56

Homes for Sale near The Downtown School

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  • /40

    $1,245,000

    • 4 Beds
    • 6 Baths
    • 4,272 Sq Ft

    1016 West Rd, Manchester Center, VT 05255

    Manchester Village...an award winning architect transformed this "Sears & Roebuck" mini farmstead indo Living Art! Masterful execution of architectural detail at every turn. Circular landscaped drive ties the residence, garages, and the an impressive party barn together for year round use. The substantial covered stone porch enters the arts & crafts foyer.. with study to one side, ahead the

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 357-7462

    1016 West Rd, Manchester Center, VT 05255
  • /15

    $115,000

    • Land
    • 2.9 Acres
    • $39,655 per Acre

    Lot 3 Route 11 30, Winhall, VT 05340

    Spectacular West and Southerly Views over Manchester Valley and boasts a bird's eye view across to the Equinox Mountain!Located on the Manchester side of Winhall, this property is at the end of a private lane offering privacy... engineered and offering VT Waste Water and Potable Water Supply Permit: WW-2-3614, design for 3 BR single family residence. Bordered by the Green Mountain Nat'l

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 808-6197

    Lot 3 Route 11 30, Winhall, VT 05340
  • /60

    $1,600,000

    • 5 Beds
    • 4.5 Baths
    • 4,243 Sq Ft

    397 Fern Hill, Dorset, VT 05251

    Take a drive up Nichols Hill Road to Fern Hill and head to the very top of the long bending driveway to find a serene, picturesque artist’s retreat 3 minutes from historic Dorset Village. Refreshingly private, quiet and secluded, drenched in natural light. With broad mountain vistas of Mother Myrick and Merck Forest, the top of the property backs gently into a beautiful private forest. The entire

    Agent Photo

    Laura Beckwith

    Josiah Allen Real Estate, Inc.

    (802) 644-3043

    397 Fern Hill, Dorset, VT 05251
  • /36

    $699,000

    • 4 Beds
    • 3 Baths
    • 2,400 Sq Ft

    682 E Manchester Rd, Manchester Center, VT 05255

    Welcome to a private Vermont retreat that blends rustic post-and-beam charm with modern versatility. Nestled above the serene Bourne Brook, this property offers the perfect balance of privacy, natural beauty and convenience. The main house exudes warmth and craftmanship, and is complemented by an income producing apartment above the 2 car garage, adding flexibility for extra guests, long term

    Agent Photo

    Christopher Cummings

    Cummings & Co

    (802) 441-7038

    682 E Manchester Rd, Manchester Center, VT 05255
  • /60

    $650,000

    • 4 Beds
    • 3 Baths
    • 2,975 Sq Ft

    58 Hicks Ln, Manchester Center, VT 05255

    OPEN HOUSE SATURDAY 10/25 11AM - 1PM ~ Manchester Center VT home for sale. Classic single family Colonial on a rare in town 0.70 acre lot. Quiet dead end lane near downtown. This 4 bedroom 3 bath property offers about 3,000 SF of finished living area plus flexible bonus space. The floor plan supports daily living and weekend guests with ease for the Manchester Center lifestyle in Bennington

    Nick Sicard EXP Realty

    58 Hicks Ln, Manchester Center, VT 05255
  • /38

    $4,975,000

    • 5 Beds
    • 4 Baths
    • 6,998 Sq Ft

    527 Benson Rd, Manchester Center, VT 05255

    Boorn Brook Farm combines the rich character of history and the comfort of contemporary living with complete privacy. Established in the late 1700s, the estate near Manchester Center offers stunning views of the Mt. Equinox and the Taconic Range. Surrounded by the Green Mountain National Forest, it creates a peaceful haven that balances the old and the new. For over 50 years, Marion Gould

    Story Jenks LandVest, Inc/Woodstock

    527 Benson Rd, Manchester Center, VT 05255
  • /30

    $1,300,000

    • 11 Beds
    • 9 Baths
    • 9,560 Sq Ft

    3309 3321 Main St, Manchester, VT 05254

    A Rare Opportunity! Introducing a historically significant gem, available for the first time in over 40 years. Set in the picturesque and highly sought after Manchester Village, this timeless estate includes a grand Main House and a charming Carriage House, each situated on its own adjoining 1.27-acre lot, totaling an expansive 2.54 park-like acres. Together, the residences offer 11 bedrooms, 6

    Gregory Cutler Four Seasons Sotheby's Int'l Realty

    3309 3321 Main St, Manchester, VT 05254
  • /27

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,958 Sq Ft

    550 Finbars Forest Rd, Manchester Center, VT 05255

    Tucked away on a private two-acre lot in the heart of the Green Mountains and within the Burr & Burton Academy school district, this modern farmhouse offers a peaceful setting minutes from downtown Manchester and adjacent to Manchester Country Club. The main level features an open-concept layout with a beautifully designed kitchen at its center - rich dark cabinetry, Caesarstone quartz

    Andie Fusco Four Seasons Sotheby's Int'l Realty

    550 Finbars Forest Rd, Manchester Center, VT 05255
  • /15

    $168,000

    • Land
    • 3 Acres
    • $56,000 per Acre

    530 Finbars Forest Rd, Manchester Center, VT 05255

    If you're looking for a distinctive Manchester home site, look no further than this private, wooded lot bordering the back nine of Manchester Country Club's celebrated championship golf course. The south-facing wooded lot offers the perfect blend of privacy, exquisite golf course views, and the distant backdrop of the rolling Green Mountain ridge. The location is as central as it is nestled in

    Jamie Luke TPW Real Estate

    530 Finbars Forest Rd, Manchester Center, VT 05255
  • /9

    $1,350,000 New Construction

    • 3 Beds
    • 4.5 Baths
    • 3,415 Sq Ft

    3746 Main St Unit A, Manchester, VT 05255

    Last Available Unit– This final Monarch on Main townhome is Luxury Living in Historic Manchester Village at its finest. Available Winter 2026, this premier Monarch on Main property offers the rare opportunity to own a thoughtfully designed townhome- front unit- in the heart of Manchester Village. Imagine an easy stroll to fine dinning, shopping and evening events. This three-level residence

    Britt Wohler

    3746 Main St Unit A, Manchester, VT 05255
  • /3

    $329,000

    • Land
    • 9.3 Acres
    • $35,376 per Acre

    1347 Morse Hill Rd, Dorset, VT 05251

    Discover the perfect blend of privacy and convenience with this 9.3 acre parcel nestled in one of Southern Vermont's most desirable locations. Enjoy sweeping mountain views and peaceful surroundings just minutes from the charming and historic towns of Dorset and Manchester, known for boutique shopping, fine dining, and year-round cultural attractions. It's a short drive to skiing and many other

    Deborah Hanst

    1347 Morse Hill Rd, Dorset, VT 05251
  • /56

    $1,849,000

    • 3 Beds
    • 2.5 Baths
    • 3,450 Sq Ft

    139 Prospect St, Manchester, VT 05254

    Set against Equinox Mountain and just minutes from the thriving center of Manchester, this timeless and elegant home has been thoughtfully renovated to honor age-old craftsmanship while embracing modern building science to create a beautiful, healthy, and inviting space. Recent renovations include a comprehensive rebuild and expansion of the upper floor, Marvin windows and patio doors, charming

    Cheyanne Pugliese

    139 Prospect St, Manchester, VT 05254
  • /27

    $1,200,000

    • 2 Beds
    • 1 Bath
    • 1,056 Sq Ft

    233 Squires Rd, Manchester Center, VT 05255

    Discover a rare opportunity to live and work amidst the serene beauty of Manchester, Vermont. This fully renovated 2-bedroom, 1-bath contemporary ranch, with leased solar array, is nestled on nearly 19 acres, offering a harmonious blend of modern comfort and entrepreneurial potential.The open-concept design features a spacious kitchen and living area, complemented by energy-efficient

    Mark Triller Real Broker LLC

    233 Squires Rd, Manchester Center, VT 05255
  • /20

    $649,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    27 Owls Head Hill Ln, Dorset, VT 05251

    Charming Raised Ranch on 2 Acres – Dorset, VTWelcome to your new home in the heart of Dorset! Nestled on a beautifully landscaped 2-acre corner lot, this inviting raised ranch offers privacy, comfort, and versatile living space.3 Bedrooms | 2 Full Baths | 2-Car Attached GarageStep inside to find a bright living room that flows seamlessly into the eat-in kitchen, perfect for everyday

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    27 Owls Head Hill Ln, Dorset, VT 05251
  • /22

    $375,000

    • 3 Beds
    • 2 Baths
    • 1,344 Sq Ft

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340

    Escape to the mountains in this charming A-frame, ideally located between the bustling town of Manchester and the area's best ski mountains. This home is your perfect base for year-round adventure, putting you just minutes from world-class skiing, hiking, mountain biking, and shopping.Inside, you'll find a comfortable layout featuring 3 bedrooms, 2 bathrooms, and a home office that can

    Robin Apps Four Seasons Sotheby's Int'l Realty

    3 Kimball Hill Rd Unit 1, Winhall, VT 05340
  • /52

    $725,000

    • 3 Beds
    • 4 Baths
    • 2,274 Sq Ft

    490 Barnumville Rd, Manchester Center, VT 05255

    490 Barnumville Road is a beautifully sited Manchester, Vermont home offering comfort, convenience, and classic Vermont charm on 1.78 flat, usable acres. Surrounded by peaceful views and just minutes from downtown Manchester, this property combines tranquil living with unbeatable access to everything the area has to offer — from ski and snowboard mountains to hiking trails, shopping, groceries,

    David Shehadi Josiah Allen Real Estate, Inc.

    490 Barnumville Rd, Manchester Center, VT 05255
  • /55

    $10,300,000 New Construction

    • 6 Beds
    • 9 Baths
    • 10,993 Sq Ft

    551 West Fields, Manchester, VT 05254

    Discover "the pinnacle of luxury living" in the heart of Manchester Village! Crafted by Breen Builders and Ramsay Gourd Architect, every detail reflects superior craftsmanship and timeless elegance! From the very foundation to the finishing touches, attention to detail and commitment to quality shine through! Experience the perfect blend of luxury and convenience in this stunning 10,000 sq.ft

    Sunny Breen Josiah Allen Real Estate, Inc.

    551 West Fields, Manchester, VT 05254
  • /2

    $425,000

    • Land
    • 3 Acres
    • $141,667 per Acre

    lot B Frost Pond Rd, Dorset, VT 05251

    Private but not remote. Dorset West Road Location nearby Dorset and Manchester. Nice mountain views.Waste water permit in place for 5 BR, 8 person occupancy.

    Charles Mauro Josiah Allen Real Estate, Inc.

    lot B Frost Pond Rd, Dorset, VT 05251
  • /60

    $1,190,000

    • 6 Beds
    • 7 Baths
    • 5,400 Sq Ft

    2001 Depot St, Manchester Center, VT 05255

    LOCATION, LOCATION: Just 8 minutes to Bromley and 20 minutes to Stratton, yet close to Manchester’s dining, shopping, fishing, golf, and the Horse Show. Built as a bed & breakfast, this fully furnished and impeccably maintained 6-bedroom, 7-bath retreat offers over 5,400 sq ft on 2 private acres—ideal as a primary home, vacation getaway, or rental investment. With a strong history as a successful

    Steven Bryant TPW Real Estate

    2001 Depot St, Manchester Center, VT 05255
  • /60

    $5,250,000

    • 9 Beds
    • 10 Baths
    • 7,900 Sq Ft

    1184 E Manchester Rd, Manchester, VT 05255

    Peacock Hollow, a c.1790 completely private estate, is gracefully sited on 29.9 acres surrounded by sweeping mountain views, a running stream, and bordered by the forest. This rare offering combines historic character with refined updates, creating a legacy property designed for both intimate living and grand entertaining. The 5,500 square foot main residence offers five beautifully appointed

    Betsy Wadsworth Four Seasons Sotheby's Int'l Realty

    1184 E Manchester Rd, Manchester, VT 05255
  • /22

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 1,963 Sq Ft

    62 Owls Nest Cir Unit B8, Manchester, VT 05255

    This taconic with garage style unit offers formal living room with cozy gas fireplace, formal dining room, and updated galley style kitchen, three bedrooms, and two full baths and one half bath, with one car attached garage. Kitchen upgrades include: maple cabinets, granite countertops, gas range, stainless kitchenaid appliances, and hardwood flooring. This unit is located in the very desirable

    David Halligan Four Seasons Sotheby's Int'l Realty

    62 Owls Nest Cir Unit B8, Manchester, VT 05255
  • /27

    $675,000

    • 2 Beds
    • 2 Baths
    • 1,432 Sq Ft

    4928 Main St Unit 2, Manchester Center, VT 05255

    Fabulous two bedroom two bath condominium converted in 2017 in the heart of Manchester Center. Many fine features: Marvin windows, hardwood flooring, central air conditioning, forced hot air heat, private second floor sundeck, mountain views. This one level second floor unit is accessed by private elevator and offers pretty mountain views through the oversized 9 foot windows. The living room has

    David Halligan Four Seasons Sotheby's Int'l Realty

    4928 Main St Unit 2, Manchester Center, VT 05255
  • /33

    $815,000

    • 3 Beds
    • 2 Baths
    • 1,743 Sq Ft

    158 Upland Downs Rd, Manchester Center, VT 05255

    This well-maintained home is nestled on an open, sunny lot with mountain views, offering a serene and picturesque setting. The property is in move-in condition and boasts one of Manchester's best locations, providing convenient access to the town, schools, and shops, all just minutes away. It is set back from the road, surrounded by beautifully landscaped lawn, gardens, and a spacious

    Tatsiana Clark Four Seasons Sotheby's Int'l Realty

    158 Upland Downs Rd, Manchester Center, VT 05255
  • /27

    $549,000

    • 2 Beds
    • 2 Baths
    • 3,478 Sq Ft

    142 Mount Aeolus Rd, Manchester, VT 05255

    A Rare Investment Opportunity in Manchester! This versatile property offers the perfect blend of commercial and residential potential, making it an ideal choice for savvy investors or those seeking a live-work setup. The upstairs features a spacious residential rental, while the lower level was recently leased to a local daycare, providing immediate rental income.This well-maintained property

    Andrea Kaplan Four Seasons Sotheby's Int'l Realty

    142 Mount Aeolus Rd, Manchester, VT 05255
  • /40

    $439,500

    • 4 Beds
    • 3.5 Baths
    • 3,861 Sq Ft

    120 Village St, East Dorset, VT 05253

    Antique charmer in the village of East Dorset was originally built in the 1850s by famous lumberman, F.G. Harwood. An addition was added in 1900, followed by several improvements over time the colonial farmhouse boasts approximately 3,861 sq. ft. including an oversized two car garage all on 1.1 acres. With a sprawling footprint that features a primary bedroom suite with oversized closet, 4

    Jill Simon Josiah Allen Real Estate, Manchester Branch Office

    120 Village St, East Dorset, VT 05253
  • /27

    $319,000

    • 3 Beds
    • 1 Bath
    • 836 Sq Ft

    557 Beech St, Manchester Center, VT 05255

    Manchester. Let the sun shine in. Easy living on one level with 3 bedrooms. You'll enjoy sitting in the kitchen and gazing either at the mountain view or the flower garden in the backyard. Nice level area to plant a garden or play outdoor games in the yard. Detached 1 car garage, good storage and area for workbench. Quick drive into center of Manchester and minutes to the Manchester Country Club.

    Patti Trudel RE/MAX Four Seasons

    557 Beech St, Manchester Center, VT 05255
  • /40

    $1,525,000

    • 4 Beds
    • 3 Baths
    • 3,931 Sq Ft

    932 Mcnamara Rd, Dorset, VT 05251

    Tucked away at the end of a gently curved, tree-lined drive, this exceptional contemporary home blends timeless elegance with Vermont charm. A welcoming paver patio leads to the informal entry, while a marble pathway guides you to the striking formal entrance and grand foyer. Inside, locally sourced marble floors flow into rich cherry hardwoods, setting the tone for quality

    Britt Wohler

    932 Mcnamara Rd, Dorset, VT 05251
  • /48

    $3,285,000

    • 5 Beds
    • 6 Baths
    • 6,900 Sq Ft

    68 Green Peak Orchard Rd N, Dorset, VT 05253

    Located in Green Peak Orchard, this custom Greek Revival home on 9.9 aces features wide-planked floors, custom moldings, hand-plastered walls and ceilings, historic reproduction lighting and custom wainscotting & cabinetry. Slate and copper roofs as well as Vermont marble and soapstone complete the authentic details of this striking residence. The home welcomes you through a brick-floored mudroom

    Carol O`Connor Four Seasons Sotheby's Int'l Realty

    68 Green Peak Orchard Rd N, Dorset, VT 05253
  • /23

    $750,000 Open Sat 11AM - 1PM

    • 4 Beds
    • 3.5 Baths
    • 3,784 Sq Ft

    258 Mending Walls Rd, Manchester Center, VT 05255

    Nestled in the highly sought-after Mending Walls Subdivision, this beautiful 4-bedroom, 4-bathroom Colonial offers the perfect blend of comfort, space, and curb appeal. Set back on a level lot, enjoy serene mornings and evenings from the welcoming front porch overlooking the expansive front yard. The main level boasts spacious living area perfect for entertaining and everyday living. Upstairs,

    Lynn Rawson Berkshire Hathaway HomeServices Stratton Home

    258 Mending Walls Rd, Manchester Center, VT 05255
  • /40

    $549,000

    • 2 Beds
    • 2 Baths
    • 4,044 Sq Ft

    5515 Main St, Manchester, VT 05255

    Own a piece of Vermont history with this charming 1830s home, perfectly situated on Main Street in downtown. Zoned for mixed use (MU2), this versatile property offers endless possibilities-live, work, or do both in one inspiring space. The 2-bedroom, 2-bath home blends vintage Vermont character with modern comfort, featuring mini-splits for heating and cooling, a propane stove, fiber optic

    Katherine Zilkha Four Seasons Sotheby's Int'l Realty

    5515 Main St, Manchester, VT 05255
  • /40

    $6,900,000

    • 5 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    515 W Fields Rd, Manchester, VT 05254

    Enduring values expressed in stone and wood! VERMONT CRAFTMANSHIP...A WORK OF ART!! Offering a private haven just minutes from downtown, in the heart of Manchester Village, nestled in the foothills of Equinox Mtn. is this rareand exceptional 5-bedroom, 6-bathroom home....The creative design of Architect Ramsey Gourd and Master Builder Mark Breen, well knownas two of Southern Vermont's

    Sunny Breen Josiah Allen Real Estate, Inc.

    515 W Fields Rd, Manchester, VT 05254
  • /52

    $2,300,000

    • 6 Beds
    • 3 Baths
    • 3,340 Sq Ft

    215 & 221 Vt Route 30, Dorset, VT 05251

    Two homes, multiple barns and outbuildings on 69 incredible acres in Dorset, VT. Nestled in the Green Mountains, 215 Route 30 the 1780s farmhouse featuring 3 bedrooms, 2 baths with 1645 finished sqft. The second building, nestled away from the road is 221 Route 30 built in 1940 with 3 bedrooms and 2 baths. 1800 sqft. The property offers pastoral venues, mature forest, and scenic mountain views. A

    Margretta Fischer Wohler Realty Group

    215 & 221 Vt Route 30, Dorset, VT 05251
  • /43

    $1,895,000

    • 6 Beds
    • 5.5 Baths
    • 5,178 Sq Ft

    144 Taconic Rd, Manchester, VT 05255

    “The Colonial” – Queen of Taconic Avenue One of the original summer “cottages” gracing historic Taconic Avenue, The Colonial is a crown jewel of Manchester Village. Painstakingly renovated, this stately home perfectly balances old-world charm with modern sophistication. The heart of the home is a stunning new chef’s kitchen, seamlessly blending timeless design with today’s comforts. All-new

    Tom Deck Josiah Allen Real Estate, Manchester Branch Office

    144 Taconic Rd, Manchester, VT 05255
  • /24

    $595,000

    • 3 Beds
    • 2.5 Baths
    • 2,210 Sq Ft

    74 Eagle Nest Rd Unit 7, Manchester, VT 05255

    Eagle Nest in Manchester, The Only Available Unit in This Sought-After Community! Welcome to easy living at Eagle Nest, a popular cluster home development where opportunities like this are rare. This freestanding home (no shared walls, no shared noise!) is being offered for the first time and has been beautifully updated from top to bottom. Step inside to find fresh interior paint, new carpeting,

    Carol O`Connor Four Seasons Sotheby's Int'l Realty

    74 Eagle Nest Rd Unit 7, Manchester, VT 05255
  • /25

    $565,000

    • 4 Beds
    • 2.5 Baths
    • 2,408 Sq Ft

    22 Bromley Forest Rd, Bondville, VT 05340

    Welcome to your ideal Vermont retreat where comfort, style, and location converge! This upgraded 4-bedroom home, complete with a versatile bonus room, has been meticulously maintained and offers an open floor plan perfect for gathering and everyday living. The kitchen shines with stainless steel appliances and a new professional grade dual-fuel convection range. East and south facing windows

    Carrie Mathews Winhall Real Estate

    22 Bromley Forest Rd, Bondville, VT 05340
  • /47

    $599,000

    • 5 Beds
    • 3 Baths
    • 3,836 Sq Ft

    162 Highland Ave, Manchester Center, VT 05255

    Easy Investment Opportunity! Three unit multi-family. Great passive income. Turn key money maker! Spacious layout with privacy for each unit. The main level unit offers an open living dining area, three bedrooms, one-bath with mountain views off the spacious deck. The second floor offers two separate one-bedroom, one-bath units. Each unit has its own entrance. The lower level provides storage for

    Margretta Fischer Wohler Realty Group

    162 Highland Ave, Manchester Center, VT 05255
  • /40

    $179,000

    • Land
    • 0.2 Acre
    • $895,000 per Acre

    10 Partridge Hill, Manchester, VT 05255

    One of the last remaining lots in the exceptional Partridge Hill Association. This beautiful lot is situated to capture wonderful views and abbuts common land and a huge undeveloped land parcel on it's boundaries- offering a private outdoor space. The building envelope benefits from the ability to approach the parcel through the adjacent common land. Underground power and cable at the lot.

    Kim Morgan-Wohler Wohler Realty Group

    10 Partridge Hill, Manchester, VT 05255
  • /49

    $1,350,000

    • 4 Beds
    • 2.5 Baths
    • 4,634 Sq Ft

    1677 Barnumville Rd, Manchester Center, VT 05255

    This historic 19th century two-story brick Federal house was originally a popular tavern. It has been completely renovated/updated to serve today's relaxed living while retaining all classic features. A bright kitchen/dining/living great room w/fireplace is the heart of the home. A first-floor master suite includes a spa-like bath w/fireplace. There is an adjacent mudroom entrance with 1/2 bath

    R. Diedrich August

    1677 Barnumville Rd, Manchester Center, VT 05255
  • /22

    $895,000

    • Land
    • 24.08 Acres
    • $37,168 per Acre

    A Windsor Rd, Manchester, VT 05255

    Simply Extraordinary! 24.08 Acres with a State Wastewater Permit for 11 Bedrooms that includes 2 buildable lots within the acreage. With unrivaled easterly views, this parcel is the last permitted within what is now the Forest and Recreational/Farming and Rural Residential District of Manchester , Vermont. There will be no further development around this parcel. Abutted by protected lands and

    Kim Morgan-Wohler Wohler Realty Group

    A Windsor Rd, Manchester, VT 05255
  • /29

    $729,000

    • 3 Beds
    • 3.5 Baths
    • 2,262 Sq Ft

    253 Owls Head Hill Ln S, Dorset, VT 05251

    Welcome to this beautifully maintained Cape-style home tucked away on peaceful cul-de-sac with stunning mountain views. Enjoy your morning coffee on the front porch and relaxing evenings on the spacious back deck. Inside, you will find a warm and inviting layout featuring a gorgeous newer kitchen with modern finishes and ample space for cooking, gathering, and entertaining. The thoughtful floor

    Annette Gallo Real Broker LLC

    253 Owls Head Hill Ln S, Dorset, VT 05251

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