Winchester Homes under $500,000

Welcome to Winchester, a charming city nestled in the picturesque Shenandoah Valley of Virginia. Known for its rich history, vibrant arts scene, and stunning landscapes, Winchester offers a delightful blend of small-town charm and modern amenities. With its historic downtown area, you'll find an array of boutique shops, delightful cafes, and a thriving local art community. The city's heritage is celebrated through its numerous festivals and events, making it a lively place to call home.

For those seeking affordable housing options, Winchester presents an enticing opportunity with homes available under $500,000. This price point allows you to explore a variety of charming properties, from cozy single-family homes to contemporary townhouses, all set against the backdrop of the valley’s natural beauty. Many of these homes feature spacious yards, modern amenities, and easy access to local parks and recreational areas, making them ideal for families, first-time buyers, or anyone looking to downsize.

Winchester’s strong sense of community is evident in its friendly neighborhoods, where residents enjoy a blend of tranquility and convenience. With excellent schools, a robust healthcare system, and a variety of dining options, it’s no wonder that Winchester is consistently ranked as one of the best places to live in Virginia.

Whether you’re drawn to the city’s historical charm or its vibrant community spirit, Winchester offers a welcoming environment where you can find your perfect home without breaking the bank. Explore the possibilities today and discover why so many are choosing to call this lovely city their home!

Newest Winchester Homes under $500,000

$389,900

2 Beds ⋅ 2 Baths ⋅ 5112269 MLS

Nestled on 5 private acres in Winchester, you’ll find this charming ranch style home offering the perfect combination of one-level living, privacy, and outdoor recreation! Upon entering, you’ll be greeted by a large and inviting living room/kitchen with plenty of space to relax and entertain. This home offers a primary bedroom with a 1/2 bath, another generously sized bedroom, a laundry room, and a full bath on the main level. The finished basement provides even more livable space and features a pellet stove, making it a great spot for a recreation room, hobby area, or additional entertaining space. Step outside and enjoy the expansive wrap-around deck, where you can take in the peaceful views and beautiful private surroundings. The property directly abuts the Ashuelot Rail Trail, offering easy access to walking, biking, and other outdoor activities right from your own backyard! There is also plenty of room for all your toys, tools, and equipment with 2 sheds, a detached 1 car garage, and a metal carport. A detached ground-mounted solar panel system and standby generator add to the functionality of this property. Located just 20 minutes from Keene, this home offers the privacy and tranquility of country living while still being conveniently close to shopping, restaurants, schools, medical facilities, and other amenities. Whether you’re looking for a full-time residence, weekend getaway, or simply a place to enjoy the peace and beauty of southwestern New Hampshire, this property has so much to offer! Schedule your private showing today!

35 Old Spofford Rd, Winchester

$299,000

3 Beds ⋅ 2 Baths ⋅ 5112014 MLS

Welcome to a charming 1885 historic home nestled on a private 0.77 acre lot in Ashuelot (Winchester), NH. Tucked back from the road, this character rich residence seamlessly combines classic New England architecture with practical modern updates. Inside, you will find beautiful hardwood floors and an abundance of custom built ins and clever storage solutions throughout. The kitchen features sleek stainless steel appliances, opening gracefully into inviting living spaces bathed in natural light. Upstairs, the home offers three comfortable bedrooms, perfect for family, guests, or a dedicated home office setup. Major mechanical upgrades provide complete peace of mind, including a newer furnace, water heater, and oil tank, alongside a full home generator that ensures uninterrupted power year-round. An attached one car garage adds convenience and extra storage. Outdoors, the expansive front and back yards create a quiet haven for leisure, outdoor dining, or cultivating your dream garden. Nature enthusiasts will love being just minutes away from local rail trails and the vast Pisgah State Park for year-round outdoor recreation. Enjoy the tranquility of a spacious, private setting while remaining close to nearby routes and amenities. This charming property is ready to welcome you home!

4 Elderberry Ln, Winchester

$269,900

1 Beds ⋅ 1 Baths ⋅ 5111797 MLS

Located just off the beaten path yet close to amenities and major routes sits this one level home waiting for you. Open concept kitchen and living room, ample sized bedroom and 2 additional rooms in the lower level that could be used for whatever you wish; office, spare bedroom, home gym, anything! Fully functional kitchen, fully applianced and plenty of storage; including multiple lazy susans in the cabinets for convenience. Forced hot air heat as well as a wood stove for a secondary heat source. 1.71 acres, private area and ready for immediate occupancy!! Don't miss this one!

1 Oak Cir, Winchester

$319,000

1 Beds ⋅ 1 Baths ⋅ 73580409 MLS ⋅ ['Parkview'] BLDG.

Best Price 1 Bedroom at The Parkview in Winchester! An exceptional opportunity to own in Winchester at an accessible price point! This first-floor, one-bedroom Terrace level at The Parkview offers an unbeatable combination of convenience, affordability, and practical living. Positioned on the ground level for easy direct access, the unit features peaceful views of the scenic duck ponds and mature, green landscaping. Step inside to an efficient open-concept layout where the kitchen features a functional peninsula and brand-new, never-used stainless steel appliances. All inclusive monthly HOA fee. Perfect for budget-conscious buyers, investors, or downsizers, completely covers your major monthly utility expenses: heat, hot water, electricity, water/sewer, and central air conditioning. In an era of rising utility costs, this structure provides total peace of mind and simplified monthly budgeting. Residents also enjoy access to the community pool, outdoor picnic grounds, and ample open parking. The location provides premium convenience, situated just minutes from vibrant Winchester Center with its local shops, cafes, highly rated restaurants, and two MBTA commuter rail stations for a straightforward commute. Enjoy everything Winchester has to offer, from the acclaimed public school system to the nearby trails of the Middlesex Fells Reservation, alongside quick access to Route 3 and I-93. If you have been searching for a smart entry into a high-demand market or a turn-key rental property with highly predictable expenses, this unit delivers outstanding utility and location for the price. ~DIRECTIONS TO OPEN HOUSE~ park in lot to the right and walk to the rear of the building (the part with the duck ponds) it is a terrace level with its own door unit T-14 Open House Saturday 10/03 11:00AM-12:30PM.

200 Swanton St Unit T14, Winchester

$425,000

5110811 MLS

Large two family home!!! In town location. Close to schools, shopping and amenities. Many original features; staircase and lovely banister in entrance hall, moldings, fireplace surround as well as turret and alcove windows. Large units; one 2 bedroom and one 3 bedroom. All separate utilities. Well maintained property ready for you to take ownership!

42 Parker St, Winchester

$399,000

1 Beds ⋅ 1 Baths ⋅ 73579389 MLS ⋅ ['Parkview Condominiums'] BLDG.

Welcome to Parkview Condominiums in Winchester! This well-maintained 1-bedroom, 1-bathroom condo offers comfortable living in a desirable location. The spacious living room features a glass slider that opens to a private balcony overlooking the pond and garden, perfect for relaxing and enjoying the peaceful surroundings. The condo fee includes all utilities, including heat, hot water, and electricity, as well as access to the in-ground swimming pool. A private basement storage unit is also included for added convenience. With its comfortable layout, private balcony, pond and garden views, included utilities, and convenient location, this move-in-ready condo is a great opportunity you won’t want to miss!

200 Swanton St Unit 727, Winchester

$495,000

2 Beds ⋅ 1 Baths ⋅ 73578112 MLS ⋅ ['Parkview'] BLDG.

Enjoy the best of Winchester living in this beautifully updated two-bedroom condo at Parkview, just minutes from Winchester Center, local shops, dining, parks, and commuter access. A bright, open-concept layout creates an inviting flow for everyday living and entertaining. The modern kitchen features stainless steel appliances, while fresh paint throughout adds a crisp, contemporary feel. Both generously sized bedrooms offer excellent closet space and flexible living options. The living area overlooks a scenic duck pond and professionally maintained grounds, creating a peaceful setting year-round. The secure card-entry building offers ample resident parking, guest parking off Swanton Street, and access to an in-ground pool. HOA includes heat, hot water, electricity, and AC for exceptional convenience and value. One basement storage unit is included.

200 Swanton St Unit 303, Winchester

$459,900

3 Beds ⋅ 2 Baths ⋅ 5108720 MLS

Price Improvement!!!! Welcome HOME and move right in to this lovely 3 year old 2 story Colonial home!!! New Englander style featuring 3 bedrooms, 2 bathrooms and room for everyone! Enter into the home from your charming farmer's porch into a spacious living room; room for entertaining, movie or game nights and so much more!!! Expansive open concept kitchen and dining boasts fully applianced kitchen, granite countertops, large kitchen island and pantry. Sliders to your 16x12 deck off the dining room lead you to your level back yard where BBQs, yard games and gardening can take place. On the second level of the home you will find your spacious primary bedroom with walk in closet and large full bathroom. 2 additional ample sized bedrooms and laundry area complete the second floor. Close to town and amenities, walk to the town beach and boat launch, easy commute to Keene, Brattleboro and I91. This home is efficient, well built and ready for you. Don't miss the opportunity to make this wonderful home yours!!!

366 Keene Rd, Winchester

$310,000

3 Beds ⋅ 1 Baths ⋅ 5107206 MLS

Price Reduction, Motivated Seller. Welcome to this beautifully renovated single-family home featuring 3 bedrooms and thoughtful new updates throughout. This move-in-ready property offers a comfortable and inviting layout, making it an excellent choice for a first-time homebuyer or anyone looking for a great starter home. With its fresh updates and welcoming atmosphere, this home is ready for its next owner to make it their own. Situated across the road from the Ashuelot River come take a look for yourself.

73 Ashuelot Main St, Winchester

$357,900

3 Beds ⋅ 2 Baths ⋅ 5105670 MLS

Generous price improvement!! Step inside this comfortable updated ranch. With 3 bedrooms, including the primary with en suite, this home is designed for easy, enjoyable living with space for all. Enjoy the outdoors from the huge screened-in porch, perfect for relaxing, entertaining, or simply taking in the peaceful surroundings. An additional enclosed porch provides even more flexible living space. The home has been modified for added accessibility, features newer flooring throughout, and central A/C for year-round comfort. Peace of mind comes easy with an automatic standby generator, while the vinyl siding and metal roof provide durable, low-maintenance exterior protection. The fenced-in backyard offers a great space for pets, gardening, recreation, or simply enjoying the outdoors. For those who like to tinker or tackle projects, the basement workshop provides a dedicated workspace as well as storage. This home offers low-maintenance living at its best. A home where you can spend less time on upkeep and more time enjoying life. Interior paint needs refreshing.

10 Burt Hill Rd, Winchester

$499,900

2 Beds ⋅ 2 Baths ⋅ 5101659 MLS

Set back from the road at the end of a well-maintained driveway sits this adorable waterfront home with gorgeous views over Forest Lake! The property features an open concept kitchen/dining/living area overlooking the water, a large deck, screened in porch, 2 ample sized bedrooms plus a full bath to complete the first level. Downstairs offers a bonus bunk room, sitting area, plus bath and laundry. Add in the handy storage shed, plenty of available parking spaces, large .40 acre lot, private dock and beach area on your 103 feet of lake frontage, and you have the total package!

418 Forest Lake Rd, Winchester

$445,000

3 Beds ⋅ 2 Baths ⋅ 5096976 MLS

This year-round lakefront retreat offers 100 feet of shoreline on Forest Lake and combines comfort, character, and stunning water views. Relax on the enclosed porch or one of several decks while enjoying the peaceful lakeside setting. The open-concept living and dining area features a pellet stove and abundant windows that capture beautiful lake views throughout the seasons. Outdoor living takes center stage, whether you're enjoying your morning coffee on the porch, entertaining on the decks, or spending the day on the water. A separate mobile home that has not been used for some time and could potentially serve as a guest cottage or private accommodation for family and visitors. It includes a living room, kitchen with pantry, bedroom, bathroom, attached shed, its own septic system, and a wood stove ready for hookup. Whether you're seeking a year-round residence, vacation getaway, or a property with space for extended family and guests, this unique waterfront offering provides the perfect blend of tranquility, recreation, and lakeside living.

71 Headlands Rd, Winchester

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 .