Guilford, CT Homes for Sale

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  /37

  $2,875,000

  • 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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  /25

  $450,000

  • 1 Bed
  • 1 Bath
  • 720 Sq Ft

  36 State St, Guilford, CT 06437

  Don't miss this extraordinary opportunity to own a picture-perfect retreat just steps from the Guilford Green. Whether you're seeking a charming pied-a-terre, a weekend escape, or a sophisticated condo alternative, this well maintained residence checks every box. Thoughtful updates and modern upgrades blend with the simple character of this home. Enjoy peace of mind with a brand-new septic

  

  Janet Cronin-Rumanoff

  William Pitt Sotheby's Int'l

  (475) 445-1124

  36 State St, Guilford, CT 06437
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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

  $1,000,000

  • 6 Beds
  • 3.5 Baths
  • 3,197 Sq Ft

  11 Island Bay Cir, Guilford, CT 06437

  LOCATION, LOCATION, LOCATION! Nestled within a peaceful cul-de-sac just around the corner from the beach, this one-of-a-kind, custom-built Cape Cod-style home blends timeless charm with a contemporary flair. Located on desirable Island Bay Circle, enjoy the convenience of being minutes from the downtown village, restaurants, shopping, and the shoreline. This thoughtfully designed 6-bedroom,

  Rose Ciardiello William Raveis Real Estate

  11 Island Bay Cir, Guilford, CT 06437
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  /38

  $1,100,000

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

  604 W Lake Ave, Guilford, CT 06437

  This private estate is a rare sanctuary of refinement and serenity, nestled at the end of a long drive and abutting preserved conservation land with direct access to hiking and horseback riding trails right from your backyard. Just minutes from the Historic Green, where charming boutiques and top-tier dining await, the setting perfectly balances seclusion and convenience. A gracious brick-floored

  Linda Toscano Coldwell Banker Realty

  604 W Lake Ave, Guilford, CT 06437
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  /36

  $875,000

  • 4 Beds
  • 2.5 Baths
  • 3,020 Sq Ft

  20 Andy Ln, Guilford, CT 06437

  Welcome to 20 Andy Lane, Guilford- Nestled at the end of a tranquil cul-de-sac and bordering conservation land, this captivating 4-bedroom, 2.5-bath colonial offers gracious living space infused with timeless New England charm and functionality. Inside, gleaming hardwood floors run throughout the main level, highlighting the home's well-maintained condition. At the heart of the home, the light

  Abbey Scott William Raveis Real Estate

  20 Andy Ln, Guilford, CT 06437
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  /39

  $899,000

  • 3 Beds
  • 3.5 Baths
  • 4,177 Sq Ft

  102 Leetes Island Rd, Guilford, CT 06437

  Nestled at the end of a private enclave of just three homes, this beautiful Colonial-style residence blends timeless charm with modern comfort in the picturesque shoreline town of Guilford, Connecticut. A grand yet welcoming foyer sets the stage for the refined interiors of this thoughtfully designed home. The living room centers around a cozy fireplace, while the cathedral-ceilinged family room

  Kathleen Moniello Coldwell Banker Realty

  102 Leetes Island Rd, Guilford, CT 06437
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  /34

  $799,900

  • 3 Beds
  • 2 Baths
  • 1,222 Sq Ft

  52 Seaside Ave, Guilford, CT 06437

  Here is your chance to own a slice of heaven! Enjoy your morning coffee while you take in the picturesque Connecticut coastline and relax each evening in the comfort of your quiet and serene backyard with a level lot and water view. Perfectly situated within walking distance to Jacob's Town Beach, a park/playground, the historic Guilford town green, shops, and the town docks, this is a property

  Lindsay Walsh Coldwell Banker Realty

  52 Seaside Ave, Guilford, CT 06437
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  /36

  $1,875,000

  • 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 western exposure view showcases the 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, deck access, Dining

  Kirsten Adams William Pitt Sotheby's Int'l

  66 High St Unit 36, Guilford, CT 06437
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  /40

  $2,950,000

  • 3 Beds
  • 2.5 Baths
  • 3,024 Sq Ft

  66 High St Unit 17, Guilford, CT 06437

  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

  Barbara Goetsch William Pitt Sotheby's Int'l

  66 High St Unit 17, Guilford, CT 06437
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  /40

  $3,250,000

  • 3 Beds
  • 2.5 Baths
  • 2,571 Sq Ft

  66 High St Unit 40, Guilford, CT 06437

  Experience Elevated Living at The Residences at 66 High Street. Step into a lifestyle of sophistication and comfort-where luxury amenities meet cosmopolitan charm. This expansive third-floor residence in the Leete Building is one of the largest in the community and offers breathtaking, unobstructed views of the West River, Long Island Sound, and Faulkner's Island. Thoughtfully designed with 3

  Nicole White William Raveis Real Estate

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

  $1,295,000

  • 4 Beds
  • 3 Baths
  • 2,405 Sq Ft

  131 Elm St, Guilford, CT 06437

  Antique Country Farmhouse Meets Modern Amenities! A beautiful blend of heritage and modern comfort, 131 Elm Street is a thoughtfully restored Antique-style farmhouse that has been lovingly maintained and tastefully upgraded by its current owners. Nestled in the heart of North Guilford, this property is more than just a home-it's a serene retreat and an expression of creativity. Step inside and

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

  131 Elm St, Guilford, CT 06437
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  /40

  $899,000

  • 4 Beds
  • 3.5 Baths
  • 4,526 Sq Ft

  522 Peddlers Rd, Guilford, CT 06437

  Privately set on a corner lot of a cul-de-sac abutting West Woods, this expanded contemporary home offers a stylish blend of natural beauty, captivating design, and modern comfort. With 3,246 SF above grade plus a 1,280 SF finished lower level, the layout provides a balance of bold, open spaces and quiet, intimate rooms. Soaring ceilings in the foyer, family room, and primary suite create a a

  Linda Toscano Coldwell Banker Realty

  522 Peddlers Rd, Guilford, CT 06437
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  /36

  $829,000

  • 4 Beds
  • 2.5 Baths
  • 4,076 Sq Ft

  81 Red Barns Rd, Guilford, CT 06437

  Welcome to 81 Red Barns Rd, a charming, spacious and very well maintained home located in the beautiful town of Guilford. This property of 3276 sq ft with an additional finished basement of 800 sq ft boasts a perfect blend of modern amenities and classic New England charm. The home features 4 bedrooms, 3 bathrooms, and a generous living space that is perfect for both relaxing and entertaining.

  Susan Wagner Berkshire Hathaway NE Prop.

  81 Red Barns Rd, Guilford, CT 06437
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  /40

  $829,900

  • 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

  $875,000

  • 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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  /36

  $1,675,000

  • 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

  5 Luxury Townhouse Condominiums NESTELED PRIVATELY BEHIND 2614 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

  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

  5 Luxury Townhouse Condominiums, NESTLED PRIVATELY BEHIND 2614 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

  John Campbell Compass Connecticut, LLC

  2 Woods 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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  /21

  $209,900

  • 1 Bed
  • 1 Bath
  • 769 Sq Ft

  22 River Colony, Guilford, CT 06437

  Lovely townhouse in River Colony complex. Quiet and desirable wooded location. Open concept living room with wood-burning fireplace, dining area, and kitchen with granite counters, stainless steel appliances, and tons of counter and cabinet space. Step outside the sliders to the Trex deck and take in the beautiful views. Large remodeled bathroom. Shared laundry area. 2 parking spaces. Convenient

  Eric Schuell RE/MAX Right Choice

  22 River Colony, Guilford, CT 06437
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  /7

  $40,000

  • 776 Sq Ft

  379 Whitfield St, Guilford, CT 06437

  Waterfront - Guilford. Set Sail in Style and experience the charm of Guilford Yacht Club, a premier marina in one of Connecticut's most picturesque coastal towns. This 46-foot slip offers ample space and immediate access to Long Island Sound, ensuring effortless adventures on the water. Guilford is rich in history and natural beauty, making it an ideal destination for boaters. At the Guilford

  Linda Coyle William Raveis Real Estate

  379 Whitfield St, Guilford, CT 06437
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  /39

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,127 Sq Ft

  120 Highwoods Dr, Guilford, CT 06437

  Located in one of Guilford's quiet and desirable neighborhoods, this mid-century modern gem offers the ease of single-level living with a unique and thoughtfully designed floor plan. Large windows invite natural light throughout the home, highlighting the warm tones of durable composite wood flooring. Set on a private level lot with a low-maintenance yard, this property is perfect for those

  Tim Galvin William Raveis Real Estate

  120 Highwoods Dr, Guilford, CT 06437
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  /37

  $630,000

  • 4 Beds
  • 5 Baths
  • 4,415 Sq Ft

  206 Peddlers Rd, Guilford, CT 06437

  Bring your vision to this expansive 4-bedroom, 5-bath Cape-style home, offering generous square footage, flexible living space, and endless potential for updates. With a thoughtful layout and timeless character, this property can easily accommodate a variety of needs and lifestyles. The exterior features a distinctive blend of brick, stone, and wood, giving the home classic curb appeal. Inside,

  Douglas Ledewitz Pulse Realty LLC

  206 Peddlers Rd, Guilford, CT 06437
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  /40

  $1,495,000

  • 3 Beds
  • 4 Baths
  • 3,590 Sq Ft

  5 Rockland Rd, Guilford, CT 06437

  The most INCREDIBLE modern home you've ever laid eyes on.This architectural masterpiece on over 4 acres of absolute privacy. Designed with meticulous attention to detail, this contemporary retreat showcases live sawn random-width wood floors & custom doors throughout. The dramatic 25-foot wood ceiling in the great room soars above Anderson walls of glass, seamlessly blending indoor luxury with

  Susan Santoro William Pitt Sotheby's Int'l

  5 Rockland Rd, Guilford, CT 06437
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  /23

  $440,000

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

  80 Seaview Terrace Unit 12, Guilford, CT 06437

  Step into coastal sophistication with this three-story townhouse, gracefully positioned in the Seaview Terrace Community of Guilford. The grandeur of the home is immediately apparent upon entry, where a soaring foyer with a convenient coat closet welcomes you into a space where expansiveness meets comfort. The staircase leads to the main living area, where an open-concept design facilitates

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

  80 Seaview Terrace Unit 12, Guilford, CT 06437
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  /37

  $529,000

  • 3 Beds
  • 2.5 Baths
  • 1,936 Sq Ft

  550 W Lake Ave, Guilford, CT 06437

  Charming Country Retreat in Sought-After Guilford! Welcome to your private oasis! Nestled on a spacious, serene lot in highly desirable Guilford, this beautifully updated home offers the perfect blend of comfort, functionality, and charm. Step inside to discover gleaming hardwood floors throughout the main level, a sun-filled living room with a cozy fireplace, and a renovated kitchen featuring a

  Bobby Moran Coldwell Banker Realty

  550 W Lake Ave, Guilford, CT 06437
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  /10

  $189,000

  • 1 Bed
  • 1 Bath
  • 839 Sq Ft

  19 Polpis Ln, Guilford, CT 06437

  Desirable end unit in secluded section of complex. Main bedroom on 1st flr. Possible second bedroom on upper level (loft). Open space with fireplace. Minor cosmetic repairs needed

  Robert Bishop Bishop, Edward & Roberts, LLC

  19 Polpis Ln, Guilford, CT 06437
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  /19

  $719,000

  • 4 Beds
  • 2.5 Baths
  • 3,227 Sq Ft

  310 Weatherly Trail, Guilford, CT 06437

  This modern home on a spacious 1.5 acre lot in a peaceful cul-de-sac subdivision features three levels of living space with open floor plan, hardwood floors, cathedral ceilings and walls of glass for normal light. The remodeled kitchen has cherry cabinets granite countertops, custom built-ins, and top-of-the line S.S. appliances. Additional features include cozy living room with new gas

  Mim Beardsley Houlihan Lawrence WD

  310 Weatherly Trail, Guilford, CT 06437
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  /25

  $425,000

  • 2 Beds
  • 1 Bath
  • 1,008 Sq Ft

  72 Prospect Hill Rd, Guilford, CT 06437

  72 Prospect Hill Rd is in a lovely setting - conveniently located with a peaceful ambiance. The curb appeal is excellent and the house will grab your attention. Stone wall, level flat lot, nice size deck in the back. This location is fantastic, close to shopping, golf course and I-95. The 2 bedroom home offers one floor living with washer and dryer on main floor. The kitchen and bathroom have

  Tim Galvin William Raveis Real Estate

  72 Prospect Hill Rd, Guilford, CT 06437
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  /37

  $625,000

  • 3 Beds
  • 2 Baths
  • 2,190 Sq Ft

  200 Sachem Head Rd, Guilford, CT 06437

  Welcome to this beautifully maintained Colonial-style home, perfectly situated on a 1.04-acre lot! From the moment you arrive, you'll appreciate the pride of ownership & thoughtful updates throughout this spacious home. Step inside to find a large living room that seamlessly flows into the eat-in kitchen-ideal for everyday living & entertaining alike. The kitchen is a chef's dream, featuring

  Lauren Freedman Coldwell Banker Realty

  200 Sachem Head Rd, Guilford, CT 06437
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  /37

  $1,150,000

  • 3 Beds
  • 3.5 Baths
  • 2,965 Sq Ft

  140 Podunk Rd, Guilford, CT 06437

  Tucked away on over 8 private acres and surrounded by nearly 600 acres of protected preserve, 140 Podunk Road is a rare modern country retreat just minutes from the Guilford Green. Built in 2012 with exceptional craftsmanship, this custom Tidewater-style Cape offers just under 3,000 sq ft of thoughtfully designed living space, where timeless elegance meets nature's tranquility. The main level

  Heidi DeRusso Coldwell Banker Realty

  140 Podunk Rd, Guilford, CT 06437
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  /34

  $3,100,000

  • 6 Beds
  • 6 Baths
  • 3,948 Sq Ft

  48 Andrews Rd, Guilford, CT 06437

  Waterfront - GUILFORD - CONTEMPORARY - THE WHALE HOUSE-Architecturally Designed by Peter Woerner. First time available in 25 years. Set on 3.39 Acres. Designed to capture large ground to sky views, southerly over Little Harbor as well as Long Island Sound. With its walls of glass, high ceilings & numerous Transom windows this Unique Designed Home allows for natural views to flow easily through

  Joseph Piscitelli Coldwell Banker Realty

  48 Andrews Rd, Guilford, CT 06437
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  /23

  $525,000

  • 2 Beds
  • 2 Baths
  • 1,256 Sq Ft

  138 White Birch Dr, Guilford, CT 06437

  Well maintained ranch offers private beach access, golfing nearby and numerous hiking opportunities. The exterior has been recently painted and there are hard wood floors throughout. The primary bedroom has vaulted ceilings, ensuite bathroom, 2 large closets and a walkout to the patio. The kitchen has updated cabinets and opens to a large dining area. The seasonal sunroom has vaulted ceilings,

  Susan Fair Fair Realty

  138 White Birch Dr, Guilford, CT 06437
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  /12

  $475,000

  • 4 Beds
  • 1 Bath
  • 1,448 Sq Ft

  872 Nut Plains Rd, Guilford, CT 06437

  Charming opportunity in prime Guilford Location! Discover the potential of this unique property situated in a highly desirable residential neighborhood, just minutes from downtown Guilford, the Green, schools, golf course, beaches, and I-95. Surrounded by newly constructed homes, this picturesque lot features mature trees, flowering bushes, and even a small pond-offering a serene, nature-rich

  Tim Galvin William Raveis Real Estate

  872 Nut Plains Rd, Guilford, CT 06437
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  /40

  $1,950,000

  • 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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  /37

  $690,000

  • 3 Beds
  • 2 Baths
  • 2,040 Sq Ft

  102 Colonial Rd, Guilford, CT 06437

  A drive-by will not do this property justice! This Sachems Head home has plenty to offer - inside and out. The setting is a natural sanctuary. Perennial beds and mature plantings provide everchanging colors and blooms from early spring through fall. The open hillside behind is dotted with rock outcroppings, stone walls, and lush gardens. The Acorn Deck House has the cool vibe of a mid-century

  Laurie Trulock Compass Connecticut, LLC

  102 Colonial Rd, Guilford, CT 06437
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  /38

  $4,750,000

  • 4 Beds
  • 4.5 Baths
  • 4,325 Sq Ft

  250 Joshua Point Rd, Guilford, CT 06437

  Welcome to an unparalleled living experience at 250 Joshua Point Road, Guilford, CT. This magnificent Nantucket style home offers the perfect blend of luxury, comfort, and breathtaking views, making it an ideal sanctuary for those seeking the finest in coastal living. This prestigious 2 acre estate sits at the end of a peninsula and boasts direct access to the serene waters of Long Island Sound,

  Jane Von Holzhausen Coldwell Banker Realty

  250 Joshua Point Rd, 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

  $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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