44 houses for sale in Winding Ways

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

Luxurious Custom Estate Just Outside the Village of Skaneateles! Discover this exquisite custom-built 4-bedroom, 4.5-bathroom Colonial, perfectly situated on 1.14 private acres in a serene, park-like setting. Located in the highly coveted Skaneateles School District, this beautiful home seamlessly blends classic elegance with high-end modern functionality. The main level features an open-concept gourmet kitchen with a stunning custom cherry breakfast bar, complemented by a separate scullery—an entertainer’s dream. Host elegant gatherings in the formal dining room, or unwind in the expansive, light-filled living room that opens to a stone patio with breathtaking sunset views. A private study offers the ideal home office during the week, with a cozy wood stove perfect for relaxing on the weekends. The second level boasts an expansive primary suite along with a private in-law suite, complete with a comfortable sitting area and fireplace. The partially finished basement provides generous a

Welcome to this beautifully renovated 4-bedroom, 2-bath ranch, ideally located just 2.5 miles from the charming Village of Skaneateles. Filled with natural light and thoughtfully updated throughout, this spacious, open-concept home offers modern style and comfortable living. The stunning eat-in kitchen features brand-new stainless steel appliances, custom cabinetry, granite countertops, and stylish lighting, making it the perfect space for everyday living and entertaining. Both bathrooms have been tastefully remodeled with timeless tile selections, quality fixtures, and neutral finishes that provide a fresh, elegant backdrop for your personal style. Each of the four generously sized bedrooms offers ample closet space, providing comfort and functionality for family and guests alike. Step outside to the expansive deck overlooking the level backyard—an ideal setting for outdoor dining, entertaining, or simply relaxing and enjoying the beautiful Upstate New York summers. Fresh landscaping

Exceptional eastside lakefront living just 3 miles from the village. Experience the best of Skaneateles waterfront living in this impeccably designed Three bedroom two and half bath transitional home, ideally situated on the coveted Eastside of Skaneateles Lake. Built just five years ago, this thoughtfully crafted residence combines timeless style with exceptional functionality and easy. Maintenance living. The open and inviting floor plan is designed to capture breathtaking lake views throughout the main living spaces. The first floor features two luxurious ensuite bedrooms, plus a powder room, providing exceptional flexibility for guests or one-level living along with a first floor laundry room. At the heart of the home is an impressive Great Room with fireplace, framed by expansive views of the lake. The adjoining large chef's kitchen offers abundant workspace and is perfectly suited for both everyday living and entertaining. Step outside onto the generous lake-facing deck, where mo

Experience the timeless beauty of Skaneateles Lake from this exceptional waterfront retreat, privately nestled on 1.13 acres with 91 feet of pristine, level shoreline. Offering an extraordinary opportunity to own on one of the Finger Lakes' most coveted lakes in the award winning Skaneateles School District. This property showcases crystal-clear waters, breathtaking sunrise views, and the peaceful setting that defines luxury lakefront living. Tucked among mature trees for added privacy, the charming three-bedroom seasonal camp exudes warmth and character, featuring a spacious primary bedroom and inviting living spaces designed for effortless lakeside living. A separate bunkhouse provides additional accommodations for guests, creating the perfect setting for hosting family and friends or building cherished summer traditions. Step outside to enjoy endless days on the water from your private dock. Whether boating, swimming, fishing, paddleboarding, or simply soaking in the spectacular sce

Discover the charm of Skaneateles at 915 Mottville Road! This prime location offers easy access to Baxter, Skaneateles Fields Spa, and the Charlie Major Nature Trail. Just a short drive away, the Village of Skaneateles awaits with its delightful shops, eateries, and stunning waterfront. Whether you’re seeking a personal retreat or a Airbnb venture, this property is your gateway to all the Skaneateles area has to offer. Don’t miss out on this incredible opportunity—come explore 915 Mottville Road today!

Experience the best of Skaneateles Lake from this extraordinary custom-built Nantucket style waterfront home, where crystal-clear water, breathtaking sunsets and sweeping 180 degree views create an unforgettable setting. With 105 ft of pristine lake frontage, this meticulously maintained home is offered for the very 1st time. Featuring 4 Bedrooms and 4 Full Baths, the open concept design is perfect for entertaining while capturing water views from nearly every window. A stunning handcrafted staircase and woodworking is by master craftsman Mateo Bartolotta. The dramatic Great Room showcases soaring ceilings, a wall of windows and an impressive floor-to-ceiling stone gas fireplace. The beautifully appointed Kitchen features custom cabinetry, Viking stove, Asko dishwasher, Sub Zero refrigerator and overlooks the spacious Dining Room that adjoins the spectacular Screened Porch. Overlooking the lake, it's the perfect space to begin your morning and enjoy sunsets in the evenings. A first flo

Perched above the clear waters of Skaneateles Lake, this split-level ranch offers breathtaking lake views and 150 feet of shared, permanent lake access with docks—providing an exceptional opportunity to enjoy one of Central New York's most sought-after waterfront destinations. Inside, you'll find hardwood floors throughout, four spacious bedrooms and 2 ½ updated baths, including primary suite with a private bath. The newer kitchen features modern appliances, abundant cabinetry, immersive garden views from the breakfast area, and flows seamlessly into the open dining and living areas. Filled with natural light, the living room is anchored by a cozy wood-burning fireplace, creating the perfect gathering space. The main entry level offers a versatile family room with a second wood-burning fireplace, custom built-ins, and a classic mantel, along with a fourth bedroom that is ideal for guests or a home office. An additional partially finished lower level provides flexible space for a recrea

Welcome home to this beautifully maintained 3-bedroom, 2-bath ranch ideally situated near Owasco Lake. This home is filled with natural light, the inviting layout offers comfortable one-level living with bright, open spaces perfect for everyday life and entertaining alike. Step outside to a stunning stamped concrete patio featuring a built-in concrete block fireplace—an ideal setting for relaxing evenings, summer gatherings, or enjoying your morning coffee. The private backyard extends your living space and creates the perfect outdoor retreat. Located just minutes from Owasco Lake this home offers close proximity to boating, fishing, and all the recreation the Finger Lakes are known for. Whether you're looking for a year-round residence or a peaceful place close to the water, this property combines comfort, convenience, and an exceptional location

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

Welcome to this custom-built Skaneateles retreat on picturesque Amerman Road, where breathtaking lake views, a private 3-acre setting, and exceptional amenities create the perfect place to call home. Offering 4 bedrooms, 2.5 bathrooms, a finished lower level, pole barn, and private basketball court, this property delivers the ideal blend of comfort, recreation, and country living. Step inside and immediately embrace the relaxed lake lifestyle. The welcoming foyer opens to a dedicated dining area that seamlessly flows into the beautifully appointed kitchen featuring white shaker cabinetry, granite countertops, stainless steel appliances, and a charming baker’s nook perfect for meal prep and entertaining. The spacious living room is the heart of the home, showcasing stunning panoramic lake views, a cozy gas fireplace, and custom built-in bookshelves that add warmth and character. Upstairs, the generous primary suite is designed to maximize the spectacular views and serves as a peaceful r

Located in the Skaneateles School District, this spacious home offers over 1,700 square feet of living space with three bedrooms, two baths, and an detached two-car pole barn, all situated on 3.5 acres of land. The property is in need of some repairs, but with improvements, it has incredible potential to become a beautiful country retreat overlooking a scenic pond. A rare opportunity to own acreage, privacy, and peaceful surroundings in a highly desirable location

Set on a private acre in the heart of the Village of Skaneateles, this premier Village Estate offers 207 feet of prime lakefront and simply some of the best views on the lake, an exceedingly rare combination paired with the ease of walking to every shop and restaurant the Village has to offer. Thoughtfully designed to capture the timeless charm and character of the Village's beloved old homes, the residence delivers every comfort of luxurious new construction, a true celebration of classic meets contemporary. Exceptional natural materials and masterful craftsmanship reveal themselves at every turn, from rich walnut paneling to intricately detailed millwork rarely found today. This is a home built for living well, where mornings begin with coffee and lake views from the primary suite's private deck, and evenings unfold effortlessly around one of the many fireplaces or at the boathouse's covered porch right over the water. Professionally designed and decorated from the ground up, this ho

Discover the timeless charm of this beautifully built Skaneateles Waterfront Stone home, ideally situated on 2.11 acres on the desirable Eastside, just 1.7 miles mile from the Village downtown area. With it's Slate Roof, Cut Quarry Stone exterior walls, poured concrete foundation, hot water heat, with 2 zoned air conditioning, natural gas, and classic craftsmanship, this special property offers the perfect blend of character, comfort, and convenience. The inviting, three. Bedroom, two and a.a-half bath residence features hardwood floors throughout, 4 wood burning fireplaces, a graceful sweeping staircase, and the added luxury of an elevator, workshop in the basement along with a finished area with hardwood floors and a oversized garage with walk up storage above plus a additional outbuilding for your boat, water toys and hobbies. House built from 1946-1968. Adding to its appeal, the property includes 20 FEET of deeded Skaneateles Lake Waterfront. Ideal for a dock, boat hoist, and unfor

A complete renovation has transformed this bright and charming village-edge home. Beautifully styled and exceptionally welcoming, it features stunning new kitchen and baths, new flooring, trim and doors, fresh exterior and interior paint, newer windows and HVAC system with mini-split air conditioning. The open main level offers a spacious living room flowing into the kitchen and dining area, while the finished lower level includes a family room and large office with an adjacent full bath—ideal for working from home or accommodating guests. Outside, the private, landscaped lot boasts mature trees, an expansive two-level deck, and patio for relaxing or entertaining. Natural gas and public water add to the ease of ownership, with boutiques, restaurants and the lake all just a short walk away. Simply move in and enjoy! Delayed showings and negotiations until Sunday (September 13th) at 12pm. Open house sunday 12-2pm

Beloved Skaneateles village landmark, currently operating as a successful Bed & Breakfast, and now being offered as a stunning residence. 2 W Lake St is a premier desired location; at the edge of the commercial / historic district; across the street from iconic lakeside Clift Park, anchoring a waterside row of private residences, and adjacent to Skaneateles' best restaurants and local shops; this lovely Victorian is a once in lifetime opportunity to own. Spectacularly renovated for modern living, but thoughtfully designed to showcase original hardwood floors and vintage tile, bevelled and leaded glass windows, hand carved pocket doors, and soaring ceilings. The first floor features a grand foyer highlighted by a Waterford chandelier; leading to two timelessly classic living rooms overlooking the lake and park; an elegant sun filled dining room; cooks' kitchen (nicely appointed with granite island & countertops, new stainless appliances, and recently professionally painted); beautiful l

Move right in and enjoy this wonderful lakefront retreat, tucked along Russells Landing on a paved private lake lane just off West Lake Road. This 1939 cottage delivers all the charm and character you'd hope for, one bedroom plus a screened sleeping porch overlooking the water, wood paneling throughout, and a stone fireplace to gather around on cool evenings, while outside a permanent dock and mooring make it easy to bring the boat right home and a shale beach area gives you a spot to wade in or just sit with your feet in Skaneateles Lake's famously clear water. Spend the day out on the boat, then wind down with s'mores around the bonfire as the sun sets over the water, and when you're ready for a change of pace, the Village of Skaneateles with all its shops, dining, and charm is just a short drive or boat ride away. Thanks to being sold turn-key with parking for up to four cars and an electric dryer, this easy-to-love retreat is ready for its next owners to start making memories from

This listing includes an additional approved building lot. The well-maintained, 3-bedroom, 1 full. And 1 half-bath RANCH is located within the Skaneateles School District. Enjoy peace of mind with a brand-new roof installed on the house September 5, 2026. Experience beautiful country views and the tranquility of a quiet road! The home offers comfortable one-level living with thoughtfully finished spaces that provide plenty of room to spread out, relax, and entertain. Step inside to a bright and welcoming interior featuring fresh paint, beautiful hardwood floors in the main living areas, and new carpeting in all three bedrooms. Not included in the square footage is the partially finished lower level, which includes a media room featuring a dual-fuel pellet and corn stove, creating a cozy and inviting atmosphere during the cooler months. The basement also provides a half bath, excellent storage, and flexibility for a variety of needs. A two-car attached garage offers convenient access to

Welcome to this amazing Colonial in the heart of the village, where timeless character meets thoughtful updates. From the moment you arrive, the stunning wrap-around porch sets the tone for this charming and inviting home—an incredible space for relaxing, entertaining, and enjoying the neighborhood. Inside, beautiful original charm and character can be found throughout. The updated eat-in kitchen features quartz countertops, stainless steel appliances, and a convenient pantry. Hardwood floors flow throughout the home, while the first-floor laundry adds everyday convenience. The generously sized living room is a warm and inviting gathering space, complete with a wood-burning fireplace with a classic brick surround and built-in cabinetry on both sides. Upstairs, you'll find three spacious bedrooms. The generously sized primary suite offers a private bath and a walk-in California closet. The two additional bedrooms share a full bath with a spacious vanity and shower. A truly exceptional f

Light-filled and charming, this bright Cape Cod home is ideally located just outside the village limits, only steps from the school campus and less than a mile from the village center. Enjoy easy access to local shops, restaurants, and the lake while coming home to a property full of warmth and character. The curb appeal is simply adorable, featuring lush landscaping and classic white picket fencing in both the front and backyard. Designed for convenient first-floor living, the home offers an open floor plan with an abundance of windows that fill the space with natural light. The inviting living room showcases beautiful hardwood floors and a freestanding gas stove, creating a cozy focal point. The dining area opens to a spacious deck overlooking the quaint, private backyard—perfect for relaxing or entertaining. The kitchen is well-appointed with granite countertops, attractive cabinetry, and a generous walk-in pantry. The spacious first-floor primary suite includes ample closet space a

Beautiful contemporary home set on 2 acres of tranquil countryside, offering generous living spaces and thoughtful finishes throughout. An additional buildable 2.10 acres is included in the sale. The tiled entryway opens to a spacious living room with gleaming hardwood floors and a brick fireplace creating a warm and welcoming atmosphere. Adjacent is a formal dining room, also featuring hardwood flooring The large eat-in kitchen is bright, spacious, and practical, with abundant windows, and cabinetry, stainless-steel appliances, solid surface counter tops and island for extra seating. Sliding patio doors lead to an expansive vinyl deck overlooking the property—an ideal setting for entertaining or enjoying quiet evenings outdoors. The main level also includes a convenient laundry area and a half bath with a granite vanity and vessel sink. The finished basement offers a comfortable family room, egress windows, substantial storage, and an exterior door leading to a large utility room grea

For those seeking a home in one of Skaneateles' most sought after settings, 27 Leitch Avenue represents a rare and exceptional opportunity. This home holds special historical significance, as it was the first home to be'placed' on Leitch Avenue. Constructed in 1830, as part of the famed Greek Revival style mansion, Roosevelt Hall, in the late 1860's during the middle of winter, it was separated and then dragged across the frozen lake. The structure was hauled up Leitch Ave. Cut into two homes and placed on previously dug three foot thick foundations. Nestled in an established neighborhood, the proximity to both the historic Village and award winning schools, make it a location with strong desirability. As you enter the home, note the comfortable Living Room with original wide plank floors, a large wood burning Fireplace w/custom Mantle, which connects to a second area with myriad possibilities. The light filled Dining Room w/ hardwood floors and floor to ceiling windows has been design

Welcome home to this charming 3-bedroom, 2-full-bath home offering a great combination of comfort, updates, and convenience. Located just outside the village and within walking distance to shops, restaurants, and other local amenities, this home is ready for its next owner. New updated furnace, hot water tank, roof, driveway, exterior doors, and spray foam insulation, helping provide added efficiency and peace of mind. Inside, you’ll find a comfortable floor plan with plenty of room to relax and entertain. The inviting sunroom is the perfect spot to enjoy your morning coffee, unwind at the end of the day, or create an additional sitting or entertaining space. Outside, the property continues to impress with a welcoming front porch and a custom-built shed providing excellent storage for tools, lawn equipment, recreational gear, and more. The updated driveway adds to the home’s curb appeal and everyday convenience. With three bedrooms, two full bathrooms, many major updates already comple

This gracious, well-maintained, 4-bedroom, 2 ½ bath home is perfectly located just over the village line in a friendly neighborhood cul-de-sac of well-spaced homes. It’s beautifully positioned on a hill that offers views, privacy, abundant natural light, and quiet. A maple tree-framed driveway leads to the front door, which is hidden from street view, ensuring safe front-porch deliveries, & there is ample visitor parking. The front porch & the spacious deck have beadboard ceilings & allow you to entertain a large group or simply relax & enjoy your serene surroundings. A mature River Birch tree shades the deck in summer, while winter sun brightens the house. Because the home faces NW and SE, you'll often enjoy lovely sunrises and sunsets. Enter the 2-story foyer with hardwood floors. A spacious dining room has hardwood floors. The beautiful living room features a refined fireplace and an atrium door to the covered deck. Each downstairs room could serve a different purpose: the den as an

Absolutely fabulous year-round lakefront living where the views take center stage. From the moment you walk through the door, a wall of glass—three expansive sliders—frames breathtaking, unobstructed views of the lake. Extensively remodeled by Tom Buff in 2000, with custom cabinetry by Bartolotta and recently styled and furnished by Lisa Terhune of Impeccably Done, every detail has been thoughtfully considered. The open main level is designed for entertaining, with a spacious kitchen featuring a large island & commercial-style range, generous dining area, comfortable living space and a gas fireplace. Three sets of sliders open directly to the expansive deck, creating a seamless connection between the house and lake. Just steps from the deck is an exceptional waterfront setup featuring a permanent dock complemented by a seasonal dock configuration with built-in seating & steps directly into the water. An incredibly rare shale beach provides additional space at the water's edge—perfect f

Charming, Updated Ranch on 1.5 Acres in Skaneateles. Welcome home to this beautifully updated three-bedroom ranch set on 1.5 private acres, just minutes from the village center. Thoughtfully renovated with exceptional craftsmanship, this home blends modern amenities with warmth and character. The stunning eat-in kitchen features white quartz countertops, custom cabinetry, stainless steel appliances, and gorgeous tile flooring. Hardwood floors flow throughout the living room and all three bedrooms. The spacious primary bedroom is filled with natural light and offers built-in closet cabinetry. The additional two bedrooms are generously sized. The first-floor bathroom has been completely renovated with a tiled shower, and beautiful vanity. The lower walk-out level provides wonderful additional living space, including a stylish bar area with cabinetry, beverage refrigerator, and butcher-block countertop. A second beautifully renovated bathroom features penny-tile flooring, a tiled shower w

Welcome to 3826 Highland Avenue, a beautifully updated Skaneateles home where thoughtful renovations, stylish finishes and comfortable living are found conveniently located just minutes from the village center. Extensively improved inside and out within the last several years, this move-in-ready home offers the kind of updates buyers appreciate with the ease of single story living. At the heart of the home is a gorgeous, renovated kitchen, gutted to the studs and redesigned with new cabinetry, an induction range, updated appliances, recessed lighting and abundant work space. The open, inviting layout flows easily into the living areas where the gas fireplace, built-in shelves and hardwood floors add warmth and charm. A former garage was thoughtfully converted to create a spacious primary suite, complete with vaulted ceiling, double closets, ensuite bath and nearby laundry. The newly finished lower level features luxury vinyl plank flooring and an additional 651 sq ft (to total 2200 sq

Everything is new! Be the first to live in the home since it was rebuilt from the studs out. This super-insulated, energy efficient home was completely rebuilt with the intention of making it the owners' primary home. Every system, surface, and finish is new, with exceptional quality and attention to detail throughout. Hardwood floors throughout the main level flow between a large living room, formal dining room, and spacious kitchen with dove-tailed wood cabinetry, 2 floor to ceiling pantries, quartz countertops, a full stainless appliance suite and 36” workstation sink. New Karastan carpeting in the three upstairs bedrooms. The primary suite offers two closets, an ensuite bath with double vanity, quartz counters, 6’ walk-in shower with Vigo glass door and rainfall head, and a private water closet. Two additional bedrooms share a full bath with tiled tub/shower, rainfall head, quartz vanity with Kohler medicine cabinet. Mitsubishi Intelli-HEAT dual-fuel heat pump, spray-foam insulatio