Guilford, CT Homes for Sale with Acreage

Privately set on 3.6 picturesque acres, this exceptional equestrian estate offers the perfect balance of luxury living, resort-style amenities, and a true horse property lifestyle. Built in 2004 and recently refreshed, the home features 4 bedrooms, 4 full baths, and beautifully designed spaces that blend comfort, sophistication, and effortless functionality. A dramatic two-story foyer opens to a

Linda Toscano Coldwell Banker Realty

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

Set on over four park-like acres in sought-after Guilford, this stately custom built colonial blends exceptional craftsmanship with refined modern living. Thoughtfully enhanced by the current owner, the home features integrated smart home technology paired with curated, high-end upgrades, creating a seamless balance of innovation and timeless design. A dramatic two-story foyer with marble floors

Linda Toscano Coldwell Banker Realty

Custom-Built Mediterranean Estate | Privately sited on 1.84 acres in the highly sought-after Woodlands subdivision, this stunning Country French-inspired residence combines timeless craftsmanship with architectural elegance. A grand two-story foyer with marble flooring and a sweeping spiral staircase sets the tone for the sophisticated interiors. Lovely millwork and custom built-ins are showcased

Rose Ciardiello William Raveis Real Estate

Tucked within a double cul-de-sac in the coveted Woodlands neighborhood, this renovated Colonial offers the perfect blend of luxury and comfort. Imagine morning walks on nearby Eastwoods trails, afternoons spent outdoors, and evenings gathered in a home designed for both everyday living and effortless entertaining. This sunlit home feels refined yet welcoming, with hardwood floors, custom

Rose Ciardiello William Raveis Real Estate

Absolutely stunning 5+ bedroom light-filled home offers the perfect blend of elegance & modern updates. A dramatic 2-story foyer with a striking contemporary fixture sets the tone. The living room with glass French doors offers flexibility as a first-floor office. The oversized family room features a soaring ceiling, custom built-ins & stone fireplace, flowing seamlessly into the remodeled

Susan Santoro William Pitt Sotheby's Int'l

Set at the end of a quiet cul-de-sac, this beautifully renovated 5-bedroom, 3.5-bath colonial delivers the space, privacy, and finishes today's buyers are searching for - all on 3.19 private acres. Step through the dramatic two-story foyer with a chandelier and sidelights into a home thoughtfully updated from top to bottom. The main level flows seamlessly from the formal living room - anchored by

Mustafa Muaremi Coldwell Banker Realty

This 4-bedroom Cape Cod offers a nice sense of privacy, set back on a quiet cul-de-sac street. Sitting on 1.21 acres, there is plenty of outdoor space to enjoy, including a brand-new deck that's perfect for grilling or relaxing. The interior is light and bright with hardwood floors throughout, updated kitchen and bathrooms. It's a great opportunity for anyone looking for a comfortable home with a

Rob McConville RE/MAX Heritage

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

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

A spacious, lightfilled Cape welcomes you with a firstfloor primary suite featuring a dramatic wall of windows, custom fireplace with builtins, an atrium door opening to the patio and pool area, plus a flexible dressing room or office and a full bath with a tub/shower combination. The home offers an elegant formal living room with its own fireplace, a formal dining room ideal for gatherings, and

Carol Cangiano Coldwell Banker Realty

A spacious home offering 2,336 square feet of living space set on 1.3 acres. The main level features a comfortable flow between the living room, dining room, and kitchen, with a fireplace adding a central focal point. Hardwood flooring is present throughout much of the home, and a first-floor bedroom provides flexible use of space. The upper level includes the primary bedroom with a walk-in

Jeremy Oliver William Raveis Real Estate

Exceptional Contemporary Direct Waterfront Estate. Located in Guilford, CT, on a private cove of Little Harbor, this stunning home has a private Beach, pier / dock and pool. Built in 1969 and designed by renowned architect Judith Chafee, the thoughtfully designed open-concept floor plan maximizes water views from almost every room and boundless natural light throughout. The Living Room, with

Kirsten Adams William Pitt Sotheby's Int'l

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

Welcome to this stunning new construction Colonial located in the heart of North Guilford, offering 2,800(Additional 900 Square feet of finished basement) square feet of living space on a private 1.9 acre lot. Situated in the sought-after Mountain View subdivision on Jans Way, this home is one of only seven exclusive parcels, providing a rare combination of privacy, space, and modern design. The

Matthew Murchison Berkshire Hathaway NE Prop.

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

Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout.

Jane Cardarelli William Raveis Real Estate

"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 mini-splits, a new roof, fresh interior paint, and gleaming hardwood floors. The main level features an open living area with wood stove, offering

Tim Galvin William Raveis Real Estate

Serene Living at 507 Little Meadow Road Discover the perfect blend of coastal charm and modern comfort in this beautifully inviting 4-bedroom, 2-bathroom expanded Raised Ranch. Nestled on over an acre of level, lightly wooded land, this home offers a private sanctuary on one of Guilford's most scenic roads. The heart of the residence is a stunning vaulted-ceiling sunroom, complete with skylights,

Jaider Osorno Alpha Capital Realty, LLC

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