Homes for Sale near The Country School

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  $22,000

  • 680 Sq Ft

  379 Whitfield St Unit BN2534, Guilford, CT 06437

  Guilford Yacht Club has been recently dredged to allow easy access to Long Island Sound. This Private club has a vibrant community of boaters waiting for you to join in on the fun. Just a few minutes and you are on the water making the best of your times with family and friends. Take advantage of the club pool and amenities. Pump out and fuel are nearby or on premises. Water, electricity and

  Rod Cross Coldwell Banker Realty

  379 Whitfield St Unit BN2534, Guilford, CT 06437
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  /40

  $600,000 Coming Soon

  • 3 Beds
  • 2 Baths
  • 1,453 Sq Ft

  41 Preble Dr, Guilford, CT 06437

  ONE FLOOR LIVING ranch style home in the desirable Rolf Gardens neighborhood, just a short stroll to the Guilford Green. This 3-bedroom, 2 full bath residence offers the ease of one level living paired with an exceptional in town lifestyle. Step inside to find a thoughtfully designed layout featuring a dining room with gas fireplace that flows seamlessly into a step-down living room. The

  Rose Ciardiello William Raveis Real Estate

  41 Preble Dr, Guilford, CT 06437
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  /40

  $699,900

  • 4 Beds
  • 2.5 Baths
  • 1,954 Sq Ft

  217 Stonehedge Ln, Guilford, CT 06437

  WELCOME to 217 Stonehedge Lane, a beautifully updated retreat set on nearly an acre where comfort, style, & year-round enjoyment come together effortlessly. Sunlight pours across the hardwood floors that flow throughout, creating a warm, seamless feel from the moment you step inside. The main living area offers a built-in entertainment system with an electric fireplace that brings both ambiance &

  Jenn Fusarelli RE/MAX Right Choice

  217 Stonehedge Ln, Guilford, CT 06437
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  $2,175,000 Coming Soon

  • 4 Beds
  • 3.5 Baths
  • 3,754 Sq Ft

  200 Whitfield St, Guilford, CT 06437

  Possibly the most admired of the historic homes closeby to the storied Guilford Town Green and Jacobs Beach, the Captain Joel Stone House, c.1853 is now seeking a new owner. This remarkable grand Italian Villa offers quite a pedigree having been built by a wealthy steamship owner, Joel Stone, son of the second lighthouse keeper of beloved Faulkner's Island. The quality of this gracious home with

  Margaret Muir William Pitt Sotheby's Int'l

  200 Whitfield St, Guilford, CT 06437
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  /38

  $2,875,000

  • 5 Beds
  • 5.5 Baths
  • 7,139 Sq Ft

  37 Lantern Hill Rd, Madison, CT 06443

  An unbeatable location, 37 Lantern Hill is set in one of Madison's most desirable in-town neighborhoods. Close to sandy beaches, charming town center and the Madison Country Club, recreation and everyday conveniences are right at your doorstep. Traditional by design with ten foot ceilings, abundant natural light and generously scaled rooms that create an airy feel, ideal for relaxing or

  Margaret Muir William Pitt Sotheby's Int'l

  37 Lantern Hill Rd, Madison, CT 06443
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  /30

  $23,500

  • 680 Sq Ft

  379 Whitfield St Unit BN1034, Guilford, CT 06437

  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

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

  379 Whitfield St Unit BN1034, Guilford, CT 06437
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  /40

  $1,995,000

  • 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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  /40

  $675,000

  • 3 Beds
  • 2 Baths
  • 1,476 Sq Ft

  441 Water St, Guilford, CT 06437

  Just one mile from the historic Guilford Green, this like-new Contemporary Farmhouse offers a rare blend of modern comfort, coastal charm, and beautiful natural views. Set on one acre with views of the marsh and West River, the home is designed to feel both private and connected to one of Guilford's most desirable village settings. The open floor plan is ideal for everyday living and

  Willard Finkle Coldwell Banker Realty

  441 Water St, Guilford, CT 06437
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  /2

  $1,675,000 Coming Soon

  • 4 Beds
  • 2.5 Baths
  • 4,022 Sq Ft

  420 Summer Hill Rd, Madison, CT 06443

  Privately positioned on nearly two acres in one of Madison's most desirable areas, this expansive Colonial offers a rare combination of privacy, scale, and convenience. Surrounded by natural beauty, the property feels secluded while remaining just minutes from the shoreline and Madison's charming town center, known for its dining, boutique shops, and coastal New England character. A true

  Adriana Radu Coldwell Banker Realty

  420 Summer Hill Rd, Madison, CT 06443
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  /40

  $2,995,000

  • 3 Beds
  • 3 Baths
  • 2,983 Sq Ft

  66 High St Unit 38, Guilford, CT 06437

  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

  Rose Ciardiello William Raveis Real Estate

  66 High St Unit 38, Guilford, CT 06437
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  /40

  $550,000

  • 4 Beds
  • 2 Baths
  • 2,280 Sq Ft

  174 Whitfield St, Guilford, CT 06437

  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

  Sally Tucker Coldwell Banker Realty

  174 Whitfield St, Guilford, CT 06437
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  /40

  $625,000 Open Sat 11AM - 2PM

  • 3 Beds
  • 2.5 Baths
  • 1,848 Sq Ft

  15 Cornfield Ln, Madison, CT 06443

  Welcome to 15 Cornfield Lane, a charming Colonial style home nestled on a quiet cul-de-sac, offering both privacy and convenience on over 1.5 acres of land. This well-maintained home features a spacious and functional floor plan, perfect for everyday living and entertaining. The main level includes a bright kitchen, formal dining room, and two inviting living spaces, along with a convenient half

  Miranda Micarelli Coldwell Banker Realty

  15 Cornfield Ln, Madison, CT 06443
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  /25

  $769,900

  • 3 Beds
  • 5 Baths
  • 3,107 Sq Ft

  2455 Boston Post Rd Unit 9, Guilford, CT 06437

  Welcome to The Landing at Guilford, a luxury townhome community offering modern design, quality construction, and low-maintenance living in one of the shoreline's most desirable locations. This well-appointed 2-bedroom residence with flexible space for a potential third bedroom features an open-concept layout with a beautifully designed kitchen complete with Viking stainless steel appliances,

  Katelin Rosello Social & Co Realty

  2455 Boston Post Rd Unit 9, Guilford, CT 06437
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  /37

  $925,000

  • 4 Beds
  • 2.5 Baths
  • 2,976 Sq Ft

  85 Fawn Brook Cir, Madison, CT 06443

  A Shoreline Masterpiece: Custom Cape Cod Living on 1.10 Private Acres Welcome to 85 Fawn Brook Circle, an immaculate Cape Cod retreat nestled at the end of a quiet, picturesque cul-de-sac. This 4-bedroom, with a first floor primary suite; 2.5-bathroom home has been thoughtfully reimagined with a level of detail rarely seen. Rich hardwood floors flow through every room, complemented by crisp

  Colette Harron William Pitt Sotheby's Int'l

  85 Fawn Brook Cir, Madison, CT 06443
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  /40

  $3,995,000 New Construction

  • 6 Beds
  • 6 Baths
  • 6,216 Sq Ft

  405 Whitfield St Unit 2, Guilford, CT 06437

  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,

  Rose Ciardiello William Raveis Real Estate

  405 Whitfield St Unit 2, Guilford, CT 06437
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  /40

  $980,000

  • 3 Beds
  • 2.5 Baths
  • 2,896 Sq Ft

  95 Chestnut Hill Rd, Killingworth, CT 06419

  Located on one of the most charming streets in Killingworth sits a one-of-a-kind antique post & beam modernized & converted barn; c. 1725. Situated on 8.7 acres with direct access to the Hammonasset River, this home is a peaceful retreat steeped in history-previously serving as the summer guest cottage for the Johnson & Johnson family. A welcoming foyer w/ cathedral ceiling leads to a majestic

  Sue Knapp William Pitt Sotheby's Int'l

  95 Chestnut Hill Rd, Killingworth, CT 06419
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  /34

  $725,000 Open Thu 4:30PM - 6:30PM

  • 3 Beds
  • 2 Baths
  • 2,248 Sq Ft

  602 Durham Rd, Madison, CT 06443

  602 Durham Road delivers the lifestyle living by the shoreline is known for, starting the moment you pull into the circular driveway. The covered front porch sets the tone, but the backyard is the headline: a resort-caliber outdoor environment anchored by an in-ground pool, hot tub, covered patio with TV, outdoor kitchen with built-in grill, oversized high-top bar, pizza oven, basketball court,

  Heidi DeRusso Coldwell Banker Realty

  602 Durham Rd, Madison, CT 06443
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  /33

  $1,975,000

  • 4 Beds
  • 2 Baths
  • 3,882 Sq Ft

  441 Opening Hill Rd, Madison, CT 06443

  Updated 4 bedroom 2 Full bath Cape on 15+ Acres of rolling Meadows and woods bordering State Forest and over 800 feet of frontage on Opening Hill. Extensive updating includes new windows and doors, original wide-board refinishing in the original building. A new kitchen in the cathedral ceilinged family room addition with deck that commands beautiful views of two spring fed, stocked ponds below

  Steve Adkins Berkshire Hathaway NE Prop.

  441 Opening Hill Rd, Madison, CT 06443
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  /21

  $2,700,000

  • 4 Beds
  • 3.5 Baths
  • 2,786 Sq Ft

  121 Middle Beach Rd, Madison, CT 06443

  Set along the coveted shoreline of Madison, this pristine coastal retreat seamlessly blends timeless antique charm, the finest modern conveniences and extensive Long Island Sound views. Thoughtfully updated while preserving its character, the home offers an inviting and sophisticated atmosphere throughout. A stunning family room serves as the heart of the home. It features dramatic

  Meig Walz Newcomb Coldwell Banker Realty

  121 Middle Beach Rd, Madison, CT 06443
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  /31

  $850,000

  • Land
  • 3.67 Acres
  • $231,608 per Acre

  4 Boston Post Rd, Madison, CT 06443

  Rarely does a Legacy Property, with a "Shovel-Ready" vision, arrive with the hardest yards of coastal development already complete. East River Landing is a fully de-risked, 3.67-acre asset at the Madison/Guilford gateway, combining an extensive marina income opportunity with unprecedented residential scalability. Approved Maritime Asset. Forget proposed plans-this is a fully built, 46-slip marina

  Michael Barnes Silver and Oak Realty

  4 Boston Post Rd, Madison, CT 06443
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  /40

  $539,000

  • 4 Beds
  • 1.5 Baths
  • 1,988 Sq Ft

  599 Durham Rd, Guilford, CT 06437

  Charming cape offering a flexible floor plan in a highly desirable location just moments from the historic Guilford Green. This inviting property blends classic New England character with everyday versatility, featuring natural sun filled living spaces that can easily adapt to your lifestyle. Enjoy a warm and welcoming atmosphere, complemented by timeless details and comfortable flow throughout.

  Jane Cardarelli William Raveis Real Estate

  599 Durham Rd, Guilford, CT 06437
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  /40

  $2,800,000 Coming Soon

  • 4 Beds
  • 6 Baths
  • 4,854 Sq Ft

  85 Garnet Park Rd, Madison, CT 06443

  A home that captures you-and doesn't let go. Nestled along the quiet edge of the Neck River, this is one of those rare offerings where design, setting and detail immediately leave an impression. From the moment you arrive, the front porch sets the tone for what unfolds beyond it. Inside, every space feels considered. A true designer's home where nothing is overlooked and nothing is left to

  Nicole White William Raveis Real Estate

  85 Garnet Park Rd, Madison, CT 06443
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  /22

  $1,150,000

  • 2 Beds
  • 2.5 Baths
  • 2,208 Sq Ft

  15 Cambridge Dr, Madison, CT 06443

  Welcome to this beautifully maintained two-bedroom condominium offering 2,208 square feet of thoughtfully designed living space in pristine condition. Above the flood plains, this home features an inviting open floor plan, this home seamlessly blends comfort and style-perfect for both everyday living and entertaining. At the heart of the home is a stunning chef's kitchen, complete with high-end

  Meig Walz Newcomb Coldwell Banker Realty

  15 Cambridge Dr, Madison, CT 06443
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  /22

  $749,000

  • Land
  • 8,276 Sq Ft
  • $3,942,105 per Acre

  885 Boston Post Rd, Madison, CT 06443

  Fully approved and ready to go, this exceptional commercial lot is situated in the heart of vibrant downtown Madison. Boasting approvals for a 5,000 square foot building the property includes a brand-new septic system, 13 designated parking spaces with additional parking options, and unbeatable proximity to restaurants, shopping, the train station, and I-95. Imagine welcoming clients or customers

  Michael Hvizdo Coldwell Banker Realty

  885 Boston Post Rd, Madison, CT 06443
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  /15

  $300,000

  • Land
  • 2.68 Acres
  • $111,940 per Acre

  2680 Long Hill Rd, Guilford, CT 06437

  Set in the desirable North Guilford area, this expansive parcel offers a rare opportunity to create a private retreat surrounded by natural beauty. With a thoughtfully configured layout and generous frontage along Long Hill Road, the property provides both usability and a sense of seclusion. The land features a blend of open and wooded areas, allowing flexibility for a custom home, outdoor living

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

  2680 Long Hill Rd, Guilford, CT 06437
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  /40

  $1,699,900

  • 3 Beds
  • 2.5 Baths
  • 2,661 Sq Ft

  7 Linden Ln, Madison, CT 06443

  Beautiful waterfront post-and-beam home offering breathtaking views of the tidal marsh, osprey nest, and beyond. Set on a peaceful corner lot along a quiet one-way lane, this property borders conservation land and is just a short walk to East Wharf Beach. The open-concept living and dining areas are filled with natural light and designed to capture the scenery, with large windows and direct

  Heather Smith Our Home Realty Advisors

  7 Linden Ln, Madison, CT 06443
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  /9

  $1,235,000

  • Land
  • 1.02 Acres
  • $1,210,784 per Acre

  8 Old Route 79, Madison, CT 06443

  Great commercial lot - signalize corner, level and cleared. A rare opportunity for Developers and Investors. Located at the strategic Junction of Old route 79 and Durham Road . One minute to I-95. The property boasts exceptional visibility an accessibility from both north and southbound traffic. Short distance to downtown MADISON, this site is ideal for a variety of commercial ventures, including

  Thomas Simjian Keller Williams Coastal

  8 Old Route 79, Madison, CT 06443
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  /38

  $699,000

  • 4 Beds
  • 2 Baths
  • 2,240 Sq Ft

  507 Little Meadow Rd, Guilford, CT 06437

  Serene Living at 507 Little Meadow Road Discover the perfect blend of coastal charm and modern comfort in this beautifully inviting 4-bedroom, 2-bathroom expanded Raised Ranch. Nestled on over an acre of level, lightly wooded land, this home offers a private sanctuary on one of Guilford's most scenic roads. The heart of the residence is a stunning vaulted-ceiling sunroom, complete with skylights,

  Jaider Osorno Alpha Capital Realty, LLC

  507 Little Meadow Rd, Guilford, CT 06437
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  /40

  $2,195,000

  • 5 Beds
  • 3 Baths
  • 3,172 Sq Ft

  15 Highland Terrace, Madison, CT 06443

  COME SEE THIS ONE OF KIND FULLY RENOVATED MADISON HOME WITH PRIVATE BEACH RIGHTS!!! Just 300 feet from the sand, this home was once a traditional raised ranch and now has been brilliantly redesigned into a spacious 'elevated ranch' with an open-concept floor plan that feels airy, bright, and made for entertaining! Step into coastal luxury with this fully reimagined Madison home, where every

  John Cronin Century 21 AllPoints Realty

  15 Highland Terrace, Madison, CT 06443
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  /38

  $4,000,000

  • 5 Beds
  • 6 Baths
  • 5,657 Sq Ft

  45 Island Ave, Madison, CT 06443

  Exceptionally located less than a tenth of a mile from both the town green and beaches - with your own private beach access - this stunning residence sits on 1.57 secluded acres and has been completely re-imagined with uncompromising attention to detail and the finest materials. The home offers 16 thoughtfully designed rooms. Sun filled interiors feature over sized windows and expansive sight

  Meig Walz Newcomb Coldwell Banker Realty

  45 Island Ave, Madison, CT 06443
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  /20

  $696,000

  • 4 Beds
  • 1.5 Baths
  • 2,060 Sq Ft

  60 Three Mile Course, Guilford, CT 06437

  Live, Love, Laugh and Play a short walk to Guilford Center, Library, Public Transportation, Dining and Shopping! The expanded Cape offers a newer Great Room addition offering the perfect space to entertain in style with doors to yard and future patio. The adjacent kitchen was updated 6yrs ago when addition was added and boast granite counters, SS appliances and adjacent original dining room for

  Diane Beckwith Popolizio William Raveis Real Estate

  60 Three Mile Course, Guilford, CT 06437
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  /39

  $545,000

  • 2 Beds
  • 2.5 Baths
  • 1,728 Sq Ft

  23 Hampshire Rd Unit 23, Madison, CT 06443

  Welcome to Kensington North, a highly desirable condo community in the heart of Madison. This well-located unit offers a wonderful opportunity to create your ideal home in a sought-after setting. The main level features a spacious living and dining area, perfect for everyday living and entertaining. The eat-in kitchen offers great potential with sliders to the sunroom and patio as well as being

  Laurie Mazzeo William Pitt Sotheby's Int'l

  23 Hampshire Rd Unit 23, Madison, CT 06443
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  /5

  $20,000

  • 720 Sq Ft

  379 Whitfield St Unit CS936, Guilford, CT 06437

  Enjoy convenient and carefree boating from this recently dredged boat slip. Direct and easy access to Long Island Sound to enjoy your time on the water. Ownership includes Guilford Yacht Club membership with a fun and vibrant community of boaters. Take advantage of the club pool and the seasonal activities. Pump-out services on premises and fuel is nearby. Winter Boat storage available.

  Rod Cross Coldwell Banker Realty

  379 Whitfield St Unit CS936, Guilford, CT 06437
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  /33

  $649,900

  • 4 Beds
  • 3 Baths
  • 3,300 Sq Ft

  73 Airline Rd, Clinton, CT 06413

  Privacy and versatility meet shoreline convenience! Set on 3.17 serene acres, 73 Airline Road is perfectly located just minutes from the vibrant town centers of Clinton and Madison, and a short drive to the iconic beaches of Hammonasset State Park. The upper level features a bright, open-concept floor plan with vaulted ceilings and hardwood floors. The chef's kitchen is a standout, boasting GE

  Matt Diamond Houlihan Lawrence WD

  73 Airline Rd, Clinton, CT 06413
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  /13

  $599,999

  • 3 Beds
  • 2 Baths
  • 1,143 Sq Ft

  179 Route 81, Killingworth, CT 06419

  DO NOT ENTER PRIVATE DRIVE - AGENT MUST accompany You - Private drive brings you to 2.9 beautiful acres. House is being sold AS IS, but the value is in the land. The property includes a raised ranch house, a two car garage and another out building, a wonderful pond with bridge. Location very convenient to Route 81.

  John Izzo William Raveis Real Estate

  179 Route 81, Killingworth, CT 06419
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  /40

  $1,700,000 New Construction

  • 4 Beds
  • 3.5 Baths
  • 3,284 Sq Ft

  539A Boston St, Guilford, CT 06437

  Brand NEW CONSTRUCTION. Move in Ready! This modern, luxurious 3284sf, 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

  Anne Marie Straka Compass Connecticut, LLC

  539A Boston St, Guilford, CT 06437
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  /40

  $1,500,000

  • 5 Beds
  • 5 Baths
  • 5,310 Sq Ft

  7 Caleb Ct, Guilford, CT 06437

  Absolutely stunning 5+ bedroom light-filled home offers the perfect blend of elegance & modern updates. A dramatic 2-story foyer with a striking contemporary fixture sets the tone. The living room with glass French doors offers flexibility as a first-floor office. The oversized family room features a soaring ceiling, custom built-ins & stone fireplace, flowing seamlessly into the remodeled

  Susan Santoro William Pitt Sotheby's Int'l

  7 Caleb Ct, Guilford, CT 06437
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  /28

  $365,000

  • 4 Beds
  • 2 Baths
  • 1,236 Sq Ft

  409 Boston St, Guilford, CT 06437

  Rare opportunity in desirable Guilford. This 9 room, 3-bedroom, 2-bath Raised Ranch sits on .46 acres with marshland and wooded views behind the home, creating a peaceful backdrop with abundant birdlife. Hardwood floors, dining room, large rear three season porch and a light-filled layout provide a solid starting point. The unfinished lower level offers expansion potential. Detached

  Steven Rivkin Planet Realty, LLC

  409 Boston St, Guilford, CT 06437

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