Winchester Homes under $1 million

Welcome to Winchester, a charming city nestled in the picturesque Shenandoah Valley of Virginia. Known for its rich history, vibrant arts scene, and stunning natural landscapes, Winchester is a delightful blend of small-town charm and modern amenities. With its historic downtown area, featuring beautifully preserved 18th and 19th-century architecture, residents and visitors can enjoy a variety of boutique shops, delightful cafes, and cultural attractions, including the renowned Museum of the Shenandoah Valley.

For those looking to call Winchester home, the good news is that the city offers an array of beautiful homes priced under $1 million. Whether you’re seeking a cozy single-family residence, a spacious townhome, or a charming historic property, Winchester has something to suit every taste and lifestyle. Many of these homes boast unique architectural details, spacious yards, and proximity to local parks and schools, making them ideal for families and individuals alike.

Winchester’s community spirit is palpable, with numerous events and festivals throughout the year, including the popular Apple Blossom Festival, which celebrates the region's agricultural heritage. Outdoor enthusiasts will appreciate the nearby hiking trails, scenic parks, and the breathtaking views of the Blue Ridge Mountains.

With its affordable housing options and a welcoming atmosphere, Winchester is not just a place to live; it’s a place to thrive. Discover your perfect home in this enchanting city, where history meets modern living and community bonds flourish. Your dream home awaits in Winchester!

Newest Winchester Homes under $1 million

$899,000

3 Beds ⋅ 1 Baths ⋅ 73585414 MLS

Charming ranch offering 1,313 square feet of main living area plus an additional 260 square feet of flexible basement space ready for finishing. Built in 1955 and set on a generous 15,800-square-foot lot, this home seamlessly blends comfortable interior living with exceptional outdoor space. Key updates include a new roof installed in 2020 and an updated electrical panel in 2023. The inviting layout features a bright living room centered around a classic fireplace, which flows effortlessly into the formal dining room and functional kitchen. Step right outside to a large deck overlooking an expansive, lush backyard—providing a wonderful setting for outdoor dining and gatherings. The sun-filled primary suite serves as a quiet retreat, complemented by two additional versatile bedrooms.

39 Henry Street, Winchester

$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

$1,000,000

3 Beds ⋅ 1 Baths ⋅ 73581744 MLS

Storybook charm meets relaxed, easy living in this inviting Winchester Colonial, ideally located near the natural beauty of the Fells Reservation, Muraco Elementary, and convenient commuter routes. Set on a lovely lot with mature plantings, the property offers a private-feeling outdoor setting, a detached two-car garage, and pretty, original architectural details throughout. Inside, natural light fills the freshly painted interior. The fireplaced living room with wood stove flows seamlessly into the updated kitchen and dining room, creating an easy connection for everyday living and entertaining. The dining room opens to a bright, welcoming sunroom - an ideal spot for morning coffee, reading, or enjoying views of the surrounding yard. Upstairs, two generously sized bedrooms are joined by a third bedroom with a walk-up to additional attic storage, and a charming full bath. The lower level provides even more versatility with a finished bonus room, laundry, plentiful storage and exterior access. Thoughtfully maintained and move-in ready, this home combines timeless architectural character with smart updates and practical spaces designed for today’s lifestyle.

23 Stone Ave., Winchester

$700,000

2 Beds ⋅ 2 Baths ⋅ 73581469 MLS ⋅ ['Wedgewood Place'] BLDG.

Easy one-floor living in Winchester Center with garage parking for one car! Fabulous location near town center, TRAIN, shopping, restaurants, schools and library. Enjoy the open layout with extra wall of beautiful kitchen cabinets, large peninsula/eating bar, fireplace, balcony and a nook for a desk or whatever you wish. Large primary bedroom has two windows, large walk-in closet and full bath. Second bedroom is across hall from laundry and bath with shower. Air handler and condenser replaced in 2022. Central air throughout. Hot water heater and water shutoff installed - 2018. The additional storage unit is off the main lobby for easy access. Amenities include 2 elevators, inviting POOL and onsite rubbish pickup. Perfect home for first time buyers, downsizers, anyone commuting to Boston or in search of a vibrant town center lifestyle.

666 Main Street Unit 217, 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

$974,900

3 Beds ⋅ 3 Baths ⋅ 73575764 MLS

A rare opportunity to own a detached home in Winchester under $1M—with the space, privacy and flexibility often missing from condo or townhome living. Tired of or can't imagine paying an HOA fee on top of fighting rising interest rates? Skip the added cost, lock in (REFI LATER) a lower monthly payment, and get more value at 258 Cross Street! The property is set on a level, fenced corner lot with a side-street driveway, ACCESSIBLE FROM RIVER STREET, parking for 4 cars, and offering 3 bedrooms, a versatile bonus room (4 beds on public record), 2.5 baths and a layout that can adapt as your needs change. The main level blends classic character with everyday function, featuring hardwood floors, crown molding, arched openings, bay windows and an updated eat-in kitchen with stone counters, upgraded cabinetry, stainless appliances and gas cooking. A brand-new first-floor powder room adds convenience for everyday living and entertaining. Upstairs, two generously sized bedrooms are joined by two updated full baths, including a larger bath with double vanity, tiled shower and soaking tub. The finished third floor provides a third bedroom plus an additional flex space ideal for a home office, fitness room, playroom, hobby space or guests. Major recent improvements, besides the unused, first floor half bath, include brand-new central AC and a newly sodded yard. Current owners have also invested considerably into improvements from the kitchen (countertops/appliances/backsplash/flooring), to the main bathroom remodel on the 2nd floor, and even a rebuilding of the lower two staircases to increase functionality. Outside, enjoy a fenced backyard, patio, storage shed and rare off-street parking for four vehicles. The full basement provides additional laundry and storage space. Convenient to Winchester Center, local shops and dining, the commuter rail, the Middlesex Fells and major routes connecting Boston, Cambridge, Burlington and the surrounding metro area. Previously prepared conceptual expansion plans are available for buyers interested in exploring future possibilities.

258 Cross St, Winchester

$769,000

2 Beds ⋅ 2 Baths ⋅ 73575558 MLS ⋅ ['Wedgewood Place Condominiums'] BLDG.

Don't miss this beautifully appointed 2-bedroom, 2 bath unit at Wedgewood Place, a waterfront condominium community that is centrally located in downtown Winchester. Magnificent new kitchen with custom cabinets, quartz counter tops and stainless-steel appliances that looks out at a bright and sunny, spacious open living and dining room and small home office area. Featuring a wood burning fireplace and a private balcony with exceptional views of the pool and garden, perfect for your morning coffee. Beautiful wide plank hardwood floors throughout. Custom vanities and quartz counter tops in both bathrooms. The generous Primary bedroom features custom walk-in closet and large en-suite with separate vanity area. Fresh paint and new light fixtures are among the many upgrades. New elevators and upgraded pool. One level living at its best. Enjoy the serene setting of Wedge Pond and park area right next door or take a short stroll to Winchester's amazing shops and restaurants. Public transportation outside your front door, short walk to train, 2 stops, 20 min and you are in Boston. Covered parking! Additional storage in garage.

666 Main St Unit 310, Winchester

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