Fairfield Real Estate

Homes for Sale with a Pool in Fairfield, CT

Welcome to your dedicated resource for homes for sale with a pool in Fairfield, 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 Fairfield, 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 Fairfield, CT

Be the First to Know About New Fairfield Homes

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

See Homes Before Everyone Else

Fairfield Real Estate Map Search

Search by Lifestyle
  Advanced Search   Market Reports   Home Value   Connect

All Homes for Sale with a Pool in Fairfield, CT

$3,850,000
5 Beds ⋅ 5 Baths ⋅ 24181784 MLS
This is why so many people fall in love with Southport. Set on an extraordinary .83-acre parcel in the heart of the Village, this circa 1874 residence captures the charm, character, and lifestyle that have made Southport one of New England's most treasured coastal communities. Approached by a long drive and set well back from Harbor Road, the home enjoys a level of privacy rarely found in the Village. Hidden from the road, it offers a sense of seclusion that is increasingly difficult to find. Rich with period details and timeless architectural character, the 5 bedroom, 4 full and 1 half bath home sits at one of the highest points on Harbor Road, where cooling summer breezes are a welcome feature. The property also includes a classic antique barn, pool, pool house, attached one-car garage, and detached two-car garage, creating a setting ideal for both everyday living and entertaining. While the home presents an exceptional opportunity for renovation and enhancement, its greatest assets cannot be replicated: its setting, scale, history, and location. For the next steward, it offers the chance to reimagine a treasured Southport property while preserving its authenticity and charm. Enjoy a quintessential Southport lifestyle with easy access to the Village, train station, Pequot Yacht Club, and the soon-to-open Southport General Store and Rose Hill Kitchen. Last offered for sale in 1989, opportunities like this rarely come to market. A true Southport gem ready for its next chapter

406 Harbor Rd, Fairfield
$3,399,900
5 Beds ⋅ 8 Baths ⋅ 24194239 MLS
Old-world craftsmanship meets modern indulgence. Set on a peaceful, tree-lined street,this home offers total privacy and timeless curb appeal. Soaring ceilings, hand-finished millwork, and custom detail are evident throughout. This grand 5BR/6.5BA light filled residence pairs classic entertaining spaces - formal LR, formal DR, & a wood-paneled library w/wet bar & full BA-with modern amenities such as a two-story FR w/ stone FP, a stunning windowed sunroom overlooking the beautiful grounds,& an impressive chef's kitchen boasting custom appliances, double sub zero, island, & dual butler's pantries.Thoughtful proportions create a seamless flow, a home as comfortable day-to-day as it is for grand-scale entertaining.The opulent primary suite is a spa retreat onto itself, w/ dual baths, dual walk-in closets,& a private sauna.The second floor offers 3 add'l en-suite BRs w/ built-ins and large closets. The third floor offers a great room w/ custom built-ins, plus an additional BR and full BA . The lower level feat a recently upgraded state-of-the-art movie theater, gym, game room, & workshop for a serious hobbyist. The expansive, landscaped grounds offer true serenity, w/ English gardens framing a resort-caliber pool and spa in a backyard built for entertaining. Timeless elegance, tucked within The Ridge - a gated enclave w/ a staffed gatehouse, clubhouse, pool & tennis courts just minutes to Fairfield and Westport amenities. Truly a special offering w/ultimate privacy& convenience.

344 Fence Row Dr, Fairfield
$2,950,000
4 Beds ⋅ 4 Baths ⋅ 24196292 MLS
Ideally located in one of Fairfield's most desirable beach neighborhoods, this beautiful custom-built FEMA compliant home combines premium construction and efficiency with high-end finishes throughout. Unique features include 2x6 framing, steel beam support, energy efficient foam insulation, dual HVAC and tankless hot water systems, a gorgeous custom kitchen with Thermador appliances and honed granite countertops, an incredible home theater system, a 3-floor elevator, a spacious bonus room with views of Long Island Sound, an oversized garage with a gym or if you prefer, space for a 3rd car; and to top it all off, a saltwater swim spa overlooking a lush, professionally landscaped yard. Just steps to deeded beach access, and minutes to the playground, tennis and bocce courts, Fairfield's vibrant town center and Metro North train station. This stunning home isn't going to last - schedule your showing before it's gone.

679 Rowland Rd, Fairfield
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.