansive updated kitchen with breakfast area, 3 bedrooms, and office perfect for working from home. The primary suite features a beautiful new bathroom addition with radiant heated floors, while a bonus TV/playroom above the garage provides additional space to relax, work, or play. A standout feature is the walk-out lower level, which includes a complete accessory dwelling with its own kitchen, living room, bedroom, full bath, and private entrance. Ideal for extended family, guests, an au pair, or multigenerational living, this though

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

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitche

FrogPond Estate is New Canaan's most striking modern Scandinavian offering-an architectural achievement set on 2.25 private acres just moments from town and train. With 11,836+ sq. ft. of sunfilled, designdriven living space, this 7 bed, 9.5bath custom residence delivers soaring 12ft ceilings, bespoke millwork, designer lighting, and walls of glass that erase the line between indoors and out. A showstopping doubleisland gourmet kitchen anchors the open main level, perfect for quiet daily living or largescale entertaining. The estate's fully independent 1,190 sq. ft. Cottage-with separate address and utilities-adds a private bedroom, office, full bath, island kitchen, laundry, and a flexible loft ideal for guests, extended family, staff, or professional use. Thoughtfully scaled yet beautifully finished, it elevates FrogPond into a true multidwelling compound. Pool is open. Landscaping complete. Showready today. A rare modern sanctuary-private, polished, and unlike anything else in the m

Turn-key, move in ready modern townhouse located in the heart of downtown New Canaan, this home offers three floors of elegant living with the feel of a single-family residence and the convenience of low-maintenance living. The renovated open floor plan features a state of the art newer chef's kitchen, a breakfast nook, island, and a light-filled living room/dining room with a fireplace. The main floor offers a study or additional bedroom with its own fireplace and large windows. On the second floor, you will find the owner suite featuring- a renovated luxury bathroom with soaking tub, shower, 2 vanities, two walk-in fitted closets-along with two additional bedrooms, a full bath, and a laundry area. The lower level provides nearly 1,000 square feet of additional walk out living space with fireplace large recreation room and a patio. Outside, the walk-out lower level leads to a private patio and yard, offering a quiet oasis which backs up to a Bristow Park Bird Sanctuary and Mead Park.

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

Ideally located on a private lot in close proximity to public and private schools, 25 Hillcrest Rd. is located on a low traffic street on New Canaan's lower west side within minutes of the Merritt Parkway, Talmadge Hill train station and down town New Canaan. Spanning close to 8,000 sq ft, the transitional floor plan masterfully blends open concept spaces with more intimate, private spaces. Featuring 9' ceilings throughout and a clean, contemporary design aesthetic, the gracious home is perfect for entertaining large crowds while at the same time comfortable for everyday living. Entering through the custom designed front door, you are welcomed by a grand foyer with unobstructed views through the living room to the private backyard. As you move through the home, the centrally located family room is connected to both the large formal dining room and the gourmet kitchen which is flooded with natural light through six over sized windows. Featuring a clean, white design aesthetic the kitche

HIGHEST and BEST: TUES, AUGUST 25TH AT 12PM* Welcome to this private North Stamford retreat set on 1.58 acres of beautiful, secluded property. This 4-bedroom Colonial offers spacious living areas and an impressive outdoor setting designed for relaxing and entertaining. A 30-foot sunroom with sliders opens to the expansive backyard and pool area. The heated gunite pool is the centerpiece of the property, featuring an expansive stone terrace and waterfall feature. Pool improvements include a new gunite floor and tile in 2021, plus a new filter and electrical box in 2025. The property also offers a pool cabana with electricity, whole-house generator, deer fencing, mature landscaping, and a newly paved and sealed driveway. Inside, the home offers a mix of classic character and updates, including renovated bathrooms, Anderson windows, French doors, updated well systems, and hardwood flooring. A rare 4-car garage setup includes two attached garages plus an oversized detached barn with heat a

FrogPond Estate is New Canaan's most striking modern Scandinavian offering-an architectural achievement set on 2.25 private acres just moments from town and train. With 11,836+ sq. ft. of sunfilled, designdriven living space, this 7 bed, 9.5bath custom residence delivers soaring 12ft ceilings, bespoke millwork, designer lighting, and walls of glass that erase the line between indoors and out. A showstopping doubleisland gourmet kitchen anchors the open main level, perfect for quiet daily living or largescale entertaining. The estate's fully independent 1,190 sq. ft. Cottage-with separate address and utilities-adds a private bedroom, office, full bath, island kitchen, laundry, and a flexible loft ideal for guests, extended family, staff, or professional use. Thoughtfully scaled yet beautifully finished, it elevates FrogPond into a true multidwelling compound. Pool is open. Landscaping complete. Showready today. A rare modern sanctuary-private, polished, and unlike anything else in the m

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

Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush landscape inside. At the heart of the home, a newly updated gourmet kitchen serves as a culinary showpiece. The primary suite is a true retreat, offering a private balcony, fireplace, and the rare luxury of dual bathrooms. Each of the six bedrooms in the main house features an ensuite bath, ensuring absolute privacy for family and guests alike. The amenities rival the world's finest resorts: a walk-out lower level equipped with a theater and wine room, and a 30x50 lagoon-style pool. The 2020-built pool house (700+ sq. ft.) provides a full guest experience with its own kitchen, bath, and flexible sl

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

Beyond a private gated entrance and sweeping circular drive lies a 2.5-acre sanctuary that redefines New Canaan luxury. Originally envisioned by Douglas Carter Architects and recently reimagined by its designer-owner, this estate seamlessly merges architectural pedigree with contemporary soul. The residence spans four finished levels, where soaring ceilings and walls of glass invite the lush landscape inside. At the heart of the home, a newly updated gourmet kitchen serves as a culinary showpiece. The primary suite is a true retreat, offering a private balcony, fireplace, and the rare luxury of dual bathrooms. Each of the six bedrooms in the main house features an ensuite bath, ensuring absolute privacy for family and guests alike. The amenities rival the world's finest resorts: a walk-out lower level equipped with a theater and wine room, and a 30x50 lagoon-style pool. The 2020-built pool house (700+ sq. ft.) provides a full guest experience with its own kitchen, bath, and flexible sl

Tucked away on a tranquil 1.2 acre lot in desirable North Stamford, this classic 4-Bedroom, 2.5 Bath Colonial offers a rare opportunity to create rhe home of your dreams. Enter the Foyer of the home and be welcomed by the traditional layout and generously sized rooms. The Main Level features the Living Room, Kitchen, Formal Dining Room, generously sized Family Room with a Fireplace and a sliding glass door to an enclosed Porch, Powder Room and Laundry Room. The Upper level features a Primary En-Suite Bedroom, over-sized Bedroom/Office, 2 additional Bedrooms and a shared Hall Bath. The partially finished Lower Level, Deck, and pristine wood floors complete the picture. Enjoy the peace and serenity of North Stamford living while being just minutes away from the Merritt Parway,Downtown Stamford, and Metro North. Home is equipped with a whole house generator and central AC for your convenience

Turn-key, move in ready modern townhouse located in the heart of downtown New Canaan, this home offers three floors of elegant living with the feel of a single-family residence and the convenience of low-maintenance living. The renovated open floor plan features a state of the art newer chef's kitchen, a breakfast nook, island, and a light-filled living room/dining room with a fireplace. The main floor offers a study or additional bedroom with its own fireplace and large windows. On the second floor, you will find the owner suite featuring- a renovated luxury bathroom with soaking tub, shower, 2 vanities, two walk-in fitted closets-along with two additional bedrooms, a full bath, and a laundry area. The lower level provides nearly 1,000 square feet of additional walk out living space with fireplace large recreation room and a patio. Outside, the walk-out lower level leads to a private patio and yard, offering a quiet oasis which backs up to a Bristow Park Bird Sanctuary and Mead Park.

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. Recent updates include the kitchen, which is a chef's delight, with gorgeous views of the pool and property. The luxurious primary suite includes a newly redone 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 horse stalls. The basement offers great flex space and a gym. Elegant, updated, and set in

BACK ON THE MARKET. Buyers could not perform. Welcome to 150 Wildwood Road, an exceptional new construction that perfectly blends timeless colonial architecture with modern sophistication. Set on 1.12 private acres in one of Stamford's most private neighborhoods, this 9,000+ sqft masterpiece showcases superior craftsmanship and thoughtful design by respected local builder known for quality and attention to detail. Four fully finished levels of lux living, designed for everyday comfort and entertaining. From the moment you enter, you're greeted by a 2-story foyer, sun-filled open spaces, and exquisite white oak detail trim. The main level features a grand foyer, expansive family room/EIK with custom fireplaces, dining rm, living room w wood burning fireplace. The gourmet chef's kitchen has Thermador appliances, custom cabinetry, and generous center island-all opening to a light-filled breakfast area and spacious fam room lead to a huge deck overlooking backyard. The serene primary suite

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

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

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

Cherished by the same family for nearly 30 years, this beautifully updated Colonial sits on a desirable New Canaan cul-de-sac that has recently welcomed multi-million-dollar new construction - offering exceptional value at this price point, just moments from town. The recently renovated kitchen opens to a spacious layout ideal for both everyday living and entertaining, complemented by a large living room with fireplace, a formal dining room and a Great Room with soaring cathedral ceiling that is a showstopper. Upstairs, the primary bedroom is joined by three additional sun-filled bedrooms, all with hardwood floors that carry the home's warmth throughout. Outside, a private deck overlooks a beautifully landscaped yard framed by mature evergreens - great for gathering or play. This is a home where all that's left to do is move in

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

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 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