Please submit highest and best by 5PM Monday, October 6th. Classic Lines. Creative Soul. Located on one of Sasco Hill's most beloved streets, this classic Colonial offers timeless curb appeal and a highly walkable lifestyle. Inside, thoughtful architectural details - arched doorways, original built-ins, and natural light throughout - create a warm, character-rich feel. The main level begins with a gracious sitting room and a window-lined office, both opening into the heart of the home: a crisp, updated kitchen, sunlit dining area, and comfortable family room that flows easily for everyday living. Upstairs, the primary suite offers a quiet retreat with a walk-in dressing area and updated bath, while three additional bedrooms - each with its own unique shape and charm - share a full hall bath. The finished lower level adds flexibility, with dedicated areas for media, play, and fitness. A welcoming front porch, three-car garage, and spacious driveway - perfect for play or overflow parking - round out the property. Just minutes from Southport Village, Fairfield Center, beaches, restaurants, and the train, this is a home that offers both character and convenience in one of the area's most desirable locations.
Est. $10,242 per month, based on comparable rentals
Sale and tax history for 88 Overhill Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24129674
Apr 7, 2026
Sold
$1,610,000
$397/sq ft
Oct 13, 2025
Pending
—
Oct 8, 2025
Contingent
—
Oct 2, 2025
Listed
$1,399,000
$345/sq ft
Sep 29, 2025
Coming Soon
$1,399,000
$345/sq ft
Public Records
Jul 20, 2020
Sold
$899,000
$222/sq ft
Smart MLS #170297840
Jul 22, 2020
Listing Removed
—
Jul 15, 2020
Sold
$899,000
$222/sq ft
May 24, 2020
Contingent
—
May 23, 2020
Listed
$899,000
$222/sq ft
Sasco Hill: Expanded and renovated with charm and character on a sought-after quiet street, this perfect location is not only walkable to dining, but to Southport Village, Train, beach, harbor and both Southport/Fairfield town centers. Curated with love inside and out, the owners have lovingly added an expansive family room and master bedroom, opened up the floor plan, restyled the kitchen and baths and re-designed the exterior and property. Relax on the wide front porch, enjoy a sip of wine on the rear lanai, snuggle in the hammock nestled between mature trees, play Ping Pong, basketball, etc on the paved drive (3 CAR GAR) that doubles as a sports court for this family. Inside, the crisp, white kitchen w/ Quartz tops opens to dining room and spacious family room. The living room with fireplace opens to their room of tranquility (the perfect sized sunny alcove for writing, office, reading). The artists niche doubles as laundry. Full bath and mudroom are offset from access to a broad rear deck. Equally spacious, the second floor features master bedroom with walk in closet and full bath, a second suite with ante room, bedroom, and closets, in addition to a full hall bath servicing bedrooms 3 and 4. The walk/out lower level adds an entire floor for entertaining, including media/family room, office/play room, WINE ROOM and access to the lanai. Also note the hobby room w/ sink and added storage rooms. We love this home because it offers the big 3 - Location, Character & Style.