Guilford, CT Homes for Sale with Acreage

Bluff Head Estates! Picture your perfect summer evening: pool lights glowing, a warm breeze, and friends laughing around a fire pit on a massive deck-welcome to 216 Bluff View Drive. Tucked away in Guilford's desirable North Guilford Neighborhood, this 4-bedroom, 2.5-bath open-concept Colonial delivers 3,410 square feet of pure comfort across two beautifully styled levels. The home boasts

Jules Gaughran - Etes William Pitt Sotheby's Int'l

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

Steve Wollman Wollman Realty

Experience the perfect blend of elegance, privacy, and shoreline living in this Mediterranean-style Colonial. 3 miles to downtown Guilford, ideally situated just up the road from a public beach. Set high above the flood plain, flood insurance is not required, offering peace of mind along with a coveted coastal lifestyle. Stately brick pillar entrance welcomes you to this 4 bedroom, 3 1/2 bath

Rose Ciardiello William Raveis Real Estate

Perfectly sited on 2.75 private acres overlooking a sweeping lawn, this distinguished Georgian Revival estate makes an unforgettable first impression, approached by a circular driveway that creates a true sense of arrival. Recently refreshed with newly painted interiors and enhanced landscaping, the property presents beautifully from the moment you enter. Once a Connecticut Designer Showhouse,

Linda Toscano Coldwell Banker Realty

Where New England architecture meets timeless elegance! Experience the pinnacle of shoreline living in this spectacular waterfront estate, perfectly positioned on a private, peninsula-like setting in Sachem's Head community. Boasting breathtaking, panoramic views of Long Island Sound, this 1930s residence is a masterwork of historic character and unique architectural artistry. The home's rich

Ana Russo William Pitt Sotheby's Int'l

Set on a large, level lot at the end of a quiet cul-de-sac, this lovingly maintained one-owner ranch offers the ease of true one-level living in a peaceful and private setting. A welcoming double front door opens to a spacious, open floor plan designed for comfortable everyday living. The kitchen is enhanced by a skylight that fills the space with natural light, and flows seamlessly into the

Linda Toscano Coldwell Banker Realty

Buyers who need an extra room for possible in-law, additional 900 sf above garage has three rooms and Bar / kitchenette, hardwood floors, bathroom and separate entrance. Touch of Tuscany awaits you at this shoreline property. This over 3,000 sq. ft. spacious four bedroom, den, two and a half bath, four car garage, home has room for everyone. Located at the end of a cul-de-sac it's close to

Lani Liu-Helisch Sovereign Properties

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

Bailey Mannix Sunset Creek Realty, LLC

Welcome to 81 Briarwood Drive, a beautifully maintained 3-bedroom, 3 full-bath home offering the perfect blend of comfort, versatility, and homestead living in one of Guilford's most peaceful neighborhoods. The permitted, mostly finished walk-out basement adds exceptional living space with luxury vinyl flooring, a full bath, laundry hookups, and plumbing already in place for a future kitchenette,

Teresa Peruzzi Dan Combs Real Estate

Welcome to Jans Way - Where Luxury Meets Lifestyle in the Heart of North Guilford this breathtaking brand-new Colonial is the new construction opportunity you've been waiting for, offering an impressive 2,734 square feet of beautifully designed living space plus an additional 900 square feet of fully finished walk-out basement, totaling an extraordinary 3,634 square feet of move-in ready

Thomas Simjian Keller Williams Coastal

Rarely do you find such a gem as the new construction on Blue Hills Dr! Nestled in a tranquil neighborhood at the end of a cul-de-sac and surrounded by lush woods, this under construction home promises to be your dream home. No expense was spared in this perfectly done dream home. Handsome hardwood floors and recessed lighting run through this entire home, enhancing all of the other features that

Joseph Gregory Toledo Realty

Welcome to 838 Little Meadow Road in Guilford! Built in 2015 and meticulously maintained, this 3-bedroom, 2.1-bath Colonial offers the perfect combination of modern comfort, thoughtful design, and an ideal location. Hardwood floors flow throughout, while high ceilings, crown molding, and abundant natural light create a warm, inviting atmosphere. The bright white kitchen features Frigidaire

Heather Dacey William Raveis Real Estate

Perfect elegance is waiting in The Woodlands at the end of a double Cul de sac!! Entertain in style with amenities to please everyone, all year long. The foyer will greet you and formal dining room awaits your dinner parties. The kitchen, perfected to be the heart of the home, offers dining at the center island or built-in table, both with granite countertops. Kitchen seamlessly flows into the

Diane Beckwith Popolizio William Raveis Real Estate

Coming soon..... Historic Charm, Modern Living - On 3+ Acres in Guilford If you've been searching for something truly different, this is it. This beautifully crafted 1700s reproduction home sits on over three peaceful acres and stands alone as a property with no comparable in all of Guilford. Character abounds throughout - three fireplaces, including a stunning walk-in fireplace, give every room

Steven Koleno Beycome of Connecticut

Privately sited on 2.38 acres along a quiet cul-de-sac, this charming Cape offers a rare opportunity to embrace a secluded, nature-filled setting without sacrificing convenience. The property provides exceptional privacy and scenic natural surroundings, all just minutes from Guilford's vibrant town center, shoreline beaches, acclaimed restaurants, shops, and everyday amenities. Thoughtfully

Melanie Scull William Pitt Sotheby's Int'l

A MAGNIFICENT REVIVAL & TIMELESS BLEND OF SOMETHING OLD & SOMETHING NEW. One of the finest restorations in New England, the Pitkin mansion is a true historical treasure. Carefully dismantled & moved to its current site in 1955, the property is nestled within nearly 4 acres of mature trees, manicured lawns, & magical gardens. This classic revival will be celebrated by the most discerning antique

Kiara Rusconi William Raveis Real Estate

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.

Joseph Piscitelli Coldwell Banker Realty

Just one mile from the historic Guilford Green, this like-new Contemporary Farmhouse offers a rare blend of modern comfort, coastal charm, and beautiful natural views. Set on one acre with views of the marsh and West River, the home is designed to feel both private and connected to one of Guilford's most desirable village settings. The open floor plan is ideal for everyday living and

Willard Finkle Coldwell Banker Realty

A serene sanctuary, a historic experience. Newly restored, 50 Ledge Hill Road is a rare 1870 parsonage on a tranquil six and a half acres, yet conveniently located to Yale New Haven and the shoreline towns. Inside, the versatile layout offers five bedrooms, one-and-a-half baths (tastefully renovated), an enormous, exposed beam living room, generous family room, and mudroom. At the heart of the

Melanie Abbott William Pitt Sotheby's Int'l

Welcome to 737 Leetes Island Road, a stone's throw from Shell Beach, one of Guilford's most desirable shoreline areas! With some TLC, the potential for this property is endless! Situated on beautiful grounds, 737 embraces all the natural elements of this area...salt water breeze coupled with lightly wooded, open space. This property was known as the "Marilyn House", as it was said that Marilyn

Carissa Mastriano GRL & Realtors, LLC

Welcome to Waystone Farm, an award-winning, energy-efficient 8+ acre mini-estate and potential horse property. Proud winner of the 2016 Highly Insulated Passive House Standard Award, this estate masterfully blends sustainability with luxury living.The main residence features newly refinished hardwood floors and a bright, open floor plan. A sun-filled great room flows into the chef's kitchen,

Bette Zollshan William Pitt Sotheby's Int'l

Set in a serene Guilford location, this welcoming oneowner home has been cherished for over 50 years and offers comfort, space, and the beauty of natural surroundings. The main living areas feature an easy, functional flow ideal for gatherings, while large windows bring in soft light and views of the property. The kitchen, dining, and living spaces support both everyday routines and special

Heidi Maria Rubertone eXp Realty

Custom built with exceptional craftsmanship and attention to detail, this stunning coastal-area estate sits on one of the largest properties in the neighborhood with water views from every room, three separate deeds totaling approximately two acres, including two separate waterfront lots, with one being the perfect site for your future docking needs. Designed for both luxury and comfort, the home

janet colello Century 21 AllPoints Realty

"Vermont in Guilford": Extraordinary hilltop privacy surrounded by woods and fields in North Guilford. This well-maintained 3-bedroom, 1.5-bath home with attached 2-car garage is ideally sited atop a hill in a desirable setting. Recent updates include new garage foundation, mini-splits, a new roof, fresh interior paint, and gleaming hardwood floors. The main level features an open living area

Tim Galvin William Raveis Real Estate

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

Barbara Goetsch William Pitt Sotheby's Int'l

Don't miss this adorable one-level home, thoughtfully updated to offer the perfect blend of charm, comfort, and flexibility. Nestled on a scenic country road, the property sits on 1.7 acres with ample room for future expansion if desired. Ideal for first-time buyers, down-sizers, or anyone seeking peaceful country living. Bright and airy throughout, the home features an open floor plan with

Kim Vigliotti Coldwell Banker Realty

Positioned on a premier corner lot at the end of a quiet cul-de-sac with 3.19 private acres, this exceptional 5-bedroom, 3.5-bath Colonial is being reintroduced with a significant improvement package. Before closing, the seller will install a NEW ROOF, NEW HEATING and COOLING systems, a New Rear Deck, improvements to the wraparound front porch, and additional landscaping enhancements, offering

Mustafa Muaremi Coldwell Banker Realty

Set on 5.65 secluded acres in the heart of Madison, this exceptional English Georgian custom home offers a rare blend of timeless architecture, refined craftsmanship, and natural beauty. Surrounded by mature woodlands, the property is a private retreat, complete with a gently winding stream and the preserved stone remnants of a historic mill-an evocative nod to the land's rich past. Inside, the

Mark McElrath William Pitt Sotheby's Int'l