Guilford Real Estate

Homes for Sale with a Pool in Guilford, CT

Welcome to your dedicated resource for homes for sale with a pool in Guilford, CT. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Guilford, CT agents, Dave Jones Realty specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

< 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 Homes for Sale with a Pool in Guilford, CT

215 Uncas Point Rd, Guilford
$35,000,000
6 Beds ⋅ 5 Baths ⋅ 24034137 MLS
Waterfront.. Sachems Head - Welcome to a Unique opportunity to purchase some of the finest waterfront properties to ever become available on the entire Connecticut Shoreline. Combined 3 properties span 13.03 rolling green Acres w/1900 feet of waterfront, 3 Docks, Boat Lift, Vineyard, Orchards, Beautiful Gardens, Fruit Trees, Tennis/Basketball Court, Go Kart Track, 2 Houses and a Carriage House. The Main House, a testament to exceptional craftsmanship, showcases approximately 5,534 square feet of living space, with six well-appointed bedrooms and 4.1 bathrooms. Designed with the finest materials, this home seamlessly blends timeless elegance and modern conveniences, providing a harmonious living environment. Outdoor area includes a Pool, Spa & Outdoor kitchen. Guest House with 3,583 sq feet, 3 bedrooms, 3 baths, Separate 942 sq ft. 1 bedroom in-law/ staff quarters. This property shares a Common border with the main residence. The separated property which can possibly be subdivided into 2 building sites, features a Carriage House, Dock & Sandy Beach. To say there are many possibilities here would be an enormous understatement! Private residence, Family compound or High-end development. Bring your Dream here; this opportunity will not let you down. All 3 properties must be sold together unless otherwise agreed to by the current owners. Please respect the privacy of current owners. BY APPOINTMENT ONLY. Taxes represent all 3 properties.

215 Uncas Point Rd, Guilford
345 Vineyard Point Rd, Guilford
$5,750,000
4 Beds ⋅ 8 Baths ⋅ 24212653 MLS
Privately nestled high on 4+ sweeping acres, in the prestigious, yet quietly refined, Sachem's Head enclave in Guilford, CT, this 2012 modern Mediterranean residence commands panoramic views of Long Island Sound. Grand yet classic interiors unfold in tasteful Palm Beach-inspired finishes, creating an atmosphere of understated elegance. Soaring ceilings, a floating stairway & multiple sets of formidable french doors welcome sea breezes to actively flow through the home, imparting the true "air" of coastal living. The primary suite sanctuary is situated on the main level, offering seamless single-floor living and an elegant elevator delivers effortless access to all levels in the home. The massive white kitchen overlooks Long Island Sound and has Calcutta countertops, a festive green pantry, Wolfe and SubZero appliances & cozy fireplace. Outside, an elevated pool/spa terrace has a relaxed resort-like vibe & connects the main home to the 1BR (5th BR)/2FBA w/kitchen guest house. The 4-stall barn, w/paddock, whispers of equestrian possibilities or creative studio use. The 5-bay heated-floor garage accommodates 7 cars. Solar energy systems lend a thoughtful green footprint, appealing to those who value sustainability. This is one of the larger parcels in Sachem's Head, come feel how this property seems transported from Malibu or Napa Valley, yet remains distinctly low-key New England. Masterfully constructed & impeccably maintained. Under 2hr drive from NYC & 20min to Yale.

345 Vineyard Point Rd, Guilford
66 High St Unit 38, Guilford
$2,995,000
3 Beds ⋅ 3 Baths ⋅ 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
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.

How much is your home worth?

Get instant property value now!