334 properties for sale in Guilford Historic Town Center

Coastal Paradise in the Heart of Madison! Welcome to one of Madison's most desirable shoreline beach communities, where coastal charm, breathtaking views, and endless outdoor recreation come together to create the perfect seaside retreat. This delightful cottage offers spectacular views of Fence Creek Salt Marsh and a glimpse of Long Island Sound. Kayak or paddleboard from the beach one block away (or directly from the back yard at high tide), enjoy morning walks along the ocean, stroll into town for coffee, and embrace the relaxed Connecticut shoreline lifestyle. Inside, this charming home features 2 bedrooms, 1 bath, and 3 additional rooms that capture the beauty of the surrounding landscape. Large windows invite natural light and showcase the stunning marsh vistas. The deck is ideal for entertaining or simply unwinding while taking in the abundant bird life. After a day at the beach, rinse off in the outdoor shower. Central air conditioning and heat offer three-season living, with t

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

Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated. Level agricultural acreage stretches across the property, bordered by old farm stonewalls. Outstanding potential-whether your vision is a hobby or gentleman's farm, livestock, or equipment storage. Ideal for multi-generational living for those seeking shared but private living. Investors seeking income producing property, entrepreneurial minded, and creatives looking for a home office, in-home gym with full bath, and studio space. The property has two separate septic systems and utilities offering true independence. Farmhouse style home is enchanting with 3-bedrooms. Dual staircases with private

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

Welcome to this beautifully maintained Colonial offering over 2,100 square feet of comfortable living space on a generous 0.64-acre lot in one of Branford's most desirable shoreline locations. Just minutes from Stony Creek, Branford Harbor, beaches, marinas, restaurants, shopping, and I-95, this home combines classic New England charm with modern updates and everyday convenience. Step inside to discover a bright and inviting floor plan. Boasting a formal dining and living rooms on the first floor creating warm, welcoming spaces for entertaining family and friends. A separate family room provides additional flexibility for relaxing or working from home. Upstairs, the large primary bedroom features splenty of natural light, creating a peaceful retreat at the end of the day. Two additional bedrooms and an office/laundry area offer versatility for remote work, or growing families. Additionally, there is a two car garage with an amazing studio apartment over it. Outside, enjoy your own priv

Private.Pastoral.Purposeful. Available for the first time in decades. This rare 4-acre compound offers a Farmhouse style home, a guest house, 3-car garage with additional storage, and attached in-home gym, office equipped with bathroom, and artist's studio. This legacy property delivers both on location and acreage offering a one-of-a-kind sequestered compound that simply cannot be replicated. Level agricultural acreage stretches across the property, bordered by old farm stonewalls. Outstanding potential-whether your vision is a hobby or gentleman's farm, livestock, or equipment storage. Ideal for multi-generational living for those seeking shared but private living. Investors seeking income producing property, entrepreneurial minded, and creatives looking for a home office, in-home gym with full bath, and studio space. The property has two separate septic systems and utilities offering true independence. Farmhouse style home is enchanting with 3-bedrooms. Dual staircases with private

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

Welcome to this beautifully maintained Colonial offering over 2,100 square feet of comfortable living space on a generous 0.64-acre lot in one of Branford's most desirable shoreline locations. Just minutes from Stony Creek, Branford Harbor, beaches, marinas, restaurants, shopping, and I-95, this home combines classic New England charm with modern updates and everyday convenience. Step inside to discover a bright and inviting floor plan. Boasting a formal dining and living rooms on the first floor creating warm, welcoming spaces for entertaining family and friends. A separate family room provides additional flexibility for relaxing or working from home. Upstairs, the large primary bedroom features splenty of natural light, creating a peaceful retreat at the end of the day. Two additional bedrooms and an office/laundry area offer versatility for remote work, or growing families. Additionally, there is a two car garage with an amazing studio apartment over it. Outside, enjoy your own priv

21 Chapel Drive greets you with an expansive front porch, perfectly positioned to capture the cooling breezes of Long Island Sound at the end of the street. This warm and inviting home is bathed in exceptional natural light throughout the day. Inside, the formal living and dining rooms flow seamlessly, setting the stage for elegant entertaining anchored by an expansive fireplace. The heart of the home is the kitchen where large windows frame picturesque views of the historic Pine Orchard Chapel. The open concept kitchen welcomes everyone to come and stay for a while. There is plenty of counter and storage space and there are two cooking areas: a gas stove and an electric cooktop. It is adjacent to the family room with its pretty built in China cabinet and private office overlooking the rear deck, complete with a pergola and a quiet landscaped yard and one car oversize detached garage. Upstairs, the primary suite offers a peaceful sanctuary featuring a versatile nook - ideal for a nurse

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

Everyone dreams of having a beach house. well, dreams do come true! Located in the private community of Hotchkiss Grove, residents have felt the pull of the sea for generations and homes tend to be passed down. This is an unique opportunity to purchase a stunning 1928 residence that has been thoughtfully reimagined, from top to bottom, perfectly balancing the original vintage look with the clean finishes of today. Turning onto Second Avenue the first thing you see is the private sandy association beach and the shimmering water of Long Island Sound. Nearby is the boat launch, moorings and the association owned peninsula which is used for Hotchkiss Grove Day, weddings and other social events. Located 7 houses from the water, 29 Second Avenue is a true beach house, but with a modern updated feel. The open floor plan incorporating the living room with its gas fireplace, dining room and updated kitchen is perfect for entertaining. There is a first floor bedroom with ensuite that also be can

21 Chapel Drive greets you with an expansive front porch, perfectly positioned to capture the cooling breezes of Long Island Sound at the end of the street. This warm and inviting home is bathed in exceptional natural light throughout the day. Inside, the formal living and dining rooms flow seamlessly, setting the stage for elegant entertaining anchored by an expansive fireplace. The heart of the home is the kitchen where large windows frame picturesque views of the historic Pine Orchard Chapel. The open concept kitchen welcomes everyone to come and stay for a while. There is plenty of counter and storage space and there are two cooking areas: a gas stove and an electric cooktop. It is adjacent to the family room with its pretty built in China cabinet and private office overlooking the rear deck, complete with a pergola and a quiet landscaped yard and one car oversize detached garage. Upstairs, the primary suite offers a peaceful sanctuary featuring a versatile nook - ideal for a nurse

Originally built in 1825, this residence has been thoughtfully updated to preserve its historic essence while incorporating modern conveniences. Nestled on a generous 4.38-acre lot, this extraordinary home boasts 3 spacious bedrooms and 2.5 beautifully appointed bathrooms within its expansive 3,500 square feet of living space. As you step inside, you'll be captivated by the elegant oak hardwood floors that flow throughout. The state-of-the-art kitchen is a chef's dream, showcasing exquisite Calacatta Gold marble countertops and top-of-the-line stainless steel appliances, making it perfect for both casual meals and entertaining guests. Step outside, and you'll find your own oasis featuring an inviting in-ground gunite pool, complete with a pool house, ideal for relaxation and summer gatherings. The vast property offers ample possibilities for subdivision or the construction of an additional home, providing the perfect opportunity for creating a cherished family compound. Additionally, t

This is not simply waterfront living. This is a waterfront lifestyle unlike any other. Tucked within the coveted enclave of Sachem's Head, this extraordinary estate commands direct Long Island Sound frontage with unobstructed harbor views and breathtaking sunsets. Masterfully crafted in 2003 and transformed by the current owners with uncompromising quality, the 6,000 SF+ residence is defined by Dramatic walls of glass framing endless water views from virtually every room offering seamless indoor-outdoor living. You will be immediately wowed by the jaw dropping great room with an incredible fireplace and soaring ceiling. At the heart of the home lies a stunning Poliform kitchen, the pinnacle of modern luxury, thoughtfully appointed with premium appliances and designed to delight the most discerning chef. Oversized dining area that effortlessly steps right onto the expansive Ipe deck for additional outdoor waterfront entertaining. The all glass-enclosed family room overlooks the sound as

Soaring ceilings and walls of glass define the heart of this modern Stony Creek residence, where natural light pours into the expansive living room. The dramatic open-plan living area, anchored by a sleek fireplace, seamlessly flows to an outdoor oasis-a salt-water pool accented by a tranquil waterfall and surrounded by a pool house, lounge spaces, and lush landscaping. The connection between indoors and outdoors is effortless, inviting gatherings large and small. At the core of the home, the kitchen is a culinary showpiece: high-end appliances, custom cabinetry, and striking stone surfaces create a space that's as functional as it is beautiful. The adjacent dining area and living space are ideal for entertaining, with panoramic views of the marsh adding an ever-changing backdrop. The main level features two well-appointed bedrooms, each thoughtfully integrated into the home's design for comfort and privacy. Upstairs, the primary suite is a sanctuary with private balcony, marsh views,

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

Everyone dreams of having a beach house. well, dreams do come true! Located in the private community of Hotchkiss Grove, residents have felt the pull of the sea for generations and homes tend to be passed down. This is an unique opportunity to purchase a stunning 1928 residence that has been thoughtfully reimagined, from top to bottom, perfectly balancing the original vintage look with the clean finishes of today. Turning onto Second Avenue the first thing you see is the private sandy association beach and the shimmering water of Long Island Sound. Nearby is the boat launch, moorings and the association owned peninsula which is used for Hotchkiss Grove Day, weddings and other social events. Located 7 houses from the water, 29 Second Avenue is a true beach house, but with a modern updated feel. The open floor plan incorporating the living room with its gas fireplace, dining room and updated kitchen is perfect for entertaining. There is a first floor bedroom with ensuite that also be can

Privacy and convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acres. Enjoy this 'tucked away' home yet a short walk to historic downtown Madison with its famed bookstore, shopping, restaurants and retail stores. This home has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath home which features granite countertops in kitchen and baths, hardwood floors, light and bright open floor plan, natural gas fireplace and a year-round heated sunporch which is surrounded by nature and very well will be your most favorite room! Detached single car garage plus additional resident and guest parking. Newer Samsung gas stove and Bosch dishwasher. Updated HVAC - Trane AC unit manufactures date 1/2021 and Trane furnace date 4/2021

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 exceptio

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

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

Own a remarkable piece of Branford history! Welcome to the Timothy Baldwin House, a distinguished circa-1819 Colonial listed on the National Register of Historic Places. Offering 6 bedrooms, 3 1/2 baths, over 3,400 square feet of living space, and 1.30 acres, this impressive home blends historic character with the space and flexibility today's buyers are looking for. Inside, multiple living and gathering spaces provide plenty of room to spread out. The spacious eat-in kitchen features an island, abundant cabinetry, pantry storage, and a striking stone fireplace surround. A separate family room opens directly to the backyard, while two first-floor bedrooms and a full bath offer flexibility for guests, a home office, or multigenerational living. Upstairs, the expansive primary suite includes a private bath, along with three additional bedrooms and another full bathroom. A walk-up attic and full basement provide substantial additional storage. Outside, enjoy a spacious, level yard with pl

Rare Shoreline Opportunity in Pine Orchard~Prime Coastal Investment and Lifestyle Potential. Offered on the market for the first time, this quintessential Pine Orchard property presents a rare value-add opportunity in one of Branford's most prestigious coastal neighborhoods. Situated on a generous lot steps from water access and surrounded by multi-million-dollar homes, it offers endless upside for both investors and future homeowners. For the Investor~Immediate Cash-Flow:Currently configured as a 4-unit home with clean, updated units ready to rent at full market rates ($1,500+/mo each). Historically, rents were kept intentionally low, leaving immediate upside. Value-Add Pathways:Convert the structure into 2 luxury units, explore lot-split possibilities, or transform the detached 7-bay garage into an ADU or additional income stream (subject to approvals). For the Homeowner~Coastal Living:Enjoy an enviable by-the-water location with water access right down the street. Versatile Footprin

Less than one mile from downtown Madison, this new construction home offers refined living with white oak floors, custom millwork, coffered ceilings, and abundant natural light throughout. The main level features 9-foot ceilings, a dramatic floor-to-ceiling gas stone fireplace with built-ins, a chef's kitchen with Sub-Zero and Wolf appliances, double ovens, pot filler, wet bar with wine chiller, walk-in pantry, first-floor laundry, private office, and a luxurious primary suite with soaking tub, oversized rain shower, double vanity, custom walk-in closet, and floor-to-ceiling tile. Upstairs includes four bedrooms and three full baths, walk-in closets, and a bonus room with floor-to-ceiling nickel gap and oversized French doors leading to your new home gym. Additional highlights include central vacuum system, elevated covered patio, and a high-ceiling basement (9 ft) ready for finishing. taxes are for the previous home

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 a sense of history and warmth. Over 3800 square foot of living space. The updated kitchen and refinished basement have been thoughtfully done, so the home is move-in ready while still feeling authentic to its roots. Three bedrooms on the second floor provide comfortable family living, and two additional finished rooms on the third floor give you the flexibility to grow, work from home, or host guests with ease. Step outside and you'll find a private retreat: a tranquil pond with a fountain, streams aligning the property, manicured gardens, and a pergola for morning coffee or evening gatherings. The

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 l

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 exceptio

Privacy and convenience are both found within this updated detached stand-alone Ranch home in sought after Kensington Acres. Enjoy this 'tucked away' home yet a short walk to historic downtown Madison with its famed bookstore, shopping, restaurants and retail stores. This home has been beautifully maintained and shows pride of ownership throughout. Enjoy single floor living in your 2 bedroom, 2 bath home which features granite countertops in kitchen and baths, hardwood floors, light and bright open floor plan, natural gas fireplace and a year-round heated sunporch which is surrounded by nature and very well will be your most favorite room! Detached single car garage plus additional resident and guest parking. Newer Samsung gas stove and Bosch dishwasher. Updated HVAC - Trane AC unit manufactures date 1/2021 and Trane furnace date 4/2021

Own a remarkable piece of Branford history! Welcome to the Timothy Baldwin House, a distinguished circa-1819 Colonial listed on the National Register of Historic Places. Offering 6 bedrooms, 3 1/2 baths, over 3,400 square feet of living space, and 1.30 acres, this impressive home blends historic character with the space and flexibility today's buyers are looking for. Inside, multiple living and gathering spaces provide plenty of room to spread out. The spacious eat-in kitchen features an island, abundant cabinetry, pantry storage, and a striking stone fireplace surround. A separate family room opens directly to the backyard, while two first-floor bedrooms and a full bath offer flexibility for guests, a home office, or multigenerational living. Upstairs, the expansive primary suite includes a private bath, along with three additional bedrooms and another full bathroom. A walk-up attic and full basement provide substantial additional storage. Outside, enjoy a spacious, level yard with pl

Rare Shoreline Opportunity in Pine Orchard~Prime Coastal Investment and Lifestyle Potential. Offered on the market for the first time, this quintessential Pine Orchard property presents a rare value-add opportunity in one of Branford's most prestigious coastal neighborhoods. Situated on a generous lot steps from water access and surrounded by multi-million-dollar homes, it offers endless upside for both investors and future homeowners. For the Investor~Immediate Cash-Flow:Currently configured as a 4-unit home with clean, updated units ready to rent at full market rates ($1,500+/mo each). Historically, rents were kept intentionally low, leaving immediate upside. Value-Add Pathways:Convert the structure into 2 luxury units, explore lot-split possibilities, or transform the detached 7-bay garage into an ADU or additional income stream (subject to approvals). For the Homeowner~Coastal Living:Enjoy an enviable by-the-water location with water access right down the street. Versatile Footprin