Deerfield Homes under $500,000

Our website features the best real estate search for homes, condos, land and foreclosure properties available in Deerfield and surrounding areas. It is the only site you will ever need! It is easy-to-use and updated by the official Realtor®’s database every 15 minutes.

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in your neighborhood? You can create a custom market report to see what’s active, under contract, and sold in your neighborhood!

Considering selling or refinancing your home? Get an INSTANT property valuation now!

Newest Deerfield Homes under $500,000

$419,900

3 Beds ⋅ 2 Baths ⋅ 73586167 MLS ⋅ ['Mountain View Condominium'] BLDG.

Overlooking a beautiful green pasture, this spacious half duplex townhouse condo offers a peaceful setting with plenty of room across multiple levels. The main level features hardwood floors, a generous living room, and a kitchen with white cabinetry, granite countertops, tile backsplash, and plenty of counter space. The adjoining dining area opens directly to a private deck where you can relax and take in the open views. Upstairs, the bedrooms feature vaulted ceilings, adding height and an airy feel, along with a full bath. The clean, well-maintained basement offers excellent storage and additional possibilities. An attached one-car garage adds to the ease of condo living. A significant recent improvement is the roof, replaced approximately three months ago. With spacious rooms, vaulted ceilings, a private deck overlooking the pasture, garage, and a clean basement, this Deerfield condo offers a wonderful combination of space, scenery and minutes to interstate 91.

6 Boynton Road Unit A, Deerfield

$399,000

4 Beds ⋅ 2 Baths ⋅ 73585401 MLS

90 N Main Street, Deerfield, MA, is a unique residence. Once a wallet shop dating from 1860, it was converted to a modernized single-family residence in 1960. It is situated on a sidewalked street just steps away from the village center of South Deerfield, town offices, new library, elementary and high schools. A beautiful yard adorned with pollinator species and perennials, iris, tulips, roses, lilies, jack-in-the-pulpit and more! Two first-floor bedrooms and a full bath make this home extremely functional. Complementing these are two bedrooms on the second floor and one half bath The large kitchen and dining area features ample custom made cabinets, generous counter space and a large functional fireplace. The picture windows provide a great view of the gardens and birds. A single car attached garage, full basement for utilities and substantial storage. Central air conditioning for those hot summer days! Many improvements over the years include new windows, electrical panel, hot water heater and entry doors. On the bus route, easy access to I91, the Five Colleges, restaurants and breweries. Enjoy the lighted Christmas tree atop Mt Sugarloaf. Surrounded by history, fertile farmland and farmstands offering fresh veggies, fruit and meats. Open house Sunday 10/04, 11-1pm OR shown by appointment.

90 N Main Street, Deerfield

$339,000

3 Beds ⋅ 2 Baths ⋅ 73583494 MLS

Well-maintained 3-bedroom, 1.5-bath Cape overlooking the surrounding Deerfield farmland. Offering approximately 1,357 square feet of living space, the home features a spacious eat-in kitchen, hardwood floors, fireplace and first-floor vinyl replacement windows. A first-floor bedroom and full bath provide a convenient and flexible layout, with two additional bedrooms upstairs. Enjoy the covered patio, .74-acre lot and 1-car attached garage. This solidly built home has been nicely cared for over the years and offers a comfortable setting with convenient access to Routes 5 & 10 and area amenities. (Showings Begin at Open House) **OPEN HOUSE: Saturday 10/3 and Sunday 10/4 11AM-1PM**

642 Greenfield Road, Deerfield

$239,900

3 Beds ⋅ 1 Baths ⋅ 73581742 MLS

Located in the highly sought-after town of Deerfield, just 2 miles from Historic Old Deerfield, Deerfield Academy, Eaglebrook School, and The Bement School, this charming 3-bedroom, 1-bath home offers an exciting opportunity for the savvy buyer. The wrap-around enclosed porch is perfect for morning coffee or relaxing at the end of the day, while vinyl siding and windows offer easy-care convenience. A detached garage provides additional storage, and the backyard offers space to enjoy the outdoors. While the property needs some work, several important projects have already been completed, including a renovated bathroom, fresh flooring throughout the main level, a new oil tank, and extensive tree work. Roll up your sleeves and bring your vision to life, as this property offers plenty of potential to create something truly special!

734 Greenfield Rd, Deerfield

$469,000

1 Beds ⋅ 2 Baths ⋅ 73581376 MLS

Completely remodeled and sporting an open, flexible floor plan is this 4 room,1 bedroom, 1.5 bath cottage. Located in a prime downtown location - only 5 minutes to Deerfield Academy - and within walking distance of local restaurants, school and library its an attractive option for those looking to balance work & leisure effectively. Offering 2 parking spaces with a cozy back yard patio - a lovely location to work and play given it's commercial zoning. The open floor plan sports a fully applianced kitchen/DA, living room with double sided gas fireplace, office and half bath on the first floor with spacious bedroom, 3/4 bath and laundry on the second floor. Amenities are many and include custom built-ins, pine floors, shiplap detail and more! This meticulously remodeled cottage stands out as a matchless residence that marries modern living with classic appeal. Its combination of thoughtful design elements & prime location make it the ideal place to hang your hat!

14 Sugarloaf St, Deerfield

$399,900

3 Beds ⋅ 3 Baths ⋅ 5110899 MLS

Welcome home to your spacious 3-bedroom, 3-bathroom home in desirable Deerfield, NH—complete with no HOA fees! This unique home offers plenty of space, privacy, and convenience, including garage parking underneath with direct entry into the home. The first floor features an open-concept kitchen, dining, and living area, along with a convenient half bathroom. Upstairs, you'll find two spacious bedrooms, a full bathroom, and laundry. The entire top floor is dedicated to an enormous primary suite featuring a private full bathroom and walk-in closet. Step outside from the kitchen onto the new, oversized deck, perfect for entertaining family and friends or enjoying your morning coffee. The private, fully fenced-in yard provides plenty of space for pets, gardening, or outdoor gatherings. With its spacious layout, private outdoor space, garage parking, and no HOA fees, this Deerfield condo is a must-see! Showings begin immediately.

6b North Rd, Deerfield

$499,000

4 Beds ⋅ 2 Baths ⋅ 73576109 MLS

Welcome to 24 Sugarloaf St, a charming 1920s two-family home in the heart of South Deerfield, where lovely period character meets incredible flexibility. Each spacious unit offers two bedrooms and one bathroom, with hardwood floors, stained glass details, original woodwork, generous kitchens with walk-in pantries, newer stainless steel appliances and inviting living and dining spaces. Perfect as an investment, owner-occupied home with rental income, multi-generational living, or explore the possibility of converting to a spacious single-family home. The second-floor unit includes a finished walk-up attic, ideal for an office, hobbies, storage and more. Two NEW natural gas furnaces (combo heat/on demand hot water) offer peace of mind for the colder months ahead. Other recent updates include whole house water filtration, renovated bathroom and LVP flooring in kitchen and bath in Unit 1 and more! Outside, enjoy a spacious backyard with plenty of room for gardening, gathering, play or simply relaxing. Welcoming front and side porches offer even more places to unwind, sip your morning coffee or enjoy the beautiful neighborhood surroundings. The large parking area provides room for everyone. Step outside to sidewalks leading to South Deerfield's restaurants, shops, breweries and more, all while enjoying beautiful views of Mount Sugarloaf. Close to UMass and area colleges, public and private schools. A very special property with warmth, style, space and possibilities! This is a rare find in todays market. Don't miss your chance to be the next owner of this charming home!

24 Sugarloaf St, Deerfield

$349,900

2 Beds ⋅ 2 Baths ⋅ 73571855 MLS

This inviting 1960 ranch in Deerfield offers an easy, comfortable lifestyle with convenient one-level living and a practical layout. The home includes 2 bedrooms, 1.5 baths and 1,092 square feet of well-planned living space, making it a manageable choice for those seeking simplicity without sacrificing functionality. An attached one-car garage provides direct access, everyday convenience and valuable storage for vehicles, tools or outdoor gear. The .57-acre lot offers room to relax, garden or enjoy the outdoors while remaining relatively easy to maintain. Conveniently located near I-91, Routes 5 & 10, shopping, parks and area recreation, the property makes commuting, errands and leisure activities easy to access.

260 Conway Rd, Deerfield

$330,000

2 Beds ⋅ 2 Baths ⋅ 73562272 MLS ⋅ ['Meadow Oak'] BLDG.

Welcome to Meadow Oak Condominiums, a thoughtfully designed community of just six duplex-style buildings tucked away on a peaceful dead-end street in South Deerfield. Surrounded by mature landscaping and a beautiful wooded backdrop, this 2-bedroom, 1.5-bath end unit offers approximately 1,260 sq. ft. of comfortable living space with the privacy and feel of a home combined with the ease of condo living. Inside, hardwood floors flow throughout the bright and inviting living areas, complemented by a vaulted ceiling that creates an open and airy feel. The spacious kitchen offers plenty of cabinet and counter space and opens to the dining area with direct access to a private rear deck overlooking the trees. Upstairs you’ll find two generously sized bedrooms with ample closet space and a full bath. An attached one-car garage adds everyday convenience and additional storage. Enjoy a tranquil, wooded setting and a smaller association while being conveniently located in South Deerfield—condo living without sacrificing space, privacy, or a sense of home.

5 Meadow Oak Ln Unit B, Deerfield

$299,000

2 Beds ⋅ 1 Baths ⋅ 5094238 MLS

2-bedroom, 1-bath waterfront home on Freeses Pond with 127 feet of pond frontage and beautiful water views. This is the kind of setting buyers wait for, with direct pond frontage, a peaceful natural backdrop, and the opportunity to bring new life to a property with serious potential. Set on a 0.29-acre lot, the elevation leads toward the water and creates a strong canvas for someone with vision, creativity, and a plan. Whether restored, refreshed, or reimagined, the opportunity here lies in the water, the views, and the potential! Home is sold as-is.

23 Penn Ave, Deerfield

$409,900

2 Beds ⋅ 1 Baths ⋅ 5093991 MLS

Back on the Market solely because prior buyer financing fell through - NO fault of the property. Welcome to your own waterfront retreat on Freeses Pond! This adorable 2-bedroom, 1-bath waterfront home is full of charm and has been beautifully updated (new flooring on second floor, new built in, updated bathroom, all new appliances, brand new wood stove, while keeping all the character that makes it feel so special. From the moment you walk in, you'll love the wide pine floors, cozy feel, and incredible wall of windows overlooking the water. Natural light pours into the home, and the water views are front and center, creating a peaceful backdrop you'll enjoy every day. The updated kitchen is both stylish and functional, featuring brand new appliances and a welcoming space to enjoy cooking. The bathroom has also been tastefully updated, making this home truly move-in ready. One of the standout features is the generous-sized primary bedroom overlooking the water. Imagine waking up each morning to beautiful pond views and ending your day with the calming sights and sounds of waterfront living. A mudroom, first-floor laundry with newer washer and dryer, and a newer water heater add everyday convenience, while the brand-new deck is the perfect spot for summer cookouts, morning coffee, or simply relaxing and taking in the scenery. As the seasons change, you'll have a front-row seat to nature's beauty, from sunny summer days on the water to the vibrant fall colors reflecting across the pond. Tucked away in the charming town of Deerfield, this home offers the perfect blend of waterfront living, modern updates, and timeless charm. If you've been dreaming of a cozy waterfront retreat that's full of character and ready to enjoy, this is the one. Deerfield resident only beach is approximately 7 minutes from the property - Veasey Park Beach on Pleasant Lake.

17a Penn Ave, Deerfield

$435,000

3 Beds ⋅ 1 Baths ⋅ 73523943 MLS

If you’ve been dreaming about a little more space, a little more privacy, and maybe a barn of your own, this Deerfield farmhouse might be exactly what you’ve been waiting for. Set on 6 acres, the property offers the kind of country setting that’s getting harder to find—room for animals, gardens, hobbies, or simply space to enjoy.Inside, this 1800s post & beam farmhouse has over 1,900 sq ft with 3 bedrooms, a dedicated office, exposed beams, wood accents, and plenty of the character you hope to find in an older New England home. There’s also a spacious attic for storage with potential for future expansion.And then there’s the barn. Four stalls are already in place, with additional barn space that could accommodate more. Two fenced pastures and a riding area make it especially appealing for horses, while additional acreage offers possibilities for expanding pasture or creating the homestead you’ve always pictured.Surrounded by trees and tucked into a private setting, this isn’t a cookie-cutter property—and that’s exactly the point. It’s a place with history, acreage, and plenty of opportunity for its next owner to make it their own!

271 Lower Road, Deerfield

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

board logo Copyright 2026 PrimeMLS, Inc. All rights reserved. This information is deemed reliable, but not guaranteed. The data relating to real estate displayed on this display comes in part from the IDX Program of PrimeMLS. The information being provided is for consumers’ personal, noncommercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated .