Guilford, CT Homes for Sale

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  /37

  $3,100,000

  • 4 Beds
  • 4.5 Baths
  • 6,194 Sq Ft

  24 Indigo Trail, Madison, CT 06443

  Come see this stately custom Brick English Georgian home in sought after Madison CT, nestled on a sprawling 5.65 acre lot with Neck River frontage. This exquisite 6,194 square foot colonial offers an unparalleled blend of luxury, privacy and natural beauty. With 4 bedrooms and 4.5 baths, it is designed for those who appreciate both elegance and tranquility. This unique residence is surrounded by

  

  Ron Stewart

  Houlihan Lawrence WD

  (475) 405-2519

  24 Indigo Trail, Madison, CT 06443
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  /40

  $2,650,000

  • 5 Beds
  • 7.5 Baths
  • 8,476 Sq Ft

  75 Half Mile Rd, Guilford, CT 06437

  Introducing a custom-built Adirondack-style masterpiece, set on over 5 acres of pristine land. Designed with care by the current owners, this home boasts a seamless layout, ideal for entertaining. Spacious, elegantly appointed rooms feature a custom-designed kitchen, soaring ceilings, and a stunning two-sided stone fireplace. Each bedroom is en suite, offering both privacy and luxury. The

  

  Cathy Lynch

  Coldwell Banker Realty

  (475) 255-6899

  75 Half Mile Rd, Guilford, CT 06437
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  /40

  $850,000

  • 3 Beds
  • 2.5 Baths
  • 3,488 Sq Ft

  31 Christopher Ln, Guilford, CT 06437

  Tucked into a quiet, picturesque cul-de-sac, this beautifully maintained colonial radiates timeless charm and effortless grace. From the moment you arrive, its regal presence, inviting curb appeal, and welcoming atmosphere create just the right feeling-making a lasting impression and instantly putting you at ease. Centrally located and thoughtfully designed for both lively entertaining and

  Nicole White William Raveis Real Estate

  31 Christopher Ln, Guilford, CT 06437
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  /40

  $1,399,999

  • 4 Beds
  • 2.5 Baths
  • 3,367 Sq Ft

  35 Bayberry Ln, Guilford, CT 06437

  35 Bayberry Lane-a stunning, newly rebuilt coastal retreat nestled in the highly sought-after Old Sachem Beach neighborhood. Just a short stroll from the peaceful shores of Joshua Cove, this modern 4-bedroom home offers 3,400 sq ft. of luxurious living space designed with both style & comfort in mind. The open-concept layout showcases wide-plank white oak hardwood floors, soaring vaulted ceilings

  Lauren Freedman Coldwell Banker Realty

  35 Bayberry Ln, Guilford, CT 06437
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  /31

  $999,999

  • 4 Beds
  • 3.5 Baths
  • 3,900 Sq Ft

  15 Briarwood Dr, Guilford, CT 06437

  Located in a beautiful Guilford neighborhood, no through road, this exceptional home offers a vacation inspired lifestyle with a pool and sauna inside, and a 5-mile drive to the beach! Many thoughtful improvements throughout the spacious flexible layout, with the opportunity to still make it your own. Major systems have been updated, including the septic, central air, hot water tank, electrical,

  Melanie Taylor Berkshire Hathaway NE Prop.

  15 Briarwood Dr, Guilford, CT 06437
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  /40

  $889,900

  • 4 Beds
  • 2.5 Baths
  • 2,882 Sq Ft

  387 N River St, Guilford, CT 06437

  Charming Historic Home built for Peter Chapman in 1851 by William Weld according to Keeping Society (town has different date). Currently has renovations throughout providing inviting elegance and modern conveniences. Main level renovated to include main level BR with ADA compliant full bath, new enlarged upgraded kitchen w/SS appliances, quartz counter and nearby wet bar area adjacent to den with

  Diane Beckwith Popolizio William Raveis Real Estate

  387 N River St, Guilford, CT 06437
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  /40

  $925,000

  • 3 Beds
  • 4 Baths
  • 2,279 Sq Ft

  1054 Boston Post Rd, Guilford, CT 06437

  RARE OPPORTUNITY TO OWN TWO BUILDINGS IN GUILFORD ~ Unlock the potential of this prime commercial property on the bustling Boston Post Road, just one block from Guilford's historic town Green. Within the PV zone (Post Road Village Zone District, this offering includes 2 buildings (see listing #1058 Boston Post Road) that share a driveway and provide dedicated parking; an ideal setup for

  Rose Ciardiello William Raveis Real Estate

  1054 Boston Post Rd, Guilford, CT 06437
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  /40

  $1,475,000

  • 2 Beds
  • 3 Baths
  • 1,740 Sq Ft

  13 Waterside Dr, Guilford, CT 06437

  13 Waterside Drive, Guilford, CT - A Coastal Gem on Joshua's Cove! Experience the best of waterfront living at this newly renovated coastal retreat, perfectly positioned on one of Guilford's most stunning sandy beaches. Nestled on the shores of picturesque Joshua's Cove, this 2-bedroom, 2-bathroom home-with an additional full outdoor bathroom- offers breathtaking views, a private beach, and

  Nicole White William Raveis Real Estate

  13 Waterside Dr, Guilford, CT 06437
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  /33

  $899,000

  • 4 Beds
  • 2.5 Baths
  • 3,232 Sq Ft

  141 Meadow Ridge Ln, Guilford, CT 06437

  WOW! This stunning contemporary colonial is bathed in sunlight and packed with incredible features from top to bottom. Step into the dramatic new two-story entry and be amazed. The huge family room boasts beamed cathedral ceilings, skylights, a cozy fireplace, and an abundance of windows. Gleaming hardwood floors flow throughout, leading to a banquet-sized dining room perfect for hosting. The

  Susan Santoro William Pitt Sotheby's Int'l

  141 Meadow Ridge Ln, Guilford, CT 06437
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  /39

  $1,950,000

  • 3 Beds
  • 2.5 Baths
  • 2,194 Sq Ft

  66 High St Unit 36, Guilford, CT 06437

  66 HIGH STREET - 3 bedroom, 2.5-bath condominium, boasting an impressive 2,194 SF on the 2nd floor. The views are western exposure, of marsh and Long Island Sound. Located in the prestigious community of Guilford, CT, this residence offers a harmonious blend of modern design and natural beauty. The open concept includes a sun filled Living Room, with a cozy gas fireplace, Dining Room and Kitchen,

  Kirsten Adams William Pitt Sotheby's Int'l

  66 High St Unit 36, Guilford, CT 06437
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  /38

  $885,000

  • 4 Beds
  • 3.5 Baths
  • 3,625 Sq Ft

  765 Durham Rd, Guilford, CT 06437

  Nestled on a spacious and serene .92-acre lot, this fully renovated 4-bedroom, 3.5-bath contemporary home has the perfect blend of modern design and functional living. The thoughtfully designed layout features a luxurious primary suite on the main level, ideal for convenience and privacy. Upstairs, discover a second primary suite, complete with its own private balcony, providing a peaceful

  Adam Negri Venus and Mars Properties, LLC

  765 Durham Rd, Guilford, CT 06437
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  /36

  $1,785,000

  • 2 Beds
  • 2.5 Baths
  • 2,790 Sq Ft

  66 High St Unit 15, Guilford, CT 06437

  The finest GUILFORD DOWNTOWN LIVING possible. This incredible townhouse will take your breath away! This 2800 sq ft end unit is located in the historic mill building at this luxurious complex. Combining modern living with extraordinary architecture and the finest finishes. Spectacular marsh views from every window as well as the oversized private deck. Dramatic 20' ceilings with exposed metal &

  Susan Santoro William Pitt Sotheby's Int'l

  66 High St Unit 15, Guilford, CT 06437
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  /40

  $1,800,000

  • 4 Beds
  • 5 Baths
  • 5,790 Sq Ft

  4 Woods Way, Guilford, CT 06437

  Nestled quietly off the Boston Post Road and a short drive to Guilford's Town Center, the Cottage at the Woods transports you to a quaint European village with it's striking architecture, hand cut stone work, and expansive patios with cozy fireplaces. Brilliant sunlight drenches the chef's kitchen and family room through walls of glass and french doors leading to a spacious patio. The residences

  John Campbell Compass Connecticut, LLC

  4 Woods Way, Guilford, CT 06437
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  /37

  $1,800,000

  • 3 Beds
  • 4 Baths
  • 4,804 Sq Ft

  2 Woods Way, Guilford, CT 06437

  Nestled quietly off the Boston Post Road and a short drive to Guilford's Town Center, the Cottage at the Woods transports you to a quaint European village with it's striking architecture, hand cut stone work, and expansive patios with cozy fireplaces. Brilliant sunlight drenches the chef's kitchen and family room through walls of glass and french doors leading to a spacious patio. The residences

  John Campbell Compass Connecticut, LLC

  2 Woods Way, Guilford, CT 06437
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  /34

  $1,475,000

  • 6 Beds
  • 5 Baths
  • 8,265 Sq Ft

  7 Hart Rd, Guilford, CT 06437

  After Colleen McCullough wrote her best selling novel, "The Thorn Birds" she designed and built a house to fulfill her dreams. Near her publishers in New York, yet with the seclusion of forested hills and brook where she could work in an ideal setting. From the imposing entrance at the end of a winding drive, one faces a long and beautiful foyer, opening on one side to the enormous atrium

  Sandra Calise Cenatiempo Settlers & Traders

  7 Hart Rd, Guilford, CT 06437
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  /32

  $930,000 New Construction

  • 3 Beds
  • 2.5 Baths
  • 2,800 Sq Ft

  4 Jans Way, Guilford, CT 06437

  This captivating colonial in the heart of North Guilford is 2800 sq ft located on a 1.9 acre lot. This residence is being built on one of the 7 parcels known as Mountain View subdivision on Jans Way. The main floor offers an open concept kitchen and great room, perfect for entertaining the family. Formal dining room and office are located on first floor with one half bath. Second floor features

  Matthew Murchison Berkshire Hathaway NE Prop.

  4 Jans Way, Guilford, CT 06437
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  /7

  $879,900 New Construction

  • 4 Beds
  • 2.5 Baths
  • 2,428 Sq Ft

  876 Nut Plains Rd Unit Lot 3, Guilford, CT 06437

  LAST LOT AVAILABLE - Introducing an exquisite gem nestled just a couple miles from our charming Town Green - the epitome of modern living awaits you in our brand-new, 3-home subdivision. These homes represent a harmonious blend of contemporary aesthetics, soaring ceilings, 8ft windows, and a sense of elegance, designed to captivate both your senses and your heart. Step into a world of refined

  Adrian Price Sunset Creek Realty, LLC

  876 Nut Plains Rd Unit Lot 3, Guilford, CT 06437
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  /40

  $2,195,000

  • 5 Beds
  • 9 Baths
  • 5,414 Sq Ft

  173 Highwoods Dr, Guilford, CT 06437

  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

  173 Highwoods Dr, Guilford, CT 06437
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  /28

  $425,000

  • 2 Beds
  • 2 Baths
  • 1,442 Sq Ft

  7 Copper Hill Dr, Guilford, CT 06437

  Enjoy EVERYTHING Guilford has to offer without the headaches! Public water, Natural gas, Central air, HOA managed shared Septic, 1-car garage. This detached condo in south Guilford has it all! Structured like a single family house so you and your family have plenty of privacy. Two-bedroom on the main level plus a loft room on the upper level which could be used as an office or additional bedroom.

  Jia Wu JJ HOMES REAL ESTATE, LLC

  7 Copper Hill Dr, Guilford, CT 06437
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  /35

  $499,999

  • 3 Beds
  • 1.5 Baths
  • 1,541 Sq Ft

  567 Nut Plains Rd, Guilford, CT 06437

  Tucked away in the scenic town of Guilford, 567 Nut Plains Road is a perfect blend of classic New England charm and modern updates. This beautifully maintained 1941 home sits on a 0.22-acre corner lot and offers 3-4 bedrooms, 1.5 bathrooms, and a detached garage. Step inside to a bright and inviting living room, complete with a cozy fireplace and an abundance of natural light streaming through

  Lauren Freedman Coldwell Banker Realty

  567 Nut Plains Rd, Guilford, CT 06437
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  /35

  $369,900

  • 2 Beds
  • 2 Baths
  • 1,459 Sq Ft

  16 Copper Hill Dr, Guilford, CT 06437

  Move right in to your own free-standing Cape Cod style condo without even picking up a paint brush. This home has been completely remodeled from top to bottom with high-end flooring, bathroom fixtures, appliances, kitchen cabinets and countertops, bathrooms, exterior and interior doors and more. It is located on a cul-de-sac of three homes in Copper Hill Village and is only a short distance from

  Doris Fallon William Raveis Real Estate

  16 Copper Hill Dr, Guilford, CT 06437
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  /40

  $640,000

  • 4 Beds
  • 2.5 Baths
  • 2,081 Sq Ft

  231 Whitethorn Dr, Guilford, CT 06437

  Multiple offers have been received- Highest & Best due by Wednesday 5/7 5:00. This sun-filled 4 bedroom home offers charming details throughout & a magical backyard bordering the Guilford Land Trust & Timberland trails. The sunfilled living room, currently being used as a home office, offers built-ins & a large picture window.Through the french doors is found the dining room w/ access to the

  Sue Knapp William Pitt Sotheby's Int'l

  231 Whitethorn Dr, Guilford, CT 06437
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  /39

  $599,999

  • 3 Beds
  • 2 Baths
  • 1,852 Sq Ft

  204 Sachem Head Rd, Guilford, CT 06437

  This rare and distinctive property showcases stunning post-and-beam construction throughout, full of charm and character. A newer front ramp and Trex deck with PVC railings lead from the sidewalk to the covered front entryway, offering easy and accessible entry. Upon entering, you're welcomed into a spacious living room that seamlessly flows into the dining area. A full bathroom is conveniently

  Lauren Freedman Coldwell Banker Realty

  204 Sachem Head Rd, Guilford, CT 06437
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  /40

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,027 Sq Ft

  197 Meadow Hills Dr, Guilford, CT 06437

  Lake Community Living at Meadow Hills! Welcome to 197 Meadow Hills, a beautifully maintained home tucked within a charming subdivision offering lake and beach access. Lovingly cared for, this home blends comfort, convenience, and stylish updates throughout. Open Concept Living: The main floor features 3 bedrooms, a full bathroom, and a spacious kitchen/dining/living room - perfect for gatherings

  Melissa DiPiazza RE/MAX One

  197 Meadow Hills Dr, Guilford, CT 06437
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  /34

  $520,000

  • 4 Beds
  • 2.5 Baths
  • 2,370 Sq Ft

  538 County Rd, Guilford, CT 06437

  Charming North Guilford property. Set back from the road, this 2.91 acre parcel offers quiet and privacy. Own a piece of Guilford's history. Originally the Baldwin Dudley Mill - first a grist mill, then a saw mill - it transitioned to a residence in the late 1950s. Some of the mill hardware is still integrated into the decor. Casual and comfortable, this home has a welcoming feel. The cozy,

  Laurie Trulock Compass Connecticut, LLC

  538 County Rd, Guilford, CT 06437
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  /38

  $459,000

  • 2 Beds
  • 1 Bath
  • 960 Sq Ft

  46 Sperry Dr, Guilford, CT 06437

  Beautifully Renovated 3-Bedroom Home in Guilford, CT - Move-In Ready! Welcome to this stunning, fully renovated single-family home located in the desirable shoreline town of Guilford. Boasting 2 spacious bedrooms, 1 full bathroom, and an additional room that can be used as your home office. This charming property has been completely updated in 2025 with modern finishes and high-quality

  Christopher Wihbey Dave Jones Realty, LLC

  46 Sperry Dr, Guilford, CT 06437
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  /36

  $685,000

  • 3 Beds
  • 2 Baths
  • 3,616 Sq Ft

  170 Barker Hill Dr, Guilford, CT 06437

  This light-filled contemporary home at the end of a cul-de-sac provides the serenity of natural surroundings, yet is close to everything Guilford is well known for: its historic green, specialty shops and Long Island Sound. Floor to ceiling windows and vaulted ceilings bring in lots of light. Cozy up to the wood stove to ward off the chill, or in warm weather, lounge on the paver patio. The

  Tracy Everson Century 21 AllPoints Realty

  170 Barker Hill Dr, Guilford, CT 06437
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  /21

  $675,000

  • 3 Beds
  • 2.5 Baths
  • 1,125 Sq Ft

  24 Echo Point Rd, Guilford, CT 06437

  This waterfront home offers beautiful lake views, stunning stone work and terraces throughout the property. It has 3 bedrooms and two and half baths with a 2 car garage. There is a fire pit with built in stone seating overlooking the water with a private dock. The large deck off the garage is another spectacular area with sweeping views of the water. The living room offers a wall of windows with

  Susan Fair Fair Realty

  24 Echo Point Rd, Guilford, CT 06437
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  /40

  $550,000

  • 3 Beds
  • 2 Baths
  • 1,624 Sq Ft

  259 Weatherly Trail, Guilford, CT 06437

  Set on a peaceful and private 1.36-acre lot, this Contemporary Colonial home offers comfort, style, and a connection to nature. As you enter, you'll notice the home's open layout and soaring vaulted ceilings that create a bright and airy feel. The spacious living room includes beautiful hardwood floors, a pellet stove for cozy winter nights, and sliding doors that lead to a wraparound deck -

  Daniel Lussier eXp Realty

  259 Weatherly Trail, Guilford, CT 06437
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  /29

  $370,000

  • 3 Beds
  • 1 Bath
  • 1,365 Sq Ft

  37 Dinwoodie Dr, North Branford, CT 06471

  Beautifully maintained Ranch that was extremely well cared for by its owners. Gleaming hardwood floors throughout, living room with fireplace, central air, wood burning stove in basement that heats entire house as an option. Sits quietly tucked off Rt 80 on a lightly wooded level lot that is part of the Clear Lake Improvement Association, rear yard property is a part of Clear Lake Manor. Annual

  Gena Ruocco-Lockery GRL & Realtors, LLC

  37 Dinwoodie Dr, North Branford, CT 06471
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  /40

  $529,000

  • 2 Beds
  • 2 Baths
  • 1,879 Sq Ft

  20 Copper Hill Dr Unit 20, Guilford, CT 06437

  Welcome to 20 Copper Hill Drive, a rare find in one of Guilford's most desirable communities. This 2-bedroom, 2-bath Cape Cod-style condominium offers 1,459 sq ft of thoughtfully designed living space and the feel of a single-family home with all the benefits of low-maintenance condo living. Nestled on a corner lot, this home features a two-car attached garage, full basement, and 10 total rooms,

  Devon Taylor Assael Dave Jones Realty, LLC

  20 Copper Hill Dr Unit 20, Guilford, CT 06437
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  /40

  $2,294,000

  • 4 Beds
  • 4.5 Baths
  • 4,000 Sq Ft

  412 Tanner Marsh Rd, Guilford, CT 06437

  NEW CONSTRUCTION: Discover the perfect blend of elegance and comfort in this newly constructed home, located on scenic Tanner Marsh Rd. This property boasts four luxurious bedrooms and 4.1 bathrooms, including a primary bedroom on both the first and second floors, ensuring ample privacy and convenience for all residents. Quality craftsmanship is evident in every corner, from the high-end finishes

  Diane Dupont William Pitt Sotheby's Int'l

  412 Tanner Marsh Rd, Guilford, CT 06437
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  /24

  $649,000

  • 2 Beds
  • 2 Baths
  • 2,645 Sq Ft

  0 Long Hill Farm Unit 20, Guilford, CT 06437

  It's almost pool time! and this expansive condo has its own private heated pool all it itself! Why bother fighting traffic, crowds and hassles when all you have to do is walk out the sliders. Nestled in the serene countryside of Guilford, Connecticut, 20 Long Hill Farm Road offers a tranquil retreat with a perfect blend of luxury and privacy. This stunning property boasts a beautifully designed

  Lori Vogel William Raveis Real Estate

  0 Long Hill Farm Unit 20, Guilford, CT 06437
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  /40

  $1,650,000

  • 4 Beds
  • 5.5 Baths
  • 5,630 Sq Ft

  604 W Lake Ave, Guilford, CT 06437

  This estate is a rare sanctuary of privacy and refinement, nestled at the end of a private drive and surrounded by protected land for lasting seclusion. Just minutes from the Historic Green, where boutique-lined streets and exceptional dining await, this home blends tranquility with coastal charm. A gracious brick-floored foyer welcomes guests into an interior designed for both elegance and

  Linda Toscano Coldwell Banker Realty

  604 W Lake Ave, Guilford, CT 06437
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  /28

  $649,900

  • 2 Beds
  • 1.5 Baths
  • 1,197 Sq Ft

  55 Seaside Ave, Guilford, CT 06437

  IMAGINE .90 acres of magnificent water views and walks to Jacobs Beach! It could all be yours in this sought after area of the Guilford shoreline. This special offering boasts an updated kitchen with granite counters, SS appliances and a center island for entertaining. LR features a large picture window which allows for a daily dose of unbeatable sunrises. Main bathroom has jetted tub with a

  Judie Ferraro Calcagni Real Estate

  55 Seaside Ave, Guilford, CT 06437
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  /6

  $525,000

  • 0.5 Baths
  • 846 Sq Ft

  35 Water St, Guilford, CT 06437

  35 Water Street, presently an office building ready to be converted into residential. Located directly in the heart of downtown Guilford, right across from the town post office and just steps away from the Guilford Green, Town Plaza and historical district. This prime location offers close distance to Jacobs Beach, train station and nearby highways, along with many local parks and historic

  Derek Greene Derek Greene

  35 Water St, Guilford, CT 06437
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  /37

  $499,000 Open Sat 1PM - 3PM

  • 1 Bed
  • 1.5 Baths
  • 1,712 Sq Ft

  80 Seaview Terrace Unit 12, Guilford, CT 06437

  Embrace the essence of coastal elegance in this two-story townhouse nestled within the Seaview Terrace Community. As you step through the front door, you are greeted by a grand foyer with soaring ceilings and a convenient coat closet, setting the stage for a home that blends spaciousness with warmth. Ascend the staircase to discover the heart of the home, where an open floor plan invites seamless

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

  80 Seaview Terrace Unit 12, Guilford, CT 06437
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  /40

  $5,700,000

  • 3 Beds
  • 3.5 Baths
  • 4,236 Sq Ft

  66 High St Unit 56-57, Guilford, CT 06437

  TOP OF THE WORLD. A beautiful 4000+ sf space interior designed by award winning David Scott Parker Architects, FAIA. David has designed high end residences and cultural institutions in Southampton, Rancho Sante Fe, Florida, Massachusetts & CA. The finishing touches have just been completed on what is arguably the most luxurious penthouse in the state of Connecticut. The apartment's views of the

  Margaret Muir William Pitt Sotheby's Int'l

  66 High St Unit 56-57, Guilford, CT 06437
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  /5

  $100

  • Land
  • 1.90 Acres
  • $53 per Acre

  505 Old Whitfield St, Guilford, CT 06437

  The property is being presented unpriced. Discover this unique waterfront development site in Guilford, Connecticut. Offering stunning views of Long Island Sound and the surrounding natural beauty. Situated along the shoreline, this development site presents potential for mixed-use spaces such as luxury residential, and commercial. This waterfront property presents an ideal setting for a

  Stephen Press, SIOR Press/Cuozzo Realtors

  505 Old Whitfield St, Guilford, CT 06437
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  /40

  $985,000

  • 2 Beds
  • 2 Baths
  • 3,140 Sq Ft

  575 Leetes Island Rd, Guilford, CT 06437

  This home, The Pelatiah Leete House, is an impeccably restored jewel of American History for those appreciative admirers of what little remains from this era. Every inch of this large (3140 sqft) 1710 Saltbox has been respectfully preserved with clever and practical adaptations through the centuries. This is a home for those with a touch of romanticism in their heart, who feel moved by being

  Lisa Jones Higgins Group Bedford Square

  575 Leetes Island Rd, Guilford, CT 06437

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