113 properties for sale in Sachem Head

Privately nestled high on 4+ sweeping acres, in the prestigious, yet quietly refined, Sachem's Head enclave in Guilford, CT, this 2012 modern Mediterranean residence commands panoramic views of Long Island Sound. Grand yet classic interiors unfold in tasteful Palm Beach-inspired finishes, creating an atmosphere of understated elegance. Soaring ceilings, a floating stairway and multiple sets of formidable french doors welcome sea breezes to actively flow through the home, imparting the true air of coastal living. The primary suite sanctuary is situated on the main level, offering seamless single-floor living and an elegant elevator delivers effortless access to all levels in the home. The massive white kitchen overlooks Long Island Sound and has Calcutta countertops, a festive green pantry, Wolfe and SubZero appliances and cozy fireplace. Outside, an elevated pool/spa terrace has a relaxed resort-like vibe and connects the main home to the 1BR (5th BR)/2FBA w/kitchen guest house. The 4-

A true once in a lifetime opportunity! As you wind through picturesque Sachem's Head onto Walden Hill Road, a circular driveway will lead you to an unparalleled waterview estate on almost two acres. The coastal home sits above Long Island Sound on one of the highest points in Sachem's Head and spans 5,185 square feet. The main level features walls of windows that provide unforgettable views of Long Island Sound and Faulkner's Island. The open kitchen/family room will satisfy any gourmet chef. It's a perfect space for indoor entertaining where guests can enjoy a crackling fire or step outside to an incredible bluestone patio with a fire pit for cool evening bonfires. Take in the 270 degree view of the Sound and enjoy both the sunrise and sunset. Outside entertaining is easy with a heated Pebble Tech Gunite pool, sound system, an outdoor shower, and ocean breezes. The coveted Sachem's Head Association offers amenities that include: beach access, tennis and paddle courts (approx. 600 ft f

Waterfront. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House. The Main House, a testament to exceptional craftsmanship, showcases approximately 5,534 square feet of living space, with six well-appointed bedrooms and 4.1 bathrooms. Designed with the finest materials, this home seamlessly blends timeless elegance and modern conveniences, providing a harmonious living environment. Outdoor area includes a Pool, Spa and Outdoor kitchen. Guest House with 3,583 sq feet, 3 bedrooms, 3 baths, Separate 942 sq ft. 1 bedroom in-law/ staff quarters. This property shares a Common border with the main residence. The separated property which can possibly be subdivided into

PRIVACY, VIEWS AND ONE LEVEL LIVING. Situated at the end of a cul-de-sac in highly desirable Sachems Head, this charming property captures breathtaking views of the marshlands and Sachems Head harbor. The home, extensively renovated by renown housewright Skip Broom, has an impressive vaulted ceiling living room with a wood-burning fireplace, beautiful oak bookcases and opens to a spacious dining room. Both rooms have access to a large, recently updated deck, perfect for entertaining or simply taking in the expansive scenery. This level also features three bedrooms, including a primary suite with a bathroom, abundant closet space and a private balcony overlooking the view. The other two bedrooms - one currently used as a den/office - share a full family bath. An eat-in kitchen and a separate laundry room complete this level making it ideal for easy one floor living. On the lower level, a guest suite has its own living room with fireplace, a full bath, a room for overflow guests and acce

STONY CREEK, BRANFORD - Classic Colonial charm meets coastal village living in this inviting home, well cared for and thoughtfully updated over the years. High ceilings, hardwood floors and distinctive woodwork lend warmth to the living and dining rooms, while the enclosed front porch offers a welcoming spot for morning coffee or unwinding at the end of the day. Three bedrooms and a level yard with space for gardening and outdoor gatherings round out the home's appeal. Updates include a roof, vinyl siding and gutters replaced in 2024, replacement windows and a new hot water heater installed in May 2025, among other improvements. Enjoy the pleasures of Stony Creek Village, from the beach and town dock to local restaurants, shops and hiking trails. The Legacy Theatre and Stony Creek Museum add to the village's distinctive character, with convenient access to train service and Yale

Privately set on over 2.5 beautifully maintained acres. Inside, you'll find formal living and dining rooms, a bright kitchen with newer appliances, a breakfast nook, and a large family room with a fireplace and access to the deck and backyard.The second floor features a generous primary suite with a private bath, three additional bedrooms, and a full hall bath. A finished third-floor room with new skylights and carpeting provides flexible space for a home office, playroom, or guest retreat, while the finished lower level includes a media room, laundry area, and abundant storage. Enjoy your own backyard oasis with an in-ground pool, expansive lawn, and exceptional privacy. Major updates include a new roof, skylights, and HVAC system (2023), plus a new hot water heater and kitchen appliances (2021), offering peace of mind for years to come. Ideally located just minutes from Guilford's high school, town center, beaches, marina, restaurants, and hiking trails, with convenient access to New

Discover 155 Stony Creek Road, a beautiful custom designed home privately situated on 1.5 acres of park-like grounds, just minutes from Stony Creek Village. Step inside the impressive two-story cathedral foyer, featuring a striking crystal chandelier, hardwood floors, and light-filled rooms throughout. The thoughtfully designed kitchen features a wood-burning fireplace, center island with granite countertops, and stainless-steel appliances. The adjacent dining room, with French doors, opens to the spacious family room, where a slider leads to the large deck and pergola - an ideal setting for entertaining or enjoying the tranquil surroundings. The second floor offers four generously sized bedrooms and two full bathrooms. The spacious primary suite provides a private retreat with a luxurious bathroom featuring a jetted tub, marble tile and shower. The lower level adds approximately 600 square feet of versatile living space, offering endless possibilities for a playroom, home gym, media r

Charming c.1800 farmhouse rich in historic character, set on a picturesque 1.5-acre level lot with sweeping water views of Shell Beach Lagoon stretching to Long Island Sound. Timeless details abound in this 3-bed, 1.5-bathroom home, including a welcoming porch, beautiful hardwood floors, built-ins, and a striking Stony Creek granite fireplace in the parlor. The main floor also consists of a living area and dining room, with a galley kitchen flowing into a bright great room, creating a comfortable space for everyday living. Upstairs are more views, as well as 3-bedrooms and a walk-up attic. Situated just minutes from downtown with convenient highway access for commuters, this distinctive property offers historic charm, scenic beauty, and endless possibilities. This is a rare opportunity to own a beautiful shoreline farmhouse, with the-potential to add a second residence on the property

Auction Opportunity. Please review FAQs and Property Information Package included in the additional documents on MLS. Asking price is opening bid only. Final price will be determined by competitive bidding and subject to seller confirmation. All bidding online, opening October 1 at 10am and ending October 8 at 4pm. Bidding website is available in the Property Information Package.Welcome to one of Connecticut's most desirable waterfront communities. Pine Orchard blends waterfront recreation, country club access, historic coastal character and a relaxed luxury lifestyle. For generations, families have been drawn to this unique shoreline community for its natural beauty and convenient access to New York and Boston. 60 Island View with a contemporary open floor plan concept to ensure panoramic water views from just about every room. Scenic vista views of the famed Stony Creek Thimble Islands, Long Island Sound, Pine Orchard Yacht and Country Club will always be for your viewing pleasure. E

Welcome to this spacious 5-bedroom, 2-full-bath raised ranch located in the desirable Valley Shores community of Guilford. Offering a flexible multigenerational floor plan, this home provides living space on two levels to accommodate a variety of lifestyles and needs. The main level features hardwood floors, three bedrooms, a full bath, and comfortable living and dining areas filled with potential. The lower level offers additional living space with two bedrooms, a second full bath, and endless possibilities for extended family, guests, a home office, or recreation space. Conveniently located near Guilford's charming town center, shopping, restaurants, and the beautiful Connecticut shoreline, this property combines space, flexibility, and an exceptional location. For the golf lover in you, the Guilford Lakes 9 hole public golf course is nearby. This property presents the perfect opportunity to bring your vision to life. Property is being sold AS IS. The sellers are motivated, so don't

Nestled on nearly an acre of tranquil landscape and adjacent to Westwood hiking trails, this four bedroom, two full bath home is surrounded by nature yet conveniently located. Rock walls and tended landscape in the large front yard lead into this contemporary home. On the main level, the open floor plan features a living room, dining area and kitchen with soaring ceilings and windows that showcase the surrounding natural beauty. Sliders lead to a large deck that overlooks the private, wooded back yard. A spacious loft overlooks the main level and offers wonderfully flexible space for an office, lounge or gym (the current owner uses it for the primary). Two bedrooms on the main floor and two on the lower level, each with lovely treed views, offer additional flexible space to enjoy! Also on the lower level is a flex room with sliders to a covered deck that provides shade and views. Large closets, eaves, shed and carport offer storage. This well-loved, maintained home has updates througho

Spectacular California Contemporary nestled in a private, picturesque setting in Guilford's desirable Fence Rock Association. Offering 5,114 square feet of above-grade living space, this distinctive four-bedroom residence showcases dramatic vaulted ceilings, skylights, expansive windows, and an open, light-filled floor plan. The impressive chef's kitchen features custom maple cabinetry, newly installed granite countertops, a center island, breakfast bar, oversized Sub-Zero refrigerator, Bosch double ovens and dishwasher, and JennAir cooktop. Beautifully designed living spaces include a dramatic living room with a two-sided stone fireplace, two inviting solariums (sunrooms), one with heated flooring, and a separate music room with French doors opening to the rear deck. The spacious first-floor primary suite offers vaulted ceilings, a fireplace, two walk-in closets, one with a built-in wall safe, and a private bath with jetted tub and separate shower. A remarkable home combining contempo

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

Charming 2-bedroom, 1-bath ranch conveniently located just minutes from the town center, beaches, train station, restaurants, and shopping, and within walking distance to Barbara Pine Beach! This home offers comfortable one-level living with a cozy living room featuring a wood-burning fireplace, an open kitchen flowing into the dining room and bright sunroom, and a deck directly off the kitchen, perfect for relaxing or entertaining. Two bedrooms and a full bathroom complete the main level. Laundry is located in the basement with exterior access only. Looking for additional space? The second floor offers over 800 square feet of unfinished space with endless possibilities! Create a spacious primary suite, bonus room, home office, or potential in-law setup, subject to town approvals. A great opportunity to make this home your own while enjoying all that the Connecticut shoreline has to offer!

RARE IN-TOWN GUILFORD SPRAWLING CAPE WITH WALKABLE CONVENIENCE, SHORELINE ACCESS and TIMELESS NEW ENGLAND CHARM! Enjoy privacy and space in one of Guilford's most desirable locations, situated on over 1 acre + just steps from the historic Guilford Green, local shops, restaurants, train service and shoreline amenities. Mature trees, established perennial gardens, expansive lawn and charming garden shed create a private, storybook setting for your secret garden. Home boasts 2,797 SF, 3 bedrooms and 3 full baths, the home features a flexible footprint with options for today's modern living. 1st floor offers potential for one-level living w/2 main level bedrooms and 2 full baths. Numerous options for home offices. Upstairs are 2 additional rooms and a 3rd full bath. Generously sized rooms, hardwood floors, a fireplace and 2 screened-in porches provide a smart footprint for renovation and outdoor living designs. 2-car attached garage. Public water. The property needs work but is well worth

Historic Charm Meets Exceptional Investment Opportunity in the Heart of Guilford Steeped in history and ideally located just steps from the iconic Guilford Green, this beautifully maintained circa-1850 Greek Revival property offers a rare opportunity to own one of downtown Guilford's most distinctive two-family residences. Once a single family rectory for the neighboring church, this landmark home has been thoughtfully converted into two spacious apartments while preserving its timeless architectural character. The first-floor residence features an inviting living room highlighted by a sun-filled bay window, a generous bedroom, an eat-in kitchen with direct access to a covered rear deck, a full bath complete with both a jetted tub and separate shower, and an additional dining room that easily functions as a home office, den, or guest room. Beautiful hardwood floors add warmth and character throughout the main living spaces. The second-floor apartment offers an open living and dining ar

This property would require a change-of-use from commercial to single-family for homeowners, buyer to do due diligence. Well-located antique commercial building overlooking the Guilford Mill Pond. The property features an approximately 1,200 SF ground-floor showroom with office space and restroom, currently operating as a tile showroom. Large windows provide excellent visibility and natural light. Interior stairway leads to an unfinished basement. Suitable for a variety of commercial uses including retail, gallery, or professional office - or there is potential to change to a single family as a great condo alternative. Prime location with character, flexibility, and strong visibility in the heart of Guilford. Also listed commercial MLS#: 24146465

COME EXPERIENCE THIS ONE-OF-A-KIND, FULLY RENOVATED MADISON HOME ON A RARE DOUBLE LOT WITH PRIVATE BEACH RIGHTS! Just 300 feet from the sandy shoreline, this exceptional home has been completely reimagined from a traditional raised ranch into a stunning elevated ranch with a bright, open-concept floor plan designed for modern living and effortless entertaining. Every detail has been thoughtfully curated to blend contemporary elegance with coastal charm. The main level features a spectacular chef's kitchen anchored by a nearly 10-foot white quartz island, premium appliances, and exceptional finishes. Two driveways provide ample parking, while two sets of washers and dryers offer added convenience. Multiple living spaces are bathed in natural light, including a breathtaking sunroom with brand-new oversized Marvin picture windows framing serene views toward Long Island Sound. A spacious hallway leads to a beautifully renovated full bath, a conveniently located laundry area, and the luxuri

Charming and beautifully maintained 2-bedroom, 2-full-bath ranch located south of Route 1, just a short stroll to the beach! Light and bright throughout, this inviting home features hardwood floors, thoughtful architectural details, and a warm, welcoming atmosphere. The living room offers a wood-burning fireplace with a stove insert. The eat-in kitchen features a lovely bay window, additional shelving, and a charming built-in corner hutch. The spacious primary bedroom offers two closets, while the second bedroom provides flexibility for guests, a home office, or sitting area. French doors lead to a heated enclosed porch with louvered windows, offering a wonderful place to relax and enjoy the natural light. Outside, unwind on the patio surrounded by gardens and a charming white picket fence. The current owner has made numerous improvements, including a new furnace, security system, basement waterproofing system, new wood stove insert with fully relined chimney flue, chimney cap upgrades

TURNKEY IN GUILFORD! Privacy, style and convenience come together in this beautifully renovated, free-standing 2-bedroom condominium tucked within a serene and meticulously maintained community. Single Family Feel. Thoughtfully updated with luxury finishes throughout, The beautifully remodeled kitchen opens seamlessly to the dining area, creating an inviting space for both everyday living and entertaining. For those seeking first-floor living, the main level features a spacious bedroom suite offering comfort and convenience. Upstairs, the private primary suite features new wall-to-wall carpeting, custom double closets, a beautifully renovated en suite bath and conveniently located laundry. The lower level, with fresh paint and new laminate flooring, provides additional versatile space ideal for a home office, fitness room, or bonus space. An attached two-car garage provides abundant storage and functionality, while the condominium lifestyle offers the ease of low-maintenance living. St

Eagleview at Guilford - Where Luxury Meets Lifestyle. Discover Guilford's newest luxury coastal condominium community, where superior craftsmanship, modern design, and breathtaking views of Long Island Sound redefine Connecticut shoreline living. Whether you're enjoying a sunset from your private balcony, entertaining in your chef's kitchen, or exploring Guilford's vibrant coastal village, Eagleview is more than a home, it's a lifestyle. Experience 6,200 SF of refined living space (expandable to over 8,000 SF) perfectly positioned to capture the tranquil salt marshes and shimmering expanse of Long Island Sound. Each residence includes multiple private balconies that invite you to relax and savor the natural beauty that surrounds you. Unmatched craftsmanship and comfort, this community of only 11 luxury units blends architectural excellence with everyday ease. Every residence features 10-foot ceilings, custom crown moldings, and a Chef's Dream Kitchen equipped with professional-grade ap

Live the lifestyle-a fantastic condo alternative with zero HOA fees! This completely renovated with unique touches, 1916 Cape Cod offers water views AND a truly prime location just ONE HALF MILE from Guilford Green's charming shopping, fine dining of all types, and historic churches with scenic views of the West River and surrounding salt meadows. Inside light-filled spaces showcase the bright painted interiors and rich hardwood floors throughout. The expansive chef's kitchen features Soho gray quartz countertops, a double stainless steel farmer's sink and all stainless steel appliances. Relax in the sun-drenched four-seasoned sun room offering views south towards Long Island Sound. Both bathrooms have been exquisitely updated: the main-level bath boasts quartz counters, a vessel sink, and a custom finger tiled shower, while the upper-level bath features marble flooring, crisp subway tiles as well as a luxurious marble rain shower! Out back, enjoy a private firepit area, a very useable

Welcome to 846 Long Hill RD in Guilford! Situated on a spacious 1-acre lot, this 3- bedroom 2- bathroom home offers 1,479 square feet of living space and plenty of potential for the right buyer. The property is in need of some updating and improvements making it a great opportunity for buyers looking to bring their own vision and personal touches to a home. Whether you're an investor, renovator, or buyer searching for a property you can make your own, this home provides a wonderful opportunity to create something special. This property is being sold AS-IS and is a probate sale subject to probate court approval. Bring your ideas and imagination and discover the potential that 846 Long Hill RD has to offer!

Located just off the Guilford Green and across from the Guilford Community Center, this exceptional property enjoys one of Guilford's most desirable in-town locations, with convenient access to restaurants, boutique shopping, cafes, the library, year-round community events, and major commuting routes, including I-95 and the Guilford Train Station. Originally constructed in 1888 by prominent Guilford builder George W. Seward, this distinguished Queen Anne Victorian offers over 3,800 square feet of living space featuring six bedrooms, four bathrooms, generous living and entertaining spaces, soaring ceilings, and original architectural details throughout. Originally designed as a single-family residence and currently utilized as a multi-family property, the flexible floor plan offers exceptional versatility for a variety of living arrangements. The seller has invested more than $300,000 in recent renovations, including the first-floor kitchen, first and third-floor bathrooms, a new roof,

Experience an elevated Branford shoreline lifestyle less than 200 yards from Long Island Sound, with deeded beach rights and no flood insurance required. Just around the bend, enjoy fine restaurants, scenic trails, picturesque Route 146-a favorite among cyclists-and the iconic Owenego Club, offering tennis, a beach, and waterfront dining. Set on a rare 1.28 acres, this 3,048 -square-foot residence offers privacy, space, four bedrooms, three-and-a-half baths, and thoughtfully designed living areas. The main level features a well-appointed kitchen and gracious family room with a fireplace for year-round living and entertaining. Upstairs, the bedrooms offer a peaceful retreat, comfortably separated from the main living areas. Flowing from the kitchen, an inviting living area opens to a spacious deck-ideal for morning coffee amid serene coastal surroundings. The versatile walk-out terrace level features a kitchenette and opens to the backyard patio, seamlessly connecting indoor and outdoor

Welcome to 23 Esterly Farms, an exceptional end-unit townhouse offering the perfect blend of style, comfort, and turnkey convenience in one of Madison's most sought-after condominium communities. This meticulously maintained 2-bedroom, 2.5-bath home has been thoughtfully updated throughout, allowing you to move right in and enjoy worry-free living. The sun-filled interior showcases fresh paint, all-new Harvey replacement windows, updated lighting, new window treatments, and a beautifully remodeled primary bath. The refreshed kitchen features brand-new stainless steel appliances, while the inviting living area is highlighted by a fireplace with elegant new glass doors. Additional upgrades include a new washer and dryer, delivering everyday convenience and modern functionality. Significant mechanical improvements provide added peace of mind, including a new furnace, central air condenser, and hot water heater. Nearly every major system has been updated, making this home truly move-in rea

Built by a highly regarded shoreline builder known for uncompromising attention to detail, this residence is designed for buyers who appreciate elevated finishes, enduring quality, and effortless livability. The home features an open floor plan with white oak hardwood floors, 9-foot ceilings, custom millwork, and oversized Pella windows throughout. A stunning bluestone entry leads to an elegant interior anchored by an eat-in kitchen with a 5' x 7.5' quartz island, Sub-Zero refrigeration, a six-burner Wolf gas range, double wall ovens, farmhouse sink, and wet bar with wine chiller and refrigerator drawers. The living room offers coffered ceilings, a stone-surround gas fireplace, and sliding doors to a partially covered bluestone patio, creating seamless indoor-outdoor living. The primary suite is a private retreat with a spa-inspired bath featuring a soaking tub, oversized rain shower, dual vanities, and a walk-in closet. Three additional bedrooms each include en-suite baths, complement

Mixed-use property (convertible to full commercial or multi units with town permits) 2,005 sq ft total / 1,672 sq ft finished living space. 30 acre lot with generous parking (10+ vehicles) Year built: 1893 with numerous modern updates. Rare to find a house in Guilford with city water. First Floor: Professional medical office 4 office spaces + half bath. Second Floor: 1-bedroom, living room, kitchen and full bath. Owner-occupied, well maintained Interior Features: 6 total rooms + kitchen + 1 1/2 baths-Brand-new 21 windows + 4 basement and 2 attic windows.-New electrical panel, 220 amp service. Alarm system with cameras. Public gas with new gas furnace. Central cooling + warm air system. Updated plumbing with insulated piping. Renovated bathrooms. Concrete basement floor with drainage system. Unfinished walk-up attic offering 800+ sq ft of storage or future living space. Exterior and Location Highlights: Beautiful landscaping and privacy-enhancing arborvitae fence. Newly built covered po

Welcome to 24 Village Circle! An Under Construction end unit in Guilford's newest luxury community, Village on State. This development features 25 - 2 bedroom townhomes, each having over 2000 square feet of living space, 2 car garages and full basements. 24 Village Circle is the Allendale model which allows for one level living with plenty of space for guests. On the main floor, there is the Primary bed/bath with a full tiled shower, a kitchen with stylish white cabinetry and Quartz counter tops, large Great room and Dining room which is perfect for entertaining, a half bath and laundry room. On the upper level you will find a spacious second bedroom with a full bath and walk in closet, a study and a large loft area. This model features 2,197 square feet of beautiful living space. Village on State is a short distance to the historic Guilford Green, shopping, restaurants, the town library and community center. These stunning townhomes will have the ultimate curb appeal. On the exterior

Coastal charm awaits in this inviting 1,388-square-foot Branford home, tucked within a quiet cul-de-sac just moments from the water's edge. The bright, open interior features gleaming hardwood floors, exposed wood beams, abundant windows, and French doors that create an effortless indoor-outdoor flow. The spacious kitchen offers stainless-steel appliances, generous cabinetry, ample counter space, and a large island with seating-ideal for everyday living and entertaining. Two comfortable bedrooms are complemented by flexible space that may accommodate a third bedroom, home office, or guest room. Outside, enjoy a private yard with a deck and outdoor shower, nearby water access, a charming picket fence, and detached one-car garage. The Owenego Beach and Tennis Club and several fine restaurants are just moments away along Limewood Avenue's newly completed coastal seawall and sidewalk. The property also has an established VRBO rental history, offering added appeal for buyers interested in p