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$3,500

Historic Charm Meets Modern Luxury: Carriage House Living in Downtown Guilford Experience the quintessential Shoreline lifestyle in this stunning, light-filled carriage house at 200 Whitfield Street. Tucked privately away in heart of downtown Guilford, this unique residence seamlessly blends historic architectural character with high-end, contemporary updates. Step inside to breathtaking open-concept living defined by soaring post-and-beam vaulted ceilings, exposed timber trusses, and rich wide-plank hardwood floors. The sun-drenched main space features skylights, expansive windows, and a chef's kitchen complete with white shaker cabinetry, sleek dark countertops, a gas cooktop island with breakfast bar, and stainless steel appliances. The living space flows effortlessly to a pristine, updated full bath featuring a custom tile and glass walk-in shower, alongside a convenient dedicated laundry and storage room. Every corner of this property radiates historic warmth, style, and total comfort. Best of all, your location is unmatched. Leave your car behind and take a short stroll to the historic Guilford Green, boutique shopping, local cafes, fine dining, the Guilford Free Library, and the shoreline train station. Jacobs Beach and Guilford Harbor/Marina are just down the road. An extraordinary rental opportunity in an unbeatable downtown location.

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24193549 MLS

Historic Charm Meets Modern Luxury: Carriage House Living in Downtown Guilford Experience the quintessential Shoreline lifestyle in this stunning, light-filled carriage house at 200 Whitfield Street. Tucked privately away in heart of downtown Guilford, this unique residence seamlessly blends historic architectural character with high-end, contemporary updates. Step inside to breathtaking open-concept living defined by soaring post-and-beam vaulted ceilings, exposed timber trusses, and rich wide-plank hardwood floors. The sun-drenched main space features skylights, expansive windows, and a chef's kitchen complete with white shaker cabinetry, sleek dark countertops, a gas cooktop island with breakfast bar, and stainless steel appliances. The living space flows effortlessly to a pristine, updated full bath featuring a custom tile and glass walk-in shower, alongside a convenient dedicated laundry and storage room. Every corner of this property radiates historic warmth, style, and total comfort. Best of all, your location is unmatched. Leave your car behind and take a short stroll to the historic Guilford Green, boutique shopping, local cafes, fine dining, the Guilford Free Library, and the shoreline train station. Jacobs Beach and Guilford Harbor/Marina are just down the road. An extraordinary rental opportunity in an unbeatable downtown location.

200 Whitfield St Unit Carriage House (rear), Guilford

$1,700

Walk to the Guilford green from this charming, one bedroom, second floor apartment. This unit has two entrances: the front door is a shared foyer, and leads to the living room; The side entrance, delivers you into the rear of the living room, near the eat-in kitchen with lovely pine cabinets. Conveniently off the kitchen is the large living room, offering space for a larger table or a desk, for those working from home. The bedroom is located at the front of the home, and features hard wood floors. The front hallway is another space that can hold a desk, if you're looking for more privacy. The bathroom is at the back of the home, located down the hall from the kitchen. Outside, a brand new patio is a lovely addition, shared by both units. The yard is spacious and level, providing an inviting outdoor space. A detached 2-car garage is shared with the first floor tenant (garage may be better suited for storage than for cars). Come take a look, this is a desirable, quiet, street in downtown Guilford. Apartments like this don't come around often!

1 Beds ⋅ 1 Baths ⋅ ACTIVE Status ⋅ 24193019 MLS

Walk to the Guilford green from this charming, one bedroom, second floor apartment. This unit has two entrances: the front door is a shared foyer, and leads to the living room; The side entrance, delivers you into the rear of the living room, near the eat-in kitchen with lovely pine cabinets. Conveniently off the kitchen is the large living room, offering space for a larger table or a desk, for those working from home. The bedroom is located at the front of the home, and features hard wood floors. The front hallway is another space that can hold a desk, if you're looking for more privacy. The bathroom is at the back of the home, located down the hall from the kitchen. Outside, a brand new patio is a lovely addition, shared by both units. The yard is spacious and level, providing an inviting outdoor space. A detached 2-car garage is shared with the first floor tenant (garage may be better suited for storage than for cars). Come take a look, this is a desirable, quiet, street in downtown Guilford. Apartments like this don't come around often!

37 Pearl St Unit B, Guilford

$1,599,000

Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 4-bedroom, 3.5-bathroom home is designed to captivate. Located only 1.5 miles from the quintessential Guilford Town Green, you'll enjoy the charm of local shops, restaurants, and a vibrant community. Plus, it's just 2.5 miles to the Guilford Marina, Guilford Yacht Club & Jacob's Beach. With quick highway access, proximity to Yale Medical nearby, this home truly delivers the best of convenience and lifestyle. Inside the home, be impressed with soaring 9' ceilings on both the main & upper floors, making the space feel open and inviting. The expansive Great Room, bathed in natural light, that features a sleek linear gas fireplace with a textured marble stone facade is perfect for cozy evenings or sophisticated entertaining. Step outside the sliders to an exquisite stone patio to enjoy in the warmer weather. The kitchen is a modern minimalist design with quartz countertops, stainless steel appliances & premium finishes. At its center is a waterfall edge island, where sleek quartz cascades down the sides for a clean, polished statement. A marble stone backsplash adds a touch of sophistication, tying in beautifully with the home's design. The home offers a tastefully designed main floor primary bedroom suite that is quiet & restful. Upstairs there is an ensuite bedroom, which is great for guests, & is tucked just steps away from the outdoor terrace- the ultimate spot to slip out & enjoy a quiet morning coffee.

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24191112 MLS

Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 4-bedroom, 3.5-bathroom home is designed to captivate. Located only 1.5 miles from the quintessential Guilford Town Green, you'll enjoy the charm of local shops, restaurants, and a vibrant community. Plus, it's just 2.5 miles to the Guilford Marina, Guilford Yacht Club & Jacob's Beach. With quick highway access, proximity to Yale Medical nearby, this home truly delivers the best of convenience and lifestyle. Inside the home, be impressed with soaring 9' ceilings on both the main & upper floors, making the space feel open and inviting. The expansive Great Room, bathed in natural light, that features a sleek linear gas fireplace with a textured marble stone facade is perfect for cozy evenings or sophisticated entertaining. Step outside the sliders to an exquisite stone patio to enjoy in the warmer weather. The kitchen is a modern minimalist design with quartz countertops, stainless steel appliances & premium finishes. At its center is a waterfall edge island, where sleek quartz cascades down the sides for a clean, polished statement. A marble stone backsplash adds a touch of sophistication, tying in beautifully with the home's design. The home offers a tastefully designed main floor primary bedroom suite that is quiet & restful. Upstairs there is an ensuite bedroom, which is great for guests, & is tucked just steps away from the outdoor terrace- the ultimate spot to slip out & enjoy a quiet morning coffee.

539-A Boston St, Guilford

$449,900

Ideally located between Guilford's shoreline and the Historic Green, this lovingly maintained expanded Ranch offers the ease of true one level living in one of the town's most desirable in town locations. Filled with warmth and character, the home features a spacious living room anchored by a gas fireplace with a stone surround and a huge vaulted sunroom with exposed beams that creates an inviting gathering space while overlooking the backyard and opening to a ground level deck. The flexible floor plan includes two bedrooms, a full bathroom, a den, and a private office, providing comfortable spaces for everyday living, guests, or working from home. Outside, the level yard is complemented by established gardens and offers plenty of room for outdoor enjoyment, along with a storage shed for added convenience. Recent improvements include a new roof with leaf guards, furnace, while practical amenities such as city water and an on demand whole house generator provide added comfort and peace of mind. Enjoy a highly walkable location just minutes from Guilford's historic town green with charming shops, and restaurants, walk to the marina, beach, and other beloved community amenities. A rare opportunity to enjoy a well cared for home with timeless appeal in the heart of Guilford.

2 Beds ⋅ 1 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24185320 MLS

Ideally located between Guilford's shoreline and the Historic Green, this lovingly maintained expanded Ranch offers the ease of true one level living in one of the town's most desirable in town locations. Filled with warmth and character, the home features a spacious living room anchored by a gas fireplace with a stone surround and a huge vaulted sunroom with exposed beams that creates an inviting gathering space while overlooking the backyard and opening to a ground level deck. The flexible floor plan includes two bedrooms, a full bathroom, a den, and a private office, providing comfortable spaces for everyday living, guests, or working from home. Outside, the level yard is complemented by established gardens and offers plenty of room for outdoor enjoyment, along with a storage shed for added convenience. Recent improvements include a new roof with leaf guards, furnace, while practical amenities such as city water and an on demand whole house generator provide added comfort and peace of mind. Enjoy a highly walkable location just minutes from Guilford's historic town green with charming shops, and restaurants, walk to the marina, beach, and other beloved community amenities. A rare opportunity to enjoy a well cared for home with timeless appeal in the heart of Guilford.

32 Summer St, Guilford

$1,299,900

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, the home blends timeless elegance with remarkable comfort and sophistication. A grand foyer with a dramatic staircase introduces more than 5,200 square feet of thoughtfully designed living space, where 10 foot ceilings, generously scaled rooms, and five fireplaces create warmth and sophistication throughout. At the heart of the home is a renovated kitchen thoughtfully designed with today's most desired amenities, featuring a large center island and butler's pantry that seamlessly blend style and functionality for effortless entertaining. Distinctive architectural details and one of a kind features add character throughout, including the remarkable office fireplace mantel reclaimed from a Newport mansion. The spacious bedroom level offers comfort, privacy, and flexibility, including a luxurious primary suite with a renovated ensuite bath and separate dressing room. Conveniently located minutes from the Guilford Green, boutique shopping, and renowned restaurants, this is a truly special offering that seamlessly combines timeless design, character, and an exceptional setting.

4 Beds ⋅ 5 Baths ⋅ ACTIVE Status ⋅ 24165243 MLS

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, the home blends timeless elegance with remarkable comfort and sophistication. A grand foyer with a dramatic staircase introduces more than 5,200 square feet of thoughtfully designed living space, where 10 foot ceilings, generously scaled rooms, and five fireplaces create warmth and sophistication throughout. At the heart of the home is a renovated kitchen thoughtfully designed with today's most desired amenities, featuring a large center island and butler's pantry that seamlessly blend style and functionality for effortless entertaining. Distinctive architectural details and one of a kind features add character throughout, including the remarkable office fireplace mantel reclaimed from a Newport mansion. The spacious bedroom level offers comfort, privacy, and flexibility, including a luxurious primary suite with a renovated ensuite bath and separate dressing room. Conveniently located minutes from the Guilford Green, boutique shopping, and renowned restaurants, this is a truly special offering that seamlessly combines timeless design, character, and an exceptional setting.

625 State St, Guilford

$23,500

Experience the ultimate boating lifestyle at the prestigious Guilford Yacht Club with this prime 34-foot boat slip. Nestled along the scenic River, this slip offers a front-row seat to breathtaking sunsets and immediate access to Long Island Sound. Within five minutes of leaving the channel, you'll be on your way to premier destinations like the Thimble Islands, Sag Harbor, Three Mile or Block Island. The club has been recently dredged, ensuring excellent depth and accessibility for your vessel. The docks, reconstructed in 2012, are in top-tier condition and include a large dock box for gear, with water, electricity, and cable readily available. Ownership includes a full club membership with no initiation fee, providing a resort-style experience. You'll have full use of the magnificent clubhouse, the heated pool, and professional Har-Tru tennis courts. The grounds are well maintained and there are BBQ areas perfect for social gatherings. Convenience is key with an on-site Dock House offering showers and heads, plus the option for winter boat storage. Whether you are heading out for a fishing expedition to Montauk or enjoying a quiet evening on the water, this slip represents an incredible value in a Guilford yachting community. Don't miss your chance to secure a lifestyle of luxury, recreation, and effortless nautical adventure.

ACTIVE Status ⋅ 24165818 MLS ⋅ Guilford Yacht Club BLDG.

Experience the ultimate boating lifestyle at the prestigious Guilford Yacht Club with this prime 34-foot boat slip. Nestled along the scenic River, this slip offers a front-row seat to breathtaking sunsets and immediate access to Long Island Sound. Within five minutes of leaving the channel, you'll be on your way to premier destinations like the Thimble Islands, Sag Harbor, Three Mile or Block Island. The club has been recently dredged, ensuring excellent depth and accessibility for your vessel. The docks, reconstructed in 2012, are in top-tier condition and include a large dock box for gear, with water, electricity, and cable readily available. Ownership includes a full club membership with no initiation fee, providing a resort-style experience. You'll have full use of the magnificent clubhouse, the heated pool, and professional Har-Tru tennis courts. The grounds are well maintained and there are BBQ areas perfect for social gatherings. Convenience is key with an on-site Dock House offering showers and heads, plus the option for winter boat storage. Whether you are heading out for a fishing expedition to Montauk or enjoying a quiet evening on the water, this slip represents an incredible value in a Guilford yachting community. Don't miss your chance to secure a lifestyle of luxury, recreation, and effortless nautical adventure.

379 Whitfield St Unit BN1034, Guilford

$2,995,000

Exquisitely reimagined with uncompromising attention to detail, this exceptional upper-level residence at The Residences at 66 High Street presents refined luxury in a premier in-town setting. Originally created by seamlessly merging two units, the owner collaborated with an interior designer, contractor, and master craftspeople to conceive a truly one-of-a-kind, fully customized home. The result is an expansive and impeccably executed "double" residence in the Leete Building offering approximately 3,000 square feet of meticulously maintained, sophisticated living space designed for both grand entertaining and effortless everyday comfort. A gracious living room anchored by a gas fireplace and a mounted 150-year old half hull ship model, flows seamlessly into a dining area with access to a private balcony; creating the perfect backdrop for intimate evenings or lively gatherings. The chef's kitchen and custom millwork throughout showcase superior craftsmanship, bespoke built-ins, and curated finishes of the highest caliber. The master bedroom suite is a private sanctuary, complete with its own fireplace, a dedicated office with built-in shelves, file drawers and cabinets for remote work, private balcony, a spa-inspired bath appointed with luxury fittings and steam shower, and two walk-in closets. Two additional bedrooms and beautifully designed full baths provide comfort and flexibility for guests.

3 Beds ⋅ 3 Baths ⋅ ACTIVE Status ⋅ 24155789 MLS ⋅ The Residences At 66 High Street BLDG.

Exquisitely reimagined with uncompromising attention to detail, this exceptional upper-level residence at The Residences at 66 High Street presents refined luxury in a premier in-town setting. Originally created by seamlessly merging two units, the owner collaborated with an interior designer, contractor, and master craftspeople to conceive a truly one-of-a-kind, fully customized home. The result is an expansive and impeccably executed "double" residence in the Leete Building offering approximately 3,000 square feet of meticulously maintained, sophisticated living space designed for both grand entertaining and effortless everyday comfort. A gracious living room anchored by a gas fireplace and a mounted 150-year old half hull ship model, flows seamlessly into a dining area with access to a private balcony; creating the perfect backdrop for intimate evenings or lively gatherings. The chef's kitchen and custom millwork throughout showcase superior craftsmanship, bespoke built-ins, and curated finishes of the highest caliber. The master bedroom suite is a private sanctuary, complete with its own fireplace, a dedicated office with built-in shelves, file drawers and cabinets for remote work, private balcony, a spa-inspired bath appointed with luxury fittings and steam shower, and two walk-in closets. Two additional bedrooms and beautifully designed full baths provide comfort and flexibility for guests.

66 High St Unit 38, Guilford

$1,399,000

Discover the vibrant energy of the historic town green just outside your doorstep. The inviting sidewalk guides you to the lively center, only 600 yards away. There, you'll find a treasure trove of quaint shops, restaurants, the recreational center, and cozy coffee spots to enjoy. Join in the community spirit at concerts and local events, and explore the area's rich history and character-all while residing on a spacious, nearly one-acre lot that offers a peaceful, private atmosphere. Experience the perfect fusion of timeless distinction and modern elegance in this well-maintained home, where original architectural craftsmanship has been beautifully preserved, and recent updates have brought a fresh, stylish feel to the space. Inside, you'll discover an inviting and versatile residence with numerous unique features that make this property truly one-of-a-kind. Enjoy the warm ambiance created by wide plank wood floors, original woodwork, exposed beams, and multiple fireplaces across the family room, living room, dining area, and primary bedroom. The home features 4+ bedrooms, thoughtfully arranged across two levels for privacy and comfort. Two hall-accessed bathrooms-one with a tub and one with a shower-occupy the second floor, both easily accessible from the hallway. The updated kitchen is an entertainer's dream, featuring leathered granite counters, a Subzero refrigerator, and an LG gas stove.

4 Beds ⋅ 4 Baths ⋅ ACTIVE Status ⋅ 24155372 MLS

Discover the vibrant energy of the historic town green just outside your doorstep. The inviting sidewalk guides you to the lively center, only 600 yards away. There, you'll find a treasure trove of quaint shops, restaurants, the recreational center, and cozy coffee spots to enjoy. Join in the community spirit at concerts and local events, and explore the area's rich history and character-all while residing on a spacious, nearly one-acre lot that offers a peaceful, private atmosphere. Experience the perfect fusion of timeless distinction and modern elegance in this well-maintained home, where original architectural craftsmanship has been beautifully preserved, and recent updates have brought a fresh, stylish feel to the space. Inside, you'll discover an inviting and versatile residence with numerous unique features that make this property truly one-of-a-kind. Enjoy the warm ambiance created by wide plank wood floors, original woodwork, exposed beams, and multiple fireplaces across the family room, living room, dining area, and primary bedroom. The home features 4+ bedrooms, thoughtfully arranged across two levels for privacy and comfort. Two hall-accessed bathrooms-one with a tub and one with a shower-occupy the second floor, both easily accessible from the hallway. The updated kitchen is an entertainer's dream, featuring leathered granite counters, a Subzero refrigerator, and an LG gas stove.

147 Boston St, Guilford

$3,995,000

Eagleview at Guilford - Where Luxury Meets Lifestyle. Discover Guilford's newest luxury coastal condominium community, where superior craftsmanship, modern design, and breathtaking views of Long Island Sound redefine Connecticut shoreline living. Whether you're enjoying a sunset from your private balcony, entertaining in your chef's kitchen, or exploring Guilford's vibrant coastal village, Eagleview is more than a home, it's a lifestyle. Experience 6,200 SF of refined living space (expandable to over 8,000 SF) perfectly positioned to capture the tranquil salt marshes and shimmering expanse of Long Island Sound. Each residence includes multiple private balconies that invite you to relax and savor the natural beauty that surrounds you. Unmatched craftsmanship & comfort, this community of only 11 luxury units blends architectural excellence with everyday ease. Every residence features 10-foot ceilings, custom crown moldings, and a Chef's Dream Kitchen equipped with professional-grade appliances and elegant finishes designed for both function and style. Modern conveniences include private elevators, heated 4-car garages with EV charging stations, central air, central vacuum systems, and backup generators. Flexible open floor plans allow you to create spaces that reflect your personal lifestyle and vision. Ideally situated just a 1/2 mile stroll to Jacob's Beach and the Guilford Green, Eagleview offers easy access to an array of restaurants, boutique shopping, and cafes.

6 Beds ⋅ 6 Baths ⋅ ACTIVE Status ⋅ 24138935 MLS ⋅ Eagleview Condominiums BLDG.

Eagleview at Guilford - Where Luxury Meets Lifestyle. Discover Guilford's newest luxury coastal condominium community, where superior craftsmanship, modern design, and breathtaking views of Long Island Sound redefine Connecticut shoreline living. Whether you're enjoying a sunset from your private balcony, entertaining in your chef's kitchen, or exploring Guilford's vibrant coastal village, Eagleview is more than a home, it's a lifestyle. Experience 6,200 SF of refined living space (expandable to over 8,000 SF) perfectly positioned to capture the tranquil salt marshes and shimmering expanse of Long Island Sound. Each residence includes multiple private balconies that invite you to relax and savor the natural beauty that surrounds you. Unmatched craftsmanship & comfort, this community of only 11 luxury units blends architectural excellence with everyday ease. Every residence features 10-foot ceilings, custom crown moldings, and a Chef's Dream Kitchen equipped with professional-grade appliances and elegant finishes designed for both function and style. Modern conveniences include private elevators, heated 4-car garages with EV charging stations, central air, central vacuum systems, and backup generators. Flexible open floor plans allow you to create spaces that reflect your personal lifestyle and vision. Ideally situated just a 1/2 mile stroll to Jacob's Beach and the Guilford Green, Eagleview offers easy access to an array of restaurants, boutique shopping, and cafes.

405 Whitfield St Unit 2, Guilford

$550,000

MULTIPLE OFFERS-SELLER REQUESTS HIGHEST & BEST OFFERS. Submission deadline is Friday May 23rd by 8:00 PM Exceptional Investment Opportunity - Prime Guilford Location Just steps from the vibrant Guilford Green, this historic multifamily property features two spacious 2-bedroom, 1-bathroom units on a level 0.46-acre lot. (Field card Says 2 bedrooms in each apt -4 bedrooms total- In 1st floor apt. Front room was used as 2nd bedroom. Fireplace is not currently operational. Ideal for restoration, it offers potential as an owner-occupied residence with rental income or a full investment property. Located only 0.5 miles from the train station and 1 mile from Jacobs Beach, Chittenden Park, and the town marina, with easy access to shops, restaurants, the Guilford Free Library and the Guilford Fairgrounds. Priced to reflect renovation needs and offered "As Is". Inspections are for informational purposes only. Best suited for cash buyers or those using an owner-occupied rehab loan.

4 Beds ⋅ 2 Baths ⋅ ACTIVE UNDER CONTRACT Status ⋅ 24126723 MLS

MULTIPLE OFFERS-SELLER REQUESTS HIGHEST & BEST OFFERS. Submission deadline is Friday May 23rd by 8:00 PM Exceptional Investment Opportunity - Prime Guilford Location Just steps from the vibrant Guilford Green, this historic multifamily property features two spacious 2-bedroom, 1-bathroom units on a level 0.46-acre lot. (Field card Says 2 bedrooms in each apt -4 bedrooms total- In 1st floor apt. Front room was used as 2nd bedroom. Fireplace is not currently operational. Ideal for restoration, it offers potential as an owner-occupied residence with rental income or a full investment property. Located only 0.5 miles from the train station and 1 mile from Jacobs Beach, Chittenden Park, and the town marina, with easy access to shops, restaurants, the Guilford Free Library and the Guilford Fairgrounds. Priced to reflect renovation needs and offered "As Is". Inspections are for informational purposes only. Best suited for cash buyers or those using an owner-occupied rehab loan.

174 Whitfield St, Guilford