Southbury Real Estate

Homes for Sale in Southbury, CT Between $500,000 to $550,000

Welcome to your dedicated resource for Homes for Sale Between $500,000 to $550,000 in Southbury, 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 Southbury, 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 properties currently available between $500,000 to $550,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Southbury, CT Homes for Sale Between $500,000 to $550,000

$535,000
5 Beds ⋅ 2 Baths ⋅ 24174641 MLS
Surrounded by nature, the property provides room to explore, garden, entertain, or simply enjoy a peaceful setting while remaining close to everyday conveniences. A covered porch welcomes you inside where hardwood flooring runs through much of the home. The living room features built in bookshelves, a wood stove, and large windows that fill the space with natural light. A key advantage is the three bedrooms on the main level, offering flexibility for single level living, guests, a home office, or multigenerational needs. The main level also includes an eat in kitchen with a large pantry, dining room, full bath, and a four season room overlooking the wooded surroundings. Upstairs are two additional bedrooms and a half bath with potential for expansion. The unfinished lower level includes workshop space, laundry and mechanical areas, a storage room suitable for a wine or root cellar, and a two car tandem garage. Outside you'll find an inground pool with a new liner (2024), multiple outbuildings and wood sheds (conveyed as is), and ample parking. Major updates include a new roof (2023), furnace (2023), well equipment incl pump/tank (2023), newer gutters, and new septic tank and 2 distribution boxes (August 2026). A whole house Generac generator provides added peace of mind. Possible building lot-buyer to do their due diligence. Set at the end of a private road on 2.9 wooded acres, this 5BR home offers privacy, space, and exceptional potential.

40 Oleson Dr, Southbury
$525,000
2 Beds ⋅ 3 Baths ⋅ 24199216 MLS
Nantucket inspired design, in-town location with a peaceful setting continue to make Old Field Hill one of the most desirable, non-age-restricted communities in Southbury. Beautiful pool with club house are just the start of what's available for social gatherings in addition to reading clubs, holiday cookie exchange, community newsletter and Thursday night meet-ups. The home has great natural light which promotes good energy, an updated kitchen and is absolutely turn-key!

33 Old Fld Hill Rd Unit 18, Southbury
$525,000
3 Beds ⋅ 2 Baths ⋅ 24194206 MLS
Welcome home to this beautifully updated raised ranch on a private, picturesque 1.03-acre lot. This move-in-ready home offers 3 bedrooms, 2 bathrooms, and a blend of modern comfort and country tranquility. Inside, enjoy a bright, open floor plan featuring gleaming hardwood floors, fresh paint, crown molding, and abundant natural light. The inviting living room boasts a charming brick fireplace, while the dining area opens to a spacious deck-ideal for entertaining. The fully equipped kitchen combines style and functionality. The finished walk-out lower level includes a generous family room, a convenient laundry area, and direct access to the attached 2-car garage, providing versatile living space for any lifestyle. Outside, the freshly painted deck overlooks a private, expansive yard perfect for recreation and gardening. Conveniently located near schools, shopping, restaurants, and highways, this exceptional property offers an easy commute paired with peaceful living.

208 Strongtown Rd, Southbury
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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.