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Very Cool Houses

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109 Mountainside Drive Killington VT 05751

Killington, VT109 Mountainside Drive

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5088805

  • Residential Single Family
  • PricePerSqFt 1052.41
  • Full Bath 3
  • Construction Existing
  • Bedrooms 3

This fully furnished, high end home delivers opulence from the moment you pull in. From the recently resurfaced driveway your eyes are immediately drawn to the newly installed daltile porcelain roof, offering you peace of mind for decades to come. Park your car in the 2 car garage and enter into a dedicated mudroom with copper fire slate flooring. The dedicated laundry room offers LQ Signature washer/dryer, soap stone counter top and a deep work sink. Entering into the grand foyer you will be met with floor to ceiling windows in the living room that deliver breathtaking mountain views, giving you a sense of seclusion. Unwind by the beautiful floor to ceiling stone hearth fireplace. For your comfort there is a 30,000 BTU AC in the great room. Immerse yourself into the stunning chefs kitchen with Brazilian Venata countertops, cherry cabinets and stainless steel appliances. The Bruce Kennedale Prestige maple hardwood flooring throughout the living room, dining room and kitchen adds beauty, durability and is designed to last a lifetime. The spacious primary suite located on the main floor offers a large bedroom with miles of mountain views, a walk in closet, sitting area, 9000 BTU AC, large whirlpool tub, walk in shower, double sink, toilet room and sauna. Relax in the 4 season sunroom offering 180 degree mountain views and the tranquility of the natural brook. Host a gathering on the large two wing wood deck. Whether it is a bbq or sitting by the on deck fire pit, entertaining is made easy here. Upstairs you will find 2 large ensuite bedrooms both offering incredible mountain views. Downstairs in the family room there is a Westwood Tuscany 8 foot pool table that converts to a ping pong table. Enjoy the ambiance of an additional fireplace. You will find additional sleeping space, a 3/4 bath and storage rooms as well. The property comes with 3 additional parcels which can be divided off, retained for privacy or create your family compound. This is a must see property!

Listed by Michelle Lord of Ski Country Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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324 Fellows Road Pittsfield VT 05762

Pittsfield, VT324 Fellows Road

Price$2,450,000

Est. Mortgage: $/month

MLS Number 5110057

  • Residential Single Family
  • PricePerSqFt 429.3
  • Full Bath 2
  • Address 324 Fellows Road
  • Construction Existing

Set within 210 acres of unspoiled forestland spanning Killington and Pittsfield, Vermont, The Tweed River Estate is a truly one-of-a-kind property, a private sanctuary where nature and craftsmanship meet. Designed by a renowned architect, the bespoke home is a masterwork in its own right, with exposed beams, high-end custom woodwork, and windows throughout that fill every room with light. Every detail, from the stonework to the finest materials, reflects the artistry of master stonemasons and skilled craftsmen. The house is perched above the Jimmy Dean Brook and the Tweed River, where the sound of running water settles peacefully over the property. Enveloped by forest on all sides, the stone, concrete, and timber structure sits on its mountain top setting so naturally that it feels less built than grown from the land itself, as if it had always been there. Large windows, stone patios and a second-floor porch frame views down the valley to the northeast and out across the surrounding woodland. On mornings when fog fills the valley below, the houses, elevated location gives the sensation of floating above the world on a cloud, a true private retreat. The property spans 210 acres across two contiguous parcels, the majority of which is untouched private forest in Pittsfield, with development potential on the 89-acre Killington parcel. Combining privacy, character, and genuine architectural originality, the estate remains just minutes from an impressive range of amenities, ski resorts, shops, and dining, making this a rare chance to own a home and landscape unlike any other in Vermont.

Listed by Thom Milke of Fountains Land Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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494-564 Goodaleville Road Jamaica VT 05343

Jamaica, VT494-564 Goodaleville Road

Price$2,430,000

Est. Mortgage: $/month

MLS Number 5107418

  • Residential Single Family
  • PricePerSqFt 615.66
  • Full Bath 4
  • Construction Existing
  • Bedrooms 9

TWO HOMES | 1BR BARN APARTMENT | RESTORED VINTAGE BARN | 13+ ACRES. A rare Vermont multi-residence estate offering two beautifully renovated homes, a separate 1BR barn apartment, a restored vintage barn, and more than 13 acres along the Winhall River. Thoughtfully renovated by Vermont Country Builders, Winhall River Farm blends authentic character, exceptional craftsmanship, and modern four-season comfort. One residence is a restored 4BR farmhouse once used as the summer home of renowned art historian Meyer Schapiro, with wide-plank floors, antique doors, an expanded kitchen with soapstone counters, updated baths, and custom built-ins. Schapiro's former art studio now serves as a self-contained 1BR apartment with SMEG appliances, a screened porch, and heated storage below. The second home is a reimagined historic schoolhouse with a timber-frame addition, high ceilings, generous windows, two sunrooms, restored floors, and warm architectural detail throughout. Private hot tubs and inviting outdoor living spaces complement all three residences. Extensive improvements across the property include standing-seam roofs, new Marvin windows, updated electrical and plumbing, modern insulation, mini-split heating and cooling, high-efficiency systems, new appliances, generators, and EV chargers. The 13+ acres include open fields, woods, apple trees, gardens, extensive stonework, patios, decks, and opportunities for trails, recreation, and equestrian use. Set along the Winhall River with direct access to the West River Rail Trail for walking, biking, swimming, and exploring. In the heart of ski country, just minutes from Stratton, Bromley, and Magic Mountain. An exceptional family estate, multi-generational retreat, or investment opportunity. Offered furnished and ready to enjoy, with additional acreage also available. All the hard work has been done--move in and start enjoying Vermont. Properties also offered individually as MLS #5101688 & #5101689. Seller is the listing broker.

Listed by Cheyanne Pugliese of The Haven Group

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$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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2 Dublin Road Plymouth VT 05149

MLS Number 5082041

  • Commercial
  • Address 2 Dublin Road
  • Area VT-Windsor

Echo Lake Inn represents a rare opportunity to acquire a historic, full-service Vermont inn for sale in one of New England's most sought-after resort markets. Ideally positioned along the active Route 100 corridor between Okemo Mountain Resort (±4 miles) and Killington Resort (±12 miles), this Vermont country inn benefits from powerful year-round tourism drivers - skiing, lake recreation, weddings, and destination travel. The combination of a longstanding operating history, a striking lakeside setting, and a scalable business model presents meaningful upside through professional revenue management, branding refinement, and expanded experiential programming. Be sure to ask about the details on the historic business or to schedule a tour of the facility in the near future.

Listed by Eben Viens of Berkley & Veller Greenwood Country

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$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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340 North Hartland Road Hartford VT 05001

MLS Number 5026321

  • Commercial
  • PricePerSqFt 182.59
  • Village White River Junction
  • Year Built 1967
  • Square Feet 13,144

VERY MOTIVATED SELLER!! SUPERB LOCATION!! PRIME in town Building and Land at the crossroads of I 89 and I 91 featuring a 12,000 +/- Square Foot Building on 1.40 +/- Acres. Build your business a new location along this high traffic main corridor. This Superb site is next door to Dunkin Donuts in White River Junction and would possibly be a great location for a car dealership, grocery store, restaurant or hotel. Become business neighbors with the V.A. Hospital, many prominent national hotel chains, Dunkin Donuts, McDonalds and several national automobile franchisees. Located just off I 89 & I91 in beautiful White River Jct., VT. this is a ONE OF A KIND LOCATION WITH HIGH VISIBILTY and HIGH TRAFFIC COUNT!! Seller is also willing to offer the property for $2,200,000. with less land and parking to be negotiated for the amount of land / parking area needed for each Buyers particular project.

Listed by Alex DeFelice of The Clerkin Agency,P.C.

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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662 Howe Farm Road Jamaica VT 05343

Jamaica, VT662 Howe Farm Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 4972272

  • Residential Single Family
  • PricePerSqFt 672.18
  • Full Bath 1
  • Address 662 Howe Farm Road
  • Construction Existing

Discover this renovated timber frame home nestled on 366 acres of private land. Offering a seamless blend of historic character and modern comfort, this 4 bedroom plus office, 4 and a half bathroom home showcases attention to detail. The gourmet kitchen, inviting living spaces, bonus game room and home gym are complemented by a sunlit dining space with a greenhouse sunroom, adding a touch of nature to your daily life. Multiple bedrooms give everyone in your party a private space to relax after a long day exploring the outdoors. Step outside to witness dramatic views of the rolling hills that surround the property. A tranquil pond with gazebo graces the landscape. A well-appointed barn with 5 stalls and a paddock caters to equestrian enthusiasts. Miles of trails crisscross the property, providing endless opportunities for outdoor activities. This property is subject to an Act 250 permit and enrolled in Vermont Current Use Program, securing its natural beauty for the future. Whether you are relaxing on the porch or hosting gatherings in the spacious bonus room, this estate balances seclusion and convenience. Situated in bucolic Jamaica, it is 20 minutes from Stratton and 25 minutes from Mount Snow. Let this be your four season retreat, close to the mountains in the winter, swimming holes in the summer, and stunning views all year round!

Listed by Andie Fusco and Tara van de Velde of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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33 Stone Lodge Road Winhall VT 05340

Winhall, VT33 Stone Lodge Road

Price$2,399,000

Est. Mortgage: $/month

MLS Number 5076149

  • Residential Single Family
  • PricePerSqFt 528.88
  • Full Bath 3
  • Address 33 Stone Lodge Road
  • Construction New Construction

Experience Premiere Luxury living in this newly built mountain residence with extraordinary panoramic views . Just minutes to Stratton Mountain'sTrails and move in ready, no detail has been overlooked with superior craftsmanship, energy efficiency and contemporary design. The handcrafted Timber Frame great room , defined by cathedral ceilings, wood burning stone hearth and expansive windows, showcases breathtaking views and the natural beauty of the Green Mountains.Every detail showcases a design with performance and comfort in mind:Premium lighting , hardware and plumbing fixtures, exceptional wood flooring and tile baths. A gourmet kitchen with Bosch appliances and a separate scullery offers a design well suited for entertaining and apres ski gatherings. Three levels, 4 Bedrooms/3.5 Bathswith 2 ensuite primaries, a lower level with a mega bedroom designed with bunks in mind ,a spacious game and media room that opens to the outdoors- just ready foryour active lifestyle.With the mountain enthusiast in mind, you'll appreciate the custom mud room, laundry room, and the oversized 2 car garage with expansion space above. Central AC, Water filtration system, standing seam roof and much more.You'll have the space and conveniences you look for in a Vermont mountain retreat. This home is prime for your winter season and one that you must visit in person to appreciate the exceptional quality and design. Located just minutes to the StrattonMountain Resort, this home offers an ideal balance of luxury, efficiency and Stratton's natural beauty. Neighborhood shuttle to the Stratton Base Lodge is scheduled for2027. Simply unrivaled in the marketplace. Time to settle into Mountain Living before the snow flies!

Listed by Kim Morgan-Wohler of Wohler Realty Group, Britt Wohler of WOHLER REALTY GROUP

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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111 Lakeside Avenue Milton VT 05468

Milton, VT111 Lakeside Avenue

Price$2,399,000

Est. Mortgage: $/month

MLS Number 5080285

  • Residential Single Family
  • PricePerSqFt 480.18
  • Full Bath 2
  • Address 111 Lakeside Avenue
  • Construction Existing

Extraordinary Lakefront Estate with 200' of Vermont Waterfront: Set on a private 2-acre peninsula with 200 feet of pristine lake frontage, this custom-built 2020 estate offers a rare blend of Vermont craftsmanship and modern luxury. Over 6,400 square feet unfold across a smart, sound-insulated floor plan governed by a high-end Elan home automation system controlling lighting, security, climate, irrigation, and whole-house audio. The kitchen is a showpiece - handmade Amish black walnut and maple cabinetry, dual Fisher & Paykel refrigerators, a Dacor 48" range, marble backsplash, and zoned Klipsch copper speakers. Vaulted Douglas fir ceilings anchor the great room, while the primary suite occupies its own private wing with a steam shower, chromatherapy soaking tub, heated bidet, and a 500+ sq ft closet with in-suite laundry. Outside, entertain by the salt-water, auto-chemical-balanced pool beneath a custom pergola, or unwind at the bluestone fire pit overlooking the water. Grounds include three custom water features, a private dock, greenhouse, apple orchard, and 70 flowering hydrangeas along the shoreline. A detached executive office/ADU adds a full gym, sound-proofed workspace, and three additional heated garage bays: six-plus total. Full-home Generac backup, Tesla Powerwalls, whole-house water and air purification, and Wifi 7 throughout ensure effortless, self-sufficient luxury. A true four-season Vermont retreat, minutes from everyday convenience.

Listed by Erin McCormick of KW Vermont

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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00 Vt Route 11 Peru VT 05152

Peru, VT00 Vt Route 11

Price$2,395,000

Est. Mortgage: $/month

MLS Number 5072898

  • Land
  • PricePerSqFt 10550.66
  • Address 00 Vt Route 11
  • Acreage 227
  • Area VT-Bennington

Bordering Green Mountain National Forest with sweeping views of Stratton, Bromley, and Magic Mountains, this 227 +/- acre offering in Peru, Vermont captures the scale, privacy, and natural beauty that define Southern Vermont mountain living. Spanning two distinct parcels, the offering includes 199 +/- acres bordering National Forest land and a separate 28 +/- acre parcel positioned to capture long-range mountain views and southern light throughout the day. Wooded ridgelines, natural clearings, and varied terrain create multiple potential building locations while preserving privacy and view corridors across the surrounding landscape. Imagine mornings with mountain light moving across the ridgeline, afternoons spent exploring the surrounding trails and wilderness, and winter weekends centered around nearby ski mountains just minutes away. The property offers exceptional flexibility for a private estate, multi-generational retreat, or long-term legacy holding shaped around the surrounding landscape and Vermont's four-season lifestyle. Located near Bromley Mountain and within easy reach of Magic Mountain, Stratton Mountain Resort, and the shops and dining of Manchester, the setting balances privacy and seclusion with convenient access to some of Southern Vermont's most sought-after recreation and amenities. A remarkable Southern Vermont land offering with significant acreage, Green Mountain National Forest frontage, mountain views, and exceptional proximity to the region's premier year-round destinations.

Listed by Kevin Moran of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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1462 Lake Road Panton VT 05482

Panton, VT1462 Lake Road

Price$2,395,000

Est. Mortgage: $/month

MLS Number 5091682

  • Residential Single Family
  • PricePerSqFt 584.15
  • Full Bath 2
  • Address 1462 Lake Road
  • Construction Existing

With west-facing views across Lake Champlain to the Adirondack Mountains, extensive lake frontage, and approximately 4,100 square feet of living space, 1462 Lake Road is an exceptional waterfront retreat set on nearly 17 private acres. The property offers direct access to Lake Champlain for swimming, boating, fishing, and days on the water. Stairs to the beach provide convenient shoreline access, and the property can accommodate both a dock and mooring. Inside, lake and mountain views take center stage from the moment you enter. The dramatic living room features 12-foot-plus ceilings, two fireplaces, and a wall of west-facing glass doors framing the Adirondacks beyond. The spacious kitchen opens to an inviting breakfast and family room, creating a comfortable gathering space at the heart of the home. The primary suite offers a peaceful retreat, while two separate two-bedroom guest suites, connected to the main residence by breezeways, provide privacy for family and guests. A flexible second-floor room above the garage is ideal for an office, studio, or additional guest space. Outdoors, beautifully maintained perennial gardens surround the home, complemented by a gunite pool, greenhouse, enclosed garden with raised beds, and expansive lawns leading toward the lake. A long, cedar-lined drive creates a wonderful sense of arrival and enhances the privacy of the property. Morning coffee might be accompanied by bald eagles and osprey overhead, while evenings bring Adirondack sunsets, time on the deck, and the unmistakable call of loons across the water. Despite its private setting, the property is within an easy 20- to 30-minute drive of Middlebury and Vergennes, with convenient access to restaurants, shopping, theater, golf, medical services, and other area amenities. With five bedrooms and four-and-a-half baths, 1462 Lake Road offers a rare combination of privacy, recreation, generous accommodations, and a remarkable connection to Lake Champlain.

Listed by Wade Weathers and Averill Cook of LandVest,Inc-Burlington

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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56 Handle Road Dover VT 05356

Dover, VT56 Handle Road

Price$2,395,000

Est. Mortgage: $/month

MLS Number 5063234

  • Residential Single Family
  • PricePerSqFt 399.17
  • Full Bath 5
  • Address 56 Handle Road
  • Construction Existing

Incredible Legacy Property. This extraordinary estate blends timeless elegance with modern comfort. The first floor features a welcoming den, gourmet eat in kitchen with DCS range, stainless appliances, sub- zero refrigerator and wet bar. A dining room, gracious living room, office, and butler's panty with fridge and ice maker make entertaining effortless. Five fireplaces, custom-built-ins, wood floors and beautifully tiled baths create a warm refined atmosphere. Upstairs the primary suite offers a fireplace and luxurious bath. An additional en-suite bedroom and three more bedrooms, laundry room, and two full baths provide plenty of space for family and guests. Dual staircases, tiled entry, and both front and back foyers highlight the home's thoughtful design. The grounds are equally impressive with a covered front porch that overlooks the sprawling south facing lawn with winter views of haystack. A serene screened veranda, back deck and stone patio with fire pit invite outdoor gatherings. An oversized-attached two car garage, whimsical children's playhouse and an incredible post and beam barn with full lower level perfect for all your recreational vehicles complete the offering. Exquisite gardens, stone walls and meticulous land scaping surround this rare property, ideally located across from the esteemed Hermitage Inn and exclusive Hermitage Club with easy access to all area activities.

Listed by Richard Caplan of Deerfield Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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241 Main Street Montgomery VT 05471

Montgomery, VT241 Main Street

Price$2,375,000

Est. Mortgage: $/month

MLS Number 5093135

  • Residential Single Family
  • PricePerSqFt 339.29
  • Full Bath 7
  • Address 241 Main Street
  • Construction Existing

Escape the noise, traffic, and stress of metropolitan living and embrace the timeless Vermont innkeeper lifestyle with this exceptional hospitality property near Jay Peak Resort in the heart of the Northeast Kingdom. Surrounded by rolling mountains, fresh air, and four-season recreation, this unique property offers the rare opportunity to live and work in one of New England's most scenic and sought-after destinations. Perfectly located near Jay Peak-renowned for some of the highest snowfall totals in the nation-this established inn attracts visitors year-round for skiing, snowboarding, hiking, mountain biking, golf, fall foliage, and destination travel. Whether you envision operating a boutique inn, farm-to-table restaurant, wedding venue, ski lodge, wellness retreat, or multi-use hospitality business, the possibilities here are truly endless. At the heart of the property is a welcoming restaurant and tavern space with seating for approximately 70 guests, creating an ideal setting for both travelers and locals alike. The fully equipped commercial kitchen and bar provide the infrastructure needed for a successful dining operation, special events business, or expanded hospitality concept. Cozy dining spaces, warm wood interiors, and classic Vermont character create an inviting atmosphere that guests remember and return to year after year. The inn offers comfortable guest accommodations, relaxing common areas, and the authentic charm today's travelers seek when searching for a Vermont getaway experience. Guests can unwind after a day on the slopes beside a crackling fire, enjoy the peaceful mountain setting, and immerse themselves in the beauty of the Northeast Kingdom. This highly versatile property presents incredible opportunities for entrepreneurs seeking a lifestyle change, remote investors pursuing a hospitality venture, or anyone dreaming of trading city life for mountain living.

Listed by Alex Pintair of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 7.28% last updated on Oct 1, 2026
* All Figures are estimates. Check with your bank or proposed mortgage company for actual interest rates.
This product uses the FRED® API but is not endorsed or certified by the Federal Reserve Bank of St. Louis.

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Broker Reciprocity 

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, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Data last updated October 7, 2026 4:22 AM UTC