Guilford Real Estate

Recently Sold Listings in Guilford, CT

Welcome to your dedicated resource for viewing Sold listings in Guilford, CT. As local Guilford, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights home values, selling strategies, and options like cash offers. Start exploring the most recent sold properties in Guilford, CT below, or if you are looking to sell a home in Guilford, CT contact a local agent to discuss the possibilities.

< Back to all Homes for Sale in Guilford, CT

Be the First to Know About New Guilford Homes

Stay ahead with real-time updates — no searching required.

See Homes Before Everyone Else

Guilford Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Recently Sold in Guilford, CT

$4,300,000
4 Beds ⋅ 5 Baths ⋅ 24093717 MLS
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, providing panoramic views, tranquil ambiance, and total privacy. Designed with meticulous attention to detail, the property features a harmonious blend of classic New England charm and modern sophistication. The exterior showcases elegant stonework, expansive windows, and beautifully landscaped grounds. The interior is a masterpiece of design, offering spacious and light-filled rooms. The generous foyer welcomes you to the main living spaces with soaring ceilings, and clear story windows. The open-concept first floor includes a gourmet kitchen equipped with a large island, a formal dining room, and a generous breakfast area. These areas open directly onto an expansive patio overlooking Long Island Sound and The Thimble Islands. The first floor also includes a cozy library with fireplace and private office space. The home has multiple luxurious bedrooms, each with its own en suite bathroom, including a suite on the main floor. The master suite is a private retreat, featuring a spa-like bathroom, two walk-in closets and magnificent views of the water.

250 Joshua Point Rd, Guilford
$4,200,000
4 Beds ⋅ 5 Baths ⋅ 24013187 MLS
A well-known photographer recently said, "I've been photographing properties on the waterfront for over twenty years and I have never seen a more beautifully sited house". Nestled in Sachem's Head, high on a private peninsula enjoying commanding views of Long Island Sound, the Thimble Islands and its own sandy swimming cove and dock, 31 Loyal Ledge stands tall. With 700+ feet of linear footage on the Sound & almost 360-degree water views, the 100+ year old house has been a cherished retreat to only four families. Each owner has enhanced the property with the latest upgrades completed this year focusing on updating the third floor to have an inviting living room, bedroom & new full bath.The first level offers an abundance of spaces and rooms to enjoy gracious living - a living room with a gas log fireplace and a wall of bookcases, a sunroom with five picture windows to the water, a formal dining room, and a large kitchen with both island and table seating and a cozy family room. There are also two covered, stone porches- one perfect for viewing the sun rising and the other its setting. The second floor has a large primary ensuite bedroom with a sitting area, an office and two nice sized bedrooms which share a bath. Outdoors, in addition to manicured grounds and the mesmerizing views of the islands, there are two areas perfect for entertaining - one features a fire pit, the other with a tall flagpole as its centerpiece.Watch the attached video.

31 Loyal Ledge Ln, Guilford
$3,675,000
6 Beds ⋅ 6 Baths ⋅ 170570602 MLS
Sachems Head is one of New England’s renowned coastal gems — and this home is among its crown jewels. With 6 bedrooms/5.1 baths, this custom-built, 7,655 sq-ft home occupies 2.22 acres of waterfront on Joshua Cove. Each room showcases architectural and construction excellence, from Brazilian cherrywood flooring and built-in shelving to triple-pane windows and a turret’s curved mahogany wood staircase leading to a rooftop deck with amazing vistas. The main floor is smartly divided, with the dining room, living room, home office, mudroom, powder room, and one of two primary bedrooms on one wing. The other wing features the gourmet kitchen with custom cabinets, large cherry-topped island, 5-burner Wolf gas range, Wolf double wall ovens, 2 Sub-Zero refrigerators, 2 sinks, and wine cooler, plus a built-in banquette dining area. Adjacent are the craft room and family room, which leads to both a sunroom and a spectacular bluestone deck overlooking the private yard, gardens, and waterfront. The second floor includes another primary bedroom, with a semicircular wall of windows, and spacious bath. Two of the other 4 bedrooms have their own full baths; the other 2 share one bath. This level also includes a waterfront-facing great room, exercise room, and laundry room. Value-added amenities include propane hydro air HVAC, on demand hot water, ERV air exchanger, generator, heated 2-car garage with electric-car charger, barn, irrigation, and security system. NOT in a flood zone.

281 Old Sachems Head Rd, Guilford
Start Your Search

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.