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Very Cool Houses

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2427 Monument Hill Road Hubbardton VT 05735

Hubbardton, VT2427 Monument Hill Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 5049627

  • Residential Single Family
  • Full Bath 2
  • Construction Existing
  • Bedrooms 5
  • Bathroom 4

Discover your Vermont sanctuary just 2 miles from stunning Lake Bomoseen and a short drive to the scenic Half Moon State Park! This exceptional home offers a perfect blend of natural beauty and luxurious comfort nestled within over 80 acres of lush land. Imagine waking up to breathtaking water features - a deep spring-fed pond, a majestic fifty-foot waterfall, and a tranquil year-round brook gently flowing behind the house - that create a peaceful, inspiring setting every day. This unique property boasts three distinct living areas, centered around a serene interior stone garden that invites relaxation and connection. The main house, an inviting guest wing, and a spa/living area with a swim-current pool, plunge pool, entertainment zone, cozy caf, and exercise area give everyone space to enjoy. Throughout, you'll find exceptional finishes and thoughtful upgrades, including a modernized primary kitchen, solar energy system, and mini-splits for ultimate comfort. With up to five bedrooms and separate spaces for privacy, this home is designed for creating lifelong memories in harmony with nature. The property’s expansive land offers endless outdoor adventures and privacy in a beautiful Vermont setting. Don’t miss this once-in-a-lifetime opportunity! Schedule your showing today and experience firsthand this one-of-a-kind Vermont retreat - your dream home awaits!

Listed by Michael Johnston of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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3 Overbrook Drive Dover VT 05356
Active With Contract

MLS Number 5049914

  • Residential Single Family
  • Full Bath 1
  • Address 3 Overbrook Drive
  • Construction Existing
  • Bedrooms 4

STUNNING NEW CONSTRUCTION, SPECTACULAR VIEWS, GREAT LOCATION! Set against the backdrop of Mount Snow, this just-completed luxury single-family home offers the perfect blend of modern design and spacious living. Located in the base area of the Mount Snow Resort, The OutLook at Mount Snow offers the perfect mix of mountain modern luxury and the ultimate convenience. This home features an open concept kitchen, dining, and great room, all with incredible views of Mount Snow. With three levels of spacious living, there's ample room for the whole family to relax and enjoy. Cozy up by the gas fireplaces in the living room and lower-level family room, complete with a wet bar and beverage cooler, or take in the views from every floor. The home offers convenient MOOver Shuttle access to and from Mount Snow and is just a short drive to the Hermitage Club. This home presents a rare opportunity to own a luxury, new-construction single-family residence with unmatched proximity to Mount Snow. Whether you're looking for a primary residence, a vacation home, or an investment property, this home is sure to exceed your expectations. Don't miss your chance to own a piece of mountain paradise!

Listed by John Redd and Donna Brown of Skihome Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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2493 Lake Street Addison VT 05491

Addison, VT2493 Lake Street

Price$1,499,000

Est. Mortgage: $/month

MLS Number 5062813

  • Residential Single Family
  • Full Bath 2
  • Address 2493 Lake Street
  • Construction Existing
  • Bedrooms 3

Experience the best of Vermont living in this stunning custom-designed home on 142 acres in scenic Addison. Wake up each day to breathtaking panoramic views of Lake Champlain, the Adirondack Mountains, and the Green Mountains. Built in 2007, this thoughtfully crafted residence offers a seamless blend of elegance, comfort, and connection to nature. Soaring cathedral ceilings and floor-to-ceiling windows flood the open-concept Great Room with natural light, creating a serene space to enjoy the changing seasons. The gourmet kitchen is a chef's dream with granite countertops, a center island, stainless steel appliances, and gas range. A spacious first-floor primary suite features a spa-like bath with soaking tub, tiled shower, and convenient laundry. Upstairs, two additional bedrooms, a full bath, and cozy loft provide plenty of space for guests or family. The finished walk-out basement includes a game room, theater area, and bonus room for work or play. Outdoors, explore miles of private trails, open meadows, and peaceful woods - perfect for recreation, horses, or a small hobby farm. The three-bay heated garage/barn adds versatility for storage, workshop or pickleball court. Located near Vergennes, Middlebury, and the Basin Harbor Club, with easy access to hiking, paddling, and Vermont's famed farm-to-table culture. Schedule your private showing today and come fall in love with this extraordinary Vermont retreat!

Listed by Michael Johnston of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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705 Cedar Beach Road Charlotte VT 05445

Charlotte, VT705 Cedar Beach Road

Price$1,499,000

Est. Mortgage: $/month

MLS Number 5090479

  • Residential Single Family
  • Full Bath 1
  • Address 705 Cedar Beach Road
  • Construction Existing
  • Bedrooms 2

Nestled in the historic Cedar Beach neighborhood, this rare waterfront retreat offers 300 feet of lakeshore with the opportunity to own your very own camp perched above beautiful Converse Bay. This unique mid-century A-frame captures stunning water views from every room, creating a peaceful setting filled with natural light to enhace the natural wood interior. The large 2.7 acre lot provides exceptional privacy along with plenty of space for gardening, outdoor entertaining, or simply enjoying the surrounding landscape. Relax on the spacious deck while listening to gentle waves roll in below, or gather with friends and loved ones to take in the spectacular scenery. Conveniently located near the Charlotte-Essex Ferry, just 30 minutes from Burlington International Airport and 35 minutes to Downtown Burlington, this special property offers the perfect balance of escape and accessibility.

Listed by Sean Dye and Christopher Dantzscher of BHHS Vermont Realty Group/Vergennes

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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652 Tierney Road Cavendish VT 05142

Cavendish, VT652 Tierney Road

Price$1,499,000

Est. Mortgage: $/month

Pending

MLS Number 5054888

  • Residential Single Family
  • Address 652 Tierney Road
  • Construction Existing
  • Bedrooms 4
  • Bathroom 4

Tucked discretely off a meandering country road you will find this charming 4 bedroom, 3 and 1/2 bath contemporary home sited on 40 acres of land with miles of groomed trails that include a picnic area on Twenty Mile Stream. The grand living room , anchored by a wood-burning fireplace and lined by a wall of windows , frames views of the giant swimming pond and long range mountain views that include Vermont's own Mt Ascutney. The custom designed kitchen is a chef's dream and the sun-drenched dinning area - with exposures on two sides- provides an elegant setting for intimate gatherings.The deck from the main floor offers expansive spaces for outdoor living with stairs to an upper level enclosed gazebo that gives a 360 degree view of the beautifully landscaped grounds.There are two primary bedrooms , one on the main level with ensuite bath and one on the second level . The second level also has a bedroom that looks out to the mountain views. Lower level is comprised of a game room ,exercise space and bedroom with bath. From the lower level one has access to a 3,000 sq. ft. fenced dog run and hot tub. The 3 car garage with ample storage has room for ATV"s and snow mobiles. Second floor could be finished into living space. Skiing at Okemo Mountain is 12 minutes away. VAST trails are down the road, and Fly fishing on the Black River is some of the best in Vermont. This idyllic property offers serenity for full time living or a delightful second home get away. Call for viewing.

Listed by Carol Wood of Williamson Group Sothebys Intl. Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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563 Rim Road Killington VT 05751

Killington, VT563 Rim Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 5076203

  • Residential Single Family
  • Full Bath 1
  • Address 563 Rim Road
  • Construction Existing
  • Bedrooms 4

The Queen's Croft-A Luxurious 4-Bedroom, 5-Bath Custom Vacation Home less than 2 miles to Bear Mountain. Built in 2007 and spanning three beautifully finished levels, this fully furnished and equipped 4,000 sq ft custom home offers the ideal blend of luxury, comfort, and convenience. The property features many thoughtfully designed rooms, and high quality details like heavily-insulated 2x6 construction, 12-inch on center deck framing, and 200 amp electrical service. Private Setting & Exceptional Outdoor Living located on peaceful, wooded, 1.1 acre lot, the home features a large deck for outdoor dining and relaxation, plus a private hot tub for unwinding after a day on the mountain. Ample parking ensures easy access for owners and guests alike. Designed for Mountain Living. Both the upper and lower entryways offer exceptional storage solutions, with the lower foyer offering storage for skis and boards, as well as a custom drying rack for wet boots and gear-keeping everything organized and ready for your next adventure. A striking stone, wood-burning fireplace anchors the main living area, creating a warm and inviting gathering space. Spacious & Fully Appointed. With four bedrooms and five bathrooms across three levels, the layout provides comfort and privacy for groups of all sizes, and the spacious chef's kitchen is perfectly appointed for feeding a hungry crowd. The home comes fully furnished and turnkey, allowing you to step right into the mountain lifestyle without lifting a finger. Strong Rental History. This property has an established rental track record, making it an excellent option for buyers seeking both personal enjoyment and investment potential. Don't miss this rare opportunity to own a luxurious, well maintained mountain retreat in one of Killington's most desirable locations. Ready for immediate enjoyment and income generation, call today to schedule a private showing.

Listed by Bret Williamson of Killington Valley Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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4602 Greenbush Road Charlotte VT 05445

Charlotte, VT4602 Greenbush Road

Price$1,495,000

Est. Mortgage: $/month

Pending

MLS Number 5086034

  • Residential Single Family
  • Full Bath 3
  • Address 4602 Greenbush Road
  • Construction Existing
  • Bedrooms 3

A private drive winds back through the trees, past impeccable gardens to six acres and a home that does not disappoint. This is exactly what quiet Charlotte living looks like and a home where every room reveals something worth slowing down for. The millwork is meticulous, the finishes curated, and the flow entirely natural. Cherry hardwood floors carry through a wide welcoming entry hall anchored by a stunning staircase. A powder room off the entry features a pedestal sink salvaged from Grand Central Station, the first detail that tells you this home was built by people who cared. A moody butler's bar connects to the formal dining room. The Classic Home VT kitchen renovation is exceptional: cream inset cabinetry, quartz countertops, Bosch appliances, and a glass cabinet wall that opens visually onto a sun-filled breakfast area with a double-height window bank and Adirondack views beyond. The living room is generous and warm, with a paneled fireplace wall, built-in niches, and a library alcove that steps up off the main space. French doors lead to the screened porch, a true second living room, and the large composite deck beyond it, where the gardens and western views take over completely. Upstairs, the primary suite faces west to the Adirondacks with a private balcony, soaking tub, separate shower, and walk-in closet. Two additional bedrooms share a bath that stops people mid-tour: a double pedestal sink with train station origins, skylight, black and white tile, and glass-enclosed shower. A large private bonus room with its own bath and back staircase rounds out a second floor that offers more than it promises. Detached carriage barn. Two-car garage. Greenbush Road is one of Charlotte's most coveted addresses. Schedule a private showing.

Listed by Nancy Warren of Coldwell Banker Hickok and Boardman

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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557 Bennett Hill Road Shaftsbury VT 05262

Shaftsbury, VT557 Bennett Hill Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 5077720

  • Residential Single Family
  • Full Bath 3
  • Construction Existing
  • Bedrooms 6
  • Bathroom 6

Gorgeous, renovated Colonial offering exceptional flexibility, thoughtful design, and timeless charm. This beautifully updated property features a spacious main residence along with a stunning addition that includes a full in-law suite and a private studio above ideal for guests, extended family, a home office, or potential rental income. Solar panels installed above the garage power efficient mini-split systems, and a Tesla Powerwall provides added energy independence and peace of mind. The main house offers four bedrooms, a fabulous chef's kitchen with quality finishes and generous workspace, and warm, inviting living areas filled with abundant natural light. Magnificent views of Mount Anthony and the sweeping five-acre meadow below can be enjoyed from the kitchen, dining room, living room, and screened porch-where wildlife is often part of the daily landscape. A new large enclosed porch further expands the living space, creating the perfect setting to relax or entertain year-round. Set on 17+ picturesque acres framed by classic stone walls, the property offers lovely views, open meadow, and wooded privacy with ample outdoor space to explore and enjoy. A three-car detached garage provides excellent space for vehicles, storage, or hobby use, while a workshop and spacious woodshed add exceptional functionality. Equestrian enthusiasts will appreciate the charming pony barn and paddock, completing this truly special setting. A rare opportunity to own a beautifully expanded home with multiple living options, sustainable features, and breathtaking views in a serene and private landscape.

Listed by Kelley McCarthy of Mahar McCarthy Real Estate

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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741 Cider Mountain Road Warren VT 05674

Warren, VT741 Cider Mountain Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 5089553

  • Residential Single Family
  • Full Bath 4
  • Construction Existing
  • Bedrooms 3
  • Bathroom 4

Welcome to your private retreat on Cider Mountain! Set on a beautifully private parcel with sweeping year-round views of Sugarbush Resort and Camel's Hump, this exceptional post and beam home captures everything buyers dream about when they picture Vermont living. Thoughtfully built by a well-known local specialty carpenter using locally sourced materials, the home showcases stunning hemlock throughout, beautiful maple hardwood floors, and timeless craftsmanship that gives the entire property warmth, character, and soul. A wood burning stove and fully functioning stone chimney create the perfect cozy Vermont ambiance throughout the colder months. The open concept layout creates an inviting flow throughout the home, while radiant heat adds comfort year round. Features include a first floor in-law suite, spacious primary suite with a private balcony, detached 3-car garage, greenhouse, and expansive garden space ideal for those looking to homestead, entertain, or simply enjoy a quieter way of life surrounded by nature. Large windows frame the mountains beyond, filling the home with natural light and breathtaking views in every season. The fully finished walkout lower level offers exceptional flexibility with its own private entrance, full kitchen, bathroom, and laundry area perfect for guests, recreation space, extended family, or potential multi-generational living. Outside, the property truly shines. Spend mornings on the porch watching the sunrise with a cup of coffee in hand, afternoons gardening or picking fresh berries from the numerous berry bushes throughout the property, and evenings relaxing on the spacious front porch or primary balcony soaking in the mountain views and unmatched serenity. Backing up to protected land, the setting will remain private, peaceful, and untouched for years to come. Rarely does a property combine this level of privacy, craftsmanship, acreage, flexibility, and breathtaking natural beauty in one truly unforgettable Vermont setting.

Listed by Lindsay Haley of Vermont Real Estate Company

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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50 Grouse Lane Dorset VT 05251

Dorset, VT50 Grouse Lane

Price$1,495,000

Est. Mortgage: $/month

MLS Number 5083578

  • Residential Single Family
  • Full Bath 1
  • Address 50 Grouse Lane
  • Construction Existing
  • Bedrooms 4

Custom-built Dorset Hollow estate offered for the first time since 1998. Perfectly situated on 10 private acres abutting 3,200 acres of conservation land, this 5,100 sq ft residence combines timeless quality, fine finishes, and Vermont mountain charm. Designed for comfort and entertaining, the home features 4 bedrooms, 5 bathrooms, and an attached 2-car garage. Elegant details include four fireplaces, verdi marble flooring, Marvin windows, a slate roof, and a Viessmann boiler-premier materials chosen for durability and style. The dramatic living room boasts a large wood-burning fireplace framed by 8-foot, 12-panel Marvin windows, crescent-shaped upper windows, and soaring 30-foot ceilings that fill the space with natural light. The chef's kitchen will delight serious cooks, offering THOR double ovens, a mini wood-burning brick fireplace, center island with butcher block top, verdi marble floors, soapstone counters, Wood Harbor cabinetry, and a charming built-in breakfast alcove. The formal dining room features 12-foot ceilings, crown molding, and direct access to an elevated synthetic sundeck, ideal for entertaining or relaxing outdoors. The intimate den, with its brick fireplace, wet bar, and copper sink, provides a cozy retreat for quiet evenings. A first-floor half bath and laundry room add convenience. Upstairs, a custom fluted staircase leads to two spacious guest bedrooms, a full tile bath, and a walk-in cedar closet. The primary suite (30x14) is a luxurious escape featuring a gas fireplace, 10-foot ceilings, crown moulding, and peaceful mountain views. Two walk-in closets and a spa-inspired primary bath include a sauna, whirlpool tub, tile shower, and double vanity. A fourth ensuite bedroom completes the upper level. Outdoors, the serene setting offers unmatched privacy while being just minutes from Dorset Village and Manchester amenities. This rare offering combines classic design, privacy, and enduring Vermont elegance.

Listed by David Halligan of Four Seasons Sotheby's Int'l Realty

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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1268 Myers Road Shaftsbury VT 05262

Shaftsbury, VT1268 Myers Road

Price$1,495,000

Est. Mortgage: $/month

MLS Number 5089684

  • Residential Single Family
  • Full Bath 2
  • Address 1268 Myers Road
  • Construction Existing
  • Bedrooms 4

Welcome to your paradise! This exquisite 30 acre estate offers extreme privacy, a custom home with architectural details throughout, a modern 1 BR guest apartment, an oversized 2 car garage, top notch equestrian facilities, a trout pond, playhouse and the list goes on and on. The winding driveway leads one to an enchanting compound, as it opens to overlook the exclusive estate in all of it's glory. The 3 Bedroom, 4000SF home boasts 10 foot ceilings, with reclaimed antique oak pocket doors from a nearby mansion, inlaid floors, stained glass windows, arches and a custom cherry and granite eat in island kitchen. The foyer, gracious leads to the expansive living room and kitchen overlooking the fantastic spring fed pond... there is a main level primary suite, and second floor gathering space with pond-side balcony and 2 bedrooms. The finished basement hosts a family recreation room and a sauna. Equestrian facilities are comprised of a recently built barn with 4, 12 X 12 stalls boasting ThuroBed Matress Systems, as well as a 12 X 18 foaling stall, leaving room for additional stalls. Paddocks and pastures with Ramm Flex Fencing and a USDF regulation 20m X 60m dressage arena with sand and fiber footing. There's a large shed and a 5 acre pasture. There's so much room for storage or lifestyle expansion within the main house or the building hosting the detached garage and guest house as there is a full unfinished second floor that could expand studio, exercise and office needs. This special location is convenient to area amenities yet a total feel of being away from it all! Whether you are an equestrian, or you are looking for an idyllic homestead, a place to enjoy nature and peace, and/or a property that demonstrates Vermont beauty, one shall adore this property. It is conveniently 3 hours from NYC, 1 hour from the Albany airport, and 25 minutes from Manchester, all while still feeling a world away! West Mountain Views are engaged wherever one is on the property!

Listed by Laura Beckwith of Josiah Allen Real Estate,Inc.

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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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3090 South Road Woodstock VT 05091

Woodstock, VT3090 South Road

Price$1,495,000

Est. Mortgage: $/month

Active With Contract

MLS Number 5089519

  • Residential Single Family
  • Full Bath 2
  • Address 3090 South Road
  • Construction Existing
  • Bedrooms 3

PROPERTY WILL CONTINUE TO BE SHOWN, UNTIL PENDING. Known affectionately as “Green Gable Farm,” this beautifully renovated 1884 Vermont farmhouse sits on 5 picturesque acres in Woodstock, complete with a year-round babbling brook, just minutes from South Woodstock, the Woodstock Inn Fitness Center, golf course, cross-country ski trails, mountain biking, and the Woodstock Village Green. The current owners undertook a comprehensive renovation, thoughtfully preserving the home's historic character-including original barnboard floors and exposed beams-while updating every major system and living space. New mechanicals, upgraded insulation, all new double-pane windows, central HVAC with heating and cooling, high-speed fiber internet, new baths, and a fully redesigned kitchen bring modern comfort to this classic country home. The architecturally reimagined floor plan creates an open, inviting first floor centered around a gourmet eat-in kitchen with Viking appliances, farmhouse sink and abundant workspace. A highly functional mudroom entry, marble tile floors, new laundry room, full bath, and first-floor bedroom add everyday practicality. The kitchen flows into a cozy sitting area with fireplace and additional flexible living spaces ideal for dining, reading, or entertaining. Upstairs are 2 spacious ensuite bedrooms, including a serene primary suite with dressing area, double sinks, smart toilet, glass-enclosed shower, and freestanding soaking tub overlooking stone walls, open fields, and berry patches. Sliding doors off the kitchen open to a large rear deck featuring a heated 12' swim spa for year-round enjoyment. A charming historic shed-barn offers space for a workshop, studio, or recreation area, while unfinished space above the attached two-car garage provides expansion potential.

Listed by John Snyder of Snyder Donegan Real Estate Group

$
$
%
$/month over payments
Federal 30-year interest rate: 6.48% last updated on May 28, 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.

Virtual TourSave FavoriteSchedule TourAsk A QuestionMore Details

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 June 8, 2026 11:43 PM EDT