Sachems Head Homes for Sale

Sachems Head Homes for Sale

Welcome to Sachems Head, a picturesque coastal neighborhood nestled in the heart of Guilford, Connecticut. Renowned for its stunning waterfront views and charming New England architecture, Sachems Head is a hidden gem that combines the tranquility of seaside living with the convenience of nearby urban amenities. This vibrant community is characterized by its rich history, with many homes dating back to the 19th century, each telling a unique story.

As you stroll through the tree-lined streets, you’ll discover an array of beautifully maintained properties, from classic colonial homes to modern waterfront estates. The homes for sale in Sachems Head offer a variety of styles and sizes, catering to diverse tastes and lifestyles. Whether you’re seeking a cozy cottage with ocean views or a spacious family home surrounded by nature, you’ll find a place that feels just right.

Residents enjoy access to pristine beaches, scenic parks, and a plethora of outdoor activities, including sailing, fishing, and hiking along the picturesque shoreline. The sense of community is palpable, with local events and gatherings that bring neighbors together, fostering lasting friendships.

In addition to its natural beauty, Sachems Head is conveniently located near Guilford’s charming downtown, where you can explore boutique shops, delightful eateries, and cultural attractions. With its perfect blend of coastal charm and modern conveniences, Sachems Head is not just a place to live; it’s a lifestyle to embrace. Explore the homes for sale in this enchanting neighborhood and discover the idyllic haven you’ve been dreaming of.

Newest Sachems Head Homes for Sale

345 Vineyard Point Rd, Guilford
$5,750,000
4 Beds ⋅ 8 Baths ⋅ 24212653 MLS
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 & 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 & cozy fireplace. Outside, an elevated pool/spa terrace has a relaxed resort-like vibe & connects the main home to the 1BR (5th BR)/2FBA w/kitchen guest house. The 4-stall barn, w/paddock, whispers of equestrian possibilities or creative studio use. The 5-bay heated-floor garage accommodates 7 cars. Solar energy systems lend a thoughtful green footprint, appealing to those who value sustainability. This is one of the larger parcels in Sachem's Head, come feel how this property seems transported from Malibu or Napa Valley, yet remains distinctly low-key New England. Masterfully constructed & impeccably maintained. Under 2hr drive from NYC & 20min to Yale.

345 Vineyard Point Rd, Guilford
473 Colonial Rd, Guilford
$1,995,000
3 Beds ⋅ 3 Baths ⋅ 24186090 MLS
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 access to an outdoor sitting area. There's also an attached two car garage with ample storage space.

473 Colonial Rd, Guilford
76 Sachem Head Rd, Guilford
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 24181939 MLS
Welcome to your private coastal sanctuary in the prestigious Sachem Head area of Guilford. This 5,620 sqft estate is a masterclass in luxury living, set on 2.31 wooded waterfront acres. Come up the gated driveway and step inside to discover a home designed for ultimate leisure. The living room features a bespoke custom mural and a stunning aquarium, serving as a mesmerizing feature next to French doors leading to the patio. Entertain effortlessly in your private home theatre, escape to your sauna tucked under the stairs, cook in the gourmet Wolf kitchen, or retreat to the office, where a bookshelf conceals a secret closet. The outdoor experience is unmatched. The custom pool area, equipped with an outdoor kitchen and pizza oven, is a resort-style masterpiece, featuring two integrated hot tubs and a dramatic infinity edge that blurs the line between water and nature. A heated walkway from the first-floor bathroom leads you straight to one of the hot tubs for year-round use. This home is thoughtfully designed for pet owners, featuring a dog door, dog washing station in the garage, and wiring for an electric fence to keep your companions safe. Modern sophistication meets comfort with a 2.5-bay attached garage, a Lutron Homeworks lighting system, a Crestron audio system, and a 2025 security installation. Recent mechanical updates including a 2023 furnace and serviced air handlers, ensure peak efficiency. Experience luxury at 76 Sachem Head Road. Schedule a private showing today.

76 Sachem Head Rd, Guilford
215 Uncas Point Rd, Guilford
$35,000,000
6 Beds ⋅ 5 Baths ⋅ 24034137 MLS
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 & 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 2 building sites, features a Carriage House, Dock & Sandy Beach. To say there are many possibilities here would be an enormous understatement! Private residence, Family compound or High-end development. Bring your Dream here; this opportunity will not let you down. All 3 properties must be sold together unless otherwise agreed to by the current owners. Please respect the privacy of current owners. BY APPOINTMENT ONLY. Taxes represent all 3 properties.

215 Uncas Point Rd, Guilford
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

How much is your home worth?

Get instant property value now!