Isla Bentley-Micallef

Licensed in MA
714 Bliss Road,
Longmeadow, MA 01106

Isla has a deep appreciation for the communities and character that make Western Massachusetts such a special place to call home. Having lived throughout Hampshire and Hampden County, her journey has also taken her far beyond New England — she spent many years living in Hawaii, where she developed a strong connection to diverse cultures and the importance of finding a space that truly feels like your own.

Isla earned both her bachelor’s and master’s degrees in Occupational Therapy from Bay Path University, a background that shaped her ability to apply empathy, understand individual needs, and advocate for others. Before transitioning into real estate, she spent 15 years working in the restaurant industry, where she built a reputation for reliability, attention to detail, and exceptional customer service. This experience strengthened her ability to work in fast-paced environments, anticipate clients’ needs, and deliver a high level of care — skills that naturally translate into real estate.

As a real estate professional, Isla is committed to making the buying or selling process as smooth and rewarding as possible. She takes the time to understand each client’s goals, whether that means helping first-time buyers navigate the market with confidence, finding the perfect home that fits a unique lifestyle, or assisting sellers in positioning their property to achieve the best possible outcome. She is also a strong and strategic negotiator, dedicated to advocating for her clients’ best interests and securing the most favorable terms possible. Her approach is rooted in clear communication, thoughtful guidance, and a genuine dedication to client success. Her ultimate goal is to ensure that one of the most significant purchases of a client’s life feels seamless, well-supported, and stress-free from start to finish.

Outside of work, Isla loves traveling the world, spending time at the beach, and making memories with friends, family, and her dog. These experiences continue to inspire her passion for helping others find not just a house, but a place they truly feel at home.

Whether a client is buying their first home, upgrading to their next, or preparing to sell, Isla provides personalized support every step of the way!

 

Call Isla Today!

 

You'll Be Glad You DID! 

Featured Western MA Properties

$395,000
6 Beds ⋅ 2 Baths ⋅ 73576300 MLS
Welcome to 34 Ashley St! This well-maintained two-family home offers a great opportunity for an owner-occupant, investor, or multigenerational household. Best of all, the property will be delivered fully vacant at closing, giving the new owner flexibility from day one.Both units feature bright, comfortable living spaces with large windows, hardwood floors, eat-in kitchens, full bathrooms, and spacious bedrooms. The kitchens offer plenty of cabinet and dining space, while updated lighting and neutral finishes create a clean and inviting feel. Additional rooms provide flexibility for a home office, dressing room, or extra storage.Outside, you’ll find low-maintenance siding, an enclosed front porch, a long paved driveway, and plenty of off-street parking. The large, level backyard is fully fenced and includes mature trees and a storage shed, offering plenty of space for entertaining, gardening, or relaxing outdoors.With separate entrances, versatile layouts, ample parking, and vacant delivery, this property is ready for its next owner. Lead compliance documentation is available for review. Don’t miss your opportunity to see everything 34 Ashley St has to offer!

34 Ashley St, Springfield
$399,000
3 Beds ⋅ 1 Baths ⋅ 73576290 MLS
Sunny New England Cape in Northampton. Conveniently located off Bridge Road in the Cloverdale neighborhood of Florence with Look Park, Fitzgerald Lake, JFK Middle School, Florence Center and Arcanum field nearby. Move right in or add your own personal touches. The first level features a Living Room, Dining Room and Bedroom, all with hardwood floors. With the kitchen and bath also on the same level, first floor living is attainable., A light filled sunroom is just off the living room. The 2nd floor features 2 bedrooms complete with dormer windows, closets and storage space. Newer roof, gas furnace and hot water tank (as per available records). Easy maintenance vinyl siding. Vinyl clad tilt in windows. The back yard offers plenty of open space, complete with a storage shed.

24 Grandview St, Northampton
$399,000
6 Beds ⋅ 2 Baths ⋅ 24206571 MLS
Investor opportunity! Multi-family property with great potential. Bring your vision and transform this property into a valuable investment. Sold as-is.

66-68 Miller St, Springfield
$399,000
6 Beds ⋅ 2 Baths ⋅ 73576255 MLS
Investor opportunity! Multi-family property with great potential. Bring your vision and transform this property into a valuable investment. Sold as-is.

66-68 Miller St, Springfield
$569,900
12 Beds ⋅ 3 Baths ⋅ 73576245 MLS
Opportunity awaits at 24 Dickinson St! Conveniently Located in Springfield's desirable Forest Park neighborhood, this spacious 4-family property offers an excellent opportunity for investors or owner-occupants looking to build their real estate portfolio. Each of the four units features 3 bedrooms and 1 full bath, providing a desirable and versatile layout across this two-level property. The units offer comfortable living spaces, well-appointed kitchens, tiled baths, and plenty of natural light. Roof is only 3 years old, newer furnaces. This is a substantial multi-family property with strong income-producing potential. Don't miss the opportunity to add this four-unit property to your investment portfolio or explore the possibilities of owner occupancy! All four units are currently rented below market rents, offering significant potential for future income growth.

24 Dickinson St., Springfield
$375,000
6 Beds ⋅ 2 Baths ⋅ 73576202 MLS
Discover an exceptional opportunity at 30 Santa Barbara, Springfield, MA. This multi-family property spans 2118 square feet of living space, offering a unique blend of classic charm and potential. With six bedrooms, this property provides ample accommodation, catering to a variety of living arrangements. Set on a generous 5001 square foot lot, this three-story residence presents a versatile canvas for your vision. First floor unit has a finished family room in the basement. Second floor unit has 4 bedrooms and newer kitchen. Explore the possibilities of multi-generational living or investment income; schedule your viewing of this distinctive property today.

30 Santa Barbara, Springfield
$319,000
3 Beds ⋅ 2 Baths ⋅ 73576177 MLS
Welcome to this 1½-story stunning bungalow with a inviting cozy back yard. This inviting three bedroom home features a spacious, updated modern kitchen with stainless steel appliances and an open layout ideal for everyday living and entertaining, The open concept floor plan flows from the living room to the dining room The partially finished basement offers valuable additional entertainment and relaxation space, while two full bathrooms provide added convenience. Outside, enjoy the well- manicured exterior, fenced yard, and quaint backyard with a deck—perfect for relaxing or gathering with family and friends. Don’t miss the opportunity to make this charming home your own

28 Dalton Pl, Springfield
$449,999
6 Beds ⋅ 4 Baths ⋅ 73576148 MLS
ATTENTION OWNER OCCUPIED & INVESTOR BUYERS! Rare to find, 2006 built duplex with 3 bedrooms in each unit, separate utilities and off street parking. Each unit has a spacious kitchen with dining area, bright living room, and a half bathroom on the first floor; 3 bedrooms with closets and a full bathroom on the second floor; laundry area and plenty of storage in the individual basement. Very well maintained duplex. Other features & updates APO: Newly replaced heating furnace in unit 52, gas heat, vinyl siding, vinyl windows, circuit breakers, concrete foundation, large backyard & more. Duplex will be delivered with one unit vacant. Don’t miss this one!

52-54 Reed St, Springfield
$425,000
6 Beds ⋅ 4 Baths ⋅ 73576099 MLS
Welcome to 28-30 Dawes Street in Springfield, MA, a desirable side-by-side duplex built in 2013 with recent updates throughout. Both units are fully vacant, offering a great opportunity for an owner occupant, investor, or multi-generational living. With three bedrooms and one-and-a-half baths in each spacious unit, this property also offers excellent rental potential. Step into Unit 28 and you are greeted by a spacious living room with new flooring throughout. The kitchen features updated cabinetry, butcher block counters, and newer appliances. A half bath on the first floor adds everyday convenience, while upstairs you will find three generous bedrooms and a renovated full bath. Unit 30 offers the same layout and updates, giving both sides a fresh, cohesive feel. Additional highlights include fresh paint throughout, maintenance-free vinyl siding, separate heat and electricity, separated basements and laundry hookups, as well as an additional side lot parcel providing extra yard space for gardening, entertaining, recreation, and more. With its younger construction, two fully vacant units, and highly desirable side-by-side design, this property is a standout opportunity. Come see all this property has to offer and schedule your showing today!

28 Dawes St, Springfield
$320,000
3 Beds ⋅ 3 Baths ⋅ 73576016 MLS
Fall in love the moment you arrive! Tucked away on a quiet dead-end street, away from the main stretch of Roosevelt Avenue, this charming Cape offers 3 bedrooms, 2 full baths and 1,313 sq. ft. of living space on approximately half an acre. Renovated in 2018, the home features an updated kitchen with granite countertops, stainless steel appliances and recessed lighting, along with updated baths and flooring. The open dining area is perfect for entertaining, while the first floor bedroom adds flexibility. Enjoy an attached 1 Car garage, spacious rear deck and an expansive backyard and a charming storage shed, perfect for keeping gardening tools and outdoor essentials. The full unfinished basement features concrete flooring, steel beam support, interior access and excellent storage with future possibilities. Conveniently located near shopping, schools and area amenities. Come see it at our Open House Sunday, September 13th, 12:00–1:30 PM!

1100 Roosevelt Ave, Springfield
$542,000
4 Beds ⋅ 4 Baths ⋅ 73576002 MLS
An extaordinary example of classic mid-century modern design, this distinctive custom built split-level offer 3 floors of exceptional living space in Longmeadow's desirable Blueberry Hill neighborhood. Sidewalk-lined streets provide easy access to nearby schools, parks and shopping. From the moment you enter, the home makes a statement with its striking slate foyer, one-of-a-kind indoor waterfall, and wide wood staircase flanked by custom wrought iron railings. The dramatic living room features a magnificent stacked-stone fireplace extending from the hardwood floor to the vaulted ceiling. Thoughtfully preserving its original architecture and wonderfully retro finishes, the home also provides modern comfort with update state-of-the-art heating and cooling systems and new windows. Spacious, distinctive, and filled with personality, this is a home with something to discover around every corner.

326 Williams, Longmeadow
$389,900
4 Beds ⋅ 2 Baths ⋅ 73575997 MLS
Attention Investors! This well-maintained 2-family home, on a Dead End Street, offers two 2-bedroom units, each featuring hardwood floors, a bright living room, gas heat, and a sun-filled dining room. First floor bathroom and kitchen recently updated as well as the second floor bathroom. This property also includes updated front porches on both levels and updated back decks for both units and a fully fenced yard. There is a two-car garage that is currently set up as additional storage and additional off-street parking for 5 vehicles. Two owned hot water heaters installed in 2021 & 2022, two new furnaces in 2024 and new wood stove in 2025 for additional winter comfort and savings. Situated in a highly convenient central location, you're minutes from shopping, restaurants, churches, and everyday amenities. Located in the heart of the Pine Point neighborhood of Springfield. No showings until after the Open House Sunday 9/13/26.

45-47 Methuen St, Springfield
$499,000
2 Beds ⋅ 2 Baths ⋅ 73575983 MLS
LOCATION! Finishing touches being applied to this lovely new condo on the ground floor in downtown Northampton. Walk to restaurants, shopping, entertainment and everything else the eclectic city of Northampton offers. 2 Units (one up and one down) duplex located on a quiet, private side street just steps to the Mass Central Rail Trail. Rare one level living with bright open floor plan. 2 bedrooms and 1 full and one half new baths. Open plan great room with living and dining area that flows to the beautiful custom kitchen with island, quartz counters and custom modern cabinets. Half bath off front entry and gorgeous new hardwood floors throughout. Sunlight streams through the home from the large, energy efficient, new windows. New stainless appliances, new electric, new plumbing, new heating/ AC, new roof, new windows and doors.... Everything is new! Large all new basement with laundry and private storage. Huge yard offers many opportunities for playing or gardening!

26 Northern Ave Unit A, Northampton
$325,000
2 Beds ⋅ 2 Baths ⋅ 73575866 MLS
Discover comfortable, low-maintenance living in this beautifully appointed 2-bedroom, 1.5-bath condo nestled in the sought-after Woodcrest development. Thoughtfully designed across multiple levels, this home offers an ideal blend of style, comfort, and everyday functionality — perfect for buyers seeking a move-in ready property with quality finishes throughout.Step inside to find gleaming hardwood floors flowing across the entire first floor, creating a warm and inviting atmosphere for daily living and entertaining. The kitchen features durable, easy-care tile flooring, offering both style and practicality for home cooks and hosts alike. Upstairs, plush wall-to-wall carpeting adds comfort and coziness to the bedrooms and second-floor living spaces, making them the perfect retreat at the end of the day.Beyond the main living areas, the fully finished basement provides valuable bonus square footage that can be tailored to fit your lifestyle — whether that means a spacious family room, a private home office, a home gym, a media room, or additional storage. This flexible space significantly expands the home's usable footprint and adds everyday convenience.Practicality continues outside with an attached garage, offering secure, weather-protected parking along with extra room for storage and direct, convenient access into the home — an especially welcome feature during the colder months. The professionally maintained landscaping surrounding the property enhances curb appeal year-round and takes the hassle out of yard maintenance, so you can spend less time on upkeep and more time enjoying your home.Situated within the well-established and desirable Woodcrest community, this condo combines comfortable living with low-maintenance convenience in a fantastic location. With its versatile layout, quality finishes, and thoughtful features throughout, this home is ready to welcome its next owner.

2205 Boston Rd Unit F50, Wilbraham
$364,999
5 Beds ⋅ 2 Baths ⋅ 73575843 MLS
Welcome to Santa Barbara St in Springfield! This fully remodeled two-family offers a great opportunity for both investors and owner-occupants. Both units have been updated throughout, providing a clean, modern feel with move-in-ready interiors. One unit will be delivered vacant at closing, creating the perfect opportunity to house hack, choose your own tenant, or immediately take advantage of market rental potential. Each unit is separately metered, helping keep ownership expenses manageable. The property also offers off-street parking and convenient access to major highways and the Mass Pike, making commuting throughout Western Massachusetts and beyond easy.

156-158 Santa Barbara St, Springfield
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