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85 High Street, Winchester
$1,899,000
4 Beds ⋅ 3 Baths ⋅ 73596915 MLS
Discover the possibilities to make your home, Yours. Classic Colonial nestled within one of Winchester’s most desirable neighborhoods, offering timeless architecture, exceptional flexibility, within a rare setting. The first floor features an updated kitchen with slider to the scenic rear yard and oversized brick patio, casual den, half bath, formal dining room, and gracious living room with fireplace and classic built-ins. Double doors lead to a spectacular all-season porch, perfectly positioned for effortless entertaining indoors or out. The second floor offers four corner bedrooms, including a spacious primary suite with double closets, ensuite bath, and convenient laundry. The walk-up third floor invites endless possibilities with an additional bedroom and abundant closet space. Approximately 500 square feet of finished lower-level flex space provides room for a home gym, teen retreat, playroom, or office. Outside, a private, level yard offers ample space for gardens, play, and entertaining, with a generous brick patio for relaxing and gathering. The two-car heated garage features a full walk-up second floor, ideal for storage or future finishing as a studio, office, or home-away-from-home retreat. Simply a beautiful home in an exceptional location—ready to be loved from day one.

85 High Street, Winchester
3 Sunset Road, Winchester
$1,699,000
4 Beds ⋅ 3 Baths ⋅ 73596720 MLS
Welcome to 3 Sunset Road, a beautifully updated 4 BR 2.5 bath colonial with rear addition featuring a 1st floor primary option, a fabulous great room w/vaulted ceilings, and a versatile floor plan! This beautiful home is situated on a generous 1/2 acre lot in one of Winchester’s most loved neighborhoods! The large renovated kitchen with custom cabinetry & high end appliances offers plenty of room for storage, cooking and gathering and opens to a lovely dining room w/ easy access to an expansive deck overlooking the gorgeous back yard, perfect for indoor and outdoor entertaining. A warm and inviting living room features a wood-burning fireplace, while the impressive family room with soaring vaulted ceilings provides an incredible space to gather. The luxurious primary suite offers a spacious bath with double vanities, a walk-in closet, and a private sunroom, ideal for a home office, gym, or quiet retreat. Three additional bedrooms and a full updated bath complete the second level. The finished lower-level playroom offers even more flexible living space. Outside, the expansive, private backyard is truly special, offering endless possibilities for kids play, gardening, entertaining, relaxing. A wonderful opportunity to move right in and enjoy spacious living in a fantastic Winchester location, convenient to schools, shops, restaurants, and all that Winchester has to offer!

3 Sunset Road, Winchester
481 Forest Lake Rd, Winchester
$329,900
3 Beds ⋅ 1 Baths ⋅ 5116190 MLS
YOUR SCENIC LAKE-VIEW HOME AWAITS WITH EXPANDABLE VALUE! Wake up every day to beautiful water views! This 3-bedroom ranch sits just across the street from Forest Lake and perfectly blends effortless single-level living with an extraordinary equity-building opportunity. Step outside your front door to views of Forest Lake, or look inside to discover the home’s hidden gem: a sunlit 500 SF dry-walled garage boasting high vaulted ceilings and windows with lake views. While it functions beautifully as a clean oversized 1 car garage, this architectural canvas is a buyer’s dream, offering an established foundation and roof-line with the possibility of transforming into a massive heated family room or bonus space. Enjoy the quintessential New Hampshire lake lifestyle with low maintenance and easy proximity to the town beach. Whether you are looking to downsize, invest, or capture a beautiful scenic escape before winter, this property delivers immense lifestyle value. Come explore the possibilities this home offers, PLUS it's located just 15 minutes south of Keene. Showings begin at the open house Saturday 10/31 at 11-2p and Sunday 11/01 from 12-2p.

481 Forest Lake Rd, Winchester
67-69 Hemingway St, Winchester
$1,450,000
73595844 MLS
Excellent development opportunity in Winchester! This 22,403 sq. ft. lot at 67-69 Hemingway Street is approved for the construction of two townhomes, with architectural plans included in the sale. The proposed design features two spacious residences, each offering 4 bedrooms, 2.5 baths, open-concept living and dining areas, mudroom, walk in pantry, a private primary suite, outdoor living space, an attached garage, and the option to finish the basement for additional living space. Zoned RG, the property will be delivered as a vacant lot, with public water, public sewer, and natural gas available, providing an excellent opportunity for builders and developers to bring this project to life. The location offers an appealing combination of neighborhood living, outdoor recreation, and commuter convenience. Just minutes from the newly constructed Lynch Elementary School, Horn Pond's scenic walking trails, and the Tri-Community Bike Path, the property provides easy access to some of Winchester's favorite outdoor destinations. Downtown Winchester offers a vibrant mix of local shops, restaurants, cafés, and community amenities, along with commuter rail service to Boston. Convenient access to Routes 93 and 95 adds to the property's appeal. Winchester continues to be a highly desirable community with a strong buyer pool seeking quality new construction. With approvals in place, architectural plans included, and a location that appeals to today's homebuyers, this is an attractive opportunity to develop two new residences in one of the area's most sought-after markets.

67-69 Hemingway St, Winchester
37 Michigan St, Winchester
$699,000
5115957 MLS
Welcome to 37 Michigan Street, a meticulously cared-for, turnkey four-unit multi-family property offering incredible versatility, robust cash flow, and complete flexibility. The unit mix features a spacious four-bedroom open-concept layout that is ideal for an owner-occupant or high-yield rental income, complemented by one two-bedroom apartment and two one-bedroom apartments for a total of eight bedrooms across the entire building. High-quality infrastructure provides rare peace of mind, highlighted by a dependable Buderus furnace, durable metal roof, separate electric meters for each apartment, a coin-op laundry room, and a sprawling, private back yard. Situated on 8.9 wooded acres, the property boasts valuable standing timber and unlimited potential for future expansion or development with town approval. Nestled in charming Winchester, owners and tenants enjoy a vibrant Monadnock Region lifestyle with local craft tasting rooms, historic covered bridges, and peaceful paddling on the Ashuelot River. Outdoor enthusiasts will appreciate being just minutes from the 13,300-acre Pisgah State Park for hiking, mountain biking, and trail exploration, all while commuting with quick drives to Keene, Massachusetts, and Vermont. Whether you choose to house-hack by living virtually rent-free in the flagship four-bedroom home or expand your investment portfolio with an income-generating property, this presents a rare blend of charm, turnkey quality, and immediate upside.

37 Michigan St, Winchester
679 Warwick Rd, Winchester
$499,900
4 Beds ⋅ 2 Baths ⋅ 5115929 MLS
Step back in time with this 1770 post-and-beam Antique Colonial. Poised in a picturesque setting, the property welcomes you with iconic stone walls and scenic views of surrounding pastures. Inside, rich wide-pine flooring tells a story of age-old craftsmanship, anchored by three stately brick fireplaces that serve as warm, distinguished focal points. Character-rich kitchen, complete with a built-in hutch, a cozy pellet stove, and a versatile loft space. Adding immense value is the attached 50-by-20-foot barn, offering an expansive, flexible footprint for a workshop, hobby space, or extra storage. A rare opportunity to own a piece of living history. Additional acreage available. Agent interest.

679 Warwick Rd, Winchester
581 Keene Rd, Winchester
$629,000
2 Beds ⋅ 2 Baths ⋅ 5115857 MLS
Discover a unique property offering comfortable living, excellent visibility, and exceptional versatility. This property features a 1,500 SF home/living space, providing an inviting residential space, along with additional buildings and income-producing opportunities. Conveniently located on Route 10, the property offers easy access and outstanding potential for a variety of residential and business uses. In addition to the living area, the property includes a 1,500 SF commercial space and a 3,345 SF garage featuring four bays, a paint booth, and office space. The garage is nearly turnkey and could be ideal for an automotive enthusiast, mechanic, motorcycle hobbyist, or anyone seeking space for a home-based business, subject to applicable approvals. The property also has town permission to display up to ten vehicles for sale and includes a leased food truck site. With the apartment and commercial space already leased, the property offers an opportunity to enjoy rental income while exploring its many possibilities. The garage is currently leased month-to-month at below-market rent, providing flexibility for a future owner to occupy the space or maximize its income potential. The previous garage tenant paid $2,700 per month, and projected net operating income for the property is approximately $45,795 annually once the garage is leased at market rates. Serviced by private well and septic, this distinctive property combines residential living with additional space, income potential, and versatility in a convenient Winchester location. Whether you're looking for a property with room for your hobbies, space for a business, or an opportunity to supplement your income, 581 Keene Road offers a compelling combination of possibilities.

581 Keene Rd, Winchester
28 Olive St, Winchester
$1,049,900
3 Beds ⋅ 2 Baths ⋅ 73595417 MLS
Welcome to 28 Olive Street, a renovated 3-bedroom, 2-bath ranch in Winchester with 1,783 square feet of finished living space and a top-to-bottom update that lets you move right in. The main level centers on an all-new, slightly expanded eat-in kitchen that opens to an adjacent living room. A wood-burning fireplace and shiplap accent wall anchor the living room. The main living level features refinished hardwood floors, all-new doors, trim, ceilings, and lighting, plus new central AC. Three bedrooms share a completely updated full bath. Downstairs, the finished lower level adds valuable flexible space. The spacious recreation room offers plenty of space for a media area, gym, or home office, plus a second full bathroom, recessed lighting, vinyl flooring, and its own mini-split for heating and cooling. A separate utility room keeps storage, laundry, and mechanicals out of sight. The big-ticket items are done: new roof, windows, siding, electrical service, and exterior doors. The 6,527-square-foot corner lot has a private driveway, new entry stairs, and a crisp new white vinyl fence surrounding the entire property. With the heavy lifting already complete, 28 Olive Street is a rare chance to own in Winchester without the projects. Offers, if any, will be reviewed Monday at Noon.

28 Olive St, Winchester
976 Old Westport Rd, Winchester
$269,900
3 Beds ⋅ 3 Baths ⋅ 5115622 MLS
Nestled in a picturesque setting directly across from the scenic Coombs Covered Bridge, this antique farmhouse offers a blend of rustic charm and practical living space. Situated on over two sloping acres, the property features two bedrooms and a country kitchen with a cozy fireplace perfect for gathering after a long day. Livingroom features wide wood flooring and small first-floor office with a half bath provides flexible functionality, making it ideal for a home office, studio space, or bedroom. BBHW heat with large supplemental wood stove in the basement. Though the home could use some updates, its layout and charm make it a fantastic choice for a personalized renovation and the Seller will also contribute $10000 towards Buyers allowable closing costs!!

976 Old Westport Rd, Winchester
67-69 Hemingway St, Winchester
$1,450,000
8 Beds ⋅ 6 Baths ⋅ 73594547 MLS
Excellent development opportunity in Winchester! This 22,403 sq. ft. lot at 67-69 Hemingway Street is approved for the construction of two townhomes, with architectural plans included in the sale. The proposed design features two spacious residences, each offering 4 bedrooms, 2.5 baths, open-concept living and dining areas, mudroom, walk in pantry, a private primary suite, outdoor living space, an attached garage, and the option to finish the basement for additional living space. Zoned RG, the property will be delivered as a vacant lot, with public water, public sewer, and natural gas available, providing an excellent opportunity for builders and developers to bring this project to life. The location offers an appealing combination of neighborhood living, outdoor recreation, and commuter convenience. Just minutes from the newly constructed Lynch Elementary School, Horn Pond's scenic walking trails, and the Tri-Community Bike Path, the property provides easy access to some of Winchester's favorite outdoor destinations. Downtown Winchester offers a vibrant mix of local shops, restaurants, cafés, and community amenities, along with commuter rail service to Boston. Convenient access to Routes 93 and 95 adds to the property's appeal. Winchester continues to be a highly desirable community with a strong buyer pool seeking quality new construction. With approvals in place, architectural plans included, and a location that appeals to today's homebuyers, this is an attractive opportunity to develop two new residences in one of the area's most sought-after markets.

67-69 Hemingway St, Winchester
5 Forest Cir, Winchester
$2,999,000
5 Beds ⋅ 5 Baths ⋅ 73594545 MLS
New construction currently underway. Estimated completion in approximately Spring/Summer 2027. Set on an impressive 22,629 sq. ft. lot, this beautifully crafted new construction offers exceptional space, thoughtful design, and a peaceful setting with easy access to the Middlesex Fells Reservation and I-93. Designed for today's lifestyle, the main level features a welcoming foyer, elegant living and dining rooms, a spacious family room with fireplace, and a stunning chef's kitchen with a walk-in pantry and adjoining mudroom and half bath. Upstairs, the luxurious primary suite is complemented by four additional bedrooms, 4 beautifully appointed baths, and a convenient second-floor laundry room. An attached two-car garage, generous backyard, and exceptional craftsmanship throughout complete this rare opportunity to own a stunning new home on a charming side street.

5 Forest Cir, Winchester
16-18 Russell Rd, Winchester
$1,049,000
4 Beds ⋅ 2 Baths ⋅ 73594513 MLS
Welcome to 16-18 Russell Road, a classic two-family home tucked along a tranquil one-way street just a short walk from downtown Winchester. The bright upper level features 3 bedrooms and 1 bath, while the flexible lower level offers a 1-bedroom, 1-bath layout with the potential to expand to two bedrooms, providing added versatility for investors, multigenerational living, or owner-occupants looking to offset their mortgage with rental income. Hardwood floors run throughout much of the home, while ductless mini-split systems provide efficient heating and cooling, complemented by a gas forced-air system in the basement. Vinyl siding and an asphalt roof help keep exterior maintenance manageable, while ample off-street parking and a yard add everyday convenience. Located within the district for the newly built Lynch Elementary School, the home is also just a short walk to the commuter rail, a new neighborhood coffee shop, restaurants, and amenities of Winchester's vibrant town center.

16-18 Russell Rd, Winchester
18 Middlesex St, Winchester
$2,650,000
4 Beds ⋅ 5 Baths ⋅ 73593868 MLS
Inspired by the timeless villas of Europe, this exceptional residence blends classic elegance with modern design. A dramatic curved staircase and soaring architectural details introduce inviting living spaces featuring handcrafted finishes, antique beams, stone fireplaces, and expansive French doors that connect seamlessly to the outdoors. At the heart of the home, a chef’s kitchen showcases custom cabinetry, luxury appliances, and an adjoining mudroom. The outdoor setting offers a private retreat with a granite-columned loggia, heated saltwater pool, landscaped grounds with irrigation, and multiple areas for entertaining.The spa-inspired primary suite, ensuite guest bedrooms, and finished lower level with flexible bonus spaces provide comfort and versatility. Heated driveways and walkways add year-round convenience. Ideally located within walking distance of downtown, the new Lynch School, the new commuter rail station, and an array of shops and restaurants, this home offers a thoughtful balance of timeless style, modern amenities, and everyday comfort.

18 Middlesex St, Winchester
15 Foxcroft Rd, Winchester
$3,799,000
8 Beds ⋅ 6 Baths ⋅ 73593484 MLS
Welcome to 15 Foxcroft Road, an 8-bedroom home with 4 full and 2 half baths in Winchester's sought-after Flats neighborhood, offering over 7,000 sq ft on a beautiful corner lot. Two private suites make it ideal for multigenerational living, in-laws, caregivers, au pairs, or long-term guests, with ADU-style flexibility already built in. A full 2012 renovation created a large kitchen with oversized butler's pantry, a spacious family room with built-in cabinetry, a dining room, a playroom, and a mudroom with half bath on the first floor. The second floor has four more bedrooms, including a primary suite with full bath and large walk in closet. The third floor adds an additional bedroom and an office as well as cedar closet. The finished lower level features a full bar, a half bath, and ample space for a game room or media room. This property offers the unique ability to offer two suites perfect for extended family or caretakers. The first-floor suite offers single-level living with two bedrooms, a living room, and a full bath with a zero-entry shower. The second-floor suite has its own private staircase, bedroom, living room, and full bath for real independence from the main household. Outside, enjoy a fully fenced yard, wraparound porch, patio with fire pit, and an attached two-car garage. A unique and special property in one of Winchester's best neighborhoods!

15 Foxcroft Rd, Winchester
419-421 Washington St, Winchester
$1,299,000
6 Beds ⋅ 2 Baths ⋅ 73592723 MLS
An exceptional turnkey opportunity in Winchester, 419–421 Washington Street presents a beautifully refreshed two-family residence featuring significant mechanical upgrades and refined finishes throughout. Major improvements include a brand-new roof, newly paved driveway with parking for 4–5 vehicles, separate central heating and air conditioning systems, separate utilities, fresh interior and exterior paint, and beautifully refinished hardwood floors. Ideally situated near vibrant Winchester Center, enjoy convenient access to local dining, boutique shopping and commuter rail service to Boston. Proximity to Winchester Hospital, I-93, Route 128/I-95, Middlesex Fells Reservation and Winchester's highly regarded schools further enhances the appeal. Move-in ready with extensive recent improvements, this exceptional property offers an ideal opportunity for owner-occupants and investors seeking lasting value in one of Greater Boston's most desirable communities.

419-421 Washington St, Winchester
18 Surrey Road, Winchester
$2,950,000
6 Beds ⋅ 4 Baths ⋅ 73592433 MLS
Spacious seven-bedroom, four-bath home in one of the area's most sought-after neighborhoods, thoughtfully designed with the flexible living space today's lifestyles demand. Whether accommodating a multigenerational household, extended family, long-term guests, or creating dedicated work and hobby spaces, this home offers exceptional versatility. The main level features an oversized living room with an open-concept layout flowing seamlessly into the dining area and kitchen, creating the perfect gathering space for everyday living and entertaining. French doors open to a large deck, extending the living space outdoors. Two first-floor bedrooms and a full bath provide convenient options for guests, family members, or a home office. Upstairs, you'll find four additional bedrooms, including a spacious primary suite with its own private balcony, a peaceful retreat to begin and end the day. The finished lower level adds even more flexibility with a generous family room, an additional bedroom or office, and direct access to the heated three-car garage. With abundant space to grow, gather, and adapt to changing needs, this exceptional home is ready to welcome its next chapter.

18 Surrey Road, Winchester
49 Keene Rd, Winchester
$589,000
6 Beds ⋅ 4 Baths ⋅ 5114832 MLS
Welcome to this brand new, turn-key two-family home, offering the perfect opportunity for investors or owner-occupants looking to offset their mortgage! Each side of this modern duplex features an identical, spacious layout boasting 3 bedrooms and 1.5 bathrooms. Built from the ground up with contemporary living in mind, both units come with fully applianced kitchens equipped with brand-new refrigerators, stoves, microwaves, and dishwashers. Side-by-side design means no neighbors above or below you, maximizing peace and privacy. Enjoy complete independence and low maintenance with fully separate utilities for each unit, including individual meters for electricity, gas, and water. Each unit has a full basement with plenty of space for all of your needs. Whether you are an investor looking to add a premium, low-maintenance asset to your portfolio, or a homeowner looking to live in one side and let the tenant pay your mortgage, this property is a rare find.

49 Keene Rd, Winchester
Manning Hill Rd, Winchester
$59,000
5114423 MLS
Located on ROUTE 10 Manning Hill Road is where you will find this 1 acre + - building lot with driveway already on property. Level to slightly sloping wooded lot with 168' of road frontage. Easy access to all conveniences that Winchester has to offer. Only tract 1 of deed to be conveyed at time of sale.

Manning Hill Rd, Winchester
80 Nelson St, Winchester
$890,000
2 Beds ⋅ 1 Baths ⋅ 73591108 MLS
Endless possibilities in this well-loved home less than 1/3rd mile from Winchester High School. Owned by the same family since 1950, this home has been lovingly cared for and is now ready for your updates. The main floor features high ceilings, an eat-in kitchen, and a large rear family sunroom drenched in light. Upstairs you'll find a front-to-back main bedroom, full bath, and nursery, as well as a finished staircase to the third floor, which was used as additional bedroom space. Large level back yard on a quiet street means ample opportunity to entertain or expand.

80 Nelson St, Winchester
Old Swanzey Road, Winchester
$65,000
5114283 MLS
Your opportunity to build in the beautiful Monadnock Region awaits! Situated in Winchester, NH, this 2.64-acre residentially zoned parcel offers an inviting country setting with the convenience of nearby amenities. Whether you're envisioning a cozy New England retreat or a custom-built home, this property provides an opportunity to bring your plans to life. Previously perc tested, the parcel is located in a rural area where you can enjoy the charm of small-town living without feeling far removed from everyday conveniences. Winchester offers a welcoming community atmosphere, outdoor recreation, and access to the natural beauty that makes southwestern New Hampshire such a desirable place to call home. Enjoy the best of both worlds with a peaceful setting and convenient access to Keene, neighboring communities, and the Massachusetts and Vermont borders. Bring your vision and explore the possibilities of making this property your own!

Old Swanzey Road, Winchester
6 Aricia Ln, Winchester
$1,399,000
3 Beds ⋅ 3 Baths ⋅ 73590311 MLS
Situated on a quiet cul-de-sac in a desirable Winchester neighborhood surrounded by substantial homes, this well-maintained 3-bedroom, 2.5-bath Split-Level offers comfortable living and plenty of potential on a generous 19,998 sq. ft. lot. Built in 1976, the home features hardwood floors throughout and central air conditioning. The main level includes a spacious living room, formal dining room, and eat-in kitchen with access to a screened porch overlooking the backyard. Three bedrooms, including a primary suite with private bath and a renovated family bathroom, complete this floor. The lower level provides additional living space with a family room featuring a fireplace, laundry area, half bath, and direct access to the attached two-car garage. Lovingly cared for over the years, this home is ready to enjoy as is, with room to make it your own over time. Conveniently located near Vinson-Owen School, Wright-Locke Farm, and the Winchester Swim & Tennis Club, it's a great opportunity to settle into one of Winchester's sought-after neighborhoods.

6 Aricia Ln, Winchester
49 Keene Rd, Winchester
$589,000
5114050 MLS
Welcome to this brand new, turn-key two-family home, offering the perfect opportunity for investors or owner-occupants looking to offset their mortgage! Each side of this modern duplex features an identical, spacious layout boasting 3 bedrooms and 1.5 bathrooms. Built from the ground up with contemporary living in mind, both units come with fully applianced kitchens equipped with brand-new refrigerators, stoves, microwaves, and dishwashers. Side-by-side design means no neighbors above or below you, maximizing peace and privacy. Enjoy complete independence and low maintenance with fully separate utilities for each unit, including individual meters for electricity, gas, and water. Each unit has a full basement with plenty of space for all of your needs. Whether you are an investor looking to add a premium, low-maintenance asset to your portfolio, or a homeowner looking to live in one side and let the tenant pay your mortgage, this property is a rare find.

49 Keene Rd, Winchester
156 Forest Lake Rd, Winchester
$299,999
4 Beds ⋅ 1 Baths ⋅ 5113915 MLS
Discover the possibilities at this inviting property set on 1.23 private acres in Winchester, New Hampshire! Offering 4 bedrooms, 1 full bath, and a versatile bonus room, this home provides plenty of space to make it your own. Whether you're looking for room to spread out, space for hobbies, or an opportunity to create a home that reflects your personal style, there's plenty of potential here. The bonus room offers flexibility for a home office, hobby space, playroom, or additional living area, depending on your needs. A 2-car garage provides valuable space for vehicles, storage, tools, or recreational equipment. Enjoy the privacy and breathing room of a generous lot while taking advantage of all that southwestern New Hampshire has to offer. If you've been searching for a property with four bedrooms, a garage, and room to make your vision a reality, 156 Forest Lake Road is worth a closer look. Bring your ideas and explore the possibilities!

156 Forest Lake Rd, Winchester
30 Surrey Rd, Winchester
$1,985,000
4 Beds ⋅ 4 Baths ⋅ 73589478 MLS
Set on over an acre of beautifully landscaped grounds abutting acres of woodland, this extensively renovated Contemporary Cape offers exceptional privacy and a peaceful connection to nature. A thoughtfully designed open floor plan features hardwood floors, a fireplaced living room, elegant dining room, and a beamed-ceiling family room adjoining the remodeled kitchen with stone counters, stainless appliances, and island. A private great room off the foyer, with windows on three walls and a slider to the spacious deck, offers a wonderful retreat. French doors open to the expansive deck overlooking the fenced backyard and wooded surroundings. Upstairs, four bedrooms include a primary suite with custom closets and private bath. The finished walkout lower level offers flexible space for a home office, gym, or guests, with separate entrance and full bath. Stone walls, mature landscaping, a long private driveway, and two-car garage complete this exceptional home.

30 Surrey Rd, Winchester
21 Amberwood Dr, Winchester
$1,999,000
5 Beds ⋅ 4 Baths ⋅ 73588059 MLS
Welcome to this beautifully appointed and exceptionally spacious home, ideally situated in a quiet, desirable West Side Winchester neighborhood within the sought-after Vinson-Owen School district. Offering an impressive combination of elegant living spaces, flexible accommodations, and thoughtful upgrades, this home provides room for everyone while easily adapting to a variety of lifestyles. At the heart of the home is the expansive granite kitchen, designed for both everyday living and entertaining. Custom cabinetry, Thermador double ovens, a Dacor warming drawer, Sub-Zero refrigerator, wine refrigerator, recessed lighting, and an impressive 50-square-foot center island create a wonderful gathering space with plenty of room for cooking, dining, and entertaining. The kitchen flows into a comfortable family room featuring a custom-built entertainment center and electric fireplace. A gracious formal dining room showcases handcrafted molding and classic wainscoting, while additional first-floor living spaces provide tremendous flexibility for a formal living room, playroom, home office, den, or whatever best suits your needs.One of the home's most appealing features is the first-floor bedroom suite with a full bath, offering exceptional versatility for extended family, guests, an au pair, or anyone seeking the convenience of first-floor living. A dedicated laundry room on this level adds even more functionality. With multiple living areas and flexible rooms throughout the first floor, there are countless ways to create private spaces for additional family members while still enjoying plenty of room to gather together.Upstairs, the generously sized primary suite provides a relaxing retreat with vaulted ceilings, recessed lighting, double closets, and a beautifully tiled private bath with double sinks. Three additional spacious bedrooms, another full bath, and additional office space provide abundant room for family, guests, work-from-home needs, hobbies, or study areas.With its generous proportions, flexible floor plan, multiple bedroom and living configurations, and outstanding West Side location, this is a home designed to grow and change with its owners. Enjoy the peace and privacy of a quiet neighborhood while being part of the wonderful Winchester community. This is more than simply a beautiful house—it is a home offering the space, versatility, and comfort today's buyers are looking for.

21 Amberwood Dr, Winchester
20 Arthur St Unit 20, Winchester
$329,900
2 Beds ⋅ 1 Baths ⋅ 73587970 MLS
Property to be sold in as is condition. This unit is subject to the Winchester Housing Corp resale procedures. See document section for additional details. Buyer is responsible for any and all inspections needed for the sale of this unit. This unit is vacant and easy to show. See attachment for qualification calculations.

20 Arthur St Unit 20, Winchester
44 Gunn Mountain Rd, Winchester
$349,900
4 Beds ⋅ 2 Baths ⋅ 5112930 MLS
When you look for a good family home, I hope you're lucky enough to find one like this! Same owners for the past 35yrs, mountains of updates and improvements, and investment! From the plumbing, heating system, 200A electrical, hot water, appliances, siding and so much more! (see the disclosures) The icing on the cake is the 24x36' garage with two full stories! You'll walk into a large sunroom, then step into a big family kitchen, with doorways to the office and living room. A full ADA bath on the first floor has a large step in shower, whirlpool tub and laundry! Beautiful floors throughout, replacement windows and tall ceilings will make you feel right at home. The garage is absolutely amazing, has dedicated electrical service, GOBS of storage or hobby space! (Garage was $75k) This is an affordable family home in a quiet setting that you can move into with confidence and pride.

44 Gunn Mountain Rd, Winchester
39 Henry Street, Winchester
$850,000
3 Beds ⋅ 1 Baths ⋅ 73585414 MLS
Exceptional Winchester living awaits at this charming 3-bedroom ranch in the coveted Vinson-Owen district! Offering 1,313 sq. ft. of bright, comfortable space plus basement expansion potential, this home features a classic fireplace living room, formal dining, and a wonderful kitchen. Step outside to a sprawling deck and a lush, private backyard that feels like your own private retreat. Complete with a 2020 roof and 2023 electrical panel, this gem is ready to welcome its next chapter!

39 Henry Street, Winchester
15 Vinson Circle, Winchester
$18,000,000
6 Beds ⋅ 7 Baths ⋅ 73585235 MLS
A NEW BENCHMARK FOR LUXURY LIVING IN WINCHESTER. Introducing a truly one-of-a kind estate—an extraordinary new residence created without compromise on approximately one private acre at the end of a cul-de-sac. Encompassing nearly 10,000 SF, 21 rooms, 6 bedrooms and 7 baths, this remarkable property brings together architectural presence, exceptional craftsmanship, advanced technology and resort-caliber amenities rarely found in a single Greater Boston residence.Beyond its gated entrance and heated driveway, sophisticated interiors unfold through grand entertaining spaces, a statement chef’s kitchen, library/office with wet bar, glass-enclosed fitness studio, acoustically designed cinema, wine lounge and underground wine cellar. The exceptional primary suite features a luxurious dressing room and dramatic two-tier panoramic veranda overlooking the grounds.Outside, the estate transforms into a private resort: spectacular pool with waterfall, integrated spa, flame features and automatic cover; covered outdoor kitchen; sunken conversation lounge with central fire feature; covered dining terrace with fireplace; and beautifully designed grounds offering extraordinary privacy.Behind the elegance is equally impressive infrastructure: 18 heating zones, 9 cooling zones, 600-amp electrical service, approximately 2.5M BTU gas capacity, integrated AV/security, automated gated entry and a 3-car climate-conscious auto lounge with porcelain flooring and dual EV charging.Minutes from Winchester Center and convenient to Boston, this is far more than exceptional new construction. It is a meticulously conceived private estate where architecture, technology, wellness, entertainment and resort living converge—created for the buyer seeking something that simply cannot be replicated.

15 Vinson Circle, Winchester
1 Plymouth Rd., Winchester
$3,299,000
7 Beds ⋅ 8 Baths ⋅ 73585058 MLS
$50,000 BUYER INCENTIVE!!! Our seller is offering buyers a $50K credit to be used as you want. Buy down your mortgage rate, order upgrades, pay closing costs. Choice is yours! Ideally situated in one of Winchester’s most serene neighborhoods, this exceptional residence offers impressive scale, thoughtful design, and remarkable versatility in a quiet, peaceful setting. It also represents one of Winchester's best values, with tremendous square footage and an au-pair/in-law apartment. Surrounded by beautiful homes and a sense of established elegance, this is a property designed to feel both private and welcoming. Thoughtfully expanded and beautifully built, the home offers 7 bedrooms and 7.5 baths, with generous living spaces designed for both everyday comfort and effortless entertaining. At the heart of the home, a stunning chef’s kitchen opens seamlessly to a dramatic fireplaced living room with soaring cathedral ceilings, creating a warm and inviting gathering space filled with natural light. There is also a family room, also with a fireplace and large picture windows, allowing for an abundance of sunlight. Explore further and you'll find a huge butler's pantry, a must-have feature in today's homes. There is also a wet bar with a beverage fridge. This is a home that has been very thoughtfully designed for how today's buyers actually live, but what truly distinguishes it is the flexibility of design. A private two-bedroom suite offers its own living area, office, wet bar, and full bath, providing an exceptional option for an au pair, extended stays, guests, returning college students or a more private living arrangement. The finished lower level adds even more space for recreation, fitness, entertaining, or simply spreading out. Beautifully proportioned rooms, exceptional functionality, and a serene neighborhood setting come together to create a home that feels substantial yet comfortable, sophisticated yet wonderfully livable. The natural light is exceptional, and outside, an oversized lot offers plenty of play space and a deck to hang out on. Just moments from Mullen Field, close to the town center and trains and an easy trip to Lexington or Cambridge, 1 Plymouth offers a rare opportunity to enjoy exceptional space and privacy in one of Winchester’s most sought-after neighborhoods.

1 Plymouth Rd., Winchester

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