luxury houses for sale Guilford, United States

Well located at the end of a quiet cul-de-sac in the desirable Meadow Hills Lake community, this spacious 4-bedroom center hall Colonial offers the perfect balance of privacy, comfort, and neighborhood amenities, including private lake access and a sandy beach. Designed for both everyday living and entertaining, the main level features formal living and dining rooms, an eat-in kitchen, and an inviting family room with vaulted ceilings, a wood-burning fireplace, and sliding doors leading to an expansive deck. A versatile room just off the kitchen is ideal as a home office or playroom and opens to the welcoming front porch. Hardwood floors extend throughout the first level. Upstairs, the generous primary suite includes a walk-in closet and private bath, while three additional bedrooms share a full hall bath. The private backyard is a true retreat, highlighted by a newly rebuilt saltwater pool and plenty of space to relax or entertain. Enjoy the best of both worlds-a peaceful setting with exceptional community amenities, all just minutes from shopping, dining, and commuter routes.

Renovated 3-bedroom, 2-bath Raised Ranch on just over an acre of flat, level property in the Guilford Lakes neighborhood of Guilford, Connecticut. 1,760 square feet of fully updated living space,a finished lower level with fireplace offering flexible room for a family room, home office, gym, or guest space. The sun-filled main level features an updated kitchen with quartz countertops, tile backsplash, and new stove and microwave, opening into living and dining areas with hardwood floors throughout. Both full bathrooms have been completely remodeled. New flooring, interior doors, trim, lighting, fresh paint, and an updated laundry room complete a turnkey interior. The backyard is the rare part - just over an acre of open, level, usable land, uncommon at this price point on the Connecticut Shoreline. Location offers Guilford Lakes Elementary school, the Timberlands trail system, GL Golf Course, the town dog park, and Nut Plains Farm within minutes, not too mention, Krauzers and a local liquor store as well. Downtown Guilford's historic Town Green, shops, restaurants, Shoreline beaches, Yale Medical Services and commuter routes are a short drive.

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. 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. Step outside to a private deck, perfect for morning coffee or evening cocktails. Set within one of Guilford's most desirable condominium communities, residents enjoy picturesque walking paths and a private pond, all just minutes from the historic Green, shoreline beaches, shopping and dining. This unique residence offers the privacy of a single-family home with the ease of condominium living. Lovingly maintained, beautifully updated and truly move-in ready - unpack and enjoy!

Available October 1, 2026 through late May 2027. Set on 1.87 private, fenced acres on a quiet street, the home feels peaceful and tucked away while still being just minutes from I-95, shopping, dining, and the historic Guilford Green.The heart of the home is a dramatic post-and-beam great room with soaring ceilings, exposed timber beams, skylights, generous natural light, and a floor-to-ceiling stone fireplace. The main level includes a dining room and beautifully updated kitchen with farmhouse sink, induction cooktop, and double steam oven combo, plus a spacious first-floor primary suite with walk-in closet and renovated en-suite bath featuring a jetted tub and oversized rain shower. A second full bath on the main level includes a steam shower. Upstairs are two additional bedrooms, a full bath, a dedicated office, and a loft space. The current bedroom setup includes a guest room and children's room, with an additional twin bed or crib available if needed. The home is fully furnished and move-in ready, with central air conditioning, oil heat, washer and dryer, a finished basement area with Peloton (subscription required), outdoor parking, and a fenced yard.

Historic 1856 Octagon Home Just One Block from the Iconic Guilford Green. Rarely does a home of such architectural distinction and prime location become available. Crafted in 1859 by renowned local builder Edwin A. Leete, this landmark 4-bedroom, 2.5-bath octagonal residence offers a extraordinary blend of mid-19th-century character and seamless modern comfort-all just a single block from the historic Guilford Green. Inside, the distinctive eight-sided floor plan fills the home with exceptional natural light across a generous layout featuring a formal Living Room, dedicated Dining Room, and cozy Family Room. At the heart of the home is a chef-inspired, high-end custom Gulick Kitchen, beautifully appointed for both daily life and effortless entertaining. Modern infrastructure ensures year-round comfort with central air conditioning and natural gas heating. Set on a lovely, flat and fenced in .61-acre lot, the property includes a versatile detached garage providing flexible space perfect for a workshop, home studio, or bonus room. Step outside your front door to enjoy boutique shopping, fine dining, local events, and train access within minutes. A true piece of Guilford history upgraded for today's lifestyle.

Imagine strolling to the historic Guilford Green, with downtown shops, dining, and the train station just steps away! Situated on a level 0.68-acre lot, this turnkey 1920 Craftsman at 134 Union perfectly marries vintage soul with effortless modern living. A reclaimed wood ceiling warms the foyer, leading into an open-concept entertainer's dream. The chef's kitchen boasts sweeping quartz counters, a massive island, farmhouse sink, double ovens, and geometric tile. The dining room easily seats ten and flows into a cozy living room. Flawless red oak floors tie the 2,194 sq ft main living space together. Your main-level primary suite features a walk-in closet, reclaimed wood accent wall, and a luxurious spa bath with a marble double vanity and glass shower. A dedicated office, laundry room, and half bath complete the first floor. Upstairs, find three bright bedrooms and a full bath. Enjoy total peace of mind with extensive 2020 renovations including a new roof, upgraded electrical, and stunning kitchen/bath remodels. The home offers gas forced-air heat, central air, public water, and septic. Relax on the open porch overlooking a private yard with a storage shed. With a full walkout basement, this move-in-ready home is the ultimate lifestyle upgrade! If your wish is to live walking distance to the guilford green, here is your chance. Just turn the key, and move in!

Rare opportunity in Guilford! This home is currently used as a multifamily but can revert to a one family residence. Approximately 2400 sqft with the possibility of future expansion. Conveniently located close to Guilford's Historic Green, shops, restaurants, beaches and shoreline attractions.

Set on nearly two private acres in a quiet, peaceful setting, this beautifully maintained home offers more than 4,000 square feet of spacious, light-filled living. Built in 1999 and presented in excellent condition, the home features an inviting open floor plan, generously sized rooms, four large bedrooms, and two fireplaces that add warmth and character. Abundant natural light highlights the home's beautiful architectural details and creates a bright, welcoming atmosphere throughout. The expansive living spaces offer wonderful flexibility for both everyday living and entertaining, while a peaceful deck provides the perfect place to relax and enjoy the privacy and natural surroundings. A full walk-out basement offers exceptional potential for additional finished living space-ideal for a home gym, recreation room, playroom, office, or media room. Completing the property is a spacious three-car garage. Offering impressive scale, privacy, natural light, and a serene setting, this exceptional home combines comfort and versatility with timeless appeal.

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 home is thoughtfully designed for both elegant living and everyday comfort, featuring expansive, light-filled spaces and exquisite millwork throughout. The custom chef's kitchen is a true centerpiece, appointed with premium appliances, striking imported granite countertops, and impeccable detailing. A grand entryway welcomes you with a sweeping staircase and a beautifully crafted coffered ceiling, setting the tone for the quality and sophistication found in every room. Layout designed for first floor primary suite. This is a home for those who appreciate enduring design, superior construction, and a setting that feels worlds away-yet remains close to everything Madison has to offer.

Welcome to a truly exceptional living experience at The Residences at 66 High Street! This stunning three-bedroom, two-and-a-half-bathroom condo presents a rare opportunity for those seeking luxury and convenience in one of Guilford's most desirable locations. Spanning an impressive 3,148 square feet, this custom single-level home offers elegant design and modern amenities, ensuring comfort and style at every turn. Step inside to discover an exquisite open floor plan highlighted by two-inch marble and black walnut countertops, complemented by high-end finishes from Waterworks and custom built-ins throughout. Enjoy the culinary delight of a gourmet kitchen equipped with Subzero appliances, a 48 Wolf range, and two spacious walk-in pantries. The inviting living area features a gas fireplace for cozy evenings and a state-of-the-art Full Swing sports simulator that also serves as a perfect media room. This smart home boasts temperature-controlled fresh air and is easily managed via iPad. Step outside to your covered private terrace and be captivated by stunning marsh and Long Island Sound views, accompanied by refreshing salty breezes. The vibrant community offers a heated pool, fitness center, fire pit, dog park, and more, making it an ideal setting for relaxation and recreation. With easy access to the marina, beach, dining, shopping, and cultural experiences in downtown Guilford, this property epitomizes Connecticut shoreline living at its finest.

Welcome to 177 Warpas Road, a beautifully rebuilt 4 bed, 2.1 bath coastal colonial set on 1.84 acres, bordered by 185 acres of protected land trust. A lighted stone column entrance sets the tone for this home where New England style meets thoughtful modern updates. Set well back from the road, enjoy a rare sense of privacy, complemented by a fresh, updated exterior with new windows, siding, entrance portico, roof and refinished flooring (all 2025). Inside, the 1st floor layout is designed for easy living and effortless entertaining. The den with custom built-ins opens to a bright, eat-in kitchen with captivating property views. The dining area, living room and family room also offer views of the perfectly manicured and landscaped grounds. A stone fireplace and cathedral ceiling detail the family room and a wall of glass frames views of the resort-like backyard. The second floor offers an updated primary bedroom with tray ceiling. A newly created attic space provides a valuable head start for expansion with potential to add additional square footage. A roomy two-car garage adds convenience year round. Outdoors, an expansive two level patio incorporates a 2-year-old 630 square foot Timbertech deck with automatic awning that creates a shady outdoor living space. Across the lush lawn, a saltwater pool and a putting green create a true country club atmosphere. A full property irrigation system keeps the professionally maintained lawn and landscaping looking beautiful!

A rare opportunity to own one of downtown Guilford's most iconic residences, often referred to as The Spaceship, masterfully designed by architect Wilfred Armster. This striking copper-clad building, elevated on concrete stilts, was thoughtfully positioned to capture sweeping, unobstructed views of Long Island Sound-beautifully showcased from this premier front-facing unit. Enter through the oversized two -car garage, offering additional ample space for a home gym, workshop, or endless storage. Inside, the home opens to a dramatic great room where walls of glass flood the space with natural light and frame stunning water views. The expansive room with a fireplace flows effortlessly into the dining room & open kitchen, featuring a large breakfast bar, abundant cabinetry, new appliances and generous prep space-ideal for both everyday living and entertaining. The first floor also includes a versatile private space with a full bath, perfect for guests or a home office. Upstairs, the serene primary suite offers a walk-in closet, full bath, and a private sun deck overlooking with breathtaking views-your own peaceful retreat. Located just a short walk to the train station, marina, and Guilford's charming downtown filled with shops and restaurants, this is an ideal weekend escape from NYC or year-round residence. New furnace, water heater & AC. Watch the moon rise & the sun set from your one of a kind home. This small complex with low fees seldom comes to market-don't miss it.

DESIRABLE 4 BEDROOM NORTH MADISON HOME. Nestled on 2.62 peaceful, tree-lined acres in desirable North Madison, this classic yellow Colonial combines timeless New England charm with spacious, modern comfort. Offering 2,600+ square feet of beautifully appointed living space, the four-bedroom, 2.5 bath home is anchored by rich hardwood floors throughout the home. The front Living Room is spacious, the Family Room has a warm, inviting wood burning fireplace that serves as the heart of the main floor. The light-filled layout includes a finished basement that provides versatile extra rooms for a home gym, media area, or private office, while central air conditioning ensures year-round comfort throughout. An attached two-car garage adds everyday convenience to this tranquil retreat. Outside, the property opens up to an impressive bluestone patio designed for seamless outdoor entertaining, or simply taking in the scenic, natural views of your vast private grounds. The setting balances serene seclusion with easy accessibility, placing you just minutes from local hiking trails, North Madison amenities, close to Durham, with the vibrant shops and beaches of downtown Madison, 15 minutes away. Perfect for both relaxing everyday life and hosting family and friends, this classic residence captures the very best of shoreline Connecticut living.

Beautiful single family residence in MINT turnkey condition in sought-after Benton's Knoll, Sachem's Head. Quality, high-end construction provides luxurious amenities throughout. The large light-filled LR/Dr with fireplace w/ marble surround includes Hunter Douglas shades w/ sliders to the large deck off the back of the residence. The kitchen is very well equipped with a large Sub zero refrigerator, Wolf ovens, Cove dishwasher & composite countertops. A large pantry, w/ built-ins &laundry room are conveniently located adjacent to the two car garage, providing easy access to the kitchen. The floors throughout the first and second floor are hardwood white oak. The primary bedroom, located on the main level has a custom designed bathroom adorned with beautiful marble tile & a heated floor. The total square footage of this unit is 4001 sq ft - 2942 sq ft on the first and second floor; then the finished walk out basement is 1100 sq ft which provides a family room with fpl, large office and storage area with a full bathroom. This level could work for an au pair or plenty of room for extra guests and family. Walk out directly from this level to the bluestone patio and in-ground heated Gunite pool . Enjoy the ease of ownership in this special 15 unit condo complex, but with the feel of single family residences affording privacy and fantastic location, steps away from the water. Drive 6 minutes to the Guilford Green and all it has to offer.

BEACH HOME! BEACH RIGHTS! NEEDS WORK! It is not everyday that an opportunity to own a double lot in such a shoreline area. This charming English Cottage-style Cape, situated on a generous footprint for the area, is ready for it's next chapter-whether that involves a thoughtful renovation or the construction of a brand-new coastal home perhaps. Residents enjoy deeded rights to a private association sandy beach located just at the end of the street! The main residence of which there are no photos for obvious reasons once you see it (NEEDS WORK) currently features three bedrooms and 1.5 baths but adding to the property's versatility is a delightful in good condition accessory apartment, which offers a full kitchen, full bath, a private bedroom and a cozy living area anchored by a stone fireplace and two separate exterior entrances. This setup is ideal for multi-generational living, a great guest suite or potential rental income. Maybe live in this while redoing the other portion. The property is a double lot that accommodates four dedicated parking spaces - a true luxury for beachside living. Best of all, the property is located where no flood insurance is required, offering peace of mind alongside the salt air. Whether you choose to polish this unique gem or start fresh with a custom build, this is the perfect canvas for your seaside lifestyle.

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, complete with quartz counters, a large island, Thermador appliances, and induction cooktop. Designed for one-level living, the spacious primary suite is located on the first floor. In total, the home offers four bedrooms, three full, and one half bath. Amenities include a dedicated mudroom and laundry room equipped with an advanced ozone laundry system. Built to the highest green standards, the home utilizes geothermal heating and cooling, active solar, and energy efficient triple-pane windows. A full unfinished basement holds a large root cellar, while the three-car garage boasts an EV charging station and a walk-up attic storage area. A Generac generator ensures total peace of mind. Relax on one of the two Ipe covered front porches and take in the stunning grounds. This unique property features a passive solar greenhouse with cold frames, extensive garden bedding, a newly planted fruiting tree orchard, and sugar maples. Animal lovers will find a three-stall barn, two chicken coops, a duck coop, an enclosed dog park, and two large fenced pastures with hay fields.

Welcome to 38 Church Lane, where exceptional custom renovations meet a captivating Madison setting. Perched high on a large corner lot surrounded by mature trees, this thoughtfully updated 4-bedroom, 2.5 bath home offers sophisticated finishes, a flexible floor plan ideal for multi-generational living and privacy just minutes from Madison's town center and shoreline. The stunning kitchen, custom-crafted by Gedney Kitchens, features bespoke cabinetry and premium finishes, while an oversized fireplace anchors the inviting living room. The finished lower level includes a comfortable den with Vermont Castings wood-burning stove, custom Gedney wet bar, light-filled bedroom/office, and spa-inspired renovated bath with dual-head shower, heated floors, and heated towel rack. Outside, a brand-new composite deck overlooks terraced grounds with mature trees, stonework, curved pathways, and inviting spaces to garden, gather, and explore. An existing front-yard pond scape offers intriguing possibilities for future re-imagining. Hardie board siding with AZEK trim provides a remarkably low-maintenance exterior, complemented by energy-efficient windows and central air. Minutes from Madison's shops, dining, and beautiful shoreline beaches, this one-of-a-kind property truly must be experienced in person.

Looking for a home with heart and soul? One that has been lovingly maintained and thoughtfully updated? This gracious 3,800 sqft Colonial sits proudly on a beautiful lot in one of Killingworth's most desirable neighborhoods. At the heart of the home is a beautifully appointed cook's kitchen that opens seamlessly to a sun-drenched family room, where expansive windows frame views of the private backyard and surrounding natural beauty. A first-floor office provides the perfect work-from-home space, while a well-designed mudroom keeps everyday life organized. An inviting living room and charming powder room complete the main level. Upstairs, you'll find 4 generously sized bedrooms, including a spacious primary suite featuring a large walk-in closet and an elegantly updated bath. A standout feature is the exceptional play and recreation room - ideal for movie nights, sleepovers, a home gym, game room, or whatever suits your lifestyle. With access from both the 1st and 2nd floors, it offers remarkable flexibility. Need even more space? The finished 3rd floor includes a 5th bedroom and full bath, making it perfect for guests, an au pair, or a private retreat. An unfinished lower level provides excellent storage and future expansion. Surrounded by mature trees and peaceful natural beauty, this move-in ready home offers timeless appeal, generous living spaces, and a setting you'll look forward to coming home to!

Set on an elevated site, part of an exclusive peninsula known as Flying Point in the storied coastal village of Stony Creek, this historic waterfront home with private beach offers some of the very best views of both the Sound and Tuttle's Hole Cove. Nearly every room overlooks a number of the Thimble Islands. At approximately 3000 s.f., this four bedroom, three full bath home feels bright and open with high ceilings and oversized windows throughout. Wraparound outdoor space frames the water on multiple sides and includes a fabulous lower lawn area for entertaining and your own private dock puts kayaking, sailing and larger power boat fun at your doorstep. You may never have seen sunsets as beautiful as those that embrace the property all year round. A short drive from New Haven, Branford is easily reached by rail from NYC and not even 15 minutes takes you to regional air service at Tweed-New Haven airport.

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.

Remarkable property (corner lot) on Killingworth's most lovely, scenic, country road. This 5 bedroom, 3.1 bath, on 2.40 extraordinary acres (million $ back yard) is perfect for happy comfortable living and entertaining. Some of the fine additional features consist of a floor to ceiling stone fire place in the living room with wide pine floors, remodeled kitchen with cherry cabinets, stainless steel appliances, a second oven, quartz counter tops, a new primary bath with CIPOLLINO APUANO - MARBLE and heated floors, full attic with flooring, finished basement with full bath and walkout to 1100 square foot fieldstone patio (possibility for in-law situation), 100 feet of fieldstone walls, gazebo (with electric), hot tub, retractable awning, newer siding and windows, new hot water heater, additional parking off Emanual Church Road. This is not a drive by!! Come, see and witness this incredible home! Pro pictures coming soon.

Set on over 20 breathtaking, wooded acres, this property offers a rare blend of privacy, natural beauty, and flexible living. This contemporary split-level home is filled with natural light and thoughtfully positioned to capture sweeping hillside views from nearly every angle. With five bedrooms and 3.5 baths, including a private in-law suite with its own entrance, the home provides exceptional versatility for multi-generational living or guest accommodations. Outdoors, the property unfolds into a true retreat-meandering private hiking trails, a serene spring-fed pond, and open fields dotted with fruit trees create an idyllic country setting. Entertain with ease around the in-ground cement pool, surrounded by a stamped concrete patio, or host unforgettable gatherings beneath the stunning pergola dining area. Recent improvements, including a new roof make this move in ready. With its unmatched acreage, scenic vistas, and boundless potential, this is a unique opportunity to create a truly special lifestyle property in the heart of Durham.

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 from the house), kayak rack, boat launch, and possible deep water mooring. This coastal home has public water, a whole house generator, an irrigation system, security, and surveillance system, an Invisible Fence, the potential to subdivide, newer septic system (2010), an oversized 2 car garage, and no need for flood insurance. Nothing Compares.