Fairfield’s late-October market arrived with real range. Twenty-three homes were listed between October 14 and October 23, stretching from a Sasco Hill estate and a nearly $6 million beach-area build to in-town homes, university-area choices, and condominiums below $600,000.
Beyond the asking prices, several properties carry useful backstories. Prior sales help frame what has changed, while the available public permit record adds context where it documents meaningful construction or renovation work.
541 Sasco Hill Road
$6,500,000 · 5 bedrooms · 7.5 baths · 11,999 sq. ft. · Listed October 14
541 Sasco Hill Road is a 5-bedroom, 7.5-bath home in Fairfield, built in 1931 on 1.25 acres with 11,999 square feet. Highlights include heated pool, spa, and outdoor kitchen, two-story foyer behind iron gates, four en-suite bedrooms on the second level, and two primary suites with dressing rooms.
View the full listing →Listed by William Raveis Real Estate
98 Banks Place
$5,995,000 · 4 bedrooms · 5 baths · 5,699 sq. ft. · Listed October 22
98 Banks Place is a 4-bedroom, 5-bath home in Fairfield, built in 1830 on 5.44 acres with 5,699 square feet. Highlights include restored 1830 Greek Revival completed in 2017, original floors, brick, timbers, and period details, chef’s kitchen with concealed scullery, and pool, year-round spa, and bluestone patio.
The 1830 structure was not merely refreshed. The 2017 project preserved original floors, brick, timbers, reclaimed hardware, and period details while adding custom millwork, radiant-heated floors, Belgian stone, and all-new systems. The current property page records a $5.625 million price change on September 27, 2026, followed by the new $5.995 million listing on October 21.
View the full listing →Listed by Compass Connecticut, LLC
18 Merry Meet Circle
$2,300,000 · 4 bedrooms · 7 baths · 3,883 sq. ft. · Listed October 16
18 Merry Meet Circle is a 4-bedroom, 7-bath home in Fairfield, built in 1986 on 2.01 acres with 3,883 square feet. Highlights include natural stone and rich wood accents, spacious kitchen with separate dining room, expansive living room with stone fireplace, and custom stone-and-wood staircase.
View the full listing →Listed by Giner Real Estate
448 Pequot Avenue
$1,799,000 · 2 bedrooms · 2.5 baths · 1,556 sq. ft. · Listed October 20
448 Pequot Avenue is a 2-bedroom, 2.5-bath home in Fairfield, built in 1834 on 0.08 acres with 1,556 square feet. Highlights include 1834 farmhouse in Southport Village, 2016 restoration recognized by Southport Conservancy, rebuilt foundation and FEMA-height elevation, and new plumbing and electrical systems.
Fairfield’s historic profile identifies the house as an 1834 Greek Revival within Southport’s local historic district. It was remodeled in 1949 and substantially renovated in 2016, when the foundation was rebuilt and raised, original wide-plank floors were restored, plumbing and electrical systems were replaced, and steel beams were installed to open the interior. The profile notes that the 2016 renovation details have not yet been independently confirmed against permit records.
View the full listing →Listed by RE/MAX Right Choice
140 Labbance Lane
$1,695,000 · 3 bedrooms · 2.5 baths · 3,649 sq. ft. · Listed October 18
140 Labbance Lane is a 3-bedroom, 2.5-bath home in Fairfield, built in 1972 on 2.03 acres with 3,649 square feet. Highlights include brook crossing to 2 manicured acres, european-styled Greenfield Hill home, three fireplaces and built-ins, and screened porch with crown molding.
View the full listing →Listed by Higgins Group Bedford Square
88 Springer Road
$1,599,000 · 4 bedrooms · 2.5 baths · 3,421 sq. ft. · Listed October 17
88 Springer Road is a 4-bedroom, 2.5-bath home in Fairfield, built in 1995 on 0.61 acres with 3,421 square feet. Highlights include floor-to-ceiling stone fireplace in the family room, eat-in kitchen with double ovens and abundant cabinetry, primary suite with walk-in closet and Jacuzzi tub, and finished lower-level flexible-use space.
View the full listing →Listed by Coldwell Banker Realty
50 Judges Hollow Road
$1,475,000 · 4 bedrooms · 2.5 baths · 2,360 sq. ft. · Listed October 21
50 Judges Hollow Road is a 4-bedroom, 2.5-bath home in Fairfield, built in 1961 on 3.56 acres with 2,360 square feet. Highlights include screened porch surrounded by nature, hardwood floors throughout the home, updated kitchen and main-level office, and dining room opening to a private patio.
The property previously sold for $995,000 on August 3, 2023.
View the full listing →Listed by William Pitt Sotheby's Int'l
70 Southfield Road
$1,375,000 · 3 bedrooms · 2.5 baths · 1,856 sq. ft. · Listed October 21
70 Southfield Road is a 3-bedroom, 2.5-bath home in Fairfield, built in 1940 on 0.13 acres with 1,856 square feet. Highlights include 2022 renovation of first floor and part of second, open-plan kitchen with quartz counters and pantry, family room opening to expansive deck, and dining room with built-ins and living room fireplace.
The property previously sold for $1,100,000 on June 29, 2023.
View the full listing →Listed by Compass Connecticut, LLC
69 Rakoczy Avenue
$1,200,000 · 4 bedrooms · 2.5 baths · 2,843 sq. ft. · Listed October 14
69 Rakoczy Avenue is a 4-bedroom, 2.5-bath home in Fairfield, built in 2026 on 0.1 acres with 2,843 square feet. Highlights include four levels of finished living space, hardwood floors and oversized windows throughout, gas fireplace with custom built-in bookcases, and kitchen with custom cabinetry and center island.
View the full listing →Listed by Coldwell Banker Realty
45 Dogwood Lane
$1,185,000 · 4 bedrooms · 2.5 baths · 2,752 sq. ft. · Listed October 16
45 Dogwood Lane is a 4-bedroom, 2.5-bath home in Fairfield, built in 1940 on 0.18 acres with 2,752 square feet. Highlights include two wood-burning fireplaces, sun-filled living room with hardwood floors, quartz countertops and stainless-steel appliances, and family room with custom built-ins.
View the full listing →Listed by William Raveis Real Estate
125 University Drive
$1,050,000 · 3 bedrooms · 2.5 baths · 2,208 sq. ft. · Listed October 19
125 University Drive is a 3-bedroom, 2.5-bath home in Fairfield, built in 1954 on 0.24 acres with 2,208 square feet. Highlights include fully fenced backyard with room to play, deck suited to sunset dinners, updated kitchen with quartz countertops, and flexible den or informal dining area.
View the full listing →Listed by William Raveis Real Estate
15 Wheeler Park Place
$997,500 · 4 bedrooms · 3 baths · 2,528 sq. ft. · Listed October 19
15 Wheeler Park Place is a 4-bedroom, 3-bath home in Fairfield, built in 1958 on 0.5 acres with 2,528 square feet. Highlights include end-of-cul-de-sac setting in North Stratfield, seasonal lake views beside Lake Mohegan, open-concept living, dining, and kitchen area, and main-level bedroom, full bath, and laundry.
View the full listing →Listed by William Raveis Real Estate
85 Newman Place
$989,000 · 4 bedrooms · 2.5 baths · 2,338 sq. ft. · Listed October 14
85 Newman Place is a 4-bedroom, 2.5-bath home in Fairfield, built in 1917 on 0.29 acres with 2,338 square feet. Highlights include 1917 home in Stratfield Village, formal living room with hardwood floors and French doors, kitchen with cherry countertops and center island, and breakfast bar adjoining the family room.
View the full listing →Listed by William Raveis Real Estate
195 Rock Major Road
$900,000 · 3 bedrooms · 2 baths · 2,352 sq. ft. · Listed October 22
195 Rock Major Road is a 3-bedroom, 2-bath home in Fairfield, built in 1951 on 0.64 acres with 2,352 square feet. Highlights include three-bedroom ranch on over half an acre, kitchen opening to a south-facing deck, oak hardwood floors and timeless built-ins, and wood-burning fireplaces.
View the full listing →Listed by Higgins Group Real Estate
9 Millspaugh Drive
$899,000 · 3 bedrooms · 2 baths · 1,497 sq. ft. · Listed October 15
9 Millspaugh Drive is a 3-bedroom, 2-bath home in Fairfield, built in 1949 on 0.26 acres with 1,497 square feet. Highlights include cape in Fairfield’s University area, hardwood floors throughout the main living level, updated kitchen and refreshed downstairs bathroom, and three bedrooms with flexible upstairs rooms.
View the full listing →Listed by William Raveis Real Estate
100 Holiday Road
$899,000 · 4 bedrooms · 3 baths · 3,068 sq. ft. · Listed October 14
100 Holiday Road is a 4-bedroom, 3-bath home in Fairfield, built in 1979 on 0.94 acres with 3,068 square feet. Highlights include four-bedroom home on a cul-de-sac, updated kitchen with central air, two-car garage, and finished basement with half bath.
View the full listing →Listed by Brown Harris Stevens
1664 Melville Avenue
$750,000 · 3 bedrooms · 2 baths · 1,134 sq. ft. · Listed October 19
1664 Melville Avenue is a 3-bedroom, 2-bath home in Fairfield, built in 1939 on 0.17 acres with 1,134 square feet. Highlights include updated kitchen with granite countertops and five-burner gas range, first-floor bedroom with ensuite bath, living room with gas fireplace and wood mantel, and front-to-back primary bedroom upstairs.
The property previously sold for $610,000 on October 2, 2023.
View the full listing →Listed by Higgins Group Real Estate
35 Highlawn Road
$739,900 · 2 bedrooms · 2 baths · 1,602 sq. ft. · Listed October 16
35 Highlawn Road is a 2-bedroom, 2-bath home in Fairfield, built in 1941 on 0.24 acres with 1,602 square feet. Highlights include two-bedroom ranch with one-level living, finished lower level for additional living space, fenced backyard with in-ground pool, and central air with heat pump.
View the full listing →Listed by Coldwell Banker Realty
20 Carrie Circle
$729,000 · 2 bedrooms · 3 baths · 2,499 sq. ft. · Listed October 20
20 Carrie Circle is a 2-bedroom, 3-bath residence in Fairfield, built in 1998 with 2,499 square feet. Highlights include main-floor primary suite with attached garage, vaulted living room with gas fireplace, deck overlooking the backyard, and upstairs bedroom, office, and full bath.
View the full listing →Listed by Coldwell Banker Realty
15 Greenleigh Road
$689,000 · 3 bedrooms · 2 baths · 2,138 sq. ft. · Listed October 15
15 Greenleigh Road is a 3-bedroom, 2-bath home in Fairfield, built in 1957 on 0.31 acres with 2,138 square feet. Highlights include three-bedroom ranch on a corner lot, set back on a quiet cul-de-sac, living room fireplace and updated kitchen, and deck overlooking the private backyard.
View the full listing →Listed by William Raveis Real Estate
258 Bennett Street
$649,999 · 4 bedrooms · 2 baths · 1,427 sq. ft. · Listed October 21
258 Bennett Street is a 4-bedroom, 2-bath home in Fairfield, built in 1953 on 0.13 acres with 1,427 square feet. Highlights include four bedrooms and two full bathrooms, bonus room with direct backyard access, new kitchen and updated bathrooms, and new heating and cooling HVAC system.
The property previously sold for $415,000 on August 19, 2024.
View the full listing →Listed by William Raveis Real Estate
72 Toll House Lane
$585,000 · 3 bedrooms · 1 bath · 1,064 sq. ft. · Listed October 21
72 Toll House Lane is a 3-bedroom, 1-bath home in Fairfield, built in 1957 on 0.87 acres with 1,064 square feet. Highlights include four-season room overlooking the backyard, hardwood floors beneath carpeting throughout, partially finished lower level for recreation, storage, and laundry, and attached two-car garage.
View the full listing →Listed by Berkshire Hathaway NE Prop
148 Southport Woods Drive
$575,000 · 2 bedrooms · 2 baths · 1,200 sq. ft. · Listed October 21
148 Southport Woods Drive is a 2-bedroom, 2-bath residence in Fairfield, built in 1969 with 1,200 square feet. Highlights include first-floor, two-bedroom condominium, single-level living, freshly painted interior, and new air conditioning.
View the full listing →Listed by William Raveis Real Estate
This ten-day group spans several distinct Fairfield markets at once: Sasco Hill and Southport luxury, beach-area and university-area homes, Greenfield Hill acreage, and lower-maintenance condominium living.
Availability, pricing, open houses, and status can change quickly. Follow each property link for current details and the complete listing.
Listing information and public records were checked on October 23, 2026. Information is deemed reliable but not guaranteed. Permit descriptions summarize municipal records and do not establish the present condition or completion of the work. Equal Housing Opportunity.
George Cress of Real Broker represents home buyers and sellers throughout Connecticut, with a focus on Fairfield County. He combines technology, local market knowledge, and modern real estate marketing to help buyers keep more of their money and sellers generate greater interest in their homes.
For buyers, George offers flat-fee buyer representation and buyer commission rebates, providing meaningful savings alongside full-service guidance, negotiation, and support through closing. For sellers, he uses property storytelling, video, targeted digital advertising, and one of Connecticut’s largest social media audiences focused on local real estate to reach beyond traditional MLS exposure and attract more qualified interest. Through Co-List with Cress, sellers can add these marketing capabilities while continuing to work with their preferred listing agent.
Explore active Connecticut homes for sale, including listings in Fairfield, Westport, Greenwich, and other Fairfield County communities. To discuss buying or selling a home in Connecticut, contact George Cress.
George Cress
(212) 203-5251
george@cress.co
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Fairfield County, CT
Real Broker CT, LLC
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