Fairfield Real Estate

Fairfield, CT Homes for Sale

Fairfield, CT homes for sale range from starter capes near $500,000 to waterfront colonials above $2 million, with the median single-family sale price around $900,000. Dave Jones Realty has worked this Fairfield County market for decades, guiding buyers through neighborhoods that stretch from the Long Island Sound beaches to the wooded northern sections near the Merritt Parkway. The town combines historic New England architecture, two university campuses, and a Metro-North commuter line that reaches Grand Central in roughly 75 minutes.

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
Search by Price
Search by Bedrooms
Search by Bathrooms

Home Styles and Price Context

Fairfield's housing stock is dominated by colonials, capes, and Victorian-era homes, many built between 1900 and 1960. Center-hall colonials in Fairfield typically list between $750,000 and $1.4 million and average 2,200 to 3,400 square feet. Beach-area cottages and capes near Fairfield Beach Road start around $550,000, while renovated waterfront properties in Southport exceed $2.5 million. Lot sizes range from a quarter acre near the shore to over an acre in the Greenfield Hill area.

Neighborhoods

Southport

Southport is a historic village in Fairfield centered on Southport Harbor and Pequot Avenue, known for restored Federal and Greek Revival homes. Southport homes frequently sell between $1.2 million and $4 million and fall within the Mill Hill Elementary School zone.

Greenfield Hill

Greenfield Hill occupies the northern section of Fairfield and is known for its annual Dogwood Festival and larger lots averaging one to two acres. Colonial estates in Greenfield Hill commonly range from $1 million to $2.5 million.

Fairfield Beach

The Fairfield Beach area along Reef Road and Fairfield Beach Road holds cottages and year-round homes within walking distance of Jennings Beach and Penfield Beach.

Daily Life

Fairfield has two Metro-North stations, Fairfield and Fairfield Metro, providing New Haven Line service to Manhattan in about 75 minutes. The Merritt Parkway and Interstate 95 both cross the town for regional driving. Sacred Heart University and Fairfield University are both located in Fairfield and rank among the town's largest employers. Jennings Beach and Penfield Beach line the Long Island Sound shoreline, and downtown Fairfield along the Post Road offers restaurants, the Fairfield Theatre Company, and weekend shopping.

Working With a Local Agent

Dave Jones Realty has closed sales across Southport, Greenfield Hill, and the Fairfield Beach area, giving buyers direct comparison points between historic village homes and northern estate properties.

  Advanced Search   Market Reports   Home Value   Connect

Newest Homes for Sale in Fairfield, CT

$1,550,000
24187939 MLS
Exceptional development opportunity in Fairfield! Offering approved plans for a new 20-unit multifamily residential community in a highly convenient location. The proposed four-story building features 20 apartments comprised of 12 one-bedroom and 8 two-bedroom units, including 6 designated affordable housing units. Plans include elevator access, covered parking, resident lounge, fitness center, tenant storage, and professionally designed site improvements. A rare opportunity for builders and developers to acquire a shovel-ready project with thoughtfully designed floor plans and modern amenities. Conveniently located near shopping, restaurants, public transportation, I-95, and Fairfield's vibrant town center. Approved plans and supporting documentation available upon request.

110 Woodrow Ave, Fairfield
$1,549,000
5 Beds ⋅ 4 Baths ⋅ 24198508 MLS
Featured in Fairfield Magazine, this beautifully restored 1834 Cape Cod farmhouse blends nearly 200 years of history, character & modern luxury in the sought-after Osborn Hill School District. Thoughtfully expanded over 30 years by its owners, including an accomplished NYC designer, this 5BR home retains exposed beams, wide-plank floors, handcrafted millwork & multiple fireplaces. A welcoming front porch leads to a charming parlor w/FP & French doors, 1st-floor office w/built-ins, formal DR w/exposed barnwood & FP, plus a 1st-floor BR w/FP. The chef's kitchen features custom cabinetry, granite counters, oversized island, 6-burner range, wine fridge & premium appliances, opening to a sun-filled family room w/wood-paneled ceiling. 1.5 updated baths & a spacious laundry room complete the main level. Upstairs, the primary suite offers exposed beams, built-ins, WIC & spa bath w/heated floors, soaking tub, dual vanities & oversized shower, plus 2 BRs w/Juliet balconies. The attached barn is an entertainers dream w/soaring ceilings, bamboo floors, barnwood bar & stone gas FP, plus an ensuite guest BR, 2nd office & fitness/flex space. The oversized garage includes an art/craft studio w/cedar closet. Outside, the private landscaped yard invites garden parties & quiet evenings alike, w/stone patio, outdoor LR w/stone FP, dining area, bar, hot tub, outdoor shower & firepit. Minutes to downtown, beaches, Black Rock, Metro-North, shopping & dining. Very special, once-in-a-lifetime home!

2580 N Benson Rd, Fairfield
$1,499,900
4 Beds ⋅ 4 Baths ⋅ 24199290 MLS
Exceptional opportunity to own what is essentially a brand-new home in Fairfield University area. Expanded with a full second-story addition and reconstructed from the original foundation up, this remarkable residence offers 3,290 square feet of beautifully finished living space with virtually every major component newly built. Designed for today's lifestyle, the open-concept floor plan features 4 bedrooms, 4 full baths, and flexible living space across three levels. The heart of the home is a stunning chef's kitchen with Thermador appliances, quartz countertops, abundant cabinetry, and a large island, opening to a dining room with coffered ceilings, and seamless flow into the living room, creating an ideal setting for both everyday living and entertaining. A first-floor bedroom and full bath provide flexibility for guests, a home office, or multigenerational living. The second floor features a spacious primary suite with a walk-in closet and beautifully appointed primary bath, along with two additional bedrooms, another full bath, and a conveniently located laundry room. The finished third floor offers a spacious office with glass French doors, valuable bonus space perfect for a playroom, media room, or guest retreat, along with a full bath. Beyond the attractive finishes, conveniently located near Fairfield's beaches, train stations, shopping, dining, parks, and top-rated schools, 694 Jennings Road offers a rare combination of modern design, turnkey living.

694 Jennings 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.